2-Chloro-1-methylpyridinium iodide

• Catalog No.: A12820
• CAS Number: 14338-32-0
• M. F.: C6H7ClIN
• M. W.: 255.48395
• Purity: 97%

SYNONYMS

• Title: 2-氯-1-甲基碘化吡啶鎓
• IUPAC name: 2-chloro-1-methylpyridin-1-ium iodide
• IUPAC Traditional name: 2-chloro-1-methylpyridin-1-ium iodide
• Synonyms: N-Methyl-2-chloropyridinium iodide; Mukaiyama's Reagent

DATABASE IDS

• Beilstein Number: 3572320
• Merck Index: 146301
• CAS Number: 14338-32-0
• EC Number: 238-288-7
• MDL Number: MFCD00011984

PROPERTIES

• Purity: 97%
• Melting Point: ca 200°C dec.
• GHS Hazard statements: H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• Storage Warning: Moisture & Light Sensitive
• TSCA Listed: 否

REFERENCES

• Carboxylic acids are coupled with nucleophiles, YH, according to the following scheme:
  
• Applications include:
• 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.
• 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 of?-lactams from ?-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).