PRODUCTS

THIOCARBONYL DIAMIDE

Thiocarbonyl diamide acts as a precursor to sulphide to produce metal sulphides like mercury sulphide.
Thiocarbonyl diamide is structurally similar to urea, except that the oxygen atom is replaced by a sulfur atom, but the properties of urea and Thiocarbonyl diamide differ significantly.
Thiocarbonyl diamide 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

Thiocarbonyl diamide 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.
Thiocarbonyl diamide is available in Technical and Laboratory grade.

Thiocarbonyl diamide is an organosulfur compound with the formula SC(NH2)2.
Thiocarbonyl diamide is the sulfur analog of urea.

Thiocarbonyl diamide is used for Thiocarbonyl diamide's synthetic equivalence to hydrogen sulfide.
Thiocarbonyl diamide plays an important role in the construction of heterocycles.

Thiocarbonyl diamide appears as whitecrystals which is combustible and on contact with fire gives off irritating or toxic fumes.
Thiocarbonyl diamide acts as a precursor to sulphide to produce metal sulphides like mercury sulphide.

Thiocarbonyl diamide is structurally similar to urea, except that the oxygen atom is replaced by a sulfur atom, but the properties of urea and Thiocarbonyl diamide differ significantly.
Thiocarbonyl diamide is a reagent in organic synthesis.

"Thiocarbonyl diamide's" refers to a broad class of compounds with the general structure (R1R2N)(R3R4N)C=S.
Thiocarbonyl diamide's are related to thioamides, e.g. RC(S)NR2, where R is methyl, ethyl, etc.

Thiocarbonyl diamide is an organosulfur compound composed of carbon, nitrogen, hydrogen and sulfur atoms.
Thiocarbonyl diamide's chemical formula is SC(NH2)2.

As the name and Thiocarbonyl diamide's composition suggests, Thiocarbonyl diamide is very much similar to urea.
In Thiocarbonyl diamide, the oxygen atom of urea is displaced by sulfur atom.

Here you need to note that urea and Thiocarbonyl diamide are structurally similar but very different in physical and chemical properties.
Thiocarbonyl diamide is also known as thiocarbamide.

All hydrogen atoms of Thiocarbonyl diamide can be substituted by alkyl group and thus formed compounds come under the category of the class Thiocarbonyl diamide's.
Such compounds have the general formula (R1R2N) (R3R4N) C=S, where R is an alkyl group.

Thiocarbonyl diamide's is a class of Thiocarbonyl diamide compounds with the general formula (R1R2N)(R3R4N)C=S.
Thiocarbonyl diamide's general structural formula is given below –
General chemical structure of a compound of class Thiocarbonyl diamide's.

Total global production of Thiocarbonyl diamide approximately 40% is produced in Germany and another 40% in China.
Thus, Germany and China are the main manufacturers of Thiocarbonyl diamide.

Approximately 10,000 tonnes of Thiocarbonyl diamide is being produced globally in a year.
Thiocarbonyl diamide's huge production clearly states Thiocarbonyl diamide's importance in the market.

Thiocarbonyl diamide, 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, Thiocarbonyl diamide 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.
Thiocarbonyl diamide exhibits many of the chemical properties of urea, but Thiocarbonyl diamide has little commercial application.

Urea and Thiocarbonyl diamide 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 Thiocarbonyl diamide-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 Thiocarbonyl diamide-based compounds by enabling chemical tools are discussed.

Thiocarbonyl diamide is an industrial chemical and also occurs naturally in some plants and fungi.

As an industrial chemical, Thiocarbonyl diamide is used in metal finishing solutions, in the manufacture of printed circuit boards, in copper refining, and as a rust inhibitor.
Thiocarbonyl diamide may also be found in black and white photographic chemicals, and silver polish/metal cleaners.

Thiocarbonyl diamide is used as an accelerator in rubber production (e.g. neoprene), and as an antioxidant to photo paper, photographic chemicals, rubber and plastics.
Thiocarbonyl diamide is also found as an additive in etchants, cleaners and polishes.
Thiocarbonyl diamide may be used as an inhibitor in pickling baths, scavenger of heavy metals, textile dye, and fireretardant component in nylon.

Applications of Thiocarbonyl Diamide:
Thiocarbonyl diamide is an analogue of urea containing sulphur.

Thiocarbonyl diamide per se has few applications.
Thiocarbonyl diamide is mainly consumed as a precursor to Thiocarbonyl diamide dioxide, which is a common reducing agent in textile processing.

Few of Thiocarbonyl diamide applications are listed below:
Thiocarbonyl diamide is mainly used as a precursor to Thiocarbonyl diamide dioxide.
Thiocarbonyl diamide dioxide is used as a reducing agent in many chemical reactions used in textile processing.

Thiocarbonyl diamide is used in production of flame - retardant resins.
Thiocarbonyl diamide is used as a source of sulfide.

Thiocarbonyl diamide 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

Thiocarbonyl diamide 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 Thiocarbonyl diamide in presence of water and heat.
Hg2+ + SC(NH2)2 + H2O → HgS + OC(NH2)2 + 2H+

Pyrimidine derivatives are formed by using Thiocarbonyl diamide.
Thiocarbonyl diamide condense with - dicarbonyl and forms pyrimidine derivatives.

Thiocarbonyl diamide 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 Thiocarbonyl Diamide:
Thiocarbonyl diamide is used in breaking dormancy in some seed types to determine seed viability if the seed fails to germinate under normal conditions.
Thiocarbonyl diamide is also used to increase stress tolerance in plant tissues.
Thiocarbonyl diamide has been used in several tree species as a substitute for stratification of seeds.

Thiocarbonyl diamide is used in vulcanization accelerators.
Thiocarbonyl diamide is used as an auxiliary agent.

Thiocarbonyl diamide is used in silver – gelatin photographic prints.
Thiocarbonyl diamide is used in diazo paper, light – sensitive photocopy paper etc.

Thiocarbonyl diamide 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.

Thiocarbonyl diamide is also used in the solution.
Thiocarbonyl diamide is used in silver cleaning products such as TarnX.

TarnX contains Thiocarbonyl diamide, sulfamic acid and detergent.
Thiocarbonyl diamide is used in gold and silver leaching.
Lixiviants are used for this purpose and Thiocarbonyl diamide is an important ingredient of these.

Other Uses of Thiocarbonyl Diamide:
Other industrial uses of Thiocarbonyl diamide include production of flame retardant resins, and vulcanization accelerators.
Thiocarbonyl diamide is used as an auxiliary agent in diazo paper, light-sensitive photocopy paper and almost all other types of copy paper.

Thiocarbonyl diamide is also used to tone silver-gelatin photographic prints.
Thiocarbonyl diamide is used in the Clifton-Phillips and Beaver bright and semi-bright electroplating processes.
Thiocarbonyl diamide is also used in a solution with tin(II) chloride as an electroless tin plating solution for copper printed circuit boards.

Thiocarbonyl diamide is an organic compound of carbon, nitrogen, sulfur and hydrogen, with the formula CSN2H4 or (NH2)2CS.
Thiocarbonyl diamide is similar to urea, except that the oxygen atom is replaced by a sulfur atom.

The properties of urea and Thiocarbonyl diamide differ significantly because of the relative electronegativities of sulfur and oxygen.
Thiocarbonyl diamide is a versatile reagent in organic synthesis.

Thiocarbonyl diamide is prohibited from use in food.
Industrial uses of Thiocarbonyl diamide include production of flame retardant resins, and vulcanization accelerators.

Thiocarbonyl diamide is used as an auxiliary agent in diazo paper (light-sensitive photocopy paper) and almost all other types of copy paper.
Thiocarbonyl diamide is also used to tone silver-gelatin photographic prints.

The liquid silver cleaning product TarnX is essentially a solution of Thiocarbonyl diamide.
A leaching agent for gold leaching and silver leaching can be created by selectively oxidizing Thiocarbonyl diamide, bypassing the steps of cyanide use and smelting.

Another common application for use of Thiocarbonyl diamide is a common sulfur source for making semiconductor cadmium sulfide nanoparticle.
Thiocarbonyl diamide 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.

Thiocarbonyl diamide 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 Thiocarbonyl diamide.

Features of Thiocarbonyl Diamide:
Purity
Non hazardous
Long shelf life

Properties of Thiocarbonyl Diamide:
Thiocarbonyl diamide is an organosulfur compound.
Thiocarbonyl diamide's molar mass is 76.12 g.mol-1.

Thiocarbonyl diamide is a white colored compound.
Thiocarbonyl diamide is found as solid at room temperature.

Melting point of Thiocarbonyl diamide is 182 ℃.
Thiocarbonyl diamide's boiling point is 155 ℃.

Thiocarbonyl diamide's density is 1.405 g.ml-1.
Thiocarbonyl diamide is highly soluble in water.

142g of Thiocarbonyl diamide can be dissolved in one liter of water at 25 ℃.
Thiocarbonyl diamide is weakly acidic in nature.

Thiocarbonyl diamide's crystals are combustible on contact with fire.
Thiocarbonyl diamide's pH is more than 3.

Thiocarbonyl diamide is an odorless compound.
Thiocarbonyl diamide's surface tension is 1.04 10-2 N/m.

Conversion in ammonium thiocyanate – Thiocarbonyl diamide on heating above 130 ℃, forms ammonium thiocyanate.
Although upon cooling Thiocarbonyl diamide's again converts into Thiocarbonyl diamide.

Reduction – Peroxides get reduced into their corresponding diols by Thiocarbonyl diamide.
During this reduction reaction an intermediate is formed which is called endoperoxide.
Endoperoxide is a highly unstable compound.

Due to Thiocarbonyl diamide's non - volatile nature, Thiocarbonyl diamide is also used in ozonolysis of cyclic alkenes to give carbonyl compounds.
Thiocarbonyl diamide reacts with alkyl halides and forms thiols.

Production of Thiocarbonyl Diamide:
Thiocarbonyl diamide can be prepared by ammonium thiocyanate.
On heating ammonium thiocyanate, Thiocarbonyl diamide forms Thiocarbonyl diamide.

Thiocarbonyl diamide’s a reversible reaction and gives high yield at a specific temperature only.
So, Thiocarbonyl diamide is not used commonly for production of Thiocarbonyl diamide.

Most commonly calcium cyanamide is used for production of Thiocarbonyl diamide.
Hydrogen sulfide reacts with calcium cyanamide in presence of carbon dioxide and forms Thiocarbonyl diamide.

The global annual production of Thiocarbonyl diamide is around 10,000 tonnes.
About 40% is produced in Germany, another 40% in China, and 20% in Japan.
Thiocarbonyl diamide can be produced from ammonium thiocyanate, but more commonly Thiocarbonyl diamide is produced by the reaction of hydrogen sulfide with calcium cyanamide in the presence of carbon dioxide.

Structure of Thiocarbonyl Diamide:
Thiocarbonyl diamide is found in Thiocarbonyl diamide's two tautomeric forms – thione form and thiol form.
Thione form is found in larger amounts in aqueous solutions.

Thiocarbonyl diamide's thiol form is also known as isoThiocarbonyl diamide.
Thiocarbonyl diamide has planar structure.

Thiocarbonyl diamide is a covalent compound.
Thiocarbonyl diamide has a double bond between carbon and sulfur.
C=S bond distance in Thiocarbonyl diamide is 1.71 A and average of C-N distances is 1.33 A.

Structure and Bonding of Thiocarbonyl Diamide:
Thiocarbonyl diamide 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.

Thiocarbonyl diamide 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 isoThiocarbonyl diamide, can be encountered in substituted compounds such as isothiouronium salts.

Biochem/Physiol Actions of Thiocarbonyl Diamide:
Thiocarbonyl diamide is a free radical scavenger of the peroxide radical.
Thiocarbonyl diamide was shown to inhibit lipid peroxidation and ultraviolet (UV)-induced crosslinking of collagen.

Bud dormancy in plants can be inhibited by Thiocarbonyl diamide which is used as a growth stimulator.
Thiocarbonyl diamide is also known to be used in the treatment of hyperthyroidism.

Reactions of Thiocarbonyl Diamide:
The material has the unusual property of changing to ammonium thiocyanate upon heating above 130 °C.
Upon cooling, the ammonium salt converts back to Thiocarbonyl diamide.

Identifiers of Thiocarbonyl Diamide:
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 Thiocarbonyl Diamide:
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 Thiocarbonyl Diamide:
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 Thiocarbonyl diamide:
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 Thiocarbonyl Diamide:

Preferred IUPAC name:
Thiocarbonyl diamide

Other name:
Thiocarbamide