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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
238-288-7
Beilstein/REAXYS Number:
3572320
MDL number:
Assay:
97%
Product Name
2-Chloro-1-methylpyridinium iodide, 97%
InChI key
ABFPKTQEQNICFT-UHFFFAOYSA-M
InChI
1S/C6H7ClN.HI/c1-8-5-3-2-4-6(8)7;/h2-5H,1H3;1H/q+1;/p-1
SMILES string
[I-].C[n+]1ccccc1Cl
assay
97%
mp
200 °C (dec.) (lit.)
functional group
chloro
Quality Level
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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.
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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W Keese et al.
Biological chemistry Hoppe-Seyler, 366(12), 1093-1095 (1985-12-01)
2-Chloro-1-methylpyridinium iodide is a coupling reagent for peptide synthesis. By its use different peptides were synthesized with protected di- and trifunctional amino acids. While urethan-protected amino acids react free of racemization, the fragment condensation needs N-Hydroxysuccinimide, as shown by the
Efficient Transformation of Aldoximes to Nitriles Using 2-Chloro-1-methylpyridinium Iodide Under Mild Conditions
Lee Kieseung, et al.
Synthetic Communications, 34(10), 1775-1782 (2004)
Chul-Hwan Lee et al.
Molecular cell, 70(3), 422-434 (2018-04-24)
PRC2 is a therapeutic target for several types of cancers currently undergoing clinical trials. Its activity is regulated by a positive feedback loop whereby its terminal enzymatic product, H3K27me3, is specifically recognized and bound by an aromatic cage present in
Tetrahedron Asymmetry, 3, 1455-1455 (1992)
A novel cell support membrane for skin tissue engineering: Gelatin film cross-linked with 2-chloro-1-methylpyridinium iodide
Yeh Ming-kung, et al.
Polymer, 52(4), 996-1003 (2011)
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