198005

2-Chloro-1-methylpyridinium iodide

97%

• Synonym(s): Mukaiyama reagent
• Empirical Formula (Hill Notation): C₆H₇ClIN
• CAS Number: 14338-32-0
• Molecular Weight: 255.48
• Beilstein/REAXYS Number: 3572320
• EC Number: 238-288-7
• MDL number: MFCD00011984
• UNSPSC Code: 12352100
• PubChem Substance ID: 24851856
• NACRES: NA.22

Properties

• Quality Level: 200
• assay: 97%
• mp: 200 °C (dec.) (lit.)
• functional group: chloro
• SMILES string: [I-].C[n+]1ccccc1Cl
• InChI: 1S/C6H7ClN.HI/c1-8-5-3-2-4-6(8)7;/h2-5H,1H3;1H/q+1;/p-1
• InChI key: ABFPKTQEQNICFT-UHFFFAOYSA-M

Description

General description

2-Chloro-1-methylpyridinium iodide (Mukaiyama reagent), is a commonly used reagent in organic synthesis for the activation of the hydroxy group of alcohols and carboxylic acids. It is used to synthesize derivatives of esters, lactones, amides, lactams, and ketenes from the corresponding carboxylic acids. It is also used as an efficient coupling reagent in the synthesis of peptides because of its low toxicity, simple reaction conditions, and also less expensive than EDC.

Application

2-Chloro-1-methylpyridinium iodide (CMPI) can be used as:

• A dehydrating agent for the conversion of various aldoximes to nitriles, and alcohols into alkyl thiocyanates.
• A cross-linking agent to fabricate biodegradable cross-linked hyaluronic acid film and gelatin membranes for biomedical applications.
• A condensing agent to synthesize various β-lactams from β-amino acids.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves