CAS 33842-02-3 Dichloromethylidene(dimethyl)azanium (HCID 419147)

Overview

See also: Phosgeniminium chloride (annotation moved to).

Names & identifiers

Preferred name: Dichloromethylidene(dimethyl)azanium
IUPAC: dichloromethylidene(dimethyl)azanium
English name: (Dichloromethylene)dimethylammonium chloride
Molecular formula: C3H6Cl2N.Cl
Molecular weight: 162.45

Names & synonyms

UNII-LCD42T0Q0ZLCD42T0Q0ZEINECS 251-695-4Dichloromethylene-dimethyliminium chlorideNSC 111186dichloromethylidene(dimethyl)azaniumNSC-111186(Dichloromethylene)dimethylammonium chloride; Phosgeniminium chloride; Vilsmeier reagentMethanaminium, N-(dichloromethylene)-N-methyl-, chlorideVIEHE'S SALT [MI]SCHEMBL5322556DIMETHYLPHOSGENIMINIUM CHLORIDE

Show more names

N-(dichloroMethylene)-N-MethylMethanaMiniuM chlorideVIEHE''SSALTN,N-DimethylpPHOSGENIMINIUM CHLORIDEPHOSGENE IMINIUM CHLORIDEPhosgene iminium chloride,98%PHOSGENE IMINIUM CHLORIDE, TECH.n,n-dimethylphosgeniminium chloridePhosgene iMiniuM chloride, 98% 25GR

(DICHLOROMETHYLENE)DIMETHYLIMINIUM CHLORIDEQ27282916AMMONIUM, (DICHLOROMETHYLENE)DIMETHYL-, CHLORIDEMETHANAMINIUM, DICHLORODIMETHYL-, CHLORIDE (1:1)

Database identifiers

CAS: 33842-02-3
PubChem CID: 419147
UNII: LCD42T0Q0Z
Nikkaji: J82.017B

Properties

Computed structural properties

XLogP: 1.9
Topological polar surface area: 3 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 0
Rotatable bonds: 0
Heavy atoms: 6
Formal charge: 1
Complexity: 68.9

Physicochemical properties

Melting point: 183 · 183-187 °C (dec.) (lit.)
Boiling point: 267.81 °C · 267.81°C (rough estimate)
Density: 1.6902 · 1.6902 (rough estimate)
refractive index: 1.63 · 1.6300 (estimate)
storage temp.: 2 · 2-8°C
solubility: slightly sol. in Chloroform
form: Crystalline Powder
color: Light yellow
Water Solubility: hydrolysis
Sensitive: Moisture Sensitive
Merck: 14 · 14,9977
BRN: 4157987 · 4157987
InChI: 1S/C3H6Cl2N.ClH/c1-6(2)3(4)5;/h1-2H3;1H/q+1;/p-1
InChIKey: NRNFKRFWZQQDMD-UHFFFAOYSA-M
SMILES: [Cl-].C\[N+](C)=C(\Cl)Cl
CAS DataBase Reference: 33842 · 33842-02-3(CAS DataBase Reference)
FDA UNII: 42 T0Q0Z · LCD42T0Q0Z
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 5 · GHS05,GHS07
Signal word: Danger
Hazard statements: 290 · H290-H314-H335-H318
Precautionary statements: 261 · P261-P280-P305+P351+P338-P310-P234-P260-P264-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P390-P405-P406-P501-P260h-P301+P330+P331-P303+P361+P353-P501a
target organs: Respiratory system
PPE: 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes: C
Risk Statements: 14 · 14-34-37-29-22
Safety Statements: 26 · 26-36/37/39-45-8
RIDADR: 3261 · UN 3261 8/PG 3
WGK Germany: 3 · 3
F: 3 · 3-10-21
HazardClass: 8 · 8
PackingGroup: III
HS Code: 29252900 · 29252900
Storage Class: 8 A · 8A - Combustible corrosive hazardous materials
Hazard Classifications: 1 BSTOT · Skin Corr. 1BSTOT SE 3

Safety & regulation

Safety data

F: 3-10-21
PPE: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk: 3
ridadr: UN 3261 8/PG 3
hs_code: 29252900
risk_code: 14-34-37-29-22
Signal word: Danger
Symbol(GHS): GHS05,GHS07
hazard_code: C
safety_code: 26-36/37/39-45-8
hazard_class: 8
Storage Class: 8A - Combustible corrosive hazardous materials
packing_group: III
target organs: Respiratory system
Hazard statements: H290-H314-H335-H318
Hazard Classifications: Skin Corr. 1BSTOT SE 3
Precautionary statements: P261-P280-P305+P351+P338-P310-P234-P260-P264-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P390-P405-P406-P501-P260h-P301+P330+P331-P303+P361+P353-P501a

Chemistry & industry

Applications · 4 items

UsesDichloromethylene-dimethyliminium Chloride is a useful chemical reagent. It has been used in the synthesis of 12-deoxychlorovulone II analogs via chloride nucleophilic substitution reaction catalyzed by Viehe''s salt.

UsesDichloromethylene-dimethyliminium chloride was used as reagent in the synthesis of selenourea and (R)-2-(2-chloroethyl)pyrrolidine-1-carboxylic acid ethyl ester. It was used for introducing amide chloride group into activated substrates.

UsesChlorinating agent; introduces amide chloride groups into activated substrates. Building block in organic synthesis.

General DescriptionDichloromethylene-dimethyliminium chloride (Vilsmeier reagent) reacts with o-acetaminophenols under Meth-Cohn conditions to yield 2-formylpyrido[2,1-b]benzoxazoles.