(3-BROMOBENZYL)METHYLAMINE Chemical Properties

Boiling point:

231-232 °C(lit.)

Density 

1.461 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.5650(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

liquid

pka

9.32±0.10(Predicted)

color 

colourless

Sensitive 

Air Sensitive

InChIKey

QCEANFBGRBLXHN-UHFFFAOYSA-N

CAS DataBase Reference

67344-77-8

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

36

WGK Germany 

2

HS Code 

2921490060

MSDS

• Language:English Provider:SigmaAldrich

(3-BROMOBENZYL)METHYLAMINE Usage And Synthesis

Uses

(3-Bromobenzyl)methylamine is a useful intermediate used in the preparation of 2,4-diamino-6-(benzylmethylamino)quinazolines with antimalarial and antitumor activities.

Synthesis

Step B: At room temperature, 3-bromobenzaldehyde (47.5 mL, 0.4 mol) was dissolved in methanol (460 mL), followed by the addition of an aqueous solution of methylamine (35 mL, 0.4 mol, 40 wt% solution). The reaction mixture was cooled to 0 °C and sodium borohydride (22 g, 0.6 mol) was added in batches. The reaction mixture was kept stirred at 0 °C for 3.5 h and then gradually warmed up to room temperature. After completion of the reaction, the mixture was concentrated under reduced pressure and subsequently partitioned with dichloromethane and water. The aqueous layer was separated and washed with dichloromethane (3×). The organic phases were combined and washed sequentially with saturated sodium bicarbonate solution and brine, then dried over anhydrous magnesium sulfate. After filtration, the organic phase was concentrated under reduced pressure to afford the target product N-methyl-3-bromobenzylamine (76 g, 81%) as a clear oil. The product was characterized by 1H NMR (300 MHz, CDCl3): δ 7.48 (d, J = 1.5 Hz, 1H), 7.40-7.37 (m, 1H), 7.24-7.16 (m, 2H), 3.73 (s, 2H), 2.45 (s, 3H).

References

[1] Patent: US2007/21408, 2007, A1. Location in patent: Page/Page column 94; 103
[2] Journal of Medicinal Chemistry, 1981, vol. 24, # 2, p. 140 - 145
[3] Patent: WO2009/149258, 2009, A2. Location in patent: Page/Page column 21; 48
[4] Patent: US2014/275101, 2014, A1. Location in patent: Paragraph 0072; 0145; 0146
[5] Patent: WO2015/127559, 2015, A1. Location in patent: Page/Page column 55; 56

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