2,6-Dichlorobenzoxazole Chemical Properties

Melting point:

49-51°C

Boiling point:

110°C/13mmHg(lit.)

Density 

1.522±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-0.96±0.30(Predicted)

form 

fused solid

color 

White

InChI

InChI=1S/C7H3Cl2NO/c8-4-1-2-5-6(3-4)11-7(9)10-5/h1-3H

InChIKey

LVVQTPZQNHQLOM-UHFFFAOYSA-N

SMILES

O1C2=CC(Cl)=CC=C2N=C1Cl

CAS DataBase Reference

3621-82-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2934999090

2,6-Dichlorobenzoxazole Usage And Synthesis

Chemical Properties

This product is solid, insoluble in water, soluble in chlorobenzene.

Uses

2,6-Dichlorobenzoxazole is used in the synthesis of 2-(3-(2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy)propoxy)-5-(trifluoromethyl)benzo[d]oxazole, an insecticide against Spodoptera exigua.

Synthesis

General procedure for the synthesis of 2,6-dichlorobenzoxazole from 6-chlorobenzo[d]oxazole-2(3H)-thione: In a 500-mL four-neck reaction flask, 50 g (0.27 mol) of 6-chlorobenzo[d]oxazole-2(3H)-thione, 300 mL of toluene, and 40 g (0.135 mol) of tris(trichloromethyl)carbonate were added. The reaction mixture was slowly warmed to 50°C and the temperature was continued at a rate of 0.5°C/min, holding the temperature for 10 minutes after each 10°C increase. When the temperature reached 105°C, the reaction was maintained for 1 hour. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure (the initial vacuum was maintained at -0.07 MPa, and when the temperature was raised to 100°C-110°C, the vacuum was increased to -0.095 MPa to completely evaporate the solvent). After evaporation, the residue was removed while hot and cooled and crystallized to give 50.82 g of 2,6-dichlorobenzoxazole with a product purity of 98.1% and a molar yield of 98.4%.

References

[1] Patent: CN102432559, 2016, B. Location in patent: Paragraph 0020; 0037; 0038
[2] Patent: WO2018/37223, 2018, A1. Location in patent: Page/Page column 197; 198
[3] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 7, p. 1975 - 1980
[4] Journal of Organic Chemistry, 2009, vol. 74, # 8, p. 3229 - 3231
[5] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 9, p. 3044 - 3049

2,6-Dichlorobenzoxazole(3621-82-7)Related Product Information

• 2-Chlorobenzoxazole
• 6-Chloro-2-benzoxazolethiol
• 5-BROMO-2-BENZOXAZOLINONE 97
• 5-Fluorobenzoxazole
• 5-Chloro-2-methylbenzoxazole
• 2-Chloro-5-fluorobenzoxazole
• 5-CHLOROBENZOXAZOLE
• 2-Mercaptobenzoxazole
• Benzoxazole
• Chlorobenzene
• 2,5-DICHLOROBENZOXAZOLE
• CYCLO-CLENBUTEROL
• 5-(2,4-Dichlorophenyl)-1,3-oxazole-4-carboxylic acid
• 2,6-Dichlorobenzoxazole
• 3-[(4,7-Dichlorobenzoxazole-2-ylmethyl)amino]-5-ethyl-6-methylpyridine-2(1H)-one,3-(4,7-Dichlorobenzoxazole-2-ylmethylamino)-5-ethyl-6-methyl-2(1H)-pyridinone
• 2-Chloroxazole
• 5,6-DICHLOROBENZOXAZOLINONE
• 5-Ethyl-6-methyl-3-[2-(4,7-dichlorobenzoxazole-2-yl)ethyl]-2(1H)-pyridinone