2-Bromophenethylamine

2-Bromophenethylamine Property

Boiling point:

253 °C(lit.)

Density 

1.396 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.5770(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Liquid

pka

9.52±0.10(Predicted)

color 

Clear colorless to slightly yellow

Sensitive 

Air Sensitive

CAS DataBase Reference

65185-58-2(CAS DataBase Reference)

Safety

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-27-36/37/39-45

RIDADR 

UN 2735 8/PG 2

WGK Germany 

3

HazardClass 

8

PackingGroup 

Ⅱ

HS Code 

29214990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

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

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

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

P363Wash contaminated clothing before reuse.

P405Store locked up.

2-Bromophenethylamine Chemical Properties,Usage,Production

Chemical Properties

Clear colorless to slightly yellow liquid

Uses

2-(2-Bromophenyl)ethylamine is used as a pharmaceutical intermediate.

General Description

May darken in storage

Synthesis

The general procedure for the synthesis of o-bromophenethylamine from o-bromobenzyl cyanide was as follows: 1 M borane-tetrahydrofuran complex (BH3-THF, 200 mL, 0.2 mol) was slowly added dropwise to a solution of 2-bromobenzyl cyanide (20.0 g, 0.1 mol) in tetrahydrofuran (THF, 100 mL) at 0 °C for 30 min. Subsequently, the reaction mixture was heated to reflux for 24 hours. Upon completion of the reaction, the reaction was quenched with methanol (MeOH, 50 mL) and 6 M hydrochloric acid (HCl, 50 mL) at 0 °C, and then the mixture was heated and refluxed again for 4 hours. The reaction solution was concentrated under reduced pressure and the residue was diluted with distilled water (H2O, 300 mL) and washed with ethyl acetate (EA, 75 mL × 2). The aqueous layer was neutralized with 15% sodium hydroxide (NaOH) solution and then extracted with ethyl acetate (EA, 75 mL × 2). The organic layers were combined, dried with anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to afford the target product o-bromophenethylamine (2a) as a yellow oil (17.4 g, 85.2% yield). High-resolution mass spectrometry (HRMS) calculated value C8H11NBr [M + H]+ 200.0069, measured value 200.0068. nuclear magnetic resonance hydrogen spectrum (1H NMR, 500 MHz, CDCl3) δ 7.58 (d, J = 8.0 Hz, 1H), 7.35-7.31 (m, 2H), 7.15 (t, J = 7.0 Hz, 1H). 2.79 (m, 4H), 1.18 (m, 2H). Nuclear magnetic resonance carbon spectrum (13C NMR, 125 MHz, DMSO-d6) δ 139.8,132.9,131.6,128.6,128.2,124.3,42.4,40.3.

References

[1] Journal of Organic Chemistry, 2008, vol. 73, # 24, p. 9627 - 9632
[2] Patent: US2002/198251, 2002, A1
[3] Tetrahedron, 1996, vol. 52, # 21, p. 7525 - 7546
[4] Tetrahedron, 1998, vol. 54, # 25, p. 7121 - 7126
[5] ChemCatChem, 2014, vol. 6, # 2, p. 538 - 546