(3-FLUOROBENZYL)METHYLAMINE Chemical Properties

Boiling point:

183-184 °C (lit.)

Density 

1.015 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.4990(lit.)

Flash point:

152 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

Liquid

pka

9.39±0.10(Predicted)

color 

Colorless to tan

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-41

Safety Statements 

26-36/39

RIDADR 

UN 2735 8/PG III

WGK Germany 

2

HazardClass 

8

PackingGroup 

III

HS Code 

29214990

MSDS

• Language:English Provider:SigmaAldrich

(3-FLUOROBENZYL)METHYLAMINE Usage And Synthesis

Chemical Properties

Colorless liquid

Synthesis

Step A: Methylamine (15.3 mL, 40% aqueous solution, 177 mmol) was slowly added dropwise to a stirred solution of 3-fluorobenzaldehyde (20.0 g, 161 mmol) in methanol (150 mL) at room temperature. The reaction mixture was cooled to 0 °C after 6 h of continuous stirring at room temperature, followed by batchwise addition of sodium borohydride (6.10 g, 161 mmol). After removal of the cooling bath, the reaction mixture was gradually warmed to room temperature and stirring was continued for 16.5 hours. Upon completion of the reaction, the reaction was quenched with deionized water and carefully acidified with 2N hydrochloric acid. The acidified mixture was extracted with dichloromethane (3 times). The aqueous phase was subsequently alkalized with 6N sodium hydroxide solution and again extracted with dichloromethane (4 times). All organic phase extracts were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the target product N-methyl-3-fluorobenzylamine (21.51 g, 96% yield) as a clarified oil. Its 1H NMR (300 MHz, CDCl3) data were as follows: δ 7.32 (td, J = 7.5, 1.7 Hz, 1H), 7.28-7.19 (m, 1H), 7.14-6.98 (m, 2H), 3.80 (s, 2H), 2.45 (s, 3H), 1.47 (br s, 1H).

References

[1] Patent: US2006/111393, 2006, A1. Location in patent: Page/Page column 26-27

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