10447-93-5

Basic information

• Product Name: 1,5-dimethyl-1H-imidazole
• Synonyms: 1,5-Dimethylimidazole; 1H-imidazole, 1,5-dimethyl-
• CAS NO: 10447-93-5
• Molecular Formula: C₅H₈N₂
• Molecular Weight: 96.1304
• Mol File: 10447-93-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 221°C at 760 mmHg
• Flash Point: 84.8°C
• Density: 0.98g/cm³
• Vapor Pressure: 0.163mmHg at 25°C
• Refractive Index: 1.518
• CAS DataBase Reference: 1,5-dimethyl-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-dimethyl-1H-imidazole(10447-93-5)
• EPA Substance Registry System: 1,5-dimethyl-1H-imidazole(10447-93-5)

Safety Data

• Hazardous Substances Data: 10447-93-5(Hazardous Substances Data)

Usage

Type of compound

Heterocyclic organic compound

Structure

Five-membered ring with two nitrogen atoms and two methyl groups attached at the 1 and 5 positions

Industrial applications

Corrosion inhibitor in the oil and gas industry

Uses

Building block in the synthesis of pharmaceuticals and agrochemicals

Potential applications

Electrochemistry and catalysis

Versatility

Wide range of uses in different industries

Upstream product

• 694-31-5 1,5-dimethyl-1H-pyrazole 
• 531-35-1 isopilocarpine 
• 20485-43-2 1-methyl-2-imidazolecarboxylic acid 
• 74-88-4 methyl iodide 

Downstream Products

• 930-62-1 2,4-Dimethylimidazole 
• 7464-68-8 1,5-dimethyl-4-nitro-1H-imidazole 
• 850429-57-1 2,4-dibromo-1,5-dimethyl-1H-imidazole 
• 158585-81-0 4-bromo-1,5-dimethyl-1H-imidazole 
• 235426-31-0 2-bromo-1,5-dimethyl-1H-imidazole 
• 95740-72-0 (1,5-dimethylimidazole)(tetra-m-tolylporphyrinato)oxoiron(IV) 
• 7664-41-7 ammonia 
• 64-19-7 acetic acid 
• 74-89-5 methylamine 
• 79080-35-6 4-cyano-1,5-dimethylimidazole 
• 79080-37-8 2-cyano-1,5-dimethylimidazole 

Relevant articles and documents

Carboxylate protection for the synthesis of 4,5-disubstituted 1-methylimidazoles

Using the carboxylate function as a readily removed blocking group for the 2-position, a regioselective synthesis of diverse 4,5-disubstituted 1-methylimidazoles has been developed starting from 1-methyltribromoimidazole, 5.

Photochemistry of Phenyl-Substituted 1-Methylpyrazoles

Direct irradiation of 1-methyl-4-phenylpyrazole (2) in methanol results in regiospecific phototransposition to 1-methyl-4-phenylimidazole (4) and in photocleavage to (E)/(Z)-3-(N-methylamino)-2-phenylpropenenitrile (5) and (E)/(Z)-2-(N-methylaimno)-1-phenylethenyl isocyanide (6). Deuterium labeling confirms that the phototransposition occurs via the P4 permutation pathway. Separate experiments show that 5 and 6 undergo (Z) → (E) isomerization and photocyclization to imidazole 4. Quantum yields for these reactions show that the sequence 2 → 6 → 4 is a major pathway for the P4 phototransposition of 2 → 4. Isocyanides were also detected as intermediates in the P4 phototransposition of a variety of other pyrazoles confirming the generality of this pathway in pyrazole photochemistry. Direct irradiation of 1-methyl-5-phenylpyrazole (3) resulted in the formation of 1-methyl-5-phenylimidazole (7), 1-methyl-2-phenylimidazole (8), and 1-methyl-4-phenylimidazole (4). Deuterium labeling revealed that these products were formed by P4, P6, and P7 permutation pathways, respectively. (E)/(Z)-3-(N-methylamino)-3-phenylpropenenitrile (9) and (E)/(Z)-2-(N-methylamino)-2-phenylethenyl isocyanide (10) photocleavage products were also formed in this reaction. Irradiation of 3 in furan solvent did not result in phototransposition but led to the formation of endo and exo adducts formed by Diels-Alder reaction of furan with 4-phenyl-5-methyl-1,5-diazabicyclo[2.1.0]pent-2-ene. This constitutes the first direct evidence for the formation of a 1,5-diazabicyclo[2.1.0]hex-2-ene from photolysis of a pyrazole and is consistent with the electrocyclic ring closure - heteroatom migration mechanism suggested for the P6 and P7 phototranspositions.