3018-12-0

Basic information

• Product Name: Dichloroacetonitrile
• Synonyms: 2,2-Dichloroethanenitrile;Dichloroacetonitrile 1g [3018-12-0];Dichloroacetonitrile, Standard for GC,>=99.5%(GC);25kgs kfaft paper bag;DICHLOROACETONITRILE;1,1-Dichlorocarbonitrile;Acetnitrile,dichloro-;dichloro-acetonitril
• CAS NO: 3018-12-0
• Molecular Formula: C₂HCl₂N
• Molecular Weight: 109.94
• EINECS: 221-159-4
• Product Categories: C1 to C5;Cyanides/Nitriles;Nitrogen Compounds;Alpha Sort;D;DAlphabetic;DIA - DIC;Volatiles/ Semivolatiles;Chemical Class;ChloroVolatiles/ Semivolatiles;DIA - DICAnalytical Standards;Halogenated;Nitriles;Agrochemical;Pyridines ,Heterocyclic Acids;Pharmaceutical Intermediates
• Mol File: 3018-12-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 110-112 °C(lit.)
• Flash Point: 96 °F
• Appearance: colourless liquid
• Density: 1.369 g/mL at 25 °C(lit.)
• Vapor Pressure: 21.7mmHg at 25°C
• Refractive Index: n20/D 1.44(lit.)
• Storage Temp.: 0-6°C
• Solubility: soluble in Methanol
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• BRN: 1739029
• CAS DataBase Reference: Dichloroacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: Dichloroacetonitrile(3018-12-0)
• EPA Substance Registry System: Dichloroacetonitrile(3018-12-0)

Safety Data

• Hazard Codes: C
• Statements: 10-22-34
• Safety Statements: 26-36/37/39-45-25-16
• RIDADR: UN 2920 8/PG 2
• WGK Germany: 3
• RTECS: AL8465000
• F: 9-19
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 3018-12-0(Hazardous Substances Data)

Usage

Description

Dichloroacetonitrile is a clear, colourless liquid with versatile chemical properties. It is a valuable compound in the field of organic synthesis due to its ability to participate in various chemical reactions, making it a key component in the production of a range of chemical products.

Uses

Used in Pharmaceutical Industry:
Dichloroacetonitrile is used as a reactant for the synthesis of Chiral α, α-dichloro-β-aminonitriles through Pd-catalyzed enantioselective Mannich-type reactions with imines. These chiral compounds are essential in the development of pharmaceuticals, as they can exhibit different biological activities and selectivity.
Used in Chemical Synthesis:
In the chemical synthesis industry, Dichloroacetonitrile is used as a reactant to produce α, α-dialkyl-substituted nitriles by alkylation reactions with trialkylboranes in the presence of a phenoxide base. This application is crucial for the creation of various organic compounds with diverse applications.
Used in Agrochemical Industry:
Dichloroacetonitrile is utilized in the synthesis of halogenated pyridines via copper-catalyzed reactions with methacrolein. These halogenated pyridines are important intermediates in the development of agrochemicals, such as pesticides and herbicides.
Used in Material Science:
Dichloroacetonitrile is used in the preparation of α,α-dichloro-β-hydroxy nitriles by condensation reactions with aldehydes and ketones in the presence of an alkoxide base. These compounds can be used as building blocks for the development of new materials with specific properties.
Used in Environmental Analysis:
Dichloroacetonitrile can be employed in the development of efficient methods for the extraction and determination of common volatile halogenated disinfection by-products using the static headspace technique coupled with gas chromatography-mass spectrometry. This application is vital for monitoring and controlling water quality, ensuring public health and safety.
Used in Synthesis of Selenium Heterocycles:
In the field of organoselenium chemistry, Dichloroacetonitrile is used to synthesize selenium heterocycle derivatives via Diels–Alder cyclization with selenoaldehydes. These selenium-containing compounds have potential applications in various areas, including pharmaceuticals, materials science, and agrochemicals.

Air & Water Reactions

Burns slowly, emitting a thick black smoke, but will not flash . Water soluble.

Reactivity Profile

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.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition Dichloroacetonitrile emits toxic fumes of chlorine, cyanides and nitrogen oxides.

Fire Hazard

Dichloroacetonitrile is probably combustible.

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.

Purification Methods

Purify the nitrile by distillation or by gas chromatography. [Beilstein 2 IV 506.] FLAMMABLE.

Upstream product

• 128-09-6 N-chloro-succinimide 
• 372-09-8 cyanoacetic acid 
• 683-72-7 dichloroacetamide 
• 594-65-0 trichloroacetamide 
• 91983-99-2 Dichloressigsaeure-<(dichlor-phenyl-phosphoranyliden)-amid> 
• 545-06-2 trichloroacetonitrile 
• 77197-84-3 N-benzylideneperchlorovinylamine 
• 74-89-5 methylamine 
• 100-46-9 benzylamine 
• 75-05-8 acetonitrile 
• 820-10-0 DL-methionine sulfone 
• 16887-00-6 chloride 
• 921-01-7 rac-cysteine 
• 3130-87-8 ASPARAGINE 

Downstream Products

• 1194709-11-9 [(4R)-2-dichloromethyl-5t-(4-nitro-phenyl)-4,5-dihydro-oxazol-4r-yl]-methanol 
• 76738-28-8 (R)-((R)-2-dichloromethyl-4,5-dihydro-oxazol-4-yl)-(4-nitro-phenyl)-methanol 
• 25126-19-6 (1RS,2SR)-2-(2,2-dichloro-acetylamino)-1-phenyl-propane-1,3-diol 
• 24223-54-9 (RS)-((SR)-2-dichloromethyl-4,5-dihydro-oxazol-4-yl)-(4-nitro-phenyl)-methanol 
• 575-17-7 (+/-)-[2-dichloromethyl-5t-(4-nitro-phenyl)-4,5-dihydro-oxazol-4r-yl]-methanol 
• 24223-54-9 (RS)-((RS)-2-dichloromethyl-4,5-dihydro-oxazol-4-yl)-(4-nitro-phenyl)-methanol 
• 683-72-7 dichloroacetamide 
• 73217-29-5 2,2-dichloro-acetamide oxime 
• 5311-21-7 2,4,6-Tris-dichlormethyl-sym.-triazin 
• 594-65-0 trichloroacetamide 
• 2648-61-5 2,2-dichloroacetophenone 
• 64326-74-5 4-(N-benzenesulfonyl-2,2-dichloro-acetimidoyl)-morpholine 
• 5829-84-5 2,4-Dichloro-4-phenyl-butyronitrile 
• 4158-37-6 2-chlorobutyronitrile 

Relevant articles and documents

-

-

-

-

Transformation of chlorinated aliphatic compounds by ferruginous smectite

A series of chlorinated aliphatic compounds (RCI, including carbon tetrachloride (PCM), 1,1,1-trichloroethane (TCA), 1,1,2,2-tetrachloroethane (TeCA), pentachloroethane (PCA), hexachloroethane (HCA), trichloroethene (TCE), tetrachloroethene (PCE), trichloronitromethane (chloropicrin, CP), and trichloroacetonitrile (TCAN)) was reacted with ferruginuous smectite (sample SWa-1 from The Source Clays Repository), SWa, in aqueous suspension under anoxic conditions. Compounds highly polarizable or sharing substituents that facilitate charge delocalization adsorbed faster by reduced (SWa-R) than by unaltered (SWa-U) clay, indicating stronger dipole-dipole interactions between the substituents and the clay surface and/or hydrating water molecules. The reduction of the clay accelerated RCI adsorption up to 100-fold. Incubations with SWa-R promoted RCI reduction (CP, TCAN) or dehydrochlorination (TeCA and PCA). The reduction of structural Fe catalyzes the transformation of RCI via Bronsted and Lewis-basic promoted pathways. This study indicates that oxidation state of the structural Fe in SWa greatly alters surface chemistry and has a large impact on clay-organic interactions.

Chemistry of the biosynthesis of halogenated methanes: C1-organohalogens as pre-industrial chemical stressors in the environment?

We have chemical evidence that in the biosynthesis of the halomethanes C1H(4-n),X(n) (n = 1-4) three different pathways of biogenic formation have to be distinguished. The formation of methyl chloride, methyl bromide, and methyl iodide, respectively, has to be considered as a methylation of the respective halide ions. The dihalo- and trihalomethanes are formed via the haloform and/or via the sulfo-haloform reaction. The possible formation of tetrahalomethanes may involve a radical mechanism. Methionine methyl sulfonium chloride used as substrate in the incubation together with chloroperoxidase (CPO) and H2O2 gave high yields of monohalomethanes only. We were able to show that next to the CPO/H2O2 driven haloform reaction of carbonyl activated methyl groups also methyl-sulphur compounds - e.g. dimethylsulfoxide, dimethylsulfone, and the sulphur amino acid methionine - can act as precursors for the biosynthesis of di- and trihalogenated methanes. Moreover, there is some but not yet very conclusive evidence for an enzymatic production of tetrahalogenated methanes. In our experiments with chloroperoxidase involving amino acids and complex natural peptide based substrates, dihalogenated acetonitriles and several other volatile halogenated but yet unidentified compounds were formed. On the basis of these experiments we like to suggest that biosynthesis of halogenated nitriles occurs in general and therefore a natural atmospheric background should exist for halogenated acetonitriles and halogenated acetaldehydes, respectively.