2-BROMO-6-METHYLANILINE

2-BROMO-6-METHYLANILINE Property

Boiling point:

105-107 °C/205 mmHg (lit.)

Density 

1.4780 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.6030(lit.)

Flash point:

215 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

2.39±0.10(Predicted)

Appearance

Off-white to yellow Solid-Liquid Mixture

InChI

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

InChIKey

LDUCMSVRKKDATH-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

53848-17-2(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2921430090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

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

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

2-BROMO-6-METHYLANILINE Chemical Properties,Usage,Production

Uses

2-Bromo-6-methylaniline can be used as a reactant to synthesize:

• Alkyl substituted bromoindazole building blocks by Pd-catalyzed Suzuki coupling reaction with various vinyl boronic acids.
• Difluoropyridoindole via Pd-catalyzed intramolecular Heck reaction with difluoropiperidinone.
• 4-Methyl-N-phenyl-1H-benzo[d]imidazol-2-amine by one-pot Cu-catalyzed domino C-N cross-coupling reaction with iodobenzene and thiourea.

Synthesis

The general procedure for the synthesis of 2-bromo-6-methylaniline from 3-bromo-2-nitrotoluene was as follows: tellurium (21.6 g, 169.4 mmol) and sodium borohydride (15.0 g, 396 mmol) were dissolved in 575 mL of anhydrous ethanol under the protection of nitrogen, heated and refluxed for 1 h and then cooled to room temperature. Subsequently, a solution of 3-bromo-2-nitrotoluene (7.32 g, 33.8 mmol) dissolved in 25 mL of ethanol was added all at once and the reaction mixture was stirred for 2 hours at room temperature. After completion of the reaction, the reaction mixture was filtered through diatomaceous earth (CELITE). The filtrate was evaporated under reduced pressure and the residue was dissolved in about 200 mL of ether, washed with saturated brine and dried over anhydrous magnesium sulfate. Finally, the solvent was evaporated to give 2.66 g (42% yield) of 2-bromo-6-methylaniline as a dark liquid.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3177 - 3180
[2] Patent: US2004/110815, 2004, A1. Location in patent: Page/Page column 18
[3] Patent: WO2005/16892, 2005, A1. Location in patent: Page/Page column 68
[4] Chemische Berichte, 1937, vol. 70, p. 2427,2430
[5] Yakugaku Zasshi, 1837, vol. 58, p. 1,7