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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:
3572320
EC Number:
238-288-7
MDL number:
MFCD00011984
UNSPSC Code:
12352100
PubChem Substance ID:
24851856
NACRES:
NA.22
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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

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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.[1][2]

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.[1][3]
  • A cross-linking agent to fabricate biodegradable cross-linked hyaluronic acid film and gelatin membranes for biomedical applications.[2][4]
  • A condensing agent to synthesize various β-lactams from β-amino acids.[5]

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000216828
MKCQ8116
SHBN1306
SHBL2695
SHBL4383

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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
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
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)
Tetrahedron Asymmetry, 3, 1455-1455 (1992)
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)
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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