26628-67-1

Basic information

• Product Name: N-METHYL-4,4'-METHYLENEDIANILINE
• Synonyms: 4-((4-aminophenyl)methyl)-n-methyl-benzenamin;4-((4-aminophenyl)methyl)-n-methylbenzenamine;n-methyl-4,4’-methylenedi-anilin;N-METHYL-4,4'-METHYLENEDIANILINE;4-[[4-(methylamino)phenyl]methyl]aniline
• CAS NO: 26628-67-1
• Molecular Formula: C₁₄H₁₆N₂
• Molecular Weight: 212.29
• Product Categories: Nitrogen Compounds;Organic Building Blocks;Polyamines
• Mol File: 26628-67-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 61-63 °C(lit.)
• Boiling Point: 390.8°Cat760mmHg
• Flash Point: 224.5°C
• Appearance: /
• Density: 1.113g/cm³
• CAS DataBase Reference: N-METHYL-4,4'-METHYLENEDIANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-METHYL-4,4'-METHYLENEDIANILINE(26628-67-1)
• EPA Substance Registry System: N-METHYL-4,4'-METHYLENEDIANILINE(26628-67-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: BY5700000
• Hazardous Substances Data: 26628-67-1(Hazardous Substances Data)

Usage

General Description

N-Methyl-4,4′-methylenedianiline (4-(4-aminobenzyl)-N-methylaniline) is a 4,4′-methylenedianiline derivative. It has been synthesized by the methylation of 4,4′-methylenedianiline using formaldehyde and characterized by 1H NMR and mass spectrometry. It has been reported to be the one of the urinary metabolites during the in vivo metabolism of 4,4′-[14C]- methylenebis(N,N-dimethyl)benzamine (reduced Michler′s ketone, RMK) in Osborne-Mendel rats.

Upstream product

• 186581-53-3 diazomethane 
• 75815-93-9 4-methylaminophenylmercury chloride 
• 62-53-3 aniline 
• 50-00-0 formaldehyd 
• 28539-02-8 1-Hydroxymethyl-1H-benzotriazole 
• 101-77-9 4,4'-diamino diphenyl methane 
• 616-38-6 carbonic acid dimethyl ester 
• 129075-89-4 4-[(benzotriazol-1-yl)methyl]phenylamine 
• 100-61-8 N-methylaniline 

Downstream Products

• 24650-10-0 2,4'-methylene-dicyclohexyldiamine 
• 648900-91-8 N-methyl-4,4'-diaminodicyclohexylmethane 
• 1761-71-3 4,4'-diaminodicyclohexylmethane 
• 70906-77-3 2,2'-methylene-dicyclohexyl-diamine 

Relevant articles and documents

SILICA-BASED ZINC CATALYSTS. THEIR PREPARATION AND USE IN THE ALKOXYCARBONYLATION OF AMINES

The present invention relates to silica-based heterogeneous zinc compounds which are suitable as catalysts in the reaction of amines with dialkyl carbonates to produce carbamates. The catalysts have the formula [SiO2]-CH2-CHR-X-COOZn[Y], wherein [SiO2] represents a silica carrier selected from the group consisting of ordered mesoporous silica and irregular amorphous narrow pore silica, R represents a moiety selected from the group consisting of hydrogen, -CH3, and -CH2CH3, preferably hydrogen, X is an aliphatic chain of 2 to 11 carbon atoms that optionally comprises ether moieties and [Y] represents a mono anion. The invention is also directed towards a method for the preparation of the aforementioned compounds and towards method for the alkoxycarbonylation of amines.

Benzotriazole Mediated Synthesis of Methylenebisanilines

Methylenebisanilines and methylenebis(N,N-dialkylaniline)s are prepared by the reactions of 1-hydroxymethylbenzotriazole with anilines and with N,N-dialkylanilines under acidic conditions.Isolation of the intermediate 4-(benzotriazol-1-ylmethyl)anilines and the N,N-dialkyl analogues and their reactions with anilines allow the efficient preparation of both symmetrical and unsymmetrical members of both product classes.

Alkylidene Transfer from Monochloroalkylmercury(II) Compounds to Aromatic Amines; Selective C-Alkylation

αα-Diarylalkane derivatives have been synthesized from monochloroalkylmercury(II) compounds in a noncarbenoid alkylidene transfer reaction which takes place selectively on the aromatic ring.A mechanism is suggested for this process.Intermediate products are prepared by alternative routes to ascertain their participation in the course of the reaction.As a consequence, two different aryl groups can be successively incorporated into the alkane molecule.