2-Chlorobenzoxazole Chemical Properties

Melting point:

7 °C(lit.)

Boiling point:

201-202 °C(lit.)

Density 

1.345 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.566(lit.)

Flash point:

185 °F

storage temp. 

Inert atmosphere,2-8°C

form 

Powder

pka

0.62±0.10(Predicted)

color 

White

Water Solubility 

Not miscible in water.

BRN 

115982

InChI

InChI=1S/C7H4ClNO/c8-7-9-5-3-1-2-4-6(5)10-7/h1-4H

InChIKey

BBVQDWDBTWSGHQ-UHFFFAOYSA-N

SMILES

O1C2=CC=CC=C2N=C1Cl

CAS DataBase Reference

615-18-9(CAS DataBase Reference)

NIST Chemistry Reference

Benzoxazole, 2-chloro-(615-18-9)

EPA Substance Registry System

Benzoxazole, 2-chloro- (615-18-9)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36/37/39-37/39-36

WGK Germany 

3

RTECS 

DM4680000

F 

10

TSCA 

Yes

HS Code 

29349990

MSDS

• Language:English Provider:2-Chlorobenzoxazole
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Chlorobenzoxazole Usage And Synthesis

Chemical Properties

clear yellow liquid

Uses

2-Chlorobenzoxazole was used in the synthesis of 2-(2-naphthylamino)benzoxazole via reaction with 2-amino-1-naphthalenesulfonic acid.

Synthesis

General procedure for the synthesis of 2-chlorobenzoxazole from 2-mercaptobenzoxazole: 2-mercaptobenzoxazole (10 mmol, 1.51 g) was suspended in SOCl2 (50 mL), and a few drops of DMF were added as catalyst. The reaction mixture was heated to reflux for 5 hours. After completion of the reaction, the solvent was removed by evaporation. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/EtOAc, 10:1) to afford the target compound as a colorless oil in 69.7% yield.

Purification Methods

Purify it by fractional distillation, preferably in a vacuum. [Siedel J Prakt Chem 42 456 1890, Katz J Am Chem Soc 75 712 1953, Meyer & Sigel J Org Chem 42 2769 1977, Beilstein 27 H 43, 27 II 17.]

References

[1] Patent: US4517370, 1985, A
[2] Heteroatom Chemistry, 2001, vol. 12, # 3, p. 151 - 155
[3] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5374 - 5379
[4] Patent: CN108794421, 2018, A. Location in patent: Paragraph 0028-0030
[5] Tetrahedron, 1986, vol. 42, # 14, p. 3905 - 3912

2-Chlorobenzoxazole(615-18-9)Related Product Information

• Benzoxazole
• Fenoxaprop-p-ethyl
• Sulfamethoxazole
• Isoxazole
• 1,2,4-Trichlorobenzene
• Famoxadone
• (2R)-2-[4-(6-Chlorobenzoxazole-2-yloxy)phenoxy]propionic acid
• 5-Chlorobenzoxazole-2(3H)-thione
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• 2-Chloro-3-ethylbenzoxazolium tetrafluoroborate
• 2,5-Dichlorobenzooxazole
• 5-CHLOROBENZOXAZOLE
• 2-METHY-5-CHLOROBENZOXAZOLE
• 2-Hydroxy-5-chlorobenzoxazole
• Ethyl 5-(4-chlorophenyl)oxazole-4-carboxylate
• Ethyl 5-(2,3-dichlorophenyl)oxazole-4-carboxylate
• 2-MERCAPTO-5-CHLOROBENZOXAZOLE
• BENZOXAZOLE, 2-CHLORO-5-METHOXY-