62366-53-4

Basic information

• Product Name: 1H-Imidazole-2-carboxylicacid,1-methyl-,methylester(9CI)
• Synonyms: 1H-Imidazole-2-carboxylicacid,1-methyl-,methylester(9CI);Methyl 1-Methyl-1H-iMidazole-2-carboxylate;1-methyl-1H-Imidazole-2-carboxylic acid methyl ester;methyl 1-methylimidazole-2-carboxylate
• CAS NO: 62366-53-4
• Molecular Formula: C₆H₈N₂O₂
• Molecular Weight: 140.14
• Product Categories: CARBOXYLICESTER
• Mol File: 62366-53-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 90-94℃/0.6Torr
• Flash Point: 100 °C
• Appearance: /
• Density: 1.18 g/cm³
• Storage Temp.: 2-8°C
• PKA: 4.00±0.25(Predicted)
• CAS DataBase Reference: 1H-Imidazole-2-carboxylicacid,1-methyl-,methylester(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Imidazole-2-carboxylicacid,1-methyl-,methylester(9CI)(62366-53-4)
• EPA Substance Registry System: 1H-Imidazole-2-carboxylicacid,1-methyl-,methylester(9CI)(62366-53-4)

Safety Data

• Hazardous Substances Data: 62366-53-4(Hazardous Substances Data)

Usage

General Description

1H-Imidazole-2-carboxylicacid,1-methyl-,methylester(9CI) is a chemical compound with the molecular formula C6H7N2O2. It is an ester of 1-methyl-1H-imidazole-2-carboxylic acid, and is commonly used in the synthesis of pharmaceuticals and agrochemicals. 1H-Imidazole-2-carboxylicacid,1-methyl-,methylester(9CI) is known to have anti-inflammatory and antioxidant properties, and is also used as an intermediate in the production of various drugs and organic compounds. It is a white crystalline solid with a melting point of 144-146°C and is soluble in organic solvents such as ethanol and acetone. However, it is sparingly soluble in water. This chemical compound is a versatile building block in organic synthesis and has various industrial applications due to its unique chemical properties.

Upstream product

• 616-47-7 1-methyl-1H-imidazole 
• 79-22-1 methyl chloroformate 
• 67-56-1 methanol 
• 68-12-2 N,N-dimethyl-formamide 
• 35342-89-3 1-methyl-2-(trimethylsilyl)-1H-imidazole 
• 30148-23-3 2-trichloroacetyl-1-methylimidazole 

Downstream Products

• 129378-60-5 1-methyl-N,N-dimethylimidazole-2-carboxamide 
• 864076-07-3 methyl 4-(4-tert-butoxycarbonylamino-phenyl)-1-methyl-imidazole-2-carboxylate 

Relevant articles and documents

METHOD FOR PRODUCING IMIDAZOLE-2-CARBOXYLATE DERIVATIVE OR SALT THEREOF

PROBLEM TO BE SOLVED: To develop a method for stably obtaining an imidazole-2-carboxylate derivative or salt thereof at a high yield regardless of a scale of a reaction and an addition time of a reagent, and to efficiently produce an industrially useful imidazole-2-carboxylate derivative or salt thereof. SOLUTION: There is provided a method for producing an imidazole-2-carboxylate derivative or salt thereof including: an adding step of adding an imidazole derivative or salt thereof and triethylamine into a mixed liquid of a chloroformic ester derivative and acetonitrile under the condition of -45°C to 10°C; and a reacting step of reacting the imidazole derivative or salt thereof with the chloroformic ester to obtain the imidazole-2-carboxylate derivative or salt thereof. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

AMINO ACIDS

Compounds of formula (I): Z’ -CO-A-B-NH-Z (I) wherein: Z is H or an amino protecting group; Z’ is OH, a protected or activated hydroxyl group or C1; A is an optionally substituted C5-6 arylene group; and B is an optionally substituted C5-6 arylene group.

STUDIES ON THE DILITHIATION OF 1-METHYLIMIDAZOLE. OPTIMISATION OF REACTION CONDITIONS FOR SYNTHESES OF 2,5-DISUBSTITUTED DERIVATIVES

Reaction of 1-methylimidazole with an excess of n-butyllithium yields the 2,5-dilithio intermediate.The extent of dilithiation is dependent on the solvent, reaction time, temperature and molar ratio of the lithiating agent to the substrate.Use of a chelating agent for Li(+) decreases the reaction time, temperature and molar excess of the alkyllithium required for high-yielding dilithiation.Syntheses via the dilithio intermediate of 2,5-bis(hydroxydiphenylmethyl)- (3) and 2,5-bis(methylthio)-1-methylimidazole (5), of 1-methyl-5-trimethylsilylimidazole (8), and (in poor yields) of 1-methylimidazole-2,5-dicarboxylic acid (9) and methyl 1-methylimidazole-2,5-dicarboxylate (10) are reported.