N-METHYL-N-(2-METHYLBENZYL)AMINE

N-METHYL-N-(2-METHYLBENZYL)AMINE Property

Melting point:

129 °C

Boiling point:

100-102 °C(Press: 11 Torr)

Density 

0.917±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

9.76±0.10(Predicted)

Appearance

Colorless to light yellow Liquid

Water Solubility 

Slightly soluble in water.

Safety

HazardClass 

IRRITANT

HazardClass 

8

HS Code 

2921290090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H314Causes severe skin burns and eye damage

H318Causes serious eye damage

Precautionary statements

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

N-METHYL-N-(2-METHYLBENZYL)AMINE Chemical Properties,Usage,Production

Uses

(R)-N-methyl-2-methylbenzylamine is resistant to displacement by the aqueous extractants.

Synthesis

To a methanol (MeOH) solution of 2-methylbenzaldehyde (10.0 g, 83.23 mmol) was slowly added aqueous methylamine (40%, 25.85 g, 332.9 mmol) at 25 °C. The reaction mixture was stirred continuously at 25 °C for 30 min and subsequently cooled to 0 °C. At this temperature, sodium borohydride (NaBH4, 6.30 g, 166.5 mmol) was added in batches. After addition, the reaction mixture was slowly warmed to 25 °C and stirring was continued for 1 hour. After completion of the reaction, the solvent was removed by distillation under reduced pressure. Water and dichloromethane (CH2Cl2) were added to the residue and the organic layer was separated. The organic layer was washed sequentially with saturated sodium bicarbonate (NaHCO3) solution and brine and dried over anhydrous sodium sulfate (Na2SO4). The organic phase was concentrated under reduced pressure to afford the target product N,2-dimethylbenzylamine (10.49 g, 93.2% yield) as an oil of sufficient purity for direct use in subsequent reactions. The product was detected by mass spectrometry (APCI+) showing m/z 136.3 ([M+H]+), and the nuclear magnetic resonance hydrogen spectroscopy (1H-NMR, CDCl3) data were as follows: δ 7.35-7.08 (m, 3H), 3.73 (s, 2H), 2.49 (s, 3H), 2.34 (s, 3H).

References

[1] Patent: US2006/111422, 2006, A1. Location in patent: Page/Page column 53
[2] Journal of the American Chemical Society, 1940, vol. 62, p. 910
[3] Patent: US2006/52378, 2006, A1. Location in patent: Page/Page column 111
[4] European Journal of Medicinal Chemistry, 2018, vol. 143, p. 390 - 401