4-Chloro-3-nitrobenzaldehyde Chemical Properties

Melting point:

61-63 °C (lit.)

Boiling point:

276.5°C (rough estimate)

Density 

1.4791 (rough estimate)

refractive index 

1.6000 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

4g/l

form 

Powder

color 

Off-white to light yellow to light green

Water Solubility 

4 g/L (98 ºC)

Sensitive 

Air Sensitive

BRN 

778323

CAS DataBase Reference

16588-34-4(CAS DataBase Reference)

NIST Chemistry Reference

4-Chloro-3-nitrobenzaldehyde(16588-34-4)

EPA Substance Registry System

Benzaldehyde, 4-chloro-3-nitro- (16588-34-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-43

Safety Statements 

26-36/37-36/37/39-22-36

WGK Germany 

3

F 

10

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29130000

MSDS

• Language:English Provider:4-Chloro-3-nitrobenzaldehyde
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Chloro-3-nitrobenzaldehyde Usage And Synthesis

Chemical Properties

Light yellow powder

Uses

4-Chloro-3-nitrobenzaldehyde is a potent inhibitor of VCAM-1 expression and a potential drug candidate for autoimmune and allergic inflammatory diseases.

Synthesis

General procedure for the synthesis of 4-chloro-3-nitrobenzaldehyde from 4-chlorobenzaldehyde: 4-chlorobenzaldehyde (70 g, 0.5 mol) was added in batches to a mixture of nitrosonitrous nitric acid (55 mL) and sulfuric acid (55 mL) at 5°C with continuous stirring for 2 hours. Upon completion of the reaction, the reaction mixture was slowly poured into ice water (1 L) while stirring was maintained. Subsequently, the precipitate was collected by filtration and recrystallized with ethanol/water solvent mixture to afford the target product 4-chloro-3-nitrobenzaldehyde (90 g, 97% yield) as white needle-like crystals. The melting point of the product was 62-63 °C.

References

[1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 4, p. 657 - 667
[2] European Journal of Medicinal Chemistry, 2014, vol. 77, p. 361 - 377
[3] Journal of Chemical Research, 2008, # 12, p. 722 - 724
[4] Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2013, vol. 43, # 8, p. 977 - 983
[5] Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2014, vol. 44, # 7, p. 921 - 926

4-Chloro-3-nitrobenzaldehyde(16588-34-4)Related Product Information

• 3-Nitrobenzaldehyde
• 4-Nitrobenzaldehyde
• 4-Chloro-3-nitrobenzonitrile
• Sodium 3-nitrobenzenesulphonate
• 4-Chloronitrobenzene
• 4-Chloro-3-nitrobenzoic acid
• 3-NITRO BENZALDEHYDE
• 1-Chloro-3-nitrobenzene
• 4-Chloro-3-nitrophenol
• 4-Chlorobenzaldehyde
• 4,4'-DICHLORO-3,3'-DINITROBENZOPHENONE
• Difluorochloromethane
• 4-CHLORO-2-NITROBENZALDEHYDE,4-chloro-2-nitrobenzaldehyde*crystalline
• Nitrobenzene
• Methyl 4-chloro-3-nitrobenzoate
• 4-CHLORO-3-NITROBENZAMIDE
• 4-Chloro-3,5-dinitrobenzoic acid
• 4-CHLORO-3-CHLOROSULFONYL-5-NITROBENZOIC ACID