14338-32-0

Basic information

• Product Name: 2-Chloro-1-methylpyridinium iodide
• Synonyms: 2-Chloro-1-methylpyridinium iodide,97%;2-Chloro-1-methylpyr;2-chloro-1-Methylpyridin-1-iuM iodide;2-Chloro-1-MethylpyridiniuM iodide, 97% 25GR;2-CHLORO-1-METHYLPYRIDINIUM IODIDE FOR S;1-Methyl-2-chloropyridiniuM iodide;PyridiniuM, 2-chloro-1-Methyl-, iodide (8CI,9CI);2-Chloro-1-MethylpyridiniuM Iodide, 98.0%(T)
• CAS NO: 14338-32-0
• Molecular Formula: C₆H₇ClN*I
• Molecular Weight: 255.48
• EINECS: 238-288-7
• Product Categories: Coupling Reactions (Peptide Synthesis);Peptide Synthesis;Pyridinium Compounds;Reagents for Oligosaccharide Synthesis;Synthetic Organic Chemistry;C6Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyridines;Heterocyclic Compounds;Biochemistry;Condensation & Active Esterification
• Mol File: 14338-32-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 200 °C (dec.)(lit.)
• Boiling Point: 195.5°C at 760 mmHg
• Flash Point: 72.1°C
• Appearance: Yellow/Crystalline Powder and/or Chunks
• Density: 1.7949 (estimate)
• Vapor Pressure: 0.417mmHg at 25°C
• Refractive Index: 1.546
• Storage Temp.: Store at 0-5°C
• Water Solubility: soluble
• Sensitive: Moisture & Light Sensitive
• Merck: 14,6301
• BRN: 3572320
• CAS DataBase Reference: 2-Chloro-1-methylpyridinium iodide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-1-methylpyridinium iodide(14338-32-0)
• EPA Substance Registry System: 2-Chloro-1-methylpyridinium iodide(14338-32-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-24/25-36
• RIDADR: 1759
• WGK Germany: 3
• F: 8-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 14338-32-0(Hazardous Substances Data)

Usage

Description

2-Chloro-1-methylpyridinium iodide, also known as Mukaiyama reagent, is a yellow crystalline solid commonly used in organic synthesis for the activation of the hydroxy group of alcohols and carboxylic acids. It is a versatile reagent that can be used to synthesize a variety of derivatives, including esters, lactones, amides, lactams, and ketenes.

Uses

Used in Organic Synthesis:
2-Chloro-1-methylpyridinium iodide is used as a condensation reagent for the synthesis of esters and ketenes, and for the kinetic resolution of carboxylic acids and alcohols. It is particularly useful in the formation of carboxylate esters from acids and alcohols, carboxamides from acids and amines, lactones from -hydroxy acids, and carbodiimides from N,N-disubstituted thioureas.
Used in Peptide Synthesis:
In the pharmaceutical industry, 2-Chloro-1-methylpyridinium iodide is used as an efficient coupling reagent in the synthesis of peptides. It is favored due to its low toxicity, simple reaction conditions, and being less expensive than other coupling reagents such as EDC (1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide).

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.]

InChI:InChI=1/C6H8ClN/c1-8-5-3-2-4-6(8)7/h2-6H,1H3

Upstream product

• 109-09-1 2-chloropyridine 
• 74-88-4 methyl iodide 

Downstream Products

• 250609-75-7 2-(pyrid-3-ylcarbonyl)oxy-4-[4-(2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2,6-dimethyl-phenoxysulfonyl]-benzoic acid tert-butyl ester 
• 250609-80-4 2-(pyrid-4-ylcarbonyl)oxy-4-[4-(9-bromo-2,3-dimethyl-naphtho[2, 3-b]thiophen-4-yl)-2,6-dimethyl-phenoxysulfonyl]-benzoic acid tert-butyl ester 
• 169458-43-9 (2R)-4-benzyl-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)piperazine 
• 169187-06-8 (RS)-3-benzyloxy-2-benzyloxy-methylpropanoic acid 
• 169460-24-6 (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(3,4-dimethylbenzyl)-4-[(N-methyl-N-benzylcarbamoyl)methyl]piperazine hydrochloride 
• 56-40-6 glycine 
• 104356-44-7 ethyl [2-[[2-[4[ 2-(4-fluorophenyl)-1,3-dioxolan-2-yl]-1-piperidinyl]ethyl]aminocarbonyl]-4-(phenylmethoxy)phenyl]carbamate 
• 101507-69-1 N-(p-chloro-alpha-ethyl-alpha-methylbenzyl)-1,2,3,4-tetrahydro-alpha-naphthoamide 
• 83200-08-2 2-[3-(N,N-diethylamino)-2-hydroxypropylaminocarbonyl]-3-methoxy-1-phenylindole 

Relevant articles and documents

Excellent correlation between substituent constants and pyridinium N-methyl chemical shifts

Substituents on the pyridinium ring of N-methylpyridinium derivatives, especially those on the 2- or 4-position, have a large effect on the 1H and 13C NMR chemical shifts of the N-methyl group. Reasonable correlations between the chemical shift changes and the resonance substituent constants are observed. The dual substituent parameter approach provides an excellent correlation when a combination of polar and resonance substituent constants is employed.

13-substituted milbemycin derivatives, their preparation and their use against insects and other pests

Compounds of formula (I) and salts thereof: Wherein R1 represents methyl, ethyl, isopropyl or s-butyl; and R2 represents hydrogen or alkyl. R3 represents hydrogen, optionally substituted alkanoyl, optionally substituted alkenoyl, optionally substituted alkynoyl, alkylsulfonyl, or alkoxycarbonyl, or R2 and R3 together with the nitrogen atom to which they are attached form a saturated, optionally substituted 4- to 6-membered heterocyclic ring group. The moiety -a- together with the carbon atom to which it is attached forms a 3- to 6-membered cycloalkyl group. These compounds have anthelmintic, acaricidal and insecticidal activity.

Electronic Effects on the Menschutkin Reaction. A Complete Kinetic and Thermodynamic Dissection of Alkyl Transfer to 3- and 4-Substituted Pyridines

The relationship between kinetic and thermodynamic parameters is explored for quaternization of a series of pyridines (mostly 3- and 4-substituted) with several methylating and ethylating reagents in several solvents.The reaction with methyl iodide in acetonitrile is reversible at temperatures in the neighborhood of 100 deg C so that the effect of substituents on free energy, enthalpy, and entropy for activation of the forward and reverse reactions and for the overall quaternization can be determined.A variety of experimental techniques was used to obtain rates over a range of 1013 and to determine enthalpies and entropies of reaction.The results are self-consistent and agree generally with isolated published values for similar systems.The relationship between thermodynamic and activation parameters is examined, and a gross disparity is found between free energy and enthalpy behavior compared with that of the entropies.A consistent picture of the quaternization reaction emerges, based on many studies using a variety of mechanistic probes.The transition state is "early" as far as bond formation to the base in concerned but "late" in terms of bond rupture between the transferring alkyl group and the leaving group with solvent reorganization nearly complete.Quaternization of the 3- and 4-substituted pyridines does not follow the reactivity-selectivity principle, but that of 2-substituted pyridines does.The current practice of assigning detailed bimolecular structures to transition states for substitution, addition, or elimination reactions by application of the Hammond postulate is criticized in view of its inability to handle the dominating role of solvation dynamics and because of the considerable difference in potential energy content (and therefore structure) between the transition states and the reactants or products.