102-18-1

Basic information

• Product Name: 1,2-Ethanediamine, N,N'-dimethyl-N,N'-bis(phenylmethyl)-
• Synonyms: N,N'-DIBENZYL-N,N'-DIMETHYLETHYLENEDIAMINE;Ethylenediamine, N,N'-dibenzyl-N,N'-dimethyl-;benzyl-[2-[benzyl(methyl)amino]ethyl]-methyl-amine;N,N'-dimethyl-N,N'-bis(phenylmethyl)ethane-1,2-diamine
• CAS NO: 102-18-1
• Molecular Formula: C₁₈H₂₄N₂
• Molecular Weight: 268.4
• EINECS: 203-011-0
• Mol File: 102-18-1.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 348.1°Cat760mmHg
• Flash Point: 149.5°C
• Appearance: /
• Density: 1.018g/cm³
• PKA: 7.85±0.50(Predicted)
• CAS DataBase Reference: 1,2-Ethanediamine, N,N'-dimethyl-N,N'-bis(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Ethanediamine, N,N'-dimethyl-N,N'-bis(phenylmethyl)-(102-18-1)
• EPA Substance Registry System: 1,2-Ethanediamine, N,N'-dimethyl-N,N'-bis(phenylmethyl)-(102-18-1)

Safety Data

• Hazardous Substances Data: 102-18-1(Hazardous Substances Data)

Usage

General Description

1,2-Ethanediamine, N,N'-dimethyl-N,N'-bis(phenylmethyl)-, commonly known as DMAPA, is an organic chemical compound characterized by its molecular structure, which includes two amine groups (N(CH3)2) attached to a central ethylene diamine backbone, with each amine group further substituted by phenylmethyl groups (C6H5CH2). DMAPA's role as a reagent in organic reactions, particularly in the synthesis of pharmaceuticals and polymers, underscores its significance in various industrial and research applications.

Upstream product

• 106-93-4 ethylene dibromide 
• 103-67-3 benzyl-methyl-amine 
• 17412-47-4 1.2-Bis--ethan 
• 50-00-0 formaldehyd 
• 140-28-3 N,N'-Dibenzylethylenediamine 

Downstream Products

• 727381-45-5 Pd(C₆H₅CH₂NCH₃CH₂)2(OC₁₀H₅CH₃)2 
• 727381-45-5 Pd(C₆H₅CH₂NCH₃CH₂)2(OC₁₀H₅CH₃)2 
• 50723-62-1 PdCl₂(C₆H₅CH₂NCH₃CH₂)2 

Relevant articles and documents

Group IB organometallic chemistry. XIV. Intramolecular ring-closure reactions of novel arylcopper compounds RCuI2. Synthesis of 7,8-dihydrodibenzo[f,h][1,4]dioxecin and 7,8-dihydrodibenzo-6,9-dimethyl[f,h][1,4]diazecin

The reaction of 1,2-bis{N-[2-(bromomagnesio)benzyl]-N-methylamino}ethane (III) with CuCl2 results in the formation of 1,2-bis[N-(2-cupriobenzyl)N-methylamino] ethane (I, 2,2′-Cu2RN) and of the product of intramolecular ring-closure 7,8-dihydrodibenzo-6,9-dimethyl[f,h][1,4]diazecin (VII). The formation of 2,2′-RN (VII) is explained in terms of a concerted electron-transfer/CC coupling reaction within a complex of the monomagnesium species 2,2′-MgRN (VIII) with CuCl2. Molecular weight determinations and NMR spectroscopic data for I point to a tetranuclear structure (2,2′-Cu2RN)2 in which (2,2′-Cu2RN)2 in which the two multicenter-bonded aryl groups in each of the RN ligands are arranged in a trans-manner. This structure accounts for the exclusive formation of 2,2′-RN (VII) upon thermal decomposition of I. The interaction of 1,2-bis[2-(bromomagnesio)benzyloxy] ethane (X) with CuCl2 affords the ring-closed product 7,8-dihydrodibenzo[f,h][1,4] dioxecin (IX) in addition to the organodicopper XII. Thermal decomposition of XII yields 2,2′-RO (IX) quantitatively.