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125954

Sigma-Aldrich

Dichloroacetonitrile

98%

Sinônimo(s):

2,2-Dichloroacetonitrile, Dichloromethyl cyanide

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About This Item

Fórmula linear:
Cl2CHCN
Número CAS:
Peso molecular:
109.94
Beilstein:
1739029
Número CE:
Número MDL:
Código UNSPSC:
12352100
ID de substância PubChem:
NACRES:
NA.22

Nível de qualidade

Ensaio

98%

Formulário

liquid

índice de refração

n20/D 1.44 (lit.)

p.e.

110-112 °C (lit.)

densidade

1.369 g/mL at 25 °C (lit.)

cadeia de caracteres SMILES

ClC(Cl)C#N

InChI

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

chave InChI

STZZWJCGRKXEFF-UHFFFAOYSA-N

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Aplicação

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.

Ações bioquímicas/fisiológicas

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.

Palavra indicadora

Danger

Frases de perigo

Classificações de perigo

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

Código de classe de armazenamento

3 - Flammable liquids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

96.8 °F - closed cup

Ponto de fulgor (°C)

36 °C - closed cup

Equipamento de proteção individual

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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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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