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280909

Sigma-Aldrich

(Chloromethylene)dimethyliminium chloride

95%

Synonym(s):

(Chlormethylene)dimethylammonium chloride, Arnold′s reagent, Dimethylchloroformiminium chloride, Vilsmeier reagent

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About This Item

Linear Formula:
ClCH=N(CH3)2Cl
CAS Number:
3724-43-4
Molecular Weight:
128.00
Beilstein:
3566322
EC Number:
425-970-6
MDL number:
MFCD00011868
UNSPSC Code:
12352101
PubChem Substance ID:
24856957
NACRES:
NA.22

Assay

95%

form

solid

reaction suitability

reaction type: C-C Bond Formation

impurities

<5% DMF

mp

132 °C (dec.) (lit.)

functional group

amine
chloro

storage temp.

2-8°C

SMILES string

[Cl-].C\[N+](C)=C\Cl

InChI

1S/C3H7ClN.ClH/c1-5(2)3-4;/h3H,1-2H3;1H/q+1;/p-1

InChI key

QQVDYSUDFZZPSU-UHFFFAOYSA-M

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Application

Reagent or Reactant for the synthesis of:
  • β-Lactams vis the Staudinger reaction
  • N-vinyl substituted indoles via cross coupling of NH-indoles with vinyl bromides
  • Multi ring-fused 2-pyridone-based fluorescent scaffold
  • ester prodrugs as anti-poxvirus agents
  • Trimethine cyanine dyes for sensing G-quadruplex formation
  • Phospha-isosteres via Hundsdiecker-Barton iododecacarboxylation
  • 2-Azetidinones via [2+2]-cycloaddition

Used for studying organic photosensitizers for application in dye-sensitized solar cells
Reagent used to prepare ß-lactams from ß-amino acids via carboxyl activation and cyclodehydration. Also used to convert α-aminonitriles into 4-chloroimidazoles.

Signal Word

Danger

Hazard Statements

H302,H314,H360D

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Repr. 1B - Skin Corr. 1A

Supplementary Hazards

EUH014

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK1025
BCCK4743
BCBQ4164V
BCCG8667
BCCH6242

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Tetrahedron Letters, 47, 5451-5451 (2006)
Azhar Abbas et al.
Bioorganic chemistry, 82, 163-177 (2018-10-16)
Benzohydrazide derivatives 1-43 were synthesized via "one-pot" reaction and structural characterization of these synthetic derivatives was carried out by different spectroscopic techniques such as 1H NMR and EI-MS. The synthetic molecules were evaluated for their in vitro urease inhibitory activity.
J. Chem. Res. (M), 705-705 (2005)
Martin Mlateček et al.
Dalton transactions (Cambridge, England : 2003), 44(46), 20242-20253 (2015-11-06)
The reaction of PhBCl2 with 1H-1,2,4-λ(3)-diazaphosphole in the presence of NEt3 gives a new scorpionate ligand, phenyl-tris(1,2,4-diazaphospholyl)borate (PhTdap). The coordination behaviour of this ligand toward transition and non-transition metals has been comprehensively studied. In the thallium(I) complex, Tl(PhTdap), κ(2)-N,N bonding

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