3-BROMOPHENETHYLAMINE Chemical Properties

Boiling point:

239-240 °C (lit.)

Density 

1.406 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.5740(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

Liquid

pka

9.83±0.10(Predicted)

color 

Clear colorless to light yellow

Safety Information

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 

29214200

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

3-BROMOPHENETHYLAMINE Usage And Synthesis

Chemical Properties

clear colorless to light yellow liquid

Synthesis

General procedure for the synthesis of 3-bromophenethylamine from 3-bromocyanobenzyl: An anhydrous THF (100 mL) suspension of LiAlH4 (3.04 g, 80 mmol) was cooled to -5°C. Concentrated H2SO4 (3.9 g, 40 mmol) was added slowly dropwise and the resulting mixture was stirred for 1 h at -5°C. The reaction system was then brought to room temperature. Subsequently, a THF (5 mL) solution of 3-bromobenzeneacetonitrile (9.80 g, 50 mmol) was added slowly dropwise, and the reaction system was slowly warmed to room temperature after the dropwise addition. The reaction was continued to be stirred for 1 h at room temperature, then cooled to 0 °C and the reaction was quenched by addition of a 1:1 THF:H2O mixture (12.4 mL). Et2O (50 mL) was added, followed by 3.6 M NaOH solution (24.4 mL). The mixture was filtered through diatomaceous earth and the solids were washed well with additional Et2O. The organic phases were combined, dried over Na2SO4, filtered and concentrated in vacuum to give 3-bromophenethylamine (9.7 g, 97% yield). The crude product was used directly in the subsequent reaction.1H NMR (400 MHz, CDCl3) δ 7.38-7.30 (m, 2H), 7.20-7.10 (m, 2H), 2.96 (t, J = 7.2 Hz, 2H), 2.72 (t, J = 7.2 Hz, 2H), 1.35 (br s, 2H). m/z MS (ESI): calculated value: 199; measured value: 200/202 (M+-).

References

[1] Patent: WO2007/61458, 2007, A2. Location in patent: Page/Page column 44; 78
[2] Patent: WO2004/60882, 2004, A1. Location in patent: Page 29-30
[3] Patent: US2010/204214, 2010, A1. Location in patent: Page/Page column 109-110
[4] Patent: CN103880745, 2018, B. Location in patent: Paragraph 0019; 0020; 0021; 0030; 0039
[5] Patent: US2008/171754, 2008, A1. Location in patent: Page/Page column 101-102

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