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Safety Information

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

Quality Level

200

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

280909-VAR:
280909-BULK:
280909-25G:4548174010747
280909-5G:4548174010754

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Certificates of Analysis (COA)

Lot/Batch Number
BCBQ4164V
BCCG8667
BCBF6311V
0001401130
BCBF6311

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J. Chem. Res. (M), 705-705 (2005)
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.
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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