2-Benzyl-2-thiopseudourea hydrochloride Chemical Properties

Melting point:

172-177 °C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

methanol: soluble1g/10 mL, clear, colorless to very faintly yellow

form 

powder to crystal

color 

White

Water Solubility 

250 g/L (15 ºC)

Sensitive 

Hygroscopic

Merck 

14,1146

BRN 

3656719

InChI

InChI=1S/C8H10N2S.ClH/c9-8(10)11-6-7-4-2-1-3-5-7;/h1-5H,6H2,(H3,9,10);1H

InChIKey

WJAASTDRAAMYNK-UHFFFAOYSA-N

SMILES

C1(C=CC=CC=1)CSC(=N)N.Cl

CAS DataBase Reference

538-28-3(CAS DataBase Reference)

EPA Substance Registry System

Carbamimidothioic acid, phenylmethyl ester, monohydrochloride (538-28-3)

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

36/37/39-45-28A

RIDADR 

UN 2811 6.1/PG 2

WGK Germany 

3

RTECS 

UM0738000

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

HS Code 

29309070

Toxicity

LD50 oral in rat: 27mg/kg

MSDS

• Language:English Provider:2-Benzylisothiouronium chloride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Benzyl-2-thiopseudourea hydrochloride Usage And Synthesis

Chemical Properties

off-white to light beige crystalline powder

Uses

Reagent for cobalt and nickel; identification and separation of carboxylic, sulfinic, and sulfonic acid.

General Description

S-benzylisothiourea analogs (2-benzyl-2-thiopseudourea hydrochloride), as small-molecule inhibitors of indoleamine-2,3-dioxygenase, has been studied.

Safety Profile

Poison by ingestion,intraperitoneal, subcutaneous, and intravenous routes.When heated to decomposition it emits very toxic fumesof HCl, SOx, and NOx.

Synthesis

GENERAL METHOD: Benzyl chloride (3 mmol) was dissolved with thiourea (3 mmol) in anhydrous ethanol (2 mL) and the reaction was refluxed at 95°C for 2 hours. Upon completion of the reaction, the mixture was cooled to room temperature and stirring was continued for 12 hours. The resulting precipitate was collected by filtration and washed with cold anhydrous ethanol to give the final S-benzylthiourea hydrochloride.

Purification Methods

Crystallise the chloride from 0.2M HCl (2mL/g) or EtOH and it dry in air. [Beilstein 6 III 1600.]

References

[1] Analytical Chemistry, 1987, vol. 59, # 4, p. 562 - 567
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 8, p. 2426 - 2431
[3] Journal of Pharmaceutical Sciences, 1984, vol. 73, # 3, p. 374 - 377
[4] European Journal of Organic Chemistry, 2002, # 7, p. 1163 - 1174
[5] Chemische Berichte, 1879, vol. 12, p. 575

2-Benzyl-2-thiopseudourea hydrochloride(538-28-3)Related Product Information

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