5-BROMO-3-METHYL-BENZENE-1,2-DIAMINE

5-BROMO-3-METHYL-BENZENE-1,2-DIAMINE Property

Melting point:

63 °C

Boiling point:

298.8±35.0 °C(Predicted)

Density 

1.589±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

3.31±0.10(Predicted)

Appearance

Brown to dark brown Solid

InChI

InChI=1S/C7H9BrN2/c1-4-2-5(8)3-6(9)7(4)10/h2-3H,9-10H2,1H3

InChIKey

UOFSLKHZOPVGHG-UHFFFAOYSA-N

SMILES

C1(N)=CC(Br)=CC(C)=C1N

CAS DataBase Reference

76153-06-5

Safety

HazardClass 

IRRITANT

HS Code 

2921599090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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

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.

5-BROMO-3-METHYL-BENZENE-1,2-DIAMINE Chemical Properties,Usage,Production

Uses

5-Bromo-3-methylbenzene-1,2-diamine is used as an intermediate in organic synthesis.

Synthesis

Step 1: Stannous chloride (SnCl2, 5.0 g, 26.1 mmol) was added to an ethanol (EtOH, 20 mL) suspension of 4-bromo-2-methyl-6-nitroaniline (2.0 g, 8.7 mmol). The reaction mixture was heated to reflux for 14 h, followed by cooling to room temperature and vacuum concentration. The residue was diluted with ethyl acetate (EtOAc, 100 mL) and partitioned between saturated aqueous sodium bicarbonate (NaHCO3) solution (200 mL) and water. The resulting slurry was filtered through a Celite pad and the wet filter cake was washed with ethyl acetate (3 x 50 mL). The filtrate was washed sequentially with saturated aqueous sodium bicarbonate, water, and brine, dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated in vacuum to give 1.27 g (72% yield) of 5-bromo-3-methylbenzene-1,2-diamine (72) as a yellow oil: mass spectrum (ESI) m/z = 201.1 [M + 1]+.

References

[1] Patent: WO2013/26914, 2013, A1. Location in patent: Page/Page column 130
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3072 - 3076
[3] Patent: US2005/54655, 2005, A1. Location in patent: Page/Page column 15-16
[4] Patent: US2004/44203, 2004, A1. Location in patent: Page 28
[5] Chemische Berichte, 1884, vol. 17, p. 776