125954

Dichloroacetonitrile

98%

• Synonym(s): 2,2-Dichloroacetonitrile, Dichloromethyl cyanide
• Linear Formula: Cl₂CHCN
• CAS Number: 3018-12-0
• Molecular Weight: 109.94
• Beilstein/REAXYS Number: 1739029
• EC Number: 221-159-4
• MDL number: MFCD00040886
• UNSPSC Code: 12352100
• PubChem Substance ID: 24847689
• NACRES: NA.22

Properties

• 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

Description

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.

Safety Information

• pictograms: GHS02,GHS05,GHS07
• signalword: Danger
• hcodes: H226,H302,H314
• pcodes: P210 - P233 - P280 - P301 + P312 - P303 + P361 + P353 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Flam. Liq. 3 - Skin Corr. 1B
• Storage Class: 3 - Flammable liquids
• wgk_germany: WGK 3
• flash_point_f: 96.8 °F - closed cup
• flash_point_c: 36 °C - closed cup
• ppe: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter