2-Bromo-5-methylbenzenamine

2-Bromo-5-methylbenzenamine Property

Melting point:

46°C

Boiling point:

130°C/16mmHg(lit.)

Density 

1.486 g/mL at 25 °C

refractive index 

n20/D 1.603

Flash point:

110 °C

storage temp. 

2-8°C

form 

Solid

pka

2.66±0.10(Predicted)

color 

White to Orange to Green

InChI

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

InChIKey

QTAQWOXSUFGGKH-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

53078-85-6(CAS DataBase Reference)

Safety

Hazard Codes 

Xn

Risk Statements 

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

Safety Statements 

9-26-36/37-60

RIDADR 

2811

WGK Germany 

3

HazardClass 

6.1

HS Code 

29214300

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H331Toxic if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

2-Bromo-5-methylbenzenamine Chemical Properties,Usage,Production

Chemical Properties

Brown crystal

Uses

2-Bromo-5-methylbenzenamine is an intermediate for synthesizing new indole anticancer drugs, antihypertensive drug reserpine, triptan drugs for treating migraine, indomethacin for treating rheumatism and rheumatoid arthritis, etc.

Synthesis

Preparation Example 1: General procedure for the synthesis of 2-bromo-5-methylaniline 1. 4-Bromo-3-nitrotoluene (60.35 g, 279 mmol), 5 wt% platinum-carbon catalyst (1.09 g, 0.28 mmol), and triethylamine (112.93 g, 1116 mmol) were added sequentially to the reaction flask. 2. the reaction mixture was heated to 100 °C and 99% formic acid (42.39 g, 921 mmol) was added slowly and dropwise over a period of 20 minutes. 3. The reaction temperature was maintained with continuous stirring for 12 hours. 4. Upon completion of the reaction, cooled to room temperature, ethyl acetate (100 mL) and water (100 mL) were added to the reaction mixture with thorough stirring. 5. Filter through diatomaceous earth to remove the platinum carbon catalyst. 6. Add ethyl acetate (200 mL) and water (100 mL) to the filtrate and extract. 7. The organic phase was separated and washed with deionized water (300 mL x 3 times). 8. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford the target product 2-bromo-5-methylaniline (51.30 g, 276 mmol) in 99% yield. 9. The structure of the product was confirmed by 1H-NMR (270 MHz, CDCl3): δ (ppm) 7.260 (1H, d), 6.583 (1H, ... (data not provided in full)).

References

[1] Patent: US2003/191325, 2003, A1. Location in patent: Page/Page column 8
[2] Patent: EP1820799, 2007, A1
[3] Patent: WO2006/51851, 2006, A1. Location in patent: Page/Page column 59-60
[4] Patent: WO2012/65062, 2012, A1. Location in patent: Page/Page column 89-90
[5] Journal of Fluorine Chemistry, 2002, vol. 116, # 2, p. 173 - 179