2427-03-4

Basic information

• Product Name: N,N,N'-Trimethyl-o-phenylenediamine
• Synonyms: N,N,N'-Trimethyl-o-phenylenediamine
• CAS NO: 2427-03-4
• Molecular Formula: C₉H₁₄N₂
• Molecular Weight: 150.22
• Mol File: 2427-03-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N,N,N'-Trimethyl-o-phenylenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N,N'-Trimethyl-o-phenylenediamine(2427-03-4)
• EPA Substance Registry System: N,N,N'-Trimethyl-o-phenylenediamine(2427-03-4)

Safety Data

• Hazardous Substances Data: 2427-03-4(Hazardous Substances Data)

Upstream product

• 178814-08-9 2-(1,3-dimethyl-2,3-dihydro-1H-benzimidazol-2-yl)benzoic acid 
• 3213-79-4 N,N'-dimethyl-1,2-phenylenediamine 
• 124-38-9 carbon dioxide 
• 67-56-1 methanol 
• 95-83-0 4-Chloro-1,2-phenylenediamine 

Downstream Products

• 1415407-12-3 C₂₀H₁₈Cl₂N₄O₂ 

Relevant articles and documents

Supercritical methanol as solvent and carbon source in the catalytic conversion of 1,2-diaminobenzenes and 2-nitroanilines to benzimidazoles

Benzimidazoles and N-methylbenzimidazoles were synthesized by simply heating 1,2-diaminobenzenes in supercritical methanol over copper-doped porous metal oxides. These catalysts were derived from synthetic hydrotalcites that only contain earth-abundant starting materials. The carbon equivalents needed for the construction of the benzimidazole core originated from the solvent itself, which is known to undergo reforming to hydrogen and carbon monoxide through the formation of a formaldehyde intermediate. A variety of 1,2-diaminobenzenes were converted to the corresponding mixtures of benzimidazoles and N-methylated analogues in good yields. Interestingly, the more challenging, but readily available 2-nitroanilines, which require an additional reduction step prior to cyclization, could also be successfully converted to benzimidazoles in high selectivity. Furthermore, various other alcohols were applied besides methanol, to obtain 2-alkyl- and 1,2-dialkylbenzimidazoles. Preliminary mechanistic insights into the origins of N-alkylation as well as the reactivity of the nitro derivatives are discussed.

Formal transfers of hydride from carbon-hydrogen bonds. Attempted generation of H2 by intramolecular protonolyses of the activated carbon-hydrogen bonds of dihydrobenzimidazoles

Protonolyses of carbon-hydrogen bonds can occur under suitable conditions to produce carbocations and H2. In an effort to accelerate these fundamental reactions, we have attempted to make them intramolecular by devising compounds in which carbon-hydrogen bonds designed to be particularly good formal donors of hydride are held in close proximity to acidic sites. Dihydrobenzimidazoles 4 and 11 are compounds of this type, since the carbon-hydrogen bonds at C2 are activated as formal donors of hydride by adjacent lone pairs in a dihydroaromatic ring, and acidic anilinium and carboxylic acid groups are held nearby. Unfortunately, this proximity does not lead to the formation of H2 by protonolysis; instead, other reactions intervene when compounds 4 and 11 are subjected to pyrolysis.