3-Nitrobenzyl bromide Chemical Properties

Melting point:

58-59 °C(lit.)

Boiling point:

153-154 °C (7 mmHg)

Density 

1.6841 (rough estimate)

refractive index 

1.6120 (estimate)

Flash point:

153-154°C/7mm

storage temp. 

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

solubility 

Dichloromethane, Hot Ethanol

form 

Crystalline Powder or Crystals

color 

Yellow to light brown

Water Solubility 

insoluble

BRN 

742795

InChIKey

LNWXALCHPJANMJ-UHFFFAOYSA-N

CAS DataBase Reference

3958-57-4(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 1-(bromomethyl)-3-nitro-(3958-57-4)

EPA Substance Registry System

Benzene, 1-(bromomethyl)-3-nitro- (3958-57-4)

Safety Information

Hazard Codes 

C

Risk Statements 

34-36/37

Safety Statements 

26-27-28-36/37/39-45

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

TSCA 

Yes

HazardClass 

8

PackingGroup 

II

HS Code 

29049090

MSDS

• Language:English Provider:3-Nitrobenzyl bromide
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
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3-Nitrobenzyl bromide Usage And Synthesis

Chemical Properties

Pale Yellow Crystalline Solid

Uses

3-Nitrobenzyl bromide was used in the synthesis of 1,4-disubstituted imidazoles.

Synthesis

General procedure for the synthesis of 3-nitrobenzyl bromide from 3-nitrobenzyl alcohol: Powdered 3-nitrobenzyl alcohol (0.5 mmol) was mixed with halosilanes (0.55 mmol) in a 4 mL screw-capped vial and stirred or heated at room temperature. The reaction mixture was kept at 70-75 °C for 0.5-24 h, during which the reaction progress was monitored by TLC. Upon completion of the reaction, the crude product was cooled to room temperature and the volatile by-product (TMS) was removed by evaporation under reduced pressure (30-35 °C).2O. The residue was confirmed by 1H NMR analysis. If necessary, the pure 3-nitrobenzyl bromide was purified by column chromatography on dry silica to obtain pure 3-nitrobenzyl bromide. Detailed experimental data, including isolated yields, spectral and other characterization data, are given in the Final Product Characterization section of the Supporting Information.

References

[1] Tetrahedron Letters, 2016, vol. 57, # 22, p. 2430 - 2433
[2] Organic Process Research and Development, 2002, vol. 6, # 2, p. 190 - 191
[3] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 1397 - 1405
[4] Patent: WO2014/151871, 2014, A2. Location in patent: Page/Page column 59; 60
[5] Journal of the American Chemical Society, 1949, vol. 71, p. 2137,2138,2140

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