4-BROMO-3-NITRO-BENZALDEHYDE Chemical Properties

Melting point:

104-108 °C (lit.)

Boiling point:

289.3±30.0 °C(Predicted)

Density 

1.781±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Light red to Green

λmax

295nm(CH3CN)(lit.)

InChI

InChI=1S/C7H4BrNO3/c8-6-2-1-5(4-10)3-7(6)9(11)12/h1-4H

InChIKey

SAFSVELFSYQXOV-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(Br)C([N+]([O-])=O)=C1

CAS DataBase Reference

163596-75-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-50-43-38-22

Safety Statements 

26-36-61-45-36/37

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

HS Code 

2913000090

MSDS

• Language:English Provider:SigmaAldrich

4-BROMO-3-NITRO-BENZALDEHYDE Usage And Synthesis

Uses

4-Bromo-3-nitrobenzaldehyde is a benzaldehyde derivative, mainly used as an intermediate component in organic synthesis. It can be used to prepare 4-Bromo-3-chlorobenzoic acid and other benzoic acid compounds.

Synthesis

Step 1. Synthesis of 4-bromo-3-nitrobenzaldehyde: NaNO3 (5.48 g, 64.47 mmol, 1.19 eq.) was added to a 100 mL three-necked round-bottomed flask, followed by slow addition of 98% H2SO4 (60 mL). The reaction mixture was stirred continuously for 1.5 h at 10 °C. After that, 4-bromobenzaldehyde (10 g, 54.05 mmol, 1.00 eq.) was added to the reaction system and stirring was continued for 2 h at the same temperature. The reaction process was monitored by thin layer chromatography (TLC, unfolding agent ratio EtOAc:PE = 1:5). Upon completion of the reaction, 200 g of ice was added to the reaction mixture to quench the reaction. The resulting white solid product was collected by filtration and washed thoroughly with distilled water (3 x 200 mL) to yield 4-bromo-3-nitrobenzaldehyde (11.72 g, 94% yield).

References

[1] Patent: US8080566, 2011, B1. Location in patent: Page/Page column 65
[2] Medicinal Chemistry Research, 2018, vol. 27, # 7, p. 1782 - 1791
[3] Recueil des Travaux Chimiques des Pays-Bas, 1926, vol. 45, p. 694
[4] Recueil des Travaux Chimiques des Pays-Bas, 1929, vol. 48, p. 1137
[5] Journal of the Chemical Society, 1927, p. 25

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