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 

TSCA listed

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

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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.

Synthesis

1. 15 mL of ethanol, 3 mL of water, 10 mmol of o-aminophenol, 10 mmol of carbon disulfide, and 10 mmol of potassium hydroxide were sequentially added to the reaction flask. 2. The reaction mixture was heated to 80 °C and stirred at reflux for 3 hours at this temperature. 3. Upon completion of the reaction, a small amount of zeolite was added to the mixture and filtered while hot. 4. Warm the filtrate to 70 °C and slowly pour it into a beaker containing 10 mL of warm water (preheated to 60-70 °C). 5. cool the beaker in an ice-water bath to induce precipitation of the product. 6. The precipitated white transparent needle-like crystals were collected by filtration and dried to give 1.23 g of 2-mercaptobenzoxazole in 81% yield.

References

[1] Patent: CN108794421, 2018, A. Location in patent: Paragraph 0024; 0025; 0027
[2] Heteroatom Chemistry, 2001, vol. 12, # 3, p. 151 - 155
[3] Letters in Organic Chemistry, 2010, vol. 7, # 7, p. 519 - 527
[4] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5374 - 5379
[5] Journal of Medicinal Chemistry, 1994, vol. 37, # 7, p. 913 - 923

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