| Identification | More | [Name]
2-Chloro-1-methylpyridinium iodide | [CAS]
14338-32-0 | [Synonyms]
2-CHLORO-1-METHYLPYRIDINIUM IODIDE
2-CHLORO-N-METHYLPYRIDINIUM IODIDE
CMPI
N-Methyl-2-chloropyridinium iodide~Mukaiyamas
N-Methyl-2-chloropyridiniumiodide
2-CHLORO-N-METHYLPYRIDINIUM IODIDE (CMPI)
Pyridinium, 2-chloro-1-methyl-, iodide
CMPI 2-CHLORO-1-METHYLPYRIDINIUM IODIDE
2-CHLORO-1-METHYLPYRIDINIUM IODIDE 97% | [EINECS(EC#)]
238-288-7 | [Molecular Formula]
C6H7ClIN | [MDL Number]
MFCD00011984 | [Molecular Weight]
255.48 | [MOL File]
14338-32-0.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow crystalline solid | [Melting point ]
200 °C (dec.) (lit.) | [density ]
1.7949 (estimate) | [storage temp. ]
Store at 0-5°C | [form ]
Crystalline Powder and/or Chunks | [color ]
Yellow | [Water Solubility ]
soluble | [Sensitive ]
Moisture & Light Sensitive | [Merck ]
6301 | [BRN ]
3572320 | [Exposure limits]
ACGIH: TWA 0.01 ppm | [InChI]
InChI=1S/C6H7ClN.HI/c1-8-5-3-2-4-6(8)7;/h2-5H,1H3;1H/q+1;/p-1 | [InChIKey]
ABFPKTQEQNICFT-UHFFFAOYSA-M | [SMILES]
C1(Cl)C=CC=C[N+]=1C.[I-] | [CAS DataBase Reference]
14338-32-0(CAS DataBase Reference) | [EPA Substance Registry System]
14338-32-0(EPA Substance) |
| Questions And Answer | Back Directory | [Synthesis]
In a dry reaction flask, 2-chloropyridine (1 mmol) was dissolved in hot acetone. Then, excess iodomethane was added to the reaction mixture with stirring. The resulting mixture was stirred at room temperature for three hours. After the reaction was complete, the reaction solution was directly evaporated, and the resulting solid precipitate was 2-Chloro-1-methylpyridinium iodide.  Figure: Synthetic route of 2-Chloro-1-methylpyridinium iodide |
| Hazard Information | Back Directory | [Chemical Properties]
yellow crystalline solid | [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.] |
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J & K SCIENTIFIC LTD.
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Alfa Aesar
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Energy Chemical
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