2-Mercaptobenzoxazole Chemical Properties

Melting point:

192-195 °C(lit.)

Boiling point:

360°C (rough estimate)

Density 

1.2170 (rough estimate)

refractive index 

1.5500 (estimate)

storage temp. 

Sealed in dry,Room Temperature

pka

11.03±0.20(Predicted)

form 

Crystalline Powder

color 

Beige

PH

5 (5g/l, H2O, 20℃)

Water Solubility 

SLIGHTLY SOLUBLE

BRN 

119483

InChIKey

FLFWJIBUZQARMD-UHFFFAOYSA-N

CAS DataBase Reference

2382-96-9(CAS DataBase Reference)

NIST Chemistry Reference

2(3H)-Benzoxazolethione(2382-96-9)

EPA Substance Registry System

2-Mercaptobenzoxazole (2382-96-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-25-24-36-26

WGK Germany 

3

RTECS 

DM4882500

F 

13

TSCA 

Yes

HS Code 

29349990

Toxicity

mouse,LD50,intravenous,180mg/kg (180mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04482,

MSDS

• Language:English Provider:2-Mercaptobenzoxazole
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• Language:English Provider:SigmaAldrich
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2-Mercaptobenzoxazole Usage And Synthesis

Chemical Properties

beige crystalline powder

Uses

2-Mercaptobenzoxazole is used in the surface treatment of materials. It is utilized for protection of metals from corrosion.

Preparation

2-Mercaptobenzoxazole has already been described in 1876 by Dunner (Ber. 9, (1876) page 465). 2-Mercaptobenzoxazole and its derivatives are prepared by processes which are based in principle on the reaction between o-aminophenol and alkali metal alkylxanthates. The alkali metal alkylxanthate here can either be employed as such, or it can be produced in the reaction mixture itself from an alkali, a lower alkanol and carbon disulphide.
https://patents.google.com/patent/US4677209A/en

Application

2-Mercaptobenzoxazole is a widely used organic scaffold in medicinal chemistry.
2-Mercaptobenzoxazole and their derivatives are known to posses several biological activities such as antibacterial, antifungal, antiinflammatory, insecticidal and herbicidal. 4-0xo-thiazolidines have also played an important activities as analgesic, anti-HIV, antitubercular, anthelmentic, dye-stuffs, fluorescent and as a photosensitizer. The incorporation of 4-oxothiazolidine and their 5-arylidene moieties in 2-mercaptobenzoxazole frame work has been found to enhance the activity.

Definition

ChEBI: 2-mercapto-1,3-benzoxazole is a benzoxazole.

Reactions

2-Mercaptobenzoxazole with ethyl chloroacetate and anhydrous K2C03 in the presence of dry acetone was refluxed on water bath to give ethyl-2-(mercaptobenzoxazolo)acetate.

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