5-NITRO-1,3-BENZOXAZOLE Chemical Properties

Melting point:

127-129°

Boiling point:

294.2±13.0 °C(Predicted)

Density 

1.473±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

-5.69±0.10(Predicted)

Appearance

Light yellow to brown Solid

Safety Information

HazardClass 

IRRITANT

HS Code 

2934999090

5-NITRO-1,3-BENZOXAZOLE Usage And Synthesis

Uses

5-Nitrobenzoxazole is a useful reactant for copper-catalyzed direct carboxylation of C-H bonds in benzoxazoles and related compounds with carbon dioxide.

Synthesis

To a 50 mL single-necked round-bottomed flask equipped with a magnetic stirrer was added 2-amino-4-nitrophenol (5.0 mmol, 1.0 eq.) and triethyl orthoformate (60.0 mmol, 12.0 eq.). The reaction mixture was slowly heated to 150 °C and the reaction was stirred at this temperature for 6 hours. Upon completion of the reaction, the mixture was cooled to room temperature, followed by distillation under reduced pressure to remove the excess triethyl orthoformate and the resulting ethanol by-product. The crude product was purified by silica gel column chromatography to give the final target compound 5-nitrobenzoxazole (see Table S-2).

References

[1] Angewandte Chemie - International Edition, 2011, vol. 50, # 48, p. 11511 - 11515
[2] Journal of the Chinese Chemical Society, 2015, vol. 62, # 5, p. 412 - 419
[3] Tetrahedron, 2013, vol. 69, # 32, p. 6627 - 6633
[4] Comptes Rendus Chimie, 2013, vol. 16, # 11, p. 1029 - 1034
[5] Angewandte Chemie - International Edition, 2009, vol. 48, # 48, p. 9127 - 9130

5-NITRO-1,3-BENZOXAZOLE(70886-33-8)Related Product Information

• Methyl 4-(5'-nitro-6'-hydroxylbenzoxazol-2-yl)benzate
• 5-NITRO-1,3-BENZOXAZOLE
• 2-BUTYL-5-NITRO-1,3-BENZOXAZOLE
• 5-NITRO-2-PROPYL-1,3-BENZOXAZOLE
• 2-ETHYL-5-NITRO-1,3-BENZOXAZOLE
• 2-(CHLOROMETHYL)-5-NITRO-1,3-BENZOXAZOLE
• 5-Nitrobenzoxazole-2-amine
• 2-METHYL-5-NITRO-1,3-BENZOXAZOLE
• AKOS BB-9364
• AKOS BB-9294
• 2-(4-CHLOROPHENYL)-5-NITROBENZO[D]OXAZOLE
• 2-(3,5-DICHLOROPHENYL)-5-NITROBENZO[D]OXAZOLE
• N-(5-NITRO-1,3-BENZOXAZOL-2-YL)GUANIDINE
• 5-Nitro-2-thiomethyl benzoxazole
• 3-(5-NITROBENZO[D]OXAZOL-2-YL)PHENOL
• AKOS BB-9300
• 5-NITRO-1,3-BENZOXAZOLE-2-THIOL
• 4-(5-NITROBENZO[D]OXAZOL-2-YL)PHENOL