GLYOXALINE
GLYOXALINE
Glyoxaline is useful as a buffer in the pH range of 6.2-7.8, and one of its applications is in the purification of His-tagged proteins in immobilized metal affinity chromatography (IMAC).
Glyoxaline is part of the theophylline molecule, found in tea leaves and coffee beans, which stimulates the central nervous system.
Glyoxaline is a highly polar compound, as evidenced by a calculated dipole of 3.61D, and is entirely soluble in water.
CAS Number: 288-32-4
EC Number: 206-019-2
Chemical Formula: C3H4N2
Molar Mass: 68.077 g/mol
Synonyms: imidazole, 1H-Imidazole, 288-32-4, Glyoxaline, Imidazol, Iminazole, Miazole, 1,3-Diazole, Glyoxalin, Imutex, 1,3-Diaza-2,4-cyclopentadiene, Pyrro(b)monazole, USAF EK-4733, Pyrro[b]monazole, Formamidine, N,N’-vinylene-, Glioksal [Polish], Glioksal, Methanimidamide, N,N’-1,2-ethenediyl-, IMD, CCRIS 3345, AI3-24703, NSC 60522, BRN 0103853, 1H-Imidazole, dimer, DTXSID2029616, N,N’-vinyleneformamidine, CHEMBL540, 7GBN705NH1, CHEBI:16069, N,N’-1,2-ethenediylmethanimidamide, MFCD00005183, NSC-60522, 227760-40-9, DTXCID809616, 1H-imidazol, CAS-288-32-4, Imidazole (8CI), NSC51860, Imidazole, puriss. p.a., >=99.5% (GC), EINECS 206-019-2, NSC 51860, UNII-7GBN705NH1, Immidazole, imidazole-, 1-H-imidazole, Glyoxaline solution, Imidazole, Reagent, {Pyrro[b]monazole}, 1,4-cyclopentadiene, Imidazole, ACS grade, 1H-Imidazole (9CI), IMIDAZOLE [MI], IMIDAZOLE [INCI], Imidazole buffer Solution, Formamidine,N’-vinylene-, bmse000096, bmse000790, WLN: T5M CNJ, EC 206-019-2, ENALAPRIL IMPURITY I, IMIDAZOLE [USP-RS], IMIDAZOLE [WHO-DD], NCIStruc1_001975, NCIStruc2_000693, Imidazole, LR, >=99%, 5-23-04-00191 (Beilstein Handbook Reference), MLS001055465, BDBM7882, Imidazole-buffered saline (5X), Imidazole-[2-13C,15N2], HSDB 8449, 1,3-Diaza-2,4-cyclopentadiene-, Imidazole, ReagentPlus(R), 99%, ZINC901039, Imidazole, for synthesis, 99.5%, BCP26547, HY-D0837, NSC60522, Methanimidamide,N’-1,2-ethenediyl-, Tox21_201504, Tox21_303345, s6006, STK362967, AKOS000120177, AM82000, CS-5135, DB03366, Imidazole, BioUltra, >=99.5% (GC), NCGC00090984-01, NCGC00090984-02, NCGC00257344-01, NCGC00259055-01, 2,4-Diazonia-2,4-cyclopentadiene-1-ide, BP-11451, Him, SMR000057825, 1,3-Diaza-2,4-cyclopentadiene;Glyoxaline, Imidazole, SAJ special grade, >=99.0%, Imidazole, Vetec(TM) reagent grade, 98%, DB-002018, CLOTRIMAZOLE IMPURITY D [EP IMPURITY], FT-0627179, FT-0670295, I0001, I0014, I0288, I0290, Imidazole, >=99% (titration), crystalline, EN300-19083, Imidazole Zone Refined (number of passes:30), Imidazole, ACS reagent, >=99% (titration), C01589, P17516, ENALAPRIL MALEATE IMPURITY I [EP IMPURITY], Q328692, J-200340, SILDENAFIL CITRATE IMPURITY E [EP IMPURITY], Imidazole, for molecular biology, >=99% (titration), F2190-0638, Z104472692, Imidazole, BioUltra, for molecular biology, >=99.5% (GC), Imidazole, European Pharmacopoeia (EP) Reference Standard, 4286D518-643C-4C69-BCE7-519D073F4992, Imidazole, pharmaceutical impurity standard, >=95.0% (HPLC), Imidazole, United States Pharmacopeia (USP) Reference Standard, Imidazole;1,3-diazole; glyoxaline; 1,3-diazacyclopenta-2,4-diene, ONDANSETRON HYDROCHLORIDE DIHYDRATE IMPURITY E [EP IMPURITY], ONDANSETRON HYDROCHLORIDE IMPURITY, IMIDAZOLE- [USP IMPURITY], Imidazole, anhydrous, free-flowing, Redi-Dri(TM), ACS reagent, >=99%, Imidazole, Pharmaceutical Secondary Standard; Certified Reference Material, Ondansetron impurity E, European Pharmacopoeia (EP) Reference Standard, 1,3-Diaza-2,4-cyclopentadiene, 103853 [Beilstein], 1H-Imidazol [German] [ACD/IUPAC Name], 1H-Imidazole [ACD/Index Name] [ACD/IUPAC Name], 1H-Imidazole [French] [ACD/Index Name] [ACD/IUPAC Name], 206-019-2 [EINECS], 288-32-4 [RN], 36364-49-5 [RN], Glyoxaline, imidazol, Imidazole [Wiki], MFCD00005183 [MDL number], mono-imidazole, 1,3-Diazacyclopenta-2,4-diene, 1,3-Diazole, 116421-26-2 secondary RN [RN], 146117-15-9 secondary RN [RN], 5-23-04-00191 [Beilstein], 5-dihydro-1H-imidazole, 6745-43-3 [RN], 6923-01-9 [RN], Formamidine, N,N’-vinylene-, Glyoxalin, Glyoxaline, 1, Glyoxaline, Iminazole, IMD, Imidazole buffermissing, Imidazole-buffered saline (5X), imidazole-d3, Imidazolemissing, iminazole, Imutex, Methanimidamide, N,N’-1,2-ethenediyl-, Methanimidamide, N,N-1,2-ethenediyl-, Miazole, missing, N,N’-1,2-ethenediylmethanimidamide, N,N’-vinyleneformamidine, OmniPur Imidazole – CAS 288-32-4 – Calbiochem, OmniPur(R) Imidazole, Pyrro(b)monazole, pyrro[b]monazole, STR00036, T5M CNJ [WLN]
Glyoxaline is a five-membered heterocycle that is found in many naturally occurring compounds.
Glyoxaline exhibits both acidic and basic properties.
Glyoxaline is reported to be an inhibitor of thromboxane formation.
Glyoxaline vertical spectrum and the radiationless decay have been recorded and analyzed.
Glyoxaline is useful as a buffer in the pH range of 6.2-7.8 One of the applications of Glyoxaline is in the purification of His-tagged proteins in immobilised metal affinity chromatography(IMAC).
Glyoxaline is used to elute tagged proteins bound to Ni ions attached to the surface of beads in the chromatography column.
An excess of Glyoxaline is passed through the column, which displaces the His-tag from nickel co-ordination, freeing the His-tagged proteins.
Glyoxaline has become an important part of many pharmaceuticals.
Synthetic Glyoxalines are present in many fungicides and antifungal, antiprotozoal, and antihypertensive medications.
Glyoxaline is part of the theophylline molecule, found in tea leaves and coffee beans, which stimulates the central nervous system.
Glyoxaline is present in the anticancer medication mercaptopurine, which combats leukemia by interfering with DNA activities.
Glyoxaline is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 tonnes per annum.
Glyoxaline is used by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
Glyoxaline is an organic compound with the formula C3N2H4.
Glyoxaline is a white or colourless solid that is soluble in water, producing a mildly alkaline solution.
In chemistry, Glyoxaline is an aromatic heterocycle, classified as a diazole, and has non-adjacent nitrogen atoms in meta-substitution.
Many natural products, especially alkaloids, contain the Glyoxaline ring.
These Glyoxalines share the 1,3-C3N2 ring but feature varied substituents.
This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.
Many drugs contain an Glyoxaline ring, such as certain antifungal drugs, the nitroGlyoxaline series of antibiotics, and the sedative midazolam.
When fused to a pyrimidine ring, Glyoxaline forms a purine, which is the most widely occurring nitrogen-containing heterocycle in nature.
The name “Glyoxaline” was coined in 1887 by the German chemist Arthur Rudolf Hantzsch (1857–1935).
Glyoxaline, any of a class of organic compounds of the heterocyclic series characterized by a ring structure composed of three carbon atoms and two nitrogen atoms at nonadjacent positions.
The simplest member of the Glyoxaline family is Glyoxaline itself, a compound with molecular formula C3H4N2.
Glyoxaline was first prepared in 1858.
Other Glyoxaline compounds have been known longer: allantoin (discovered in 1800) and parabanic acid were prepared in 1837 from uric acid.
The amino acid histidine and Glyoxaline decomposition product histamine have the Glyoxaline structure, as does biotin, a growth factor for both humans and yeast.
Glyoxalines, benzGlyoxalines, imidazolines, imidazolidines, and related carbenes are classes of heterocyclic compounds possessing unique chemical and physical properties.
Tremendous advances in Glyoxaline chemistry have been made in the decade since 1995, and are manifested in the large body of the literature related to Glyoxaline and Glyoxaline analogs.
This chapter reviews important developments in Glyoxaline chemistry from 1996 to 2006.
Major portions of the chapter are devoted to the reactivity and synthesis of Glyoxaline and Glyoxalines analogs.
Special attention has been given to the transformations involving transition metal catalysts and N-heterocyclic carbenes.
Theoretical, experimental, structural and thermodynamic studies, and the applications of Glyoxaline and Glyoxaline analogs are also covered.
Glyoxaline (ImH) is an organic compound with the formula C3N2H4.
Glyoxaline is a white or colourless solid that is soluble in water, producing a mildly alkaline solution.
In chemistry, Glyoxaline is an aromatic heterocycle, classified as a diazole, and has non-adjacent nitrogen atoms in meta-substitution.
Many natural products, especially alkaloids, contain the Glyoxaline ring.
These Glyoxalines share the 1,3-C3N2 ring but feature varied substituents.
This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.
Many drugs contain an Glyoxaline ring, such as certain antifungal drugs, the nitroGlyoxaline series of antibiotics, and the sedative midazolam.
When fused to a pyrimidine ring, Glyoxaline forms a purine, which is the most widely occurring nitrogen-containing heterocycle in nature.
The name “Glyoxaline” was coined in 1887 by the German chemist Arthur Rudolf Hantzsch (1857–1935).
Glyoxalines have occupied a unique position in heterocyclic chemistry, and Glyoxaline derivatives have attracted considerable interests in recent years for their versatile properties in chemistry and pharmacology.
Glyoxaline is nitrogen-containing heterocyclic ring which possesses biological and pharmaceutical importance.
Thus, Glyoxaline compounds have been an interesting source for researchers for more than a century.
The Glyoxaline ring is a constituent of several important natural products, including purine, histamine, histidine, and nucleic acid.
Being a polar and ionisable aromatic compound, Glyoxaline improves pharmacokinetic characteristics of lead molecules and thus is used as a remedy to optimize solubility and bioavailability parameters of proposed poorly soluble lead molecules.
There are several methods used for the synthesis of Glyoxaline-containing compounds, and also their various structure reactions offer enormous scope in the field of medicinal chemistry.
The Glyoxaline derivatives possess extensive spectrum of biological activities such as antibacterial, anticancer, antitubercular, antifungal, analgesic, and anti-HIV activities.
Glyoxaline nucleus forms the main structure of some well-known components of human organisms, that is, the amino acid histidine, Vit-B12, a component of DNA base structure and purines, histamine, and biotin.
Glyoxaline is also present in the structure of many natural or synthetic drug molecules, that is, cimetidine, azomycin, and metronidazole.
Glyoxaline-containing drugs have a broaden scope in remedying various dispositions in clinical medicine.
Glyoxaline was first synthesized by Heinrich Debus in 1858, but various Glyoxaline derivatives had been discovered as early as the 1840s.
His synthesis used glyoxal and formaldehyde in ammonia to form Glyoxaline.
This synthesis, while producing relatively low yields, is still used for creating C-substituted Glyoxalines.
Glyoxaline is a 5-membered planar ring, which is soluble in water and other polar solvents.
Glyoxaline exists in two equivalent tautomeric forms because the hydrogen atom can be located on either of the two nitrogen atoms.
Glyoxaline is a highly polar compound, as evidenced by a calculated dipole of 3.61D, and is entirely soluble in water.
Glyoxaline is amphoteric; that is, Glyoxaline can function as both an acid and a base.
Glyoxaline is classified as aromatic due to the presence of a sextet of π-electrons, consisting of a pair of electrons from the protonated nitrogen atom and one from each of the remaining four atoms of the ring.
Salts of Glyoxaline:
Salts of Glyoxaline where the Glyoxaline ring is the cation are known as imidazolium salts (for example, imidazolium chloride or nitrate).
These salts are formed from the protonation or substitution at nitrogen of Glyoxaline.
These salts have been used as ionic liquids and precursors to stable carbenes.
Salts where a deprotonated Glyoxaline is an anion are also well known; these salts are known as imidazolates (for example, sodium imidazolate, NaC3H3N2).
Biological Significance and Applications:
Glyoxaline is incorporated into many important biological compounds.
The most pervasive is the amino acid histidine, which has an Glyoxaline side-chain.
Histidine is present in many proteins and enzymes, e.g. by binding metal cofactors, as seen in hemoglobin.
Glyoxaline-based histidine compounds play a very important role in intracellular buffering.
Histidine can be decarboxylated to histamine.
Histamine can cause urticaria (hives) when Glyoxaline is produced during allergic reaction.
Glyoxaline substituents are found in many pharmaceuticals.
Synthetic Glyoxalines are present in many fungicides and antifungal, antiprotozoal, and antihypertensive medications.
Glyoxaline is part of the theophylline molecule, found in tea leaves and coffee beans, that stimulates the central nervous system.
Glyoxaline is present in the anticancer medication mercaptopurine, which combats leukemia by interfering with DNA activities.
A number of substituted Glyoxalines, including clotrimazole, are selective inhibitors of nitric oxide synthase, which makes them interesting drug targets in inflammation, neurodegenerative diseases and tumors of the nervous system.
Other biological activities of the Glyoxaline pharmacophore relate to the downregulation of intracellular Ca2+ and K+ fluxes, and interference with translation initiation.
Pharmaceutical derivatives:
The substituted Glyoxaline derivatives are valuable in treatment of many systemic fungal infections.
Glyoxalines belong to the class of azole antifungals, which includes ketoconazole, miconazole, and clotrimazole.
For comparison, another group of azoles is the triazoles, which includes fluconazole, itraconazole, and voriconazole.
The difference between the Glyoxalines and the triazoles involves the mechanism of inhibition of the cytochrome P450 enzyme.
The N3 of the Glyoxaline compound binds to the heme iron atom of ferric cytochrome P450, whereas the N4 of the triazoles bind to the heme group.
The triazoles have been shown to have a higher specificity for the cytochrome P450 than Glyoxalines, thereby making them more potent than the Glyoxalines.
Some Glyoxaline derivatives show effects on insects, for example sulconazole nitrate exhibits a strong anti-feeding effect on the keratin-digesting Australian carpet beetle larvae Anthrenocerus australis, as does econazole nitrate with the common clothes moth Tineola bisselliella.
Applications of Glyoxaline:
Industrial Applications:
Glyoxaline itself has few direct applications.
Glyoxaline is instead a precursor to a variety of agrichemicals, including enilconazole, climbazole, clotrimazole, prochloraz, and bifonazole.
Uses of Glyoxaline:
Glyoxaline is used as an intermediate (pharmaceuticals, pesticides, dye intermediates, auxiliaries for textile dyeing and finishing, photographic chemicals, and corrosion inhibitors) and hardener for epoxy resins.
Glyoxaline is also used in process regulators, anti-freeze agents, photographic application, laboratory applications, glues/adhesives, cement fillers or sealing compounds, paints, varnishes, lacquers, consumer cleaning and washing agents, swimming pool applications, and in publishing, printing, and reproduction of recorded media.
Glyoxaline is Karl Fischer reagent in analytical chemistry.
Glyoxaline is reagent in synthetic organic chemistry.
The bulk of Glyoxaline produced is used in the preparation of biologically active compounds.
Glyoxaline is used in the chemical industry as an intermediate in the production of pharmaceuticals, pesticides, dye intermediates, auxiliaries for textile dyeing and finishing, photographic chemicals and corrosion inhibitors.
Glyoxaline is used in cosmetics as a buffering agent
Widespread uses by professional workers:
Glyoxaline is used in the following products: laboratory chemicals and pH regulators and water treatment products.
Glyoxaline is used in the following areas: scientific research and development and health services.
Other release to the environment of Glyoxaline is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use resulting in inclusion into or onto a materials (e.g. binding agent in paints and coatings or adhesives).
Uses at industrial sites:
Glyoxaline is used in the following products: laboratory chemicals, metal surface treatment products and polymers.
Glyoxaline has an industrial use resulting in manufacture of another substance (use of intermediates).
Glyoxaline is used in the following areas: scientific research and development.
Glyoxaline is used for the manufacture of: chemicals.
Release to the environment of Glyoxaline can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates), in processing aids at industrial sites, in the production of articles and for thermoplastic manufacture.
Industrial Processes with risk of exposure:
Textiles (Fiber & Fabric Manufacturing)
Painting (Pigments, Binders, and Biocides)
Plastic Composites Manufacturing
Photographic Processing
Use in Biological Research:
Glyoxaline is a suitable buffer for pH 6.2-7.8.
Pure Glyoxaline has essentially no absorbance at protein relevant wavelenths (280 nm), however lower purities of Glyoxaline can give notable absorbance at 280 nm.
Glyoxaline can interfere with the Lowry protein assay.
Coordination Chemistry:
Glyoxaline and its derivatives have high affinity for metal cations.
One of the applications of Glyoxaline is in the purification of His-tagged proteins in immobilised metal affinity chromatography (IMAC).
Glyoxaline is used to elute tagged proteins bound to nickel ions attached to the surface of beads in the chromatography column.
An excess of Glyoxaline is passed through the column, which displaces the His-tag from nickel coordination, freeing the His-tagged proteins.
Structure and Properties of Glyoxaline:
Glyoxaline is a planar 5-membered ring, that exists in two equivalent tautomeric forms because hydrogen can be bound to one or another nitrogen atom.
Glyoxaline is a highly polar compound, as evidenced by Glyoxaline electric dipole moment of 3.67 D, and is highly soluble in water.
Glyoxaline is classified as aromatic due to the presence of a planar ring containing 6 π-electrons (a pair of electrons from the protonated nitrogen atom and one from each of the remaining four atoms of the ring).
Amphoterism:
Glyoxaline is amphoteric, which is to say that Glyoxaline can function both as an acid and as a base.
As an acid, the pKa of Glyoxaline is 14.5, making Glyoxaline less acidic than carboxylic acids, phenols, and imides, but slightly more acidic than alcohols.
The acidic proton is the one bound to nitrogen.
Deprotonation gives the imidazolide anion, which is symmetrical.
As a base, the pKa of the conjugate acid (cited as pKBH+ to avoid confusion between the two) is approximately 7, making Glyoxaline approximately sixty times more basic than pyridine.
The basic site is the nitrogen with the lone pair (and not bound to hydrogen).
Protonation gives the imidazolium cation, which is symmetrical.
Preparation of Glyoxaline:
Glyoxaline was first reported in 1858 by the German chemist Heinrich Debus, although various Glyoxaline derivatives had been discovered as early as the 1840s.
Glyoxaline was shown that glyoxal, formaldehyde, and ammonia condense to form Glyoxaline.
This synthesis, while producing relatively low yields, is still used for generating C-substituted Glyoxalines.
In one microwave modification, the reactants are benzil, benzaldehyde and ammonia in glacial acetic acid, forming 2,4,5-triphenylGlyoxaline (“lophine”).
Glyoxaline can be synthesized by numerous methods besides the Debus method.
Many of these syntheses can also be applied to different substituted Glyoxalines and Glyoxaline derivatives by varying the functional groups on the reactants.
These methods are commonly categorized by which and how many bonds form to make the Glyoxaline rings.
For example, the Debus method forms the (1,2), (3,4), and (1,5) bonds in Glyoxaline, using each reactant as a fragment of the ring, and thus this method would be a three-bond-forming synthesis.
A small sampling of these methods is presented below.
Formation of one bond:
The (1,5) or (3,4) bond can be formed by the reaction of an imidate and an α-aminoaldehyde or α-aminoacetal.
The example below applies to Glyoxaline when R1 = R2 = hydrogen.
Formation of two bonds:
The (1,2) and (2,3) bonds can be formed by treating a 1,2-diaminoalkane, at high temperatures, with an alcohol, aldehyde, or carboxylic acid.
A dehydrogenating catalyst, such as platinum on alumina, is required.
The (1,2) and (3,4) bonds can also be formed from N-substituted α-aminoketones and formamide with heat.
Glyoxaline will be a 1,4-disubstituted Glyoxaline, but here since R1 = R2 = hydrogen, Glyoxaline itself is Glyoxaline.
The yield of this reaction is moderate, but Glyoxaline seems to be the most effective method of making the 1,4 substitution.
Formation of four bonds:
This is a general method that is able to give good yields for substituted Glyoxalines.
In essence, Glyoxaline is an adaptation of the Debus method called the Debus-Radziszewski Glyoxaline synthesis.
The starting materials are substituted glyoxal, aldehyde, amine, and ammonia or an ammonium salt.
Formation from other heterocycles:
Glyoxaline can be synthesized by the photolysis of 1-vinyltetrazole.
This reaction will give substantial yields only if the 1-vinyltetrazole is made efficiently from an organotin compound, such as 2-tributylstannyltetrazole.
The reaction, shown below, produces Glyoxaline when R1 = R2 = R3 = hydrogen.
Glyoxaline can also be formed in a vapor-phase reaction.
The reaction occurs with formamide, ethylenediamine, and hydrogen over platinum on alumina, and Glyoxaline must take place between 340 and 480 °C.
This forms a very pure Glyoxaline product.
Van Leusen reaction:
The Van Leusen reaction can also be employed to form Glyoxalines starting from TosMIC and an aldimine.
The Van Leusen Glyoxaline Synthesis allows the preparation of Glyoxalines from aldimines by reaction with tosylmethyl isocyanide (TosMIC).
The reaction has later been expanded to a two-step synthesis in which the aldimine is generated in situ: the Van Leusen Three-Component Reaction (vL-3CR).
Manufacturing Methods of Glyoxaline:
In the generally applicable Radziszewski reaction, a 1,2-dicarbonyl compound is condensed with an aldehyde and ammonia in a molar ratio of 1:1: 2, respectively.
Replacement of a molar equivalent of ammonia with a primary amine leads to the corresponding 1-substituted Glyoxalines.
The reaction is usually carried out in water or a water-alcohol mixture at 50-100 °C.
Work-up may involve the usual processes (e.g., distillation, extraction, and crystallization).
Distillation leads to Glyoxaline with a purity > 99%.
The yield is generally 60-85%.
General Manufacturing Information of Glyoxaline:
Industry Processing Sectors:
All Other Basic Organic Chemical Manufacturing
Plastics Material and Resin Manufacturing
Human Metabolite Information of Glyoxaline:
Tissue Locations:
Adrenal Cortex
Adrenal Gland
Epidermis
Liver
Neuron
Placenta
Platelet
Testis
Cellular Locations:
Cytoplasm
Handling and Storage of Glyoxaline:
Safe Storage:
Separated from strong acids and food and feedstuffs.
Storage Conditions:
Keep container tightly closed in a dry and well-ventilated place.
Storage class (TRGS 510): 6.1D: Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects.
Safety of Glyoxaline:
Glyoxaline has low acute toxicity as indicated by the LD50 of 970 mg/kg (Rat, oral).
Accidental Release Measures of Glyoxaline:
Personal protection:
Use complete protective clothing including self-contained breathing apparatus.
Sweep spilled substance into covered containers.
Then wash away with plenty of water.
Cleanup Methods of Glyoxaline:
Personal precautions, protective equipment and emergency procedures:
Use personal protective equipment.
Avoid dust formation.
Avoid breathing vapors, mist or gas.
Ensure adequate ventilation.
Evacuate personnel to safe areas.
Avoid breathing dust.
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Methods and materials for containment and cleaning up:
Pick up and arrange disposal without creating dust.
Sweep up and shovel.
Keep in suitable, closed containers for disposal.
Personal protection:
Use complete protective clothing including self-contained breathing apparatus.
Sweep spilled substance into covered containers.
Then wash away with plenty of water.
Disposal Methods of Glyoxaline:
Recycle any unused portion of the material for Glyoxaline approved use or return it to the manufacturer or supplier.
Ultimate disposal of the chemical must consider:
Glyoxaline’s impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations.
If Glyoxaline is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.
Contact a licensed professional waste disposal service to dispose of Glyoxaline.
Dissolve or mix Glyoxaline with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Offer surplus and non-recyclable solutions to a licensed disposal company;
Contaminated packaging:
Dispose of as unused product.
Identifiers of Glyoxaline:
CAS Number: 288-32-4
ChEBI: CHEBI:16069
ChEMBL: ChEMBL540
ChemSpider: 773
ECHA InfoCard: 100.005.473
EC Number: 206-019-2
KEGG: C01589
PubChem CID: 795
RTECS number: NI3325000
UNII: 7GBN705NH1
CompTox Dashboard (EPA): DTXSID2029616
InChI: InChI=1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)
Key: RAXXELZNTBOGNW-UHFFFAOYSA-N
InChI=1/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)
Key: RAXXELZNTBOGNW-UHFFFAOYAS
SMILES: c1cnc[nH]1
Synonym(s): 1,3-Diaza-2,4-cyclopentadiene
Empirical Formula (Hill Notation): C3H4N2
CAS Number: 288-32-4
Molecular Weight: 68.08
Beilstein: 103853
EC Number: 206-019-2
MDL number: MFCD00005183
eCl@ss: 39161001
PubChem Substance ID: 24895975
NACRES: NA.21
EC / List no.: 206-019-2
CAS no.: 288-32-4
Mol. formula: C3H4N2
CAS number: 288-32-4
EC index number: 613-319-00-0
EC number: 206-019-2
Hill Formula: C₃H₄N₂
Molar Mass: 68.08 g/mol
HS Code: 2933 29 90
Properties of Glyoxaline:
Chemical formula: C3H4N2
Molar mass: 68.077 g/mol
Appearance: White or pale yellow solid
Density: 1.23 g/cm3, solid
Melting point: 89 to 91 °C (192 to 196 °F; 362 to 364 K)
Boiling point: 256 °C (493 °F; 529 K)
Solubility in water: 633 g/L
Acidity (pKa): 6.95 (for the conjugate acid)
UV-vis (λmax): 206 nm
Grade: ACS reagent
Quality Level: 200
Vapor pressure: <1 mmHg ( 20 °C) Assay: ≥99% (titration) Impurities: ≤0.2% water Ign. residue: ≤0.1% pH: 9.5-11.0 (25 °C, 5% in H2O) pKa (25 °C): 6.95 bp: 256 °C (lit.) mp: 88-91 °C (lit.) Cation traces: Fe: ≤0.001% SMILES string: c1c[nH]cn1 InChI: 1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5) InChI key: RAXXELZNTBOGNW-UHFFFAOYSA-N Boiling point: 256 °C (1013 hPa) Density: 1.233 g/cm3 (20 °C) Flash point: 145 °C Ignition temperature: 480 °C Melting Point: 90.5 °C pH value: 10.5 (67 g/l, H₂O, 20 °C) Vapor pressure: 0.003 hPa (20 °C) Bulk density: 500 - 600 kg/m3 Solubility: 633 g/l Molecular Weight: 68.08 XLogP3: -0.1 Hydrogen Bond Donor Count: 1 Hydrogen Bond Acceptor Count: 1 Rotatable Bond Count: 0 Exact Mass: 68.037448136 Monoisotopic Mass: 68.037448136 Topological Polar Surface Area: 28.7 Ų Heavy Atom Count: 5 Complexity: 28.1 Isotope Atom Count: 0 Defined Atom Stereocenter Count: 0 Undefined Atom Stereocenter Count: 0 Defined Bond Stereocenter Count: 0 Undefined Bond Stereocenter Count: 0 Covalently-Bonded Unit Count: 1 Compound Is Canonicalized: Yes Specifications of Glyoxaline: Assay (GC, area%): ≥ 99.0 % (a/a) Melting range (lower value): ≥ 88 °C Melting range (upper value): ≤ 91 °C Water (K. F.): ≤ 0.20 % Identity (IR): passes test Structure of Glyoxaline: Crystal structure: Monoclinic Coordination geometry: Planar 5-membered ring Dipole moment: 3.61 D Related heterocycles: BenzGlyoxaline, an analog with a fused benzene ring DihydroGlyoxaline or imidazoline, an analog where the 4,5-double bond is saturated Pyrrole, an analog with only one nitrogen atom in position 1 Oxazole, an analog with the nitrogen atom in position 1 replaced by oxygen Thiazole, an analog with the nitrogen atom in position 1 replaced by sulfur Pyrazole, an analog with two adjacent nitrogen atoms Triazoles, analogs with three nitrogen atoms Names of Glyoxaline: Regulatory process names: 1,3-Diaza-2,4-cyclopentadiene 1,3-Diazole Formamidine, N,N'-vinylene- Glioksal Glyoxalin Glyoxaline IMD Imidazol Imidazole Iminazole Imutex Methanimidamide, N,N'-1,2-ethenediyl- Miazole Pyrro(b)monazole Translated names: imidasool (et) Imidatsoli (fi) imidazol (cs) imidazol (da) Imidazol (de) imidazol (es) imidazol (hr) imidazol (hu) imidazol (pl) imidazol (ro) imidazol (sk) imidazol (sl) imidazol (sv) imidazolas (lt) imidazole (fr) imidazole (pt) imidazolo (it) imidazols (lv) Imidazool (nl) imidażol (mt) ιμιδαζόλιο (el) имидазол (bg) CAS name: 1H-Imidazole IUPAC names: (2S)-2-amino-3-(1H-imidazol-5-yl)propanoic acid 1, 3-diaea-2, 4-cyclopentadiene 1,3- diazole Imidazole 1,3-diaza-2,4-ciclopentadieno 1,3-Diaza-2,4-cyclopentadien 1,3-diaza-2,4-cyclopentadiene 1,3-Diaza-2,4-cyclopentadiene, Glyoxaline 1-H-Imidazole 1H-IMIDAZOLE 1H-Imidazole 1H-imidazole 1H-imidazole Imidazol Imidazol IMIDAZOLE Imidazole imidazole IMIDAZOLE Imidazole imidazole Preferred IUPAC name: 1H-Imidazole Systematic IUPAC name: 1,3-Diazacyclopenta-2,4-diene Trade names: Imidazole Other names: 1,3-Diazole Glyoxaline (archaic) Other identifiers: 116421-26-2 116421-26-2 146117-15-9 146117-15-9 288-32-4