A12820

2-Chloro-1-methylpyridinium iodide, 97%

CAS Number 14338-32-0 Synonyms
  • N-Methyl-2-chloropyridinium iodide
  • Mukaiyama's Reagent
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2-Chloro-1-methylpyridinium iodide, 97%

MDL: MFCD00011984
EINECS: 238-288-7

Chemical Properties

Formula: C6H7ClIN  Melting point: ca 200° dec.
Formula weight: 255.49  Sensitivity: Moisture & Light Sensitive

Literature References

Useful reagent in a wide variety of dehydrative coupling reactions. For a review of the chemistry of this and related reagents, see: Angew. Chem. Int. Ed., 18, 707 (1979). For peptide reagents, see Appendix 6.

Carboxylic acids are coupled with nucleophiles, YH, according to the following scheme:

Applications include:

Synthesis of esters: Chem. Lett., 1163 (1975); Bull. Chem. Soc. Jpn., 50, 1863 (1977); macrolides: Chem. Lett., 49 (1976); Tetrahedron Lett., 30, 3209 (1989); and strained, trans-fused -lactones: Synthesis, 493 (1983). Formation ofß-lactams from ß-amino acids: Synthesis, 210 (1979); Chem. Lett., 1465 (1984), or from carboxylic acids and imines: Tetrahedron Lett., 32, 581 (1991); cyclization of a macrocyclic amide: J Am. Chem. Soc., 111, 1157 (1989). Coupling of carboxylic acids with N,O-dimethylhydroxylamine gives the Weinreb amide: Synth. Commun., 25, 1255 (1995).

Conversion of thioureas to carbodiimides: Chem. Lett., 575 (1977); in the presence of a primary amine the guanidine is formed: J. Org. Chem., 62, 1540 (1997). Generation of ketenes from carboxylic acids: Synlett, 36 (1989).

GHS Hazard and Precautionary Statements

Hazard Statements : H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements : P261-P280-P305+P351+P338-P304+P340-P405-P501A

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Harmful or Irritant

Other References

Merck: 14,6301
Beilstein: 3572320
Harmonized Tariff Code: 2933.39
TSCA: No
2-Chloro-1-methylpyridinium iodide, 97% - CAS 14338-32-0 - Formula C6H7ClIN

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