2-Chloro-1-methylpyridinium iodide Chemical Properties

Melting point:

200 °C (dec.) (lit.)

Density 

1.7949 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Crystalline Powder and/or Chunks

color 

Yellow

Water Solubility 

soluble

Sensitive 

Moisture & Light Sensitive

Merck 

14,6301

BRN 

3572320

Exposure limits

ACGIH: TWA 0.01 ppm

InChIKey

ABFPKTQEQNICFT-UHFFFAOYSA-M

CAS DataBase Reference

14338-32-0(CAS DataBase Reference)

EPA Substance Registry System

2-Chloro-1-methylpyridinium iodide (14338-32-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-24/25-36

RIDADR 

1759

WGK Germany 

3

F 

8-21

HazardClass 

8

PackingGroup 

III

HS Code 

29333999

MSDS

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2-Chloro-1-methylpyridinium iodide Usage And Synthesis

Chemical Properties

yellow crystalline solid

Uses

2-Chloro-1-methylpyridinium iodide is a reagent in a wide variety of dehydrative coupling reactions. It is also used to form carboxylate esters from acids and alcohols, carboxamides from acids and amines, lactones from -hydroxy acids and carbodiimides from N,N-disubstituted thioureas.

Uses

Condensation reagent for the synthesis of esters and ketenes, and for the kinetic resolution of carboxylic acids and alcohols.

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.

Purification Methods

Purify it by dissolving in EtOH and adding dry Et2O. The solid is washed with Me2CO and dried at 20o/0.35mm. Store it in the dark. Attempted recrystallisation from Me2CO/EtOH/pet ether (b 40-60o) causes some exchange of the Cl substituent by I. The picrate has m 106-107o, and the perchlorate has m 212-213o. [Jones et al. J Am Chem Soc 111 1157 1989, UV and solvolysis: Barlin & Benbow J Chem Soc, Perkin Trans 2 790 1974, Beilstein 20/5 V 405.]

2-Chloro-1-methylpyridinium iodide(14338-32-0)Related Product Information

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