CAS 14338-32-0|2-chloro-1-methylpyridin-1-ium iodide|2-chloro-1-methylpyridin-1-ium iodide|2-Chloro-1-methylpyridinium iodide|2-chloro-1-methylpyridin-1-ium iodide|2-Chloro-1-methylpyridinium iodide...

General Information

Structure

Molecular Formula

C₆H₇ClIN

Molecular Mass

255.48395

Exact Mass

254.93117491

Charge

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

Canonic Smiles

Clc1cccc[n+]1C.[I-]

Isomeric Smiles

c1(cccc[n+]1C)Cl.[I-]

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

-2.8687396

LogD (pH = 7.4)

-2.8687396

Log P

-2.8687396

Molar Refractivity

34.8624

Polarizability

13.440737

Polar Surface Area

3.88

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC name

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

IUPAC Traditional name

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

Synonyms

2-Chloro-1-methylpyridinium iodide2-chloro-1-methylpyridin-1-ium iodide2-Chloro-1-methylpyridinium iodide2-氯-1-甲基吡啶碘化物Mukaiyama's Reagent2-氯-1-甲基碘化吡啶鎓N-Methyl-2-chloropyridinium iodide

Names and Identifiers

Registration numbers

MDL Number

CAS Number

PubChem SID

Beilstein Number

EC Number

PubChem CID

Merck Index

Registration numbers

Properties

Physical Property

200 °C (dec.)(lit.)

ca 200°C dec.

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

02150626

Purity: ~97%
Used to form carboxylate esters from acids and alcohols¹ , carboxamides from acids and amines² , lactones from ω-hydroxy acids³ , and carbodiimides from N,N'-disubstituted thioureas⁴ .

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

25270

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

Molecule Details

References

PubChem Literature

From Data Sources

• Chem. Lett. , 1045 (1975).

• Chem. Lett. , 575 (1977).

• Chem. Lett. , 49 (1976).

• Chem. Lett. , 1159 (1975).

• 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).

References

Bioactivity

PubChem BioAssay

Bioactivity