CAS 14338-32-0 2-Chloro-1-methylpyridinium iodide (HCID 167069)

Names & identifiers

Preferred name: 2-Chloro-1-methylpyridinium iodide
IUPAC: 2-chloro-1-methylpyridin-1-ium iodide
English name: 2-Chloro-1-methylpyridinium iodide
Molecular formula: C6H7ClIN
Molecular weight: 255.48

Names & synonyms

2-Chloro-1-methylpyridinium iodide14338-32-0Mukaiyama ReagentN-methyl-2-chloropyridinium iodidePyridinium, 2-chloro-1-methyl-, iodide1-methyl-2-chloropyridinium iodide2-Chloro-N-methylpyridinium iodide2-chloropyridine methiodideUNII-RLQ88NYZ68EINECS 238-288-7RLQ88NYZ68NSC-200739

Show more names

CMPI2-chloro-1-Methylpyridin-1-iuM iodide2-Chloro-1-methylpyridine iodide2-Chloro-1-methylpyridinium iodide,97%2-CHLORO-1-METHYLPYRIDINIUM IODIDE FOR S2-Chloro-1-methylpyrVonoprazan Impurity 139Epinastine Impurity 26 Iodide

2-Chloro-1-methylpyridinium iodide (1:1)MUKAIYAMA REAGENT [MI]DTXSID6022260NSC 200739RefChem:861302Chloropyridine methiodide1Methyl2chloropyridinium iodideDTXCID402260

Database identifiers

CAS: 14338-32-0
PubChem CID: 167069
DTXSID: DTXSID6022260
UNII: RLQ88NYZ68
EC Number: 238-288-7

Properties

Computed structural properties

Topological polar surface area: 3.9 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 1
Rotatable bonds: 0
Heavy atoms: 9
Formal charge: 0
Complexity: 74.9

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Pyridines

Physical DescriptionNearly colorless or pale yellow solid; [Merck Index] Yellow hygroscopic powder; [Acros Organics MSDS]

Physicochemical properties

Melting point: 200 °C · 200 °C (dec.) (lit.)
Density: 1.7949 · 1.7949 (estimate)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
form: Crystalline Powder and/or Chunks
color: Yellow
Water Solubility: soluble
Sensitive: Moisture & Light Sensitive
Merck: 14 · 14,6301
BRN: 3572320 · 3572320
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 · 14338-32-0(CAS DataBase Reference)
FDA UNII: 88 NYZ68 · RLQ88NYZ68
EPA Substance Registry System: 2 · 2-Chloro-1-methylpyridinium iodide (14338-32-0)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 335 · H335-H315-H319
Precautionary statements: 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-24/25-36
RIDADR: 1759 · 1759
WGK Germany: 3 · 3
F: 8 · 8-21
HazardClass: 8 · 8
PackingGroup: III
HS Code: 29333999 · 29333999
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 48 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information2-Chloro-1-methylpyridinium iodide: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryAn irritant; [Acros Organics MSDS] See 3-Chloropyridine. See Iodine for the TLV of Iodides.

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety & protection

Threshold Limit Values (TLV)0.01 [ppm], inhalable fraction and vapor, (iodides)

Safety data

F: 8-21
PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
ridadr: 1759
hs_code: 29333999
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-24/25-36
hazard_class: 8
Storage Class: 11 - Combustible Solids
packing_group: III
Hazard statements: H335-H315-H319
Precautionary statements: P261-P280a-P304+P340-P305+P351+P338-P405-P501a-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Chemistry & industry

Uses & manufacturing

UsesUsed as a condensation reagent in organic synthesis; [Merck Index]

Applications · 3 items

Uses2-Chloro-1-methylpyridinium iodide is a reagent in a wide variety of dehydrative coupling reactions. It is also used to form carboxylate esters from acids and alcohols, carboxamides from acids and amines, lactones from -hydroxy acids and carbodiimides from N,N-disubstituted thioureas.

UsesCondensation reagent for the synthesis of esters and ketenes, and for the kinetic resolution of carboxylic acids and alcohols.

General Description2-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.