3-Bromo-2-methylaniline Chemical Properties

Boiling point:

248 °C (lit.)

Density 

1.51 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.619(lit.)

Flash point:

230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

3.38±0.10(Predicted)

form 

Liquid

color 

Clear colorless to yellow to pale brown

Sensitive 

Light Sensitive

BRN 

2354213

InChI

InChI=1S/C7H8BrN/c1-5-6(8)3-2-4-7(5)9/h2-4H,9H2,1H3

InChIKey

IILVSKMKMOJHMA-UHFFFAOYSA-N

SMILES

C1(N)=CC=CC(Br)=C1C

CAS DataBase Reference

55289-36-6(CAS DataBase Reference)

NIST Chemistry Reference

3-Bromo-2-methylaniline(55289-36-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

2810

WGK Germany 

3

Hazard Note 

Harmful/Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29214300

MSDS

• Language:English Provider:2-Amino-6-bromotoluene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Bromo-2-methylaniline Usage And Synthesis

Application

3-Bromo-2-methylaniline is a 3-halo-2-methylaniline derivative. 3-bromo-2-methylaniline is an important organic intermediate (building block) to synthetize substituted aniline products. 3-Bromo-2-methylaniline may be used in the preparation of 3,4-dibromo-2-methylaniline, racemic 3,9-dibromo-4,10-dimethyl-6H,12H,5,11-methanodibenzodiazocine, a racemic derivative of Tröger’s base, 4-bromo-1H-indazole, and so on.

Chemical Properties

Colorless to pale brown liquid

Uses

3-Bromo-2-methylaniline may be used in the preparation of :

• 3,4-dibromo-2-methylaniline
• racemic 3,9-dibromo-4,10-dimethyl-6H,12H,5,11-methanodibenzodiazocine, a racemic derivative of Tr?ger′s base
• 4-bromo-1H-indazole

General Description

3-Bromo-2-methylaniline is a 3-halo-2-methylaniline derivative.

Synthesis

General procedure for the synthesis of 3-bromo-2-methylaniline from 2-bromo-6-nitrotoluene: 2-bromo-6-nitrotoluene (500 mg, 2.32 mmol) and stannous dichloride hydrate (2.62 g, 11.63 mmol) were dissolved in ethanol, and the reaction was stirred for 3 hours at 80°C. After completion of the reaction, ethanol was removed by rotary evaporation. Subsequently, the pH of the reaction mixture was adjusted with saturated aqueous sodium bicarbonate to about 8. The mixture was filtered through diatomaceous earth and the filter cake was washed with ethyl acetate. The filtrates were combined and extracted three times with ethyl acetate. Finally, the combined organic phases were dried by rotary evaporation to give 3-bromo-2-methylaniline (410 mg, 2.20 mmol) in 95% yield.

References

[1] Tetrahedron, 2008, vol. 64, # 13, p. 2938 - 2950
[2] Synlett, 2009, # 15, p. 2483 - 2486
[3] Chemical Communications, 2003, # 10, p. 1170 - 1171
[4] Organic Letters, 2011, vol. 13, # 19, p. 5220 - 5223
[5] Patent: EP3412657, 2018, A1. Location in patent: Paragraph 0104; 0108

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