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198005

Sigma-Aldrich

2-Chloro-1-methylpyridinium iodide

97%

Sinonimo/i:

Mukaiyama reagent

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About This Item

Formula empirica (notazione di Hill):
C6H7ClIN
Numero CAS:
14338-32-0
Peso molecolare:
255.48
Beilstein:
3572320
Numero CE:
238-288-7
Numero MDL:
MFCD00011984
Codice UNSPSC:
12352100
ID PubChem:
24851856
NACRES:
NA.22

Saggio

97%

Punto di fusione

200 °C (dec.) (lit.)

Stringa SMILE

[I-].C[n+]1ccccc1Cl

InChI

1S/C6H7ClN.HI/c1-8-5-3-2-4-6(8)7;/h2-5H,1H3;1H/q+1;/p-1
ABFPKTQEQNICFT-UHFFFAOYSA-M

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Categorie correlate

Descrizione generale

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.

Applicazioni

2-Chloro-1-methylpyridinium iodide (CMPI) can be used as:
  • A dehydrating agent for the conversion of various aldoximes to nitriles, and alcohols into alkyl thiocyanates.
  • A cross-linking agent to fabricate biodegradable cross-linked hyaluronic acid film and gelatin membranes for biomedical applications.
  • A condensing agent to synthesize various β-lactams from β-amino acids.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

Certificati d'analisi (COA)

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Sigma-Aldrich

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Molecular cell, 70(3), 422-434 (2018-04-24)
PRC2 is a therapeutic target for several types of cancers currently undergoing clinical trials. Its activity is regulated by a positive feedback loop whereby its terminal enzymatic product, H3K27me3, is specifically recognized and bound by an aromatic cage present in
Efficient Transformation of Aldoximes to Nitriles Using 2-Chloro-1-methylpyridinium Iodide Under Mild Conditions
Lee Kieseung, et al.
Synthetic Communications, 34(10), 1775-1782 (2004)
W Keese et al.
Biological chemistry Hoppe-Seyler, 366(12), 1093-1095 (1985-12-01)
2-Chloro-1-methylpyridinium iodide is a coupling reagent for peptide synthesis. By its use different peptides were synthesized with protected di- and trifunctional amino acids. While urethan-protected amino acids react free of racemization, the fragment condensation needs N-Hydroxysuccinimide, as shown by the
Tetrahedron Asymmetry, 3, 1455-1455 (1992)
A novel cell support membrane for skin tissue engineering: Gelatin film cross-linked with 2-chloro-1-methylpyridinium iodide
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