61985-23-7

Basic information

• Product Name: 1H-Imidazole-1-carboxylic acid, methyl ester (9CI)
• Synonyms: 1H-Imidazole-1-carboxylic acid, methyl ester (9CI);Methyl 1H-imidazole-1-carboxylate;Methylimidazolecarbamate;MImC;N-Carbomethoxyimidazole;Methyl 1H-imidazole-1-carboxylate 95%
• CAS NO: 61985-23-7
• Molecular Formula: C₅H₆N₂O₂
• Molecular Weight: 126.11334
• Product Categories: ACIDHALIDE
• Mol File: 61985-23-7.mol
• Article Data: 13

Chemical Properties

• Melting Point: 38-44°C
• Boiling Point: 219.1±23.0 °C(Predicted)
• Flash Point: 90℃
• Appearance: /
• Density: 1.22±0.1 g/cm3(Predicted)
• Storage Temp.: ?20°C
• PKA: 3.52±0.10(Predicted)
• CAS DataBase Reference: 1H-Imidazole-1-carboxylic acid, methyl ester (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Imidazole-1-carboxylic acid, methyl ester (9CI)(61985-23-7)
• EPA Substance Registry System: 1H-Imidazole-1-carboxylic acid, methyl ester (9CI)(61985-23-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 61985-23-7(Hazardous Substances Data)

Usage

Uses

Methyl 1H-imidazole-1-carboxylate can be used to prepare fluorous β-keto esters, precursors used for the synthesis of fluorinated L-carbidopa derivatives.

General Description

Methyl 1H-imidazole-1-carboxylate is a reagent developed by Heller and Sarpong for the amidation and esterification of carboxylic acids chemoselectively.

Upstream product

• 67-56-1 methanol 
• 530-62-1 1,1'-carbonyldiimidazole 
• 288-32-4 1H-imidazole 
• 1848-01-7 4-methylphenyl methyl carbonate 
• 79-22-1 methyl chloroformate 

Downstream Products

• 125990-08-1 methyl α-(p-methoxyphenylamino)-α-phenylacetate 
• 15463-92-0 dimethyl 2-phenylsuccinate 
• 1012886-58-6 methyl 2-(2-methoxyphenyl)-2-((4-methoxyphenyl)amino)acetate 
• 1012886-60-0 methyl 2-(4-fluorophenyl)-2-((4-methoxyphenyl)amino)acetate 
• 1012886-59-7 methyl 2-(3,4-dimethoxyphenyl)-2-(4-methoxyphenylamino)acetate 
• 121766-30-1 methyl 2-(4-methoxyphenyl)-2-((4-methoxyphenyl)amino)acetate 
• 1012886-61-1 methyl 2-((4-methoxyphenyl)amino)-2-(naphthalen-1-yl)acetate 
• 616-47-7 1-methyl-1H-imidazole 
• 694-85-9 1-methyl-2-pyridone 
• 104-93-8 p-methylanizole 
• 459-60-9 1-fluoro-4-methoxybenzene 
• 21048-31-7 methyl [carbonyl-¹⁸O]benzoate 
• 623-12-1 4-chloromethoxybenzene 
• 1344736-13-5 C₁₃H₁₄N₂O₂ 

Relevant articles and documents

Facile access to imidazole derivatives: Carboxylic acids and δ-lactones

The nucleophilic addition of bis-(TMS)ketene acetals to doubly N-activated imidazole under mild conditions, leads to their corresponding dihydroimidazolyl carboxylic acids in a first instance. Subsequent reaction of these acids can be efficiently turned i

Enantioselective Syntheses of Strychnos and Chelidonium Alkaloids through Regio- and Stereocontrolled Cooperative Catalysis

We describe enantioselective syntheses of strychnos and chelidonium alkaloids. In the first case, indole acetic acid esters were established as excellent partner nucleophiles for enantioselective cooperative isothiourea/Pd catalyzed α-alkylation. This provides products containing indole-bearing stereocenters in high yield and with excellent levels of enantioinduction in a manner that is notably independent of the N-substituent. This led to concise syntheses of (?)-akuammicine and (?)-strychnine. In the second case, the poor performance of ortho-substituted cinnamyl electrophiles in the enantioselective cooperative isothiourea/Ir catalyzed α-alkylation was overcome by appropriate substituent choice, leading to enantioselective syntheses of (+)-chelidonine, (+)-norchelidonine, and (+)-chelamine.

Palladium-catalyzed C3-benzylation of indoles

A general method for regioselective C3-benzylation of indoles has been developed. Various 3-substituted indoles and benzyl methyl carbonates with different electronic properties react under mild conditions to afford a diverse range of 3-benzylindolenine products in good yields.