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14338-32-0 - 2-Chloro-1-methylpyridinium iodide, 97% - N-Methyl-2-chloropyridinium iodide - Mukaiyama's Reagent - A12820 - Alfa Aesar

A12820 2-Chloro-1-methylpyridinium iodide, 97%

CAS Number
14338-32-0
Synonyms
N-Methyl-2-chloropyridinium iodide
Mukaiyama's Reagent

Size Price ($) Quantity Availability
25g 36.77
100g 111.99
500g 472.80
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2-Chloro-1-methylpyridinium iodide, 97%

MDL
MFCD00011984
EINECS
238-288-7

Chemical Properties

Formula
C6H7ClIN
Formula Weight
255.49
Melting point
ca 200° dec.
Sensitivity
Moisture & Light Sensitive
Solubility
Soluble in Methanol (50 mg/ml). Insoluble in water.

Applications

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.

Notes

Store at 4°C. Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Incompatible with oxidizing agents.

Literature References

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:

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-P362-P312-P321-P405-P403+P233-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. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,6301
Beilstein
3572320
Harmonized Tariff Code
2933.39
TSCA
No

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