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198005

2-Chloro-1-methylpyridinium iodide

97%

Synonym(s):

Mukaiyama reagent

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Size/SKUAvailabilityPrice
10 g

Estimated to ship onSeptember 08, 2026fromMILWAUKEE

$42.40
25 g

Estimated to ship onSeptember 08, 2026fromMILWAUKEE

$66.40
100 g

Estimated to ship onSeptember 08, 2026fromMILWAUKEE

$187.00
$140.25

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%

$42.40


Estimated to ship onSeptember 08, 2026Details


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Quality Segment

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

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.


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description

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description

Sulfhydryl reagent used to characterize reactive SH groups.

description

ReagentPlus®, ≥99%

description

≥99%

assay

97%

assay

≥98% (titration)

assay

≥99%

assay

≥99%

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

200

mp

200 °C (dec.) (lit.)

mp

-

mp

661 °C (lit.)

mp

62-67 °C (lit.)

functional group

chloro

functional group

-

functional group

-

functional group

ether


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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Questions

1–2 of 2 Questions  
  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/418/501/product-dating-information-06-25-mk.pdf

      Helpful?

  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

      Helpful?

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