16413-71-1

Basic information

• Product Name: N,N-dimethyl-1-(naphthalen-1-yl)methanamine
• Synonyms: N,N-dimethyl-1-(naphthalen-1-yl)methanamine
• CAS NO: 16413-71-1
• Molecular Formula: C₁₃H₁₅N
• Molecular Weight: 185.2649
• EINECS: -0
• Mol File: 16413-71-1.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 277.2°Cat760mmHg
• Flash Point: 111°C
• Appearance: /
• Density: 1.028g/cm³
• Vapor Pressure: 0.0046mmHg at 25°C
• Refractive Index: 1.604
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8?+-.0.28(Predicted)
• CAS DataBase Reference: N,N-dimethyl-1-(naphthalen-1-yl)methanamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-dimethyl-1-(naphthalen-1-yl)methanamine(16413-71-1)
• EPA Substance Registry System: N,N-dimethyl-1-(naphthalen-1-yl)methanamine(16413-71-1)

Safety Data

• Hazardous Substances Data: 16413-71-1(Hazardous Substances Data)

Usage

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

InChI:InChI=1/C13H15N/c1-14(2)10-12-8-5-7-11-6-3-4-9-13(11)12/h3-9H,10H2,1-2H3

Upstream product

• 14489-75-9 N-methyl-1-naphthalenemethylamine 
• 30354-18-8 N,N-dimethyl(methylene)ammonium chloride 
• 972-09-8 1-(tributylstannyl)naphthalene 
• 96863-56-8 dimethyl(1-naphthylmethyl)phenacylammonium bromide 
• 66-77-3 1-naphthaldehyde 
• 124-40-3 dimethyl amine 
• 68-12-2 N,N-dimethyl-formamide 
• 86-52-2 1-Chloromethylnaphthalene 
• 3815-24-5 N,N-dimethyl-1-naphthamide 
• 109522-62-5 (2-ethoxy-1,1-difluoro-2-oxoethyl)zinc(II) bromide 
• 50-00-0 formaldehyd 
• 118-31-0 (naphth-1-yl)methylamine 
• 67-56-1 methanol 
• 55210-79-2 1-(azidomethyl)naphthalene 

Downstream Products

• 1467-79-4 NCNMe₂ 
• 69517-55-1 3-Phenyl-1H,3H-benzo[de]isochromen-1-one 
• 135366-47-1 C₂₅H₂₄NPSi 
• 1365910-72-0 4-methyl-N-(m-tolyl)naphthalen-1-amine 
• 1365911-05-2 N-(4-bromophenyl)-4-methylnaphthalen-1-amine 
• 1365911-01-8 N-(4-chlorophenyl)-4-methylnaphthalen-1-amine 
• 1365910-91-3 4-methyl-N-(p-tolyl)naphthalen-1-amine 
• 1365910-41-3 N,4-dimethyl-N-phenylnaphthalen-1-amine 
• 475250-57-8 4,4,5,5-tetramethyl-2-(naphthalen-1-ylmethyl)-1,3,2-dioxaborolane 
• 66-77-3 1-naphthaldehyde 
• 35699-45-7 1-Methyl-2-naphthaldehyde 
• 138767-45-0 (8-dimethylaminomethyl)naphthylphenyldifluorosilane 
• 62142-29-4 Dimethyl-naphthalen-1-ylmethyl-phenoxymethyl-ammonium; chloride 

Relevant articles and documents

DMF as a dimethylamine equivalent in the palladium-catalyzed nucleophilic substitution of naphthylmethyl and allyl acetates

Naphthylmethyl acetates 1a and 2a were substituted by morpholine in DMPU in the presence of 2 mol% of [Pd(dba)2 + 1.5 dppe] to give products 9-10 in 66-70% isolated yield. In DMF in the presence of benzylamine, N,N-dimethylnaphthylmethylamines 11-12 were produced in 78-85% isolated yield.

Synthesis of tertiary amines by direct Br?nsted acid catalyzed reductive amination

Tertiary amines are ubiquitous and valuable compounds in synthetic chemistry, with a wide range of applications in organocatalysis, organometallic complexes, biological processes and pharmaceutical chemistry. One of the most frequently used pathways to synthesize tertiary amines is the reductive amination reaction of carbonyl compounds. Despite developments of numerous new reductive amination methods in the past few decades, this reaction generally requires non-atom-economic processes with harsh conditions and toxic transition-metal catalysts. Herein, we report simple yet practical protocols using triflic acid as a catalyst to efficiently promote the direct reductive amination reactions of carbonyl compounds on a broad range of substrates. Applications of this new method to generate valuable heterocyclic frameworks and polyamines are also included.

Reductive Coupling between C-N and C-O Electrophiles

The cross-electrophile reaction is a promising strategy for C-C bond formation. Recent studies have focused mainly on reactions with organic halides. Here we report a coupling reaction between C-N and C-O electrophiles that demonstrates the possibility of constructing a C-C bond via C-N and C-O cleavage. Several reactions between benzyl/aryl ammonium salts and vinyl/aryl C-O electrophiles have been studied. Preliminary mechanistic studies revealed that the benzyl ammoniums were activated through a radical mechanism.