37615-53-5

Basic information

• Product Name: N-METHYLDIHEXYLAMINE
• Synonyms: N N-DIHEXYLMETHYLAMINE;N-METHYLDIHEXYLAMINE;N-METHYL DI-N-HEXYLAMINE;N,N-DI-N-HEXYL METHYLAMINE;Methyldihexylamine;N,N-Dihexylmethaneamine
• CAS NO: 37615-53-5
• Molecular Formula: C₁₃H₂₉N
• Molecular Weight: 199.38
• Product Categories: Amines;C11 to C38;Nitrogen Compounds
• Mol File: 37615-53-5.mol

Chemical Properties

• Melting Point: 26°C (estimate)
• Boiling Point: 146 °C/48 mmHg(lit.)
• Flash Point: 89 °C
• Appearance: /
• Density: 0.775 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0356mmHg at 25°C
• Refractive Index: n20/D 1.433(lit.)
• PKA: 10.23±0.50(Predicted)
• CAS DataBase Reference: N-METHYLDIHEXYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-METHYLDIHEXYLAMINE(37615-53-5)
• EPA Substance Registry System: N-METHYLDIHEXYLAMINE(37615-53-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 2735 8/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 37615-53-5(Hazardous Substances Data)

Usage

Uses

Used in Polymer Synthesis:
N-Methyldihexylamine is used as a precursor in the synthesis of comb-shaped cationic poly(2,6-dimethylphenylenoxide) (PPO) polymer anion-exchange membrane (AEM). The presence of two hexyl side chains in N-Methyldihexylamine contributes to the formation of the comb-shaped structure in the resulting polymer.
Used in Energy Industry:
In the energy industry, N-Methyldihexylamine-derived AEMs are utilized for their potential applications in fuel cells and other electrochemical devices. The comb-shaped cationic PPO polymer AEMs offer improved performance characteristics, such as enhanced ionic conductivity and mechanical stability, which are crucial for the efficient operation of these devices.
Used in Chemical Research:
N-Methyldihexylamine also serves as a valuable compound in chemical research, particularly in the study of amine chemistry and the development of new synthetic methods. Its unique structure and reactivity make it an interesting subject for further investigation and potential applications in various chemical processes.

InChI:InChI=1/C13H29N/c1-4-6-8-10-12-14(3)13-11-9-7-5-2/h4-13H2,1-3H3

Upstream product

• 4385-04-0 N,N-dimethylhexylamine 
• 64-18-6 formic acid 
• 143-16-8 dihexylamine 
• 35161-70-7 N-methylhexanamine 
• 67-56-1 methanol 
• 111-26-2 hexan-1-amine 
• 111-25-1 1-bromo-hexane 
• 74-89-5 methylamine 
• 544-10-5 1-Chlorohexane 

Downstream Products

• 950901-94-7 (cyanomethyl)dihexylmethylammonium tosylate 

Relevant articles and documents

Reaction of aliphatic amines with 49% formic acid. 1-hexylamine, di-1-hexylamine, N,N-dimethyl-1-hexylamine, 1-dodecylamine, N,N-dimethyl-1-dodecylamine and N,N-dimethyl-1-butylamine

Two primary amines, 1-hexylamine 2, 1-dodecylamine 19, one secondary amine, di-1-hexylamine 18, and three tertiary amines, N,N-dimethyl-1-hexylamine 6, N,N-dimethyl-1-butylamine 3, and N,N-dimethyl-1-dodecylamine 22 were each heated at 150°C, 250°C or 350°C with 49% aqueous formic acid for varying periods of time. The aliphatic primary amines underwent easy N-formylation and subsequent reduction to give N-methyl- and N,N-dimethylalkylamines. Especially at higher temperatures, other reactions intervened including elimination of NH3 to the corresponding alkenes followed by partial double bond isomerization. Tertiary amines were more reactive at higher temperatures undergoing hydrolysis and reductive cleavages to secondary and primary amines, which subsequently followed the reaction sequences seen for primary amines. This series of saturated amines showed none of the cleavage into smaller fragments that was observed in the reductive alkylation of pyridine and 4-methylpyridine to a series of N-alkylpiperdines. This result reinforces the bis-aza-retro-Aldol-fragmentation mechanism postulated for the formation of the N-alkylpiperidines. Johann Ambrosius Barth 1997.

THE HOMOGENEOUSLY CATALYSED SYNTHESIS OF N-METHYLDIALKYLAMINES FROM N-METHYL AND N,N-DIMETHYLALKYLAMIMES

N-Methyl and N,N-dimethylalkylamines are converted into N-methyldialkylamines in good yields when heated at 180 deg C in the presence of a catalytic amount of RuCl2(Ph3P)3.

SELECTIVE CONVERSION OF PRIMARY AMINES INRO N,N-DIMETHYLALKYL- OR N,N-DIALKYLMETHYL-AMINES WITH METHANOL AND RuCl2(Ph3P)3

N,N-dimethylalkyl- or N,N-dialkylmethyl-amines are selectively obtained from the reaction between aliphatic amines and methanol at 180 deg C for 7 h in the presence of RuCl2(Ph3P)3 catalyst.