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198005

Sigma-Aldrich

2-Chloro-1-methylpyridinium iodide

97%

Synonym(s):

Mukaiyama reagent

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About This Item

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

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

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

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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)
Ming-Kung Yeh et al.
Journal of biomaterials science. Polymer edition, 23(7), 973-990 (2011-05-10)
We prepared a novel porous gelatin (GEL) sponge which was cross-linked (CL) with a zero-length crosslinker of 2-chloro-1-methylpyridinium iodide (CMPI), and compared CPMI with 1-ethyl-3,3-dimethylaminoproplycarbodiimide (EDC). The ninhydrin assay indicated that the CMPI-CL-GEL sponge had a higher degree of cross-linking
A convenient method for the construction of β-lactam compounds from β-amino acids using 2-chloro-1-methylpyridinium iodide as condensing reagent
Huang H, et al.
Chemistry Letters (Jpn), 13(8), 1465-1466 (1984)
Dmitrii V Belykh et al.
Molecules (Basel, Switzerland), 23(7) (2018-07-18)
This article focuses on the antiradical activity of a number of 2,6-diisobornylphenol-porphyrin conjugates with various spacers between the porphyrin and phenolic fragments in the model reaction of ethylbenzene oxidation initiated by azoisobutyric acid dinitrile. The study has shown that the
Jenn-Jong Young et al.
Journal of biomaterials science. Polymer edition, 15(6), 767-780 (2004-07-17)
In order to obtain much slower biodegradable films, which are often required for biomedical applications, we have developed a series of studies on heterogeneous cross-linking of hyaluronic acid (HA) films by using 2-chloro-1-methylpyridinium iodide (CMPI) or 1-ethyl-(3,3-dimethylaminopropyl)carbodiimide (EDC) as cross-linking
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