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.
일반 설명
Clear liquid.
공기와 물의 반응
Burns slowly, emitting a thick black smoke, but will not flash . Water soluble.
반응 프로필
Dichloroacetonitrile is a halogenated nitrile. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents.
건강위험
ACUTE/CHRONIC HAZARDS: When heated to decomposition Dichloroacetonitrile emits toxic fumes of chlorine, cyanides and nitrogen oxides.
화재위험
Dichloroacetonitrile is probably combustible.
Purification Methods
Purify the nitrile by distillation or by gas chromatography. [Beilstein 2 IV 506.] FLAMMABLE.
