4-Bromo-3-nitrotoluene Chemical Properties

Melting point:

31-33 °C (lit.)

Boiling point:

151.5-152.5 °C/14 mmHg (lit.)

Density 

1.578 g/mL at 25 °C (lit.)

refractive index 

1.5930 (estimate)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to lump to clear liquid

color 

White or Colorles to Yellow to Orange

Specific Gravity

1.578

FreezingPoint 

29.0 to 33.0 ℃

Sensitive 

Light Sensitive

BRN 

1945925

CAS DataBase Reference

5326-34-1(CAS DataBase Reference)

NIST Chemistry Reference

4-Bromo-3-nitrotoluene(5326-34-1)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22-20/21/22

Safety Statements 

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

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29049090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Bromo-3-nitrotoluene Usage And Synthesis

Chemical Properties

Low melting solid

Uses

4-Bromo-3-nitrotoluene may be used as a starting material in the synthesis of 2-bromo-5-methylaniline and as a reagent in the synthesis of 2-nitro-4:4′-dimethyl-diphenyl by reacting with p-iodotoluene.

General Description

4-Bromo-3-nitrotoluene (2-bromo-5-methylnitrobenzene, 1-bromo-4-methyl-2-nitrobenzene) is a halonitrobenzene. It has been synthesized from 4-methyl-2-nitroaniline and confirmed by ¹H NMR. The crystal structure of 1-bromo-4-methyl-2-nitrobenzene is found to be orthorhombic in the Pna2₁ space group. Its enthalpy of vaporization at boiling point has been determined.

Synthesis

To a Silak reaction tube equipped with a magnetic stirrer were sequentially added 6.2 mg of silver sulfate, 36.3 mg of copper acetate, 12.5 mg of 2,9-dimethyl-1,10-o-phenanthroline, 36.2 mg of 4-methyl-2-nitrobenzoic acid, and 30.9 mg of sodium bromide, followed by the addition of 4 mL of dimethyl sulfoxide as a solvent. The reaction mixture was heated and stirred at 160 °C for 24 hours under an oxygen atmosphere. Upon completion of the reaction, the reaction was quenched by addition of appropriate amount of distilled water and extracted three times with ethyl acetate (10 mL each time). The organic phases were combined and concentrated to give 29.8 mg of 4-bromo-3-nitrotoluene in 69% yield.

References

[1] Patent: CN107325002, 2017, A. Location in patent: Paragraph 0091
[2] Organic and Biomolecular Chemistry, 2018, vol. 16, # 30, p. 5416 - 5421
[3] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 2794 - 2803

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