5-Chlorobenzooxazole-2-thiol Chemical Properties

Melting point:

280-285 °C(lit.)

Boiling point:

278.7±42.0 °C(Predicted)

Density 

1.57±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

10.45±0.20(Predicted)

Appearance

Light yellow to brown Solid

InChIKey

BOBIZYYFYLLRAH-UHFFFAOYSA-N

CAS DataBase Reference

22876-19-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

DM4760000

HazardClass 

IRRITANT

HS Code 

2934999090

Toxicity

mouse,LD50,intraperitoneal,120mg/kg (120mg/kg),Medicinal Chemistry: A Series of Monographs. Vol. 4(1), Pg. 337, 1964.

MSDS

• Language:English Provider:SigmaAldrich

5-Chlorobenzooxazole-2-thiol Usage And Synthesis

Uses

5-Chloro-2-mercaptobenzoxazole may be used in the synthesis of 5-chloro-2-(4-methyl-1-piperazinyl)benzoxazole and 5-chloro-2-morpholin-4-yl-1,3-benzoxazole.

General Description

5-Chloro-2-mercaptobenzoxazole can be synthesized by reacting amino-4-chlorophenol, potassium hydroxide and carbon disulfide in ethanol.

Synthesis

Synthesis of compound 19: A mixture of potassium ethylxanthate (13.4 g, 84.0 mmol) and 4-chloro-2-aminophenol (10 g, 69.6 mmol) was dissolved in anhydrous ethanol (200 mL). The reaction mixture was stirred under reflux conditions overnight. After completion of the reaction, it was cooled to room temperature and the solvent was removed by evaporation under reduced pressure. The residue was dissolved in water (200 mL) and the pH was adjusted with acetic acid (HOAc) to 5. A solid product was precipitated, filtered and dried to afford 5-chloro-2-mercaptobenzoxazole (12.8 g, 99.1% yield).

References

[1] Patent: US2011/224269, 2011, A1. Location in patent: Page/Page column 21
[2] Patent: CN106478537, 2017, A. Location in patent: Paragraph 0025; 0026; 0037; 0038; 0048; 0049; 0062-0064
[3] Patent: US2016/168138, 2016, A1. Location in patent: Paragraph 0142-0143
[4] Patent: CN106632121, 2017, A. Location in patent: Paragraph 0031; 0032
[5] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 3, p. 907 - 911

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