2-Bromo-3-methylaniline Chemical Properties

Boiling point:

48 °C/0.03 mmHg (lit.)

Density 

1.489 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.605(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Liquid

pka

2.66±0.10(Predicted)

color 

Pale brown

InChI

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

InChIKey

VJNUZLYTGSGDHR-UHFFFAOYSA-N

SMILES

C1(N)=CC=CC(C)=C1Br

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-43-36/37/38-20/21/22

Safety Statements 

36/37-60-26-23-9

RIDADR 

2810

WGK Germany 

3

HazardClass 

6.1

HS Code 

29214300

2-Bromo-3-methylaniline Usage And Synthesis

Synthesis

Add iron powder (3.86 g, 69 mmol), water (5 mL) and concentrated HCL (0.5 mL) sequentially to a solution of commercially available 2-bromo-3-nitrotoluene (5 g, 23 mmol) in methanol (100 mL) at room temperature and heat the mixture at reflux for 125 h. Remove the solvents under reduced pressure, suspend the residue in water (400 mL) and extract with chloroform (3 x 250 mL). Dry the combined organic extracts over MGS04 and remove the solvents under reduced pressure to afford 2-bromo-3-methylphenylamine as an amber oil (4.45 g, 100percent): 1H NMR (CDC13) 5 2.30 (s, 3H), 4.00 (br s, 2H), 7.60 (m, 2H), 7.00 (t, 1H).

References

[1] Patent: WO2004/63155, 2004, A1. Location in patent: Page 120-121
[2] Journal of Organic Chemistry, 1988, vol. 53, # 6, p. 1170 - 1176
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 34, p. 11040 - 11044
[4] Angew. Chem., 2018, vol. 130, # 34, p. 11206 - 11210,5
[5] Angewandte Chemie - International Edition, 2010, vol. 49, # 40, p. 7257 - 7260

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