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

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

• 96863-55-7 dimethylacetonyl(1-naphthylmethyl)ammonium bromide 
• 96863-54-6 dimethyl(1-naphthylmethyl)cyanomethylammonium chloride 
• 124-40-3 dimethyl amine 
• 3815-24-5 N,N-dimethyl-1-naphthamide 
• 109522-62-5 (2-ethoxy-1,1-difluoro-2-oxoethyl)zinc(II) bromide 
• 14489-75-9 N-methyl-1-naphthalenemethylamine 
• 86-87-3 naphth-1-yl acetic acid 
• 67-56-1 methanol 
• 1033694-58-4 2-(naphthalen-1-yl)acetyl azide 
• 66-77-3 1-naphthaldehyde 
• 68-12-2 N,N-dimethyl-formamide 
• 50-00-0 formaldehyd 
• 118-31-0 (naphth-1-yl)methylamine 
• 55210-79-2 1-(azidomethyl)naphthalene 

Downstream Products

• 62142-29-4 Dimethyl-naphthalen-1-ylmethyl-phenoxymethyl-ammonium; chloride 
• 138767-45-0 (8-dimethylaminomethyl)naphthylphenyldifluorosilane 
• 1467-79-4 NCNMe₂ 
• 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 
• 135366-47-1 C₂₅H₂₄NPSi 
• 69517-55-1 3-Phenyl-1H,3H-benzo[de]isochromen-1-one 

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.

Difluoroalkylation of Tertiary Amides and Lactams by an Iridium-Catalyzed Reductive Reformatsky Reaction

An iridium-catalyzed, reductive alkylation of abundant tertiary lactams and amides using 1-2 mol % of Vaska's complex (IrCl(CO)(PPh3)2), tetramethyldisiloxane (TMDS), and difluoro-Reformatsky reagents (BrZnCF2R) for the general synthesis of medicinally relevant α-difluoroalkylated tertiary amines is described. A broad scope (46 examples), including N-aryl- and N-heteroaryl-substituted lactams, demonstrated an excellent functional group tolerance. Furthermore, late-stage drug functionalizations, a gram-scale synthesis, and common downstream transformations proved the potential synthetic relevance of this new methodology.

Synthesis of: N -methylated amines from acyl azides using methanol

The transformation of acyl azide derivatives into N-methylamines was developed using methanol as the C1 source via the one-pot Curtius rearrangement and borrowing hydrogen methodology. Following this protocol, various functionalised N-methylated amines were synthesized using the (NNN)Ru(ii) complex from carboxylic acids via an acyl azide intermediate. Several kinetic studies and DFT calculations were carried out to support the mechanism and also to determine the role of the Ru(ii) complex and base in this transformation.

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.

Palladium-Catalyzed Highly Regioselective Aromatic Substitution of Benzylic Ammonium Salts with Amines

An unprecedented aromatic substitution reaction of benzylic ammonium salts has been developed through palladium-catalyzed C-N bond cleavage. A range of primary and secondary amines participated in a palladium-catalyzed aromatic substitution reaction of benzylic ammonium salts, delivering sterically hindered aromatic amines in moderate to excellent yields with extremely high regioselectivity. Preliminary mechanistic studies permitted successful identification of Π-benzylpalladium complexes and Γ-vinyl allylic amines as key intermediates. This study paves the way for the use of benzylic ammonium salts in the aromatic substitution reactions.

Methyl-Selective α-Oxygenation of Tertiary Amines to Formamides by Employing Copper/Moderately Hindered Nitroxyl Radical (DMN-AZADO or 1-Me-AZADO)

Methyl-selective α-oxygenation of tertiary amines is a highly attractive approach for synthesizing formamides while preserving the amine substrate skeletons. Therefore, the development of efficient catalysts that can advance regioselective α-oxygenation at the N-methyl positions using molecular oxygen (O2) as the terminal oxidant is an important subject. In this study, we successfully developed a highly regioselective and efficient aerobic methyl-selective α-oxygenation of tertiary amines by employing a Cu/nitroxyl radical catalyst system. The use of moderately hindered nitroxyl radicals, such as 1,5-dimethyl-9-azanoradamantane N-oxyl (DMN-AZADO) and 1-methyl-2-azaadamanane N-oxyl (1-Me-AZADO), was very important to promote the oxygenation effectively mainly because these N-oxyls have longer life-times than less hindered N-oxyls. Various types of tertiary N-methylamines were selectively converted to the corresponding formamides. A plausible reaction mechanism is also discussed on the basis of experimental evidence, together with DFT calculations. The high regioselectivity of this catalyst system stems from steric restriction of the amine-N-oxyl interactions.

Controlled Reduction of Carboxamides to Alcohols or Amines by Zinc Hydrides

New protocols for controlled reduction of carboxamides to either alcohols or amines were established using a combination of sodium hydride (NaH) and zinc halides (ZnX2). Use of a different halide on ZnX2 dictates the selectivity, wherein the NaH-ZnI2 system delivers alcohols and NaH-ZnCl2 gives amines. Extensive mechanistic studies by experimental and theoretical approaches imply that polymeric zinc hydride (ZnH2)∞ is responsible for alcohol formation, whereas dimeric zinc chloride hydride (H?Zn?Cl)2 is the key species for the production of amines.

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.

Selective synthesis of mono- and di-methylated amines using methanol and sodium azide as C1 and N1 sources

A Ru(ii) complex mediated synthesis of various N,N-dimethyl and N-monomethyl amines from organic azides using methanol as a methylating agent is reported. This methodology was successfully applied for a one-pot reaction of bromide derivatives and sodium azide in methanol. Notably, by controlling the reaction time several N-monomethylated and N,N-dimethylated amines were synthesized selectively. The practical applicability of this tandem process was revealed by preparative scale reactions with different organic azides and synthesis of an anti-vertigo drug betahistine. Several kinetic experiments and DFT studies were carried out to understand the mechanism of this transformation.

Direct Synthesis of N,N-Dimethylated and β-Methyl N,N-Dimethylated amines from nitriles using methanol: Experimental and computational studies

Direct and selective synthesis of N,N-dimethylated amines from nitriles using methanol as C1 building blocks is reported using an air- and moisture-stable ruthenium complex. Following this process, various aromatic as well as aliphatic nitriles were converted to the corresponding N-methylated amines. Interestingly, tandem C-methylation as well as N-methylation was achieved by introducing multiple methyl groups. The practical aspect of this process was revealed by preparative-scale reactions with different nitriles and the synthesis of anti-allergic drug "avil". Several kinetic experiments and detailed DFT calculations were carried out to understand the mechanism of this process.