2-chloro-1-methylpyridin-1-ium iodide

• ChemBase ID: 69555
• Molecular Formular: C6H7ClIN
• Molecular Mass: 255.48395
• Monoisotopic Mass: 254.93117491
• SMILES: c1(cccc[n+]1C)Cl.[I-]
• Canonical SMILES: Clc1cccc[n+]1C.[I-]
• 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

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 14338-32-0
• EC Number: 238-288-7
• MDL Number: MFCD00011984
• Beilstein Number: 3572320
• Merck Index: 146301
• PubChem SID: 24851856; 162035281
• PubChem CID: 167069

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): -2.8687396
• LogD (pH = 7.4): -2.8687396
• Log P: -2.8687396
• Molar Refractivity: 34.8624 cm^3
• Polarizability: 13.440737 Å^3
• Polar Surface Area: 3.88 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 200 °C (dec.)(lit.); ca 200°C dec.

Safety Information

• Storage Condition: 2-8°C, Desiccate
• Storage Warning: IRRITANT; Moisture & Light Sensitive
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 36/37/38; R:22
• Safety Statements: 26; 26-37; S:36/37/39
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ~97%; ≥97.0% (AT); 95+%; 97%
• Grade: purum
• Salt Data: I-
• Empirical Formula (Hill Notation): C6H7ClIN

DETAILS

MP Biomedicals - 02150626

Purity: ~97%
Used to form carboxylate esters from acids and alcohols^1 , carboxamides from acids and amines^2 , lactones from ω-hydroxy acids^3 , and carbodiimides from N,N'-disubstituted thioureas^4 .

MP Biomedicals - 05221636

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 198005

Packaging
10, 25, 100 g in glass bottle
Application
Reagent for the kinetic resolution of alcohols and amino acids.1

Sigma Aldrich - 25270

Other Notes
Efficient coupling reagent for the preparation of various derivatives of acids1,2,3,4,5,6,7,8,9

REFERENCES

• Chem. Lett. , 1045 (1975).
• Chem. Lett. , 1159 (1975).
• Chem. Lett. , 49 (1976).
• Chem. Lett. , 575 (1977).
• 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).