14489-75-9

Basic information

• Product Name: 1-Methyl-aminomethyl naphthalene
• Synonyms: N-METHYL-1-NAPHTHALENEMETHYLAMINE;N-METHYL-1-NAPHTHYLMETHYLAMINE;N-METHYLNAPHTHALENE-1-METHYLAMINE;N-METHYL NAPHTHYLMETHYLAMINE;TIMTEC-BB SBB005765;AURORA KA-7760;1-METHYL-1-NAPHTHALENEMETHYLAMINE;1-(METHYLAMINOMETHYL)NAPHTHALENE
• CAS NO: 14489-75-9
• Molecular Formula: C₁₂H₁₃N
• Molecular Weight: 171.24
• EINECS: 238-497-3
• Product Categories: Chemical intermediate for Terbinafine;Anilines, Aromatic Amines and Nitro Compounds;Amines;Aromatics;Terbinafine;Naphthalene series
• Mol File: 14489-75-9.mol
• Article Data: 23

Chemical Properties

• Melting Point: 189.5-190 °C
• Boiling Point: 104 °C
• Flash Point: 146.629 °C
• Appearance: /
• Density: 1,05 g/cm3
• Vapor Pressure: 0.00242mmHg at 25°C
• Refractive Index: 1.6160-1.6190
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 9.38±0.10(Predicted)
• CAS DataBase Reference: 1-Methyl-aminomethyl naphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-aminomethyl naphthalene(14489-75-9)
• EPA Substance Registry System: 1-Methyl-aminomethyl naphthalene(14489-75-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 14489-75-9(Hazardous Substances Data)

Usage

Description

1-Methyl-aminomethyl naphthalene is an organic compound characterized by its yellow oil appearance. It is known for its chemical properties that make it a versatile reagent in various applications.

Uses

1. Used in Analytical Chemistry:
1-Methyl-aminomethyl naphthalene is used as a reagent for the determination of isocyanates in air. This application takes advantage of its chemical properties that allow for effective detection through UV or fluorescence methods, making it a valuable tool in environmental monitoring and industrial hygiene.
2. Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 1-Methyl-aminomethyl naphthalene serves as a key intermediate in the synthesis of terbinafine, an antifungal medication. Its role in the production process highlights its importance in the development of therapeutic agents to combat fungal infections.
3. Used in Impurity Analysis:
1-Methyl-aminomethyl naphthalene is also utilized in the analysis of impurities in terbinafine, specifically as Terbinafine EP Impurity A, Terbinafine BP Impurity A, and Terbinafine USP Related Compound A. This application ensures the quality and safety of the final pharmaceutical product by identifying and quantifying potential impurities during the manufacturing process.

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

Upstream product

• 66-77-3 1-naphthaldehyde 
• 74-89-5 methylamine 
• 86-52-2 1-Chloromethylnaphthalene 
• 593-51-1 methylamine hydrochloride 
• 135679-81-1 2,2,2-Trifluoro-N-methyl-N-naphthalen-1-ylmethyl-acetamide 
• 41004-67-5 Methyl-[1-naphthalen-1-yl-meth-(E)-ylidene]-amine 
• 41004-67-5 (±)-(2S,3R)-ethyl 1,3-dimethyl-2-(naphthalen-1-yl)-4-oxoazetidine-3-carboxylate 
• 1498015-90-9 N-methyl-N-(naphthalen-2-ylmethyl)formamide 
• 3400-38-2 methylaminomethanol 
• 3400-33-7 N-methyl-1-naphthalenecarboxamide 
• 118-31-0 (naphth-1-yl)methylamine 
• 333-27-7 methyl trifluoromethanesulfonate 
• 67-56-1 methanol 
• 55210-79-2 1-(azidomethyl)naphthalene 

Downstream Products

• 318-88-7 2-fluoro-N-methyl-N-(naphthalen-1-ylmethyl)ethanamine 
• 16413-71-1 N,N-dimethyl(naphthalen-1-yl)methanamine 
• 98978-38-2 N-<3-(1-cyclohexenyl)-2-propynyl>-N-methyl-1-naphthalenemethanamine 
• 98978-39-3 N-(3-cyclohexyl-2-propynyl)-N-methyl-1-naphthalenemethanamine 
• 98978-27-9 3--1-(2-chlorophenyl)-1-propanone 
• 98978-25-7 3--1-(2-fluorophenyl)-1-propanone 
• 104257-78-5 N-methyl-N-<3-(2,6,6-trimethyl-1-cyclohexenyl)-2-propinyl>-1-naphthalinmethanamin 
• 65472-88-0 naftifine 
• 104257-75-2 N-methyl-N-<3-(4-methyl-1-cyclohexenyl)-2-propinyl>-1-naphthalinmethanamin 
• 104257-76-3 N-<3-(6,6-dimethyl-1-cyclohexenyl)-2-propinyl>-N-methyl-1-naphthalinmethanamin 
• 104257-77-4 N-<3-(2,6-dimethyl-1-cyclohexenyl)-2-propinyl>-N-methyl-1-naphthalinmethanamin 
• 110951-66-1 methyl-[1]naphthylmethyl-(4-phenyl-benzyl)-amine 
• 98977-55-0 N-methyl-N-(3-phenylpropyl)-1-naphthalenemethanamine 
• 98977-59-4 (E)-N-methyl-N-(4-phenyl-3-butenyl)naphthalenemethanamine 

Relevant articles and documents

Determination of Isocyanates in Air by Liquid Chromatography with Fluorescence Detection

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Simple RuCl3-catalyzed N-Methylation of Amines and Transfer Hydrogenation of Nitroarenes using Methanol

Methanol is a potential hydrogen source and C1 synthon, which finds interesting applications in both chemical synthesis and energy technologies. The effective utilization of this simple alcohol in organic synthesis is of central importance and attracts scientific interest. Herein, we report a clean and cost-competitive method with the use of methanol as both C1 synthon and H2 source for selective N-methylation of amines by employing relatively cheap RuCl3.xH2O as a ligand-free catalyst. This readily available catalyst tolerates various amines comprising electron-deficient and electron-donating groups and allows them to transform into corresponding N-methylated products in moderate to excellent yields. In addition, few marketed pharmaceutical agents (e. g., venlafaxine and imipramine) were also successfully synthesized via late-stage functionalization from readily available feedstock chemicals, highlighting synthetic value of this advanced N-methylation reaction. Using this platform, we also attempted tandem reactions with selected nitroarenes to convert them into corresponding N-methylated amines using MeOH under H2-free conditions including transfer hydrogenation of nitroarenes-to-anilines and prepared drug molecules (e. g., benzocaine and butamben) as well as key pharmaceutical intermediates. We further enable one-shot selective and green syntheses of 1-methylbenzimidazole using ortho-phenylenediamine (OPDA) and methanol as coupling partners.

Epoxide-Mediated Stevens Rearrangements of α-Amino-Acid-Derived Tertiary Allylic, Propargylic, and Benzylic Amines: Convenient Access to Polysubstituted Morpholin-2-ones

A new strategy has been established for the synthesis of polysubstituted morpholin-2-ones through Stevens rearrangements of tertiary amines via in situ activation with epoxides. A range of α-amino acid-derived tertiary allylic, propargylic, and benzylic amines reacted with epoxides in the presence of zinc halide catalysts to afford structurally diverse allyl-, allenyl-, and benzyl-substituted morpholin-2-ones, respectively, in moderate-to-good yields with high regioselectivity. The process involves [2,3]- and [1,2]-Stevens rearrangements of quaternary ammonium ylide intermediates and constitutes a very convenient method to prepare polysubstituted morpholin-2-ones through tandem formation of C?N, C?O, and C?C bonds. Moreover, replacing epoxides with aziridines permitted the synthesis of polysubstituted piperazin-2-ones.