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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.
G Chwatko.; E Bald. Determination of cysteine in human plasma by high-performance liquid chromatography and ultraviolet detection after pre-column derivatization with 2-chloro-1-methylpyridinium iodide . Talanta. 2000, 52 (3), 509-515.
Jenn-Jong Young.; Kuang-Ming Cheng.; Tai-Li Tsou.; Hwan-Wun Liu.; Hsian-Jenn Wang. Preparation of cross-linked hyaluronic acid film using 2-chloro-1-methylpyridinium iodide or water-soluble 1-ethyl-(3,3-dimethylaminopropyl)carbodiimide. Journal of Biomaterials Science, Polymer Edition. 2004, 15 (6), 767-780.
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:
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).
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant