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Safety Information

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

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.

PDSCL

Deleterious substance

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

125954-100G:4548173104249
125954-25G:4548173104256
125954-VAR:
125954-BULK:
125954-500G:
125954-1KG:

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Certificates of Analysis (COA)

Lot/Batch Number
STBG2732V
STBG0931V
STBG0930V
STBF2821V
10209PD

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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)
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)
M Clemens et al.
Zentralblatt fur Hygiene und Umweltmedizin = International journal of hygiene and environmental medicine, 193(1), 91-98 (1992-06-01)
18 different swimming pool waters in the Bonn-Rhein-Sieg area were analysed for trihalogenmethanes, halogenated acetic acids, 2,2-dichloropropionic acid, dihalogenacetonitriles and chloral hydrate. Most substances mentioned above were determined in almost every sample reaching total concentrations up to 538 micrograms/l. Considering
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