N-(Chloromethylidene)-N-methylmethanaminium chloride

Base Information

• Chemical Name: N-(Chloromethylidene)-N-methylmethanaminium chloride
• CAS No.: 3724-43-4
• Deprecated CAS: 1487-66-7,92458-33-8,1512534-40-5,92458-33-8
• Molecular Formula: C₃H₇ClN*Cl
• Molecular Weight: 128.001
• Hs Code.: 29252000
• European Community (EC) Number: 425-970-6,609-368-2
• UNII: Q39V7G8776
• DSSTox Substance ID: DTXSID7044423
• Wikipedia: Vilsmeier_reagent
• Wikidata: Q27894258
• ChEMBL ID: CHEMBL3183181
• Mol file: 3724-43-4.mol

Synonyms:3724-43-4;(Chloromethylene)dimethyliminium chloride;arnold's reagent;Vilsmeier reagent;N-(Chloromethylidene)-N-methylmethanaminium chloride;(CHLOROMETHYLENE)DIMETHYLAMMONIUM CHLORIDE;Methanaminium, N-(chloromethylene)-N-methyl-, chloride;MFCD00011868;N-(chloromethylene)-N-methylmethanaminium chloride;chloromethylene dimethylammonium chloride;chloromethylidene(dimethyl)azanium;chloride;DTXSID7044423;Dimethylchloromethyliminium chloride;N-Chloromethylene-N,N-dimethyl ammonium chloride;chloro-n,n-dimethylformiminium chloride;Chloromethylenedimethylammonium chloride;Q39V7G8776;N,N-Dimethylchloromethyliminium chloride;Chloromethylene(dimethyl)ammonium chloride;EC 425-970-6;EC 609-368-2;[chloromethylene]dimethylammonium chloride;(Chloromethylene)dimethylammonium chloride (6CI,7CI);Ammonium, (chloromethylene)dimethyl-, chloride (8CI);Viismeier reagent;Dimethylchloroformiminium chloride;(Chlormethylene)dimethylammonium chloride;C3H7ClN.Cl;SCHEMBL280;C3-H7-Cl-N.Cl;CHEMBL3183181;DTXCID5024423;UNII-Q39V7G8776;Tox21_302163;GEO-04109;AKOS017345161;chlormethylene dimethylammonium chloride;FS-4034;(chloromethylene)dimethylammoniumchloride;chloromethylene-dimethylammonium chloride;chloromethylene dimethyl-ammonium chloride;N,N,-Dimethylchloromethyliminium chloride;NCGC00255861-01;(Chloromethlene)dimethyl ammonium chloride;(chloromethylidene)dimethylazanium chloride;(chloro-methylene)dimethylammonium chloride;(chloromethylene)-dimethylammonium chloride;(Chloromethylene)-dimethylammonium-chloride;(Chloromethylene)dimethyl ammonium chloride;CAS-3724-43-4;(chloro-methylen)-dimethyl-ammonium-chloride;FT-0604890;D89427;Q27894258;Methanaminium, N-(chloromethylene)-N-methyl-, chloride (1:1)

Chemical Property of N-(Chloromethylidene)-N-methylmethanaminium chloride

Chemical Property:

• Appearance/Colour: White to off-white powder
• Melting Point: 132 ºC (dec.)
• Refractive Index: 1.4525 (estimate)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 3.01000
• Density: g/cm³
• LogP: -2.47040
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: reacts
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 126.9955546
• Heavy Atom Count: 6
• Complexity: 44.9

Purity/Quality:

99.9% ^*data from raw suppliers

(Chloromethylene)dimethylammoniumChloride ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 61-20/21/22-34-22-14-35
• Safety Statements: 53-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[N+](=CCl)C.[Cl-]
• Uses: (Chloromethylene)dimethylammonium chloride is used in the synthesis of beta-lactams, n-vinyl substituted indoles and fused 2-pyridone rings and 2-azetidinones. It is used as a formylating agent and used in the preparation of anti-poxvirus agents. It is used in Staudinger reaction and Hundsdiecker-barton iododecarboxylation reaction. It is widely used for studying organic photosensitizers, which finds application in dye-sensitized solar cells. Reagent or Reactant for the synthesis of: β-Lactams vis the Staudinger reactionN-vinyl substituted indoles via cross coupling of NH-indoles with vinyl bromidesMulti ring-fused 2-pyridone-based fluorescent scaffoldester prodrugs as anti-poxvirus agentsTrimethine cyanine dyes for sensing G-quadruplex formationPhospha-isosteres via Hundsdiecker-Barton iododecacarboxylation2-Azetidinones via [2+2]-cycloadditionUsed for studying organic photosensitizers for application in dye-sensitized solar cells

Technology Process of N-(Chloromethylidene)-N-methylmethanaminium chloride

There total 13 articles about N-(Chloromethylidene)-N-methylmethanaminium chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.7%

N,N-dimethyl-formamide (68-12-2,33513-42-7) + Phthaloyl dichloride (88-95-9) → phthalic anhydride (85-44-9) + Vilsmeier reagent (3724-43-4,149409-22-3)

Guidance literature:

In toluene; for 3h; Heating;

Reference yield: 69.0%

chloroform (67-66-3,8013-54-5) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → Vilsmeier reagent (3724-43-4,149409-22-3)

Guidance literature:

chloroform; N,N-dimethyl-formamide; With oxygen; at 30 ℃; for 3h; Irradiation;

at 50 ℃; for 2h;

DOI:10.1021/acs.joc.1c00334

Reference yield:

oxalyl dichloride (79-37-8) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → Vilsmeier reagent (3724-43-4,149409-22-3)

Guidance literature:

With diethyl ether;

DOI:10.1002/hlca.19590420526

upstream raw materials:

phosgene

N,N-dimethyl-formamide

oxalyl dichloride

2,3-dichloro-5-dichloromethylene-2-cyclopentene-1,4-dione

Downstream raw materials:

4-dimethylamino-benzaldehyde

cholesteryl formate

benzenesulfonyl chloride

(β,β'-dichloro-isopropyl)-dimethyl-amine

Refernces

• 1、 -. "acyl triazole derivative and its manufacturing method". Paragraph 0053. . Retrieved 2017/04/03.
• 2、 Lechuga-Eduardo, Harim,Olivo, Horacio F.,Romero-Ortega, Moises. "Syntheses of 4-substituted 2-(trichloromethyl)quinazolines under mild conditions by benzyne [4+2] cycloaddition". . p. 5910 - 5913. Retrieved 2015/03/30.