N,N-dimethyl-1-(naphthalen-1-yl)methanamine Chemical Properties

Boiling point:

148-152 °C(Press: 16 Torr)

Density 

1.028±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

8?+-.0.28(Predicted)

Safety Information

HS Code 

2921490090

N,N-dimethyl-1-(naphthalen-1-yl)methanamine Usage And Synthesis

Uses

N,N-Dimethyl-1-(naphthalen-1-yl)methanamine is a useful reactant in organic synthesis.

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 2535, 1984 DOI: 10.1016/S0040-4039(01)81224-7

Synthesis

Sodium hydroxide (3.0 eq.), NHC-Pd(II)-Im complex 1 (1.0 mol%), water (1.0 mL), 1-chloromethylnaphthalene (0.8 mmol), and N,N-dimethylformamide (2.0 eq.) were sequentially added to the Schlenk reaction tube under nitrogen protection. The reaction mixture was stirred at 50 °C for 3 hours. After completion of the reaction, it was cooled to room temperature and the reaction mixture was extracted with ethyl acetate, the extract was washed with saturated brine and dried with anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure and the resulting crude product was purified by rapid column chromatography on silica gel (eluent: petroleum ether/ethyl acetate=5:1) to afford the pure N,N-dimethyl-1-(naphthalen-1-yl)methylamine (4t). The product was a colorless liquid with the following NMR hydrogen spectrum (300 MHz, CDCl3) data: δ 8.24 (d, J = 7.8 Hz, 1H), 7.83-7.75 (m, 2H), 7.51-7.36 (m, 4H), 3.79 (s, 2H), 2.27 (s, 6H); NMR carbon spectrum (75 MHz, CDCl3) data are as follows: δ 134.6, 133.8, 132.4, 128.4, 127.9, 127.4, 125.9, 125.5, 125.0, 124.4, 62.4, 45.6.

References

[1] Journal of Chemical Research, 2013, vol. 37, # 10, p. 611 - 614
[2] Tetrahedron, 2014, vol. 70, # 4, p. 880 - 885

N,N-dimethyl-1-(naphthalen-1-yl)methanamine(16413-71-1)Related Product Information

• 3-[Methyl(1-naphthalenylmethyl)amino]-1-phenyl-1-Propanone
• Naftifine-d3 Hydrochloride
• Naftifine Desmethyl Impurity
• Naftifine hydrochloride
• 1-Chloromethyl naphthalene
• Naftifine Impurity 9
• α-[2-[Methyl(1-naphthalenylmethyl)amino]ethyl]-Benzenemethanol
• (Z)-Naftifine HCl
• Naftifine Impurity 8