All Photos(2)

198005

Sigma-Aldrich

2-Chloro-1-methylpyridinium iodide

97%

Synonym(s):
Mukaiyama reagent
Empirical Formula (Hill Notation):
C6H7ClIN
CAS Number:
Molecular Weight:
255.48
Beilstein:
3572320
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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.

Packaging

10, 25, 100 g in glass bottle

Storage Class Code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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...
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...
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...
Ming Liu et al.
Food chemistry, 242, 338-344 (2017-10-19)
In this study, a strategy based on chemical derivatization coupled with electrospray ionizationtandem quadrupole mass spectrometry (ESI-MS/MS) for rapid and sensitive detection of FFAs in edible oils was developed. A derivative reagent (N,N-diethyl-1,2-ethanediamine, DEEA) was employed to selectively label carboxyl...
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...

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