methyl-(naphthalen-2-ylmethyl)azanium

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methyl-(naphthalen-2-ylmethyl)azanium Basic information
Product Name:methyl-(naphthalen-2-ylmethyl)azanium
Synonyms:methyl-(naphthalen-2-ylmethyl)azanium;Methyl-2-naphthaleneMethylaMine;N-Methylnaphthalene-2-methanamine;N-Methyl-1-(naphthalen-2-yl)MethanaMine;N-Methyl(naphthalen-2-yl)MethanaMine;Terbinafine Related Compound 2;N-methyl-1-(naphthalen-2-yl);2-Naphthalenemethanamine, N-methyl-
CAS:76532-33-7
MF:C12H13N
MW:171.24
EINECS:
Product Categories:Amines;Aromatics
Mol File:76532-33-7.mol
methyl-(naphthalen-2-ylmethyl)azanium Structure
methyl-(naphthalen-2-ylmethyl)azanium Chemical Properties
Melting point 232-233 °C
Boiling point 90 °C(Press: 0.02 Torr)
density 1.036±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
pka9.50±0.10(Predicted)
AppearanceColorless to light yellow Liquid
Safety Information
MSDS Information
methyl-(naphthalen-2-ylmethyl)azanium Usage And Synthesis
UsesAn intermediate in the preparation of detoxification inhibitors of the crucifer phytoalexin Brassinin, as potential fungicides against Leptosphaeria maculans.
Synthesis
2-(Bromomethyl)naphthalene

939-26-4

methyl-(naphthalen-2-ylmethyl)azanium

76532-33-7

General procedure for the synthesis of N-methyl-2-naphthalenemethylamine from 2-bromomethylnaphthalene: 2-bromomethylnaphthalene (10 g, 43 mmol) was added batchwise to a stirred mixture of 40 wt% aqueous methylamine solution (50 mL, 581 mmol) and THF (50 mL) at 0 °C. The reaction mixture was gradually warmed to room temperature and stirred continuously for 16 hours. Upon completion of the reaction, the mixture was concentrated under vacuum. The concentrated residue was dissolved in ether (Et2O), washed sequentially with 1.0 N NaOH solution and brine, and the organic phase was dried over anhydrous sodium sulfate (Na2SO4) and concentrated to dryness. Purification by silica gel fast column chromatography (eluent ratio from 98:2 to 9:1 CHCl3/methanol containing 5% NH4OH) afforded N-methyl-2-naphthalenemethylamine (3.95 g, 54% yield) as a clear oil. Its 1H NMR (400 MHz, CDCl3) data were as follows: δ 7.85 (m, 3H), 7.79 (s, 1H), 7.49 (m, 3H), 3.94 (s, 2H), 2.53 (s, 3H).

References[1] Patent: EP1226138, 2004, B1
methyl-(naphthalen-2-ylmethyl)azanium Preparation Products And Raw materials
Raw materials2-Quinolinecarboxaldehyde-->N-Methyl-2-naphthaMide-->2-(Chloromethyl)naphthalene-->Methylamine-->Diethyl ether-->2-(Bromomethyl)naphthalene-->Tetrahydrofuran-->2-Naphthaldehyde-->Chloroform-->Water
Tag:methyl-(naphthalen-2-ylmethyl)azanium(76532-33-7) Related Product Information
1-Chloro-6,6-dimethyl-2-heptene-4-yne (E)-N,6,6-triMethyl-N-(naphthalen-2-ylMethyl)hept-2-en-4-yn-1-aMine Terbinafine N-[(2E)-6,6-DiMethyl-2-hepten-4-yn-1-yl]-N-Methyl-2-naphthaleneMethanaMine Hydrochloride cis-Terbinafine Hydrochloride (E)-1-Bromo-6,6-dimethyl-2-hepten-4-yne (Z)-N,6,6-triMethyl-N-(naphthalen-1-ylMethyl)hept-2-en-4-yn-1-aMine 1-Methyl-aminomethyl naphthalene N-Methyl-2-naphthaMide 3,3-Dimethyl-1-butyne 6,6-Dimethyl-1-hepten-4-yn-3-ol Terbinafine Hydrochloride N-(2-Chlorobenzyl)-N-methylamine 1-Chloro-6,6-dimethyl-2-heptene-4-yne 1-Chloro-6,6-dimethyl-2-hepten-4-yne [2-(4-Chloro-phenyl)-ethyl]-methyl-amine N-(2,3-Dihydro-2-oxo-1H-benzimidazol-5-yl)-3-hydroxy-2-naphthalenecarboxamide Naphthol AS-E