(4-CHLORO-BENZYL)-METHYL-AMINE Chemical Properties

Boiling point:

77 °C

Density 

1.088±0.06 g/cm3(Predicted)

refractive index 

1.5380 to 1.5420

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

clear liquid

pka

9.50±0.10(Predicted)

color 

Colorless to Light yellow to Light orange

EPA Substance Registry System

Benzenemethanamine, 4-chloro-N-methyl- (104-11-0)

Safety Information

Hazard Codes 

Xi,C,Xn

Risk Statements 

22-34-52-41-37/38

Safety Statements 

23-26-36/37/39-45-39

RIDADR 

2735

TSCA 

Yes

HazardClass 

8

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

2921490090

(4-CHLORO-BENZYL)-METHYL-AMINE Usage And Synthesis

Definition

ChEBI: N-(4-chlorobenzyl)-N-methylamine is an aromatic amine.

Synthesis

General procedure for the synthesis of N-(4-chlorobenzyl)-N-methylamine from 4-chlorobenzyl chloride and monomethylamine: an aqueous solution of methylamine (40% v/v, 9.03 ml, 93.48 mmol) was slowly added to a stirred tetrahydrofuran (THF, 300 ml) solution of 4-chlorobenzyl chloride (3.00 g, 18.63 mmol) under nitrogen protection and at 0 °C. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the solvent was removed by rotary evaporation and residual water was removed by azeotropy with toluene. The crude product was purified directly by column chromatography, first using ethyl acetate (100%) as eluent, followed by a solvent mixture of ethyl acetate: methanol: triethylamine (92:5:3) as eluent, to afford the target compound, N-(4-chlorobenzyl)-N-methylamine (30), as a yellow oil (2.49 g, 81% yield). The structure of the product was determined by NMR hydrogen spectrum (1H NMR, CDCl3, 300 MHz) δ 7.25-7.18 (4H, m), 3.66 (2H, s), 2.38 (3H, s), 1.65 (1H, s); NMR carbon spectrum (13C NMR, CDCl3, 100 MHz) δ 138.6, 132.6, 129.5 (2C ), 128.4 (2C), 55.2, 35.8; high-resolution mass spectrometry (HRMS, ESI): measured value 156.0580 (M+), theoretical value of 156.0556 for C8H10NCl (M+).

References

[1] Patent: WO2010/18555, 2010, A2. Location in patent: Page/Page column 19; 23
[2] European Journal of Medicinal Chemistry, 2011, vol. 46, # 5, p. 1729 - 1742
[3] Justus Liebigs Annalen der Chemie, 1926, vol. 449, p. 264
[4] Journal of Medicinal Chemistry, 1983, vol. 26, # 3, p. 309 - 312
[5] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 13, p. 4693 - 4707

(4-CHLORO-BENZYL)-METHYL-AMINE(104-11-0)Related Product Information

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