1-Methyl-1H-imidazole-4-carboxylic acid methyl ester

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Cat Number

INT17289199

CAS Number

17289-19-9

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Product Detail Description Customer Q&A

CAS Number

17289-19-9

Storage

Room temperature

Synonyms

Methyl-N-methylimidazole-4-carboxylic acid;4-(Methoxycarbonyl)-1-methyl-1H-imidazole;1,2-diMethyl-1H-iMidazole-4-carboxylic acid

Molecular Formula

C6H8N2O2

Molecular Weight

140.14

Smiles

C1N(C)C=C(C(OC)=O)N=1

Appearance

Off-white powder

Melting Point

103℃

Boiling Point

285℃

Relative Density

1.18

pKa

3.37

General Description

1-Methyl-1H-imidazole-4-carboxylic acid methyl ester is a methyl-substituted imidazole derivative with a carboxylic ester at the C-4 position. The N-1 methyl group blocks this nitrogen, directing nucleophilic attack to the C-2 position and preventing unwanted N-alkylation side reactions in further synthesis. The ester functionality serves as a handle for hydrolysis to the acid or amidation reactions, while the imidazole ring provides two nucleophilic nitrogen sites for further transformations.

Mechanism of Action

1-Methyl-1H-imidazole-4-carboxylic acid methyl ester functions as a versatile imidazole-containing building block in pharmaceutical synthesis. The methyl ester can be selectively hydrolyzed to the corresponding carboxylic acid or transesterified, and subsequently converted to amides. The imidazole ring can participate in cyclocondensation reactions and metal-catalyzed couplings. The N-1 methyl group prevents unwanted polyalkylation and simplifies downstream synthetic steps.

Application

1-Methyl-1H-imidazole-4-carboxylic acid methyl ester is used as an intermediate in the synthesis of imidazole-containing pharmaceuticals including proton pump inhibitors (PPIs), antifungal agents, and histamine H2 receptor antagonists. The imidazole moiety is a privileged heterocycle in drug discovery due to its ability to coordinate with metal ions in enzyme active sites. It is also used in the synthesis of ionic liquids and functional materials.

What is the recommended storage condition for 1-Methyl-1H-imidazole-4-carboxylic acid methyl ester?

It should be stored at controlled room temperature in a well-sealed container, protected from moisture and direct light, to maintain its chemical integrity throughout the shelf life.

Is a Certificate of Analysis (COA) available for 1-Methyl-1H-imidazole-4-carboxylic acid methyl ester?

Yes, a fully verified COA is issued for every batch and can be shared electronically. Additional documentation such as MSDS or impurity profiles may be requested separately.

Is 1-Methyl-1H-imidazole-4-carboxylic acid methyl ester available in high-chemical-purity grade for pharmaceutical synthesis?

Yes, it is supplied in high chemical purity grades suitable for demanding pharmaceutical intermediate applications. Specifications and analytical data are available upon request.

Can 1-Methyl-1H-imidazole-4-carboxylic acid methyl ester be provided with custom specifications for synthetic applications?

Custom specifications including adjusted particle size, solvent residue limits, or additional purity testing can be arranged for qualified customers with defined requirements.

Is 1-Methyl-1H-imidazole-4-carboxylic acid methyl ester suitable for use in regulated pharmaceutical processes?

Yes, it is manufactured under quality standards consistent with regulated pharmaceutical applications, including in-process controls and release testing aligned with industry requirements.