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125954

Sigma-Aldrich

Dichloroacetonitrile

98%

Synonym(s):

2,2-Dichloroacetonitrile, Dichloromethyl cyanide

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About This Item

Linear Formula:
Cl2CHCN
CAS Number:
3018-12-0
Molecular Weight:
109.94
Beilstein:
1739029
EC Number:
221-159-4
MDL number:
MFCD00040886
UNSPSC Code:
12352100
PubChem Substance ID:
24847689
NACRES:
NA.22

Quality Level

100

Assay

98%

form

liquid

refractive index

n20/D 1.44 (lit.)

bp

110-112 °C (lit.)

density

1.369 g/mL at 25 °C (lit.)

SMILES string

ClC(Cl)C#N

InChI

1S/C2HCl2N/c3-2(4)1-5/h2H

InChI key

STZZWJCGRKXEFF-UHFFFAOYSA-N

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Application

Dichloroacetonitrile can be used as a reactant to prepare:
  • Chiral α, α-dichloro-β-aminonitriles via Pd-catalyzed enantioselective Mannich-type reaction with imines.
  • α, α-dialkyl-substituted nitriles by an alkylation reaction with trialkylboranes in the presence of phenoxide base as a base.
  • Halogenated pyridines via copper-catalyzed reaction with methacrolein.
  • α,α-dichloro-β-hydroxy nitriles by condensation reaction with aldehydes and ketones in the presence of an alkoxide base.
  • Selenium heterocycle derivatives via Diels–Alder cyclization with selenoaldehydes.
  • Dichloroacetonitrile can also be used to develop an efficient method for the extraction and determination of common volatile halogenated disinfection by-products using the static headspace technique coupled with gas chromatography-mass spectrometry.

Biochem/physiol Actions

Dichloroacetonitrile is direct-acting mutagen and induces DNA strand breaks in cultured human lymphoblastic cells. It induces apoptosis or necrosis in murine macrophage cell line via reactive oxygen intermediates-mediated oxidative mechanisms of cellular damage.

Signal Word

Danger

Hazard Statements

H226 - H302 - H314

Hazard Classifications

Acute Tox. 4 Oral - Flam. Liq. 3 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

96.8 °F - closed cup

Flash Point(C)

36 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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255858

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Isabel Montesinos et al.
Journal of chromatography. A, 1310, 113-120 (2013-09-03)
A simple and efficient method has been developed for the extraction and determination of sixteen common volatile halogenated disinfection by-products (DBPs) using the static headspace (HS) technique coupled with gas chromatography-mass spectrometry (GC-MS). The DBPs determined included trihalomethanes (THMs), halonitromethanes
M K Smith et al.
Fundamental and applied toxicology : official journal of the Society of Toxicology, 12(4), 765-772 (1989-05-01)
Dichloroacetonitrile (DCAN), a by-product of drinking water disinfection formed by reaction of chlorine with background organic materials, was evaluated for its developmental effects in pregnant Long-Evans rats. Animals were dosed by oral intubation on Gestation Days 6-18 (plug = 0)
Dichloroacetonitrile
GL Bundy
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Speciation of common volatile halogenated disinfection by-products in tap water under different oxidising agents
Montesinos I and Gallego M
Journal of Chromatography A, 1310, 113-120 (2013)
M R Roby et al.
Environmental health perspectives, 69, 215-220 (1986-11-01)
The excretion and tissue distribution of [1-14C]dichloroacetonitrile and [2-14C]dichloroacetonitrile were studied in male Fischer 344 rats and male B6C3F1 mice. Three dose levels of dichloroacetonitrile (DCAN) (0.2, 2, or 15 mg/kg) were administered to rats and two dose levels of
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