1-Methyl-aminomethyl naphthalene Chemical Properties

Melting point:

189.5-190 °C

Boiling point:

104 °C

Density 

1,05 g/cm³

refractive index 

1.6160-1.6190

storage temp. 

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

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

clear liquid

pka

9.38±0.10(Predicted)

color 

Colorless to Orange to Green

PH

10.71 at 24℃ and 10g/L

InChI

InChI=1S/C12H13N/c1-13-9-11-7-4-6-10-5-2-3-8-12(10)11/h2-8,13H,9H2,1H3

InChIKey

MQRIUFVBEVFILS-UHFFFAOYSA-N

SMILES

C1(CNC)=C2C(C=CC=C2)=CC=C1

CAS DataBase Reference

14489-75-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HS Code 

2921.49.5000

HazardClass 

IRRITANT

1-Methyl-aminomethyl naphthalene Usage And Synthesis

Uses

1-Methyl-aminomethyl naphthalene has been used as reagent for the determination of isocyanates in air by UV or fluorescence detection. 1-Methyl-aminomethyl naphthalene has been used in the preparation of key intermediate required for the synthesis of terbinafine.

Chemical Properties

Yellow Oil

Uses

Terbinafine EP Impurity A. Terbinafine BP Impurity A. Terbinafine USP Related Compound A

Synthesis

The crude product N-methyl-N-(1-naphthylmethyl)formamide prepared according to step (a) was suspended in 300 mL of 20% aqueous sodium hydroxide solution and the reaction was heated at 60-70°C for 7 hours. Upon completion of the reaction, the mixture was cooled to 25 °C and subsequently extracted with toluene (2 x 200 mL). The toluene extracts were combined and back-extracted with 3N hydrochloric acid (2 x 300 mL). The aqueous phase was decolorized with activated carbon and the pH was adjusted with 20% aqueous sodium hydroxide to 10.0. The released free base was extracted with toluene, and the toluene layers were combined and distilled to remove the solvent to give 86 g of crude product. Finally, 82 g (85% yield) of pure N-methyl-1-naphthalenemethylamine was obtained by high vacuum distillation purification.

References

[1] Patent: WO2004/80945, 2004, A1. Location in patent: Page 8
[2] Patent: WO2004/80945, 2004, A1. Location in patent: Page 9-10

1-Methyl-aminomethyl naphthalene(14489-75-9)Related Product Information

• N-Methyl-1-naphthalenemethylamine hydrochloride
• N-Methyl-1,2-benzenediamine dihydrochloride
• N-METHYL-2-(TRIFLUOROMETHOXY)ANILINE
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• methyl-(naphthalen-2-ylmethyl)azanium
• Terbinafine
• (E)-N,6,6-triMethyl-N-(naphthalen-2-ylMethyl)hept-2-en-4-yn-1-aMine
• 1-Chloro-6,6-dimethyl-2-heptene-4-yne
• (Z)-N,6,6-triMethyl-N-(naphthalen-1-ylMethyl)hept-2-en-4-yn-1-aMine
• N-Methyl-2-naphthaMide
• 3,3-Dimethyl-1-butyne
• 1-CHLORO-6,6-DIMETHYL-2-HEPTENE-4-YNE
• 6,6-Dimethyl-1-hepten-4-yn-3-ol
• Terbinafine Hydrochloride
• 4-AMINO-1,8-NAPHTHALIMIDE