3204-31-7

Basic information

• Product Name: 1,3-Dimethyl-2,3-dihydro-1H-benzimidazole
• Synonyms: 1,3-Dimethyl-1,3-dihydro-2H-benzimidazole;1,3-Dimethyl-2,3-dihydro-1H-benzimidazole
• CAS NO: 3204-31-7
• Molecular Formula: C₉H₁₂N₂
• Molecular Weight: 148.21
• Mol File: 3204-31-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 238.2°C at 760 mmHg
• Flash Point: 93°C
• Appearance: /
• Density: 1.053g/cm³
• Vapor Pressure: 0.0429mmHg at 25°C
• Refractive Index: 1.564
• PKA: 6.46±0.20(Predicted)
• CAS DataBase Reference: 1,3-Dimethyl-2,3-dihydro-1H-benzimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dimethyl-2,3-dihydro-1H-benzimidazole(3204-31-7)
• EPA Substance Registry System: 1,3-Dimethyl-2,3-dihydro-1H-benzimidazole(3204-31-7)

Safety Data

• Hazardous Substances Data: 3204-31-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H12N2/c1-10-7-11(2)9-6-4-3-5-8(9)10/h3-6H,7H2,1-2H3

Upstream product

• 4166-43-2 formic acid-(N-methyl-2-methylamino-anilide) 
• 3652-93-5 1,3-dimethyl-2-(o-hydroxyphenyl)-2,3-dihydro-1H-benzo[d]imidazole 
• 7181-87-5 1,3-dimethylbenzimidazolium Iodide 
• 769-15-3 1,3-dimethyl-benzoimidazolium 
• 124-38-9 carbon dioxide 
• 3213-79-4 N,N'-dimethyl-1,2-phenylenediamine 
• 328312-77-2 N,N'-dimethylbenzimidazolium hexafluorophosphate 
• 55342-78-4 2-H-1,3-di-tert-butyl-1,3,2-diazaphosphorinane 

Downstream Products

• 94-38-2 3-diethylamino-1-phenyl-propan-1-one 
• 3299-38-5 4-(diethylamino)butan-2-one 
• 2983-48-4 1-phenyl-3-(phenylamino)propan-1-one 
• 6220-79-7 4-phenylamino-butan-2-one 
• 122377-71-3 3-(N,N-Dibenzylamino)-1-phenyl-propan-1-on 
• 26734-07-6 4-dibenzylamino-2-butanone 
• 4166-43-2 formic acid-(N-methyl-2-methylamino-anilide) 
• 92-52-4 biphenyl 
• 7181-87-5 1,3-dimethylbenzimidazolium Iodide 
• 92-94-4 [1,1';4',1'']terphenyl 

Relevant articles and documents

Benzimidazoles as Metal-Free and Recyclable Hydrides for CO2 Reduction to Formate

We report a novel metal-free chemical reduction of CO2 by a recyclable benzimidazole-based organo-hydride, whose choice was guided by quantum chemical calculations. Notably, benzimidazole-based hydride donors rival the hydride-donating abilities of noble-metal-based hydrides such as [Ru(tpy)(bpy)H]+ and [Pt(depe)2H]+. Chemical CO2 reduction to the formate anion (HCOO-) was carried out in the absence of biological enzymes, a sacrificial Lewis acid, or a base to activate the substrate or reductant. 13CO2 experiments confirmed the formation of H13COO- by CO2 reduction with the formate product characterized by 1H NMR and 13C NMR spectroscopy and ESI-MS. The highest formate yield of 66% was obtained in the presence of potassium tetrafluoroborate under mild conditions. The likely role of exogenous salt additives in this reaction is to stabilize and shift the equilibrium toward the ionic products. After CO2 reduction, the benzimidazole-based hydride donor was quantitatively oxidized to its aromatic benzimidazolium cation, establishing its recyclability. In addition, we electrochemically reduced the benzimidazolium cation to its organo-hydride form in quantitative yield, demonstrating its potential for electrocatalytic CO2 reduction. These results serve as a proof of concept for the electrocatalytic reduction of CO2 by sustainable, recyclable, and metal-free organo-hydrides.

Neutral Organic Super Electron Donors Made Catalytic

Neutral organic super electron donors (SEDs) display impressive reducing power but, until now, it has not been possible to use them catalytically in radical chain reactions. This is because, following electron transfer, these donors form persistent radical cations that trap substrate-derived radicals. This paper unlocks a conceptually new approach to super electron donors that overcomes this issue, leading to the first catalytic neutral organic super electron donor.

Bridging amines with CO2: Organocatalyzed reduction of CO2 to aminals

The four-electron reduction of CO2 in the presence of secondary aromatic amines is described for the first time to access aminals. Under metal-free hydrosilylation conditions, the four C-O bonds of CO2 are cleaved, and the organocatalysts are able to balance the reactivity of CO2 to promote the selective formation of two C-N and two C-H bonds. The methodology enables the formation of various symmetrical and unsymmetrical aminals.