THIOUREA
THIOUREA
Thiourea acts as a precursor to sulphide to produce metal sulphides like mercury sulphide.
Thiourea is structurally similar to urea, except that the oxygen atom is replaced by a sulfur atom, but the properties of urea and thiourea differ significantly.
Thiourea is a reagent in organic synthesis.
CAS Number: 62-56-6
EC Number: 200-543-5
Chemical Formula: CH4N2S
Molar Mass: 76.12 g/mol
Synonyms: THIOUREA, Thiocarbamide, 62-56-6, Isothiourea, 2-Thiourea, Pseudothiourea, Sulourea, Thiuronium, 2-Thiopseudourea, Sulfourea, Thiocarbonic acid diamide, Urea, thio-, Carbamimidothioic acid, beta-Thiopseudourea, Thiomocovina, Urea, 2-thio-, Tsizp 34, Pseudourea, 2-thio-, Thiocarbamid, Thioharnstoff, Thiokarbamid, Sulfouren, USAF EK-497, RCRA waste number U219, carbonothioic diamide, thio-urea, UNII-GYV9AM2QAG, NSC 5033, MFCD00008067, .beta.-Thiopseudourea, 17356-08-0, GYV9AM2QAG, Urea, thio- (8CI), H2NC(S)NH2, (NH2)2CS, CHEMBL260876, CHEBI:36946, DSSTox_CID_1348, DSSTox_RID_76101, DSSTox_GSID_21348, Thiourea, 99%, extra pure, TOU, Thiomocovina [Czech], Thiourea, 99+%, for analysis, Caswell No. 855, Thiourea, 99+%, ACS reagent, sulfocarbamide, RCRA waste no. U219, CAS-62-56-6, CCRIS 588, S C (N H2)2, HSDB 1401, THIOUREA, ACS, EINECS 200-543-5, EPA Pesticide Chemical Code 080201, aminothioamide, thiopseudourea, thiourea group, AI3-03582, isothiourea group, Thiourea Solution, aminothiocarboxamide, 2-Thio-Pseudourea, Thiocarbonic diamide, 2-Thio-Urea, beta -thiopseudourea, Thiourea, homopolymer, Thiourea, 99%, Sulfourea, Thiocarbamide, WLN: ZYZUS, EC 200-543-5, Thiourea ACS Reagent Grade, Thiourea, LR, >=98%, MLS002454451, BIDD:ER0582, DTXSID9021348, [N]C(N)=S, NC([S])=N, NSC5033, HMS2234E12, HMS3369M21, AMY40190, BCP27948, NSC-5033, STR00054, ZINC8437745, Thiocarbamide,Isothiourea,2-Thiourea, Tox21_201873, Tox21_302767, BDBM50229993, STL194300, Thiourea, ACS reagent, >=99.0%, AKOS000269032, AKOS028109302, CCG-207963, MCULE-5046264236, NE10552, UN 2877, Thiourea, ReagentPlus(R), >=99.0%, NCGC00091199-01, NCGC00091199-02, NCGC00091199-03, NCGC00256530-01, NCGC00259422-01, Thiourea, >=99.999% (metals basis), BP-31025, S726, SMR000857187, Thiourea, JIS special grade, >=98.0%, Thiourea, p.a., ACS reagent, 99.0%, FT-0675198, T0445, C14415, T-3650, 10.14272/UMGDCJDMYOKAJW-UHFFFAOYSA-N.1, A833853, Q528995, Thiourea, puriss. p.a., ACS reagent, >=99.0%, doi:10.14272/UMGDCJDMYOKAJW-UHFFFAOYSA-N.1, J-524966, F0001-1650, Thiourea, Pharmaceutical Secondary Standard; Certified Reference Material, 53754-90-8, Thiourea [ACD/Index Name] [ACD/IUPAC Name] [Wiki], 200-543-5 [EINECS], 2-Thiopseudourea, 2-thiourea, 605327 [Beilstein], 62-56-6 [RN], b-Thiopseudourea, GYV9AM2QAG, MFCD00008067 [MDL number], Sulfourea, sulourea, thiocarbamide, Thioharnstoff [German] [ACD/IUPAC Name], Thiourée [French] [ACD/IUPAC Name], tiomocznik [Polish], UNII-GYV9AM2QAG, Urea, 2-thio-, Urea, thio- (8CI), YU2800000, β-thiopseudourea, β-Thiopseudourea, (NH2)2CS, 17370-85-3 [RN], 2-Thio-Pseudourea, 2-Thio-Urea, ACS, 99%, carbonothioic diamide, InChI=1S/CH4N2S/c2-1(3)4/h(H4,2,3,4), Isothiourea, Pseudothiourea, Pseudourea, 2-thio-, STR00054, sulfouren, Thiocarbamid, thiocarbonic acid diamide, Thiocarbonic diamide, Thiokarbamid, Thiomocovina [Czech], thio-urea, Thiourea ACS Reagent Grade, Thiourea|Thiocarbamide, Thiurea, Thiuronium, THU, urea, thio-, ZYZUS [WLN], β -thiopseudourea
Thiourea is used in the production and modification of textile and dyeing auxiliaries, in the leaching of ores, in the production of pharmaceuticals and pesticides, as a vulcanization accelerator, and as an auxiliary agent in diazo paper.
Thiourea is available in Technical and Laboratory grade.
Thiourea is an organosulfur compound with the formula SC(NH2)2.
Thiourea is the sulfur analog of urea.
Thiourea is used for Thiourea’s synthetic equivalence to hydrogen sulfide.
Thiourea plays an important role in the construction of heterocycles.
Thiourea appears as whitecrystals which is combustible and on contact with fire gives off irritating or toxic fumes.
Thiourea acts as a precursor to sulphide to produce metal sulphides like mercury sulphide.
Thiourea is structurally similar to urea, except that the oxygen atom is replaced by a sulfur atom, but the properties of urea and thiourea differ significantly.
Thiourea is a reagent in organic synthesis.
“Thiourea’s” refers to a broad class of compounds with the general structure (R1R2N)(R3R4N)C=S.
Thiourea’s are related to thioamides, e.g. RC(S)NR2, where R is methyl, ethyl, etc.
Thiourea is an organosulfur compound composed of carbon, nitrogen, hydrogen and sulfur atoms.
Thiourea’s chemical formula is SC(NH2)2.
As the name and Thiourea’s composition suggests, thiourea is very much similar to urea.
In thiourea, the oxygen atom of urea is displaced by sulfur atom.
Here you need to note that urea and thiourea are structurally similar but very different in physical and chemical properties.
Thiourea is also known as thiocarbamide.
All hydrogen atoms of thiourea can be substituted by alkyl group and thus formed compounds come under the category of the class Thiourea’s.
Such compounds have the general formula (R1R2N) (R3R4N) C=S, where R is an alkyl group.
Thiourea’s is a class of thiourea compounds with the general formula (R1R2N)(R3R4N)C=S.
Thiourea’s general structural formula is given below –
General chemical structure of a compound of class Thiourea’s.
Total global production of thiourea approximately 40% is produced in Germany and another 40% in China.
Thus, Germany and China are the main manufacturers of thiourea.
Approximately 10,000 tonnes of thiourea is being produced globally in a year.
Thiourea’s huge production clearly states Thiourea’s importance in the market.
Thiourea, also called thiocarbamide, an organic compound that resembles urea but contains sulfur instead of oxygen.
I.e. the molecular formula is CS(NH2)2, while that of urea is CO(NH2)2.
Like urea, Thiourea can be prepared by causing a compound with the same chemical composition to undergo rearrangement, as by heating ammonium thiocyanate (NH4SCN).
A method of preparation more commonly used consists of the addition of hydrogen sulfide to cyanamide.
Thiourea exhibits many of the chemical properties of urea, but Thiourea has little commercial application.
Urea and thiourea represent privileged structures in medicinal chemistry.
Indeed, these moieties constitute a common framework of a variety of drugs and bioactive compounds endowed with a broad range of therapeutic and pharmacological properties.
Herein, we provide an overview of the state-of-the-art of urea and thiourea-containing pharmaceuticals.
We also review the diverse approaches pursued for (thio)urea bioisosteric replacements in medicinal chemistry applications.
Finally, representative examples of recent advances in the synthesis of urea- and thiourea-based compounds by enabling chemical tools are discussed.
Thiourea is an industrial chemical and also occurs naturally in some plants and fungi.
As an industrial chemical, thiourea is used in metal finishing solutions, in the manufacture of printed circuit boards, in copper refining, and as a rust inhibitor.
Thiourea may also be found in black and white photographic chemicals, and silver polish/metal cleaners.
Thiourea is used as an accelerator in rubber production (e.g. neoprene), and as an antioxidant to photo paper, photographic chemicals, rubber and plastics.
Thiourea is also found as an additive in etchants, cleaners and polishes.
Thiourea may be used as an inhibitor in pickling baths, scavenger of heavy metals, textile dye, and fireretardant component in nylon.
Applications of Thiourea:
Thiourea is an analogue of urea containing sulphur.
Thiourea per se has few applications.
Thiourea is mainly consumed as a precursor to thiourea dioxide, which is a common reducing agent in textile processing.
Few of Thiourea applications are listed below:
Thiourea is mainly used as a precursor to thiourea dioxide.
Thiourea dioxide is used as a reducing agent in many chemical reactions used in textile processing.
Thiourea is used in production of flame – retardant resins.
Thiourea is used as a source of sulfide.
Thiourea reacts with alkyl halides and changes them into thiols.
For example, ethane – 1,2 – dithiol is prepared by 1,2 – dibromoethane.
C2H4Br2 + 2SC(NH2)2 → [C2H4(SC(NH2)2)2]Br2
[C2H4(SC(NH2)2)2]Br2 + 2KOH → C2H4(SH)2 + 2OC(NH2)2 + 2KBr
Thiourea can be used as a source of sulfide in reactions with metal ions as well.
For example, mercury sulfide is formed when mercury ion reacts with thiourea in presence of water and heat.
Hg2+ + SC(NH2)2 + H2O → HgS + OC(NH2)2 + 2H+
Pyrimidine derivatives are formed by using thiourea.
Thiourea condense with – dicarbonyl and forms pyrimidine derivatives.
Thiourea has been used:
As a component of lysis buffer for liver tissue homogenization
In 2-D sample buffer for two-dimensional in-gel protein tyrosine phosphatases (PTP) assay
In rehydration buffer for protein extraction
Uses of Thiourea:
Thiourea is used in breaking dormancy in some seed types to determine seed viability if the seed fails to germinate under normal conditions.
Thiourea is also used to increase stress tolerance in plant tissues.
Thiourea has been used in several tree species as a substitute for stratification of seeds.
Thiourea is used in vulcanization accelerators.
Thiourea is used as an auxiliary agent.
Thiourea is used in silver – gelatin photographic prints.
Thiourea is used in diazo paper, light – sensitive photocopy paper etc.
Thiourea is used in many electroplating processes such as Clifton – Philips and Beaver bright electroplating etc.
For copper printed circuits, tin(II) chloride solution is used.
Thiourea is also used in the solution.
Thiourea is used in silver cleaning products such as TarnX.
TarnX contains thiourea, sulfamic acid and detergent.
Thiourea is used in gold and silver leaching.
Lixiviants are used for this purpose and thiourea is an important ingredient of these.
Other Uses of Thiourea:
Other industrial uses of thiourea include production of flame retardant resins, and vulcanization accelerators.
Thiourea is used as an auxiliary agent in diazo paper, light-sensitive photocopy paper and almost all other types of copy paper.
Thiourea is also used to tone silver-gelatin photographic prints.
Thiourea is used in the Clifton-Phillips and Beaver bright and semi-bright electroplating processes.
Thiourea is also used in a solution with tin(II) chloride as an electroless tin plating solution for copper printed circuit boards.
Thiourea is an organic compound of carbon, nitrogen, sulfur and hydrogen, with the formula CSN2H4 or (NH2)2CS.
Thiourea is similar to urea, except that the oxygen atom is replaced by a sulfur atom.
The properties of urea and thiourea differ significantly because of the relative electronegativities of sulfur and oxygen.
Thiourea is a versatile reagent in organic synthesis.
“Thiourea’s” refers to a broad class of compounds with the general structure (R1R2N)(R3R4N)C=S.
Thiourea’s are related to thioamides, e.g. RC(S)NR2, where R is methyl, ethyl, etc.
Thiourea is prohibited from use in food.
Industrial uses of thiourea include production of flame retardant resins, and vulcanization accelerators.
Thiourea is used as an auxiliary agent in diazo paper (light-sensitive photocopy paper) and almost all other types of copy paper.
Thiourea is also used to tone silver-gelatin photographic prints.
The liquid silver cleaning product TarnX is essentially a solution of thiourea.
A leaching agent for gold leaching and silver leaching can be created by selectively oxidizing thiourea, bypassing the steps of cyanide use and smelting.
Another common application for use of thiourea is a common sulfur source for making semiconductor cadmium sulfide nanoparticle.
Thiourea is a planar molecule.
The C=S bond distance is 1.60±0.1 for a wide range of derivatives.
This narrow range indicates that the C=S bond is insensitive to the nature of the substitutent.
Thus, the thioamide, which is similar to an amide group, is difficult to perturb.
Thiourea reduces peroxides to the corresponding diols.
The intermediate of the reaction is an unstable epidioxide which can only be identified at -100 °C.
Epidioxide is similar to epoxide except with two oxygen atoms.
This intermediate reduces to diol by thiourea.
Features of Thiourea:
Purity
Non hazardous
Long shelf life
Properties of Thiourea:
Thiourea is an organosulfur compound.
Thiourea’s molar mass is 76.12 g.mol-1.
Thiourea is a white colored compound.
Thiourea is found as solid at room temperature.
Melting point of thiourea is 182 ℃.
Thiourea’s boiling point is 155 ℃.
Thiourea’s density is 1.405 g.ml-1.
Thiourea is highly soluble in water.
142g of thiourea can be dissolved in one liter of water at 25 ℃.
Thiourea is weakly acidic in nature.
Thiourea’s crystals are combustible on contact with fire.
Thiourea’s pH is more than 3.
Thiourea is an odorless compound.
Thiourea’s surface tension is 1.04 10-2 N/m.
Conversion in ammonium thiocyanate – Thiourea on heating above 130 ℃, forms ammonium thiocyanate.
Although upon cooling Thiourea’s again converts into thiourea.
Reduction – Peroxides get reduced into their corresponding diols by thiourea.
During this reduction reaction an intermediate is formed which is called endoperoxide.
Endoperoxide is a highly unstable compound.
Due to Thiourea’s non – volatile nature, Thiourea is also used in ozonolysis of cyclic alkenes to give carbonyl compounds.
Thiourea reacts with alkyl halides and forms thiols.
Production of Thiourea:
Thiourea can be prepared by ammonium thiocyanate.
On heating ammonium thiocyanate, Thiourea forms thiourea.
Thiourea’s a reversible reaction and gives high yield at a specific temperature only.
So, Thiourea is not used commonly for production of thiourea.
Most commonly calcium cyanamide is used for production of thiourea.
Hydrogen sulfide reacts with calcium cyanamide in presence of carbon dioxide and forms thiourea.
The global annual production of thiourea is around 10,000 tonnes.
About 40% is produced in Germany, another 40% in China, and 20% in Japan.
Thiourea can be produced from ammonium thiocyanate, but more commonly Thiourea is produced by the reaction of hydrogen sulfide with calcium cyanamide in the presence of carbon dioxide.
Structure of Thiourea:
Thiourea is found in Thiourea’s two tautomeric forms – thione form and thiol form.
Thione form is found in larger amounts in aqueous solutions.
Thiourea’s thiol form is also known as isothiourea.
Thiourea has planar structure.
Thiourea is a covalent compound.
Thiourea has a double bond between carbon and sulfur.
C=S bond distance in thiourea is 1.71 A and average of C-N distances is 1.33 A.
Structure and Bonding of Thiourea:
Thiourea is a planar molecule.
The C=S bond distance is 1.71 Å.
The C-N distances average 1.33 Å.
The weakening of the C-S bond by C-N pi-bonding is indicated by the short C=S bond in thiobenzophenone, which is 1.63 Å.
Thiourea occurs in two tautomeric forms, of which the thione form predominates in aqueous solutions.
The equilibrium constant has been calculated as Keq is 1.04×10−3.
The thiol form, which is also known as an isothiourea, can be encountered in substituted compounds such as isothiouronium salts.
Biochem/Physiol Actions of Thiourea:
Thiourea is a free radical scavenger of the peroxide radical.
Thiourea was shown to inhibit lipid peroxidation and ultraviolet (UV)-induced crosslinking of collagen.
Bud dormancy in plants can be inhibited by thiourea which is used as a growth stimulator.
Thiourea is also known to be used in the treatment of hyperthyroidism.
Reactions of Thiourea:
The material has the unusual property of changing to ammonium thiocyanate upon heating above 130 °C.
Upon cooling, the ammonium salt converts back to thiourea.
Identifiers of Thiourea:
Synonym(s): Thiocarbamide, Sulfourea
Linear Formula: NH2CSNH2
CAS Number: 62-56-6
Molecular Weight: 76.12
Beilstein/REAXYS Number: 605327
EC Number: 200-543-5
MDL number: MFCD00008067
PubChem Substance ID: 24900549
Typical Properties of Thiourea:
Chemical formula: CH4N2S
Molar mass: 76.12 g/mol
Appearance: white solid
Density: 1.405 g/ml
Melting point: 182 °C (360 °F; 455 K)
Solubility in water: 142 g/l (25 °C)
Magnetic susceptibility (χ): −4.24×10−5 cm3/mol
CAS Number: 62-56-6
Beilstein Reference: 605327
CHEBI:36946
ChEMBL: ChEMBL260876
ChemSpider: 2005981
ECHA InfoCard: 100.000.494
Gmelin Reference: 1604
KEGG: C14415
PubChem CID: 2723790
RTECS number: YU2800000
UNII: GYV9AM2QAG
UN number: 2811
CompTox Dashboard (EPA): DTXSID9021348
Specifications of Thiourea:
Quality Level: 200
Grade: ACS reagent
Assay: ≥99.0%
İgn. residue: ≤0.1% (as SO4)
Loss: ≤0.5% loss on drying, 105°C, 2h
mp:
170-176 °C (lit.)
174-177 °C
Solubility: H2O: passes test
SMILES string: NC(N)=S
InChI: 1S/CH4N2S/c2-1(3)4/h(H4,2,3,4)
InChI key: UMGDCJDMYOKAJW-UHFFFAOYSA-N
Some products that may contain Thiourea:
Adhesives
Cleaners
Copy Paper
Corrosion Inhibitor
Etchants
Fire-Retardant Resins
Light-Sensitive Photocopy Paper
Metal Polishes
Paint & Glue Removers
Photo Paper
Photographic Chemicals
Plastic
Rubber
Textile and Paper Dye
Neoprene (polychloroprene) Products:
Gloves
Wetsuits
Orthopedic braces/supports
Weather stripping
Keyboard wrist supports
Athletic shoes/insoles
Swim goggles
Rubber boots
Protective eyewear
Insoles
Thermocoating:
Plastic phone cards
Names of Thiourea:
Preferred IUPAC name:
Thiourea
Other name:
Thiocarbamide