198005
2-Chloro-1-methylpyridinium iodide
97%
Synonym(s):
Mukaiyama reagent
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About This Item
Empirical Formula (Hill Notation):
C6H7ClIN
CAS Number:
Molecular Weight:
255.48
Beilstein:
3572320
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Assay
97%
mp
200 °C (dec.) (lit.)
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
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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.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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