| Identification | More | [Name]
Dichloroacetonitrile | [CAS]
3018-12-0 | [Synonyms]
DICHLOROACETONITRILE
1,1-Dichlorocarbonitrile
Acetnitrile,dichloro-
dichloro-acetonitril
Dichloromethyl cyanide
dichloromethylcyanide
DICHLOROACETONITRILE, STANDARD FOR GC
Dichloroacetonitrile, 98+%
2,2-Dichloroethanenitrile | [EINECS(EC#)]
221-159-4 | [Molecular Formula]
C2HCl2N | [MDL Number]
MFCD00040886 | [Molecular Weight]
109.94 | [MOL File]
3018-12-0.mol |
| Chemical Properties | Back Directory | [Appearance]
colourless liquid | [Boiling point ]
110-112 °C(lit.) | [density ]
1.369 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.44(lit.)
| [Fp ]
96 °F
| [storage temp. ]
0-6°C
| [solubility ]
soluble in Methanol | [form ]
neat | [color ]
Colorless to Light yellow to Light orange | [Specific Gravity]
1.37 | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents. | [BRN ]
1739029 | [Exposure limits]
NIOSH: IDLH 25 mg/m3 | [CAS DataBase Reference]
3018-12-0(CAS DataBase Reference) | [IARC]
3 (Vol. 52, 71) 1999 | [NIST Chemistry Reference]
Acetonitrile, dichloro-(3018-12-0) | [EPA Substance Registry System]
3018-12-0(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R10:Flammable.
R22:Harmful if swallowed.
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S25:Avoid contact with eyes .
S16:Keep away from sources of ignition-No smoking . | [RIDADR ]
UN 2920 8/PG 2
| [WGK Germany ]
3
| [RTECS ]
AL8465000
| [F ]
9-19 | [HazardClass ]
3 | [PackingGroup ]
II | [HS Code ]
29269090 | [Hazardous Substances Data]
3018-12-0(Hazardous Substances Data) |
| Hazard Information | Back Directory | [General Description]
Clear liquid. | [Reactivity Profile]
DICHLOROACETONITRILE(3018-12-0) 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. | [Air & Water Reactions]
Burns slowly, emitting a thick black smoke, but will not flash . Water soluble. | [Health Hazard]
ACUTE/CHRONIC HAZARDS: When heated to decomposition this chemical emits toxic fumes of chlorine, cyanides and nitrogen oxides. | [Fire Hazard]
This chemical is probably combustible. | [Chemical Properties]
colourless liquid | [Uses]
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.
| [Definition]
ChEBI: Dichloroacetonitrile is an aliphatic nitrile. | [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. |
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