(4-BROMOBENZYL)METHYLAMINE Chemical Properties

Boiling point:

218-219 °C(lit.)

Density 

1.00 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

pka

9.52±0.10(Predicted)

Appearance

Colorless to light yellow Liquid

Sensitive 

Air Sensitive

InChIKey

URFJXIULELMVHV-UHFFFAOYSA-N

CAS DataBase Reference

699-03-6

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

36

WGK Germany 

2

MSDS

• Language:English Provider:SigmaAldrich

(4-BROMOBENZYL)METHYLAMINE Usage And Synthesis

Uses

N-Methyl-4-bromobenzylamine is an important chemical raw material and pharmaceutical intermediate, such as being used to prepare benzofuran-based poly(ADP-ribose) polymerase (PARP) inhibitors.

Synthesis

General procedure for the synthesis of N-methyl-4-bromobenzylamine: In an autoclave, 4-bromobenzaldehyde (2.08 g, 11.55 mmol) was mixed with a methanolic solution of 2 M methylamine (25 mL, 33.44 mmol) and the reaction was stirred at 65 °C for 4 hours. After completion of the reaction, cooled to room temperature, sodium borohydride (633 mg, 16.72 mmol) was added in batches. Stirring was continued for 30 minutes at room temperature, followed by vacuum concentration. The residue was dissolved in ethyl acetate (30 mL) and the organic layer was washed with saturated aqueous sodium bicarbonate. The aqueous phase was adjusted to pH 13 with a few drops of 1 N sodium hydroxide solution and then extracted twice with ethyl acetate. The organic extracts were combined, washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give N-methyl-4-bromobenzylamine as a colorless oil (2.04 g, 91% yield), which was used directly in the next step of the reaction.LC-MS analysis (Analytical Condition A, Zorbax SB-AQ columns, Acidic conditions): retention time t R = 0.61 min; [M + H]+ = 241.06 (acetonitrile adduct).

References

[1] Patent: WO2010/58353, 2010, A1. Location in patent: Page/Page column 77-78
[2] Patent: US2011/224210, 2011, A1. Location in patent: Page/Page column 54
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 78, # 1-4, p. 141 - 152
[4] Organic Letters, 2014, vol. 16, # 2, p. 358 - 361

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