5-Bromo-2-methylaniline Chemical Properties

Melting point:

33 °C(lit.)

Boiling point:

139 °C17 mm Hg(lit.)

Density 

1.49 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.614(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

Liquid After Melting

pka

3.38±0.10(Predicted)

color 

Clear yellow to brown

CAS DataBase Reference

39478-78-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

Hazard Note 

Harmful/Irritant

HS Code 

29214300

MSDS

• Language:English Provider:5-Bromo-2-methylaniline
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

5-Bromo-2-methylaniline Usage And Synthesis

Chemical Properties

clear yellow to brown liquid after melting

Uses

In industrial applications, 5-bromo-2-methylaniline is often used as a chemical intermediate for the synthesis of drugs, dyes or other chemicals.

Synthesis

The general procedure for the synthesis of 2-amino-4-bromotoluene from 4-bromo-2-nitrotoluene was as follows: first, 4-bromo-1-methyl-2-nitrobenzene (5 g, 23.14 mmol, 1.00 eq.), ethyl acetate (100 mL), and SnCl2-H2O (20 g) were added to a 250 mL round-bottom flask. The reaction mixture was stirred at 30 °C overnight. Upon completion of the reaction, the pH of the reaction solution was adjusted to 10 with 5 mol/L sodium hydroxide solution.Subsequently, the reaction solution was extracted with ethyl acetate (3 x 30 mL) and the organic layers were combined. The organic phase was sequentially washed with brine (3 × 50 mL), dried over anhydrous sodium sulfate and finally concentrated under reduced pressure. After the above steps, 4 g (93% yield) of 5-bromo-2-methylaniline was obtained as a brown oily product.

References

[1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 19, p. 3116 - 3127
[2] Patent: US2015/366198, 2015, A1. Location in patent: Paragraph 0132
[3] Journal of Medicinal Chemistry, 2004, vol. 47, # 26, p. 6603 - 6608
[4] Patent: WO2003/99824, 2003, A1. Location in patent: Page 23
[5] Patent: US6337351, 2002, B1. Location in patent: Example 14

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