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62-56-6 - Thiourea, 99% - Thiocarbamide - A12828 - Alfa Aesar

A12828 Thiourea, 99%

CAS Number
62-56-6
Synonyms
Thiocarbamide

Size Price ($) Quantity Availability
100g 22.05
500g 35.54
2500g 112.27
10000g 350.20
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Thiourea, 99%

MDL
MFCD00008067
EINECS
200-543-5

Chemical Properties

Formula
CH4N2S
Formula Weight
76.12
Melting point
172-178°
Density
1.405
Solubility
Soluble in water.

Applications

Reagent for organic synthesisUsed as a reagent for organic synthesis. Thiourea is a photographic fixative, and used in manufacture of resins. It acts as a catalyst for asymmetric reactions. It plays an essential role as a catalyst for highly enantio- and diastereoselective additions reaction of oxindoles to nitroolefins. It is also useful to improve the productivity of mung bean.

Notes

Stable. Incompatible with strong acids. Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Handle and store under inert gas.

Literature References

Reagent for the conversion of alkyl halides to thiols by base hydrolysis of the isothiouronium salts; see also N-Acetyl­thiourea, B21198. Cleavage of isothiouronium salts with base and alkylation of the resulting thiolate has been used as a convenient synthesis of unsymmetrical sulfides: Synth. Commun., 14, 209 (1984).

Epoxides are converted to episulfides: J. Org. Chem., 26, 3467 (1961). The 2,3-epoxy alcohols resulting from the Sharpless enantioselective epoxidation can be converted to the corresponding episulfides with retention at both centers, using Ti(O-i-Pr)4 as mediator: J. Org. Chem., 53, 4114 (1988).

Widely used in heterocyclic syntheses, e.g. of thiazoles and pyrimidines.

Has been used in a convenient synthesis of isothiocyanates from oximes via the nitrile oxide: Tetrahedron Lett., 34, 8283 (1993); see also Benzaldoxime, A12053:

Bui, T.; Syed, S.; Barbas, C. F. Thiourea-Catalyzed Highly Enantio- and Diastereoselective Additions of Oxindoles to Nitroolefins: Application to the Formal Synthesis of (+) -Physostigmine. J. Am. Chem. Soc. 2009, 131 (25), 8758-8759.

Takemoto, Y. Development of Chiral Thiourea Catalysts and Its Application to Asymmetric Catalytic Reactions. Chem. Pharm. Bull. 2010, 58 (5), 593-601.

GHS Hazard and Precautionary Statements

Hazard Statements: H351-H361-H302-H411

Suspected of causing cancer. Suspected of damaging fertility or the unborn child. Harmful if swallowed. Toxic to aquatic life with long lasting effects.

Precautionary Statements: P201-P273-P281-P264-P270-P301+P312-P308+P313-P330-P405-P501a

Obtain special instructions before use. Avoid release to the environment. Use personal protective equipment as required. Wash thoroughly after handling. Do not eat, drink or smoke when using this product. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF exposed or concerned: Get medical advice/attention. Rinse mouth. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,9367
Beilstein
605327
Hazard Class
9
Packing Group
III
Harmonized Tariff Code
2930.90
TSCA
Yes
RTECS
YU2800000

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