| | Trichloroacetonitrile Basic information |
| | Trichloroacetonitrile Chemical Properties |
| Melting point | -42 °C | | Boiling point | 83-84 °C(lit.) | | density | 1.44 g/mL at 25 °C(lit.) | | vapor pressure | 58 mm Hg ( 20 °C) | | refractive index | n20/D 1.441(lit.) | | Fp | None | | storage temp. | Store below +30°C. | | solubility | <0.1 g/100 mL at 21.5°C | | form | Liquid | | color | Clear colorless to very slightly yellow | | Odor | odor of chloral and hydrogen cyanide | | Water Solubility | <0.1 g/100 mL at 21.5 ºC | | Sensitive | Lachrymatory | | Merck | 14,9628 | | BRN | 605572 | | Exposure limits | NIOSH: IDLH 25 mg/m3 | | Stability: | Stable, but water sensitive. Incompatible with acids, water, steam. May hydrolyze in alkali or acid conditions. Flammable. | | CAS DataBase Reference | 545-06-2(CAS DataBase Reference) | | IARC | 3 (Vol. 52, 71) 1999 | | NIST Chemistry Reference | Acetonitrile, trichloro-(545-06-2) | | EPA Substance Registry System | Trichloroacetonitrile (545-06-2) |
| Hazard Codes | T,N | | Risk Statements | 23/24/25-51/53 | | Safety Statements | 45-61 | | RIDADR | UN 3276 6.1/PG 3 | | WGK Germany | 3 | | RTECS | AM2450000 | | Hazard Note | Toxic/Lachrymatory | | TSCA | Yes | | HazardClass | 8 | | PackingGroup | II | | HS Code | 29269095 | | Hazardous Substances Data | 545-06-2(Hazardous Substances Data) | | Toxicity | LD50 orally in rats: 0.25 g/kg (Smyth) |
| | Trichloroacetonitrile Usage And Synthesis |
| Chemical Properties | colourless to slightly yellow liquid | | Uses | Insecticide. | | Uses | Trichloroacetonitrile is involved as a reagent in Overman rearrangement, which is used to prepare alylic amines from allylic alcohols. It is also used to prepare bistrichloroacetimidates from diols leading to dihyrooxazines through acid catalyzed cyclization. Further, it is utilized in the synthesis of trichloroacetimidates by 1,8-Diazobicyclo[5.4.0]undec-7-ene (DBU) catalyzed addition of allylic alcohols. It finds application in the study of the methoxy methyl (MOM) catalyzed aza-Claisen rearrangement. | | Definition | ChEBI: Trichloroacetonitrile is an aliphatic nitrile and an organochlorine compound. | | General Description | Clear pale yellow liquid. | | Air & Water Reactions | Highly flammable. Insoluble in water. | | Reactivity Profile | May be sensitive to light and heat. Trichloroacetonitrile may react with water, steam, acid or acid fumes. Trichloroacetonitrile may hydrolyze under acidic or alkaline conditions. . The reaction of benzene and Trichloroacetonitrile evolves toxic chloroform and HCl gasses. (Hagedorn, F., H.-P. Gelbke, and Federal Republic of Germany. 2002. Nitriles. In Ullman Encyclopedia of Industrial Chemistry. Wiley-VCH Verlag GmbH & Co. KGaA.). | | Hazard | Strong irritant to tissue. Questionable carcinogen. | | Fire Hazard | Trichloroacetonitrile is combustible. | | Safety Profile | Poison by ingestion and
intravenous routes. Moderately toxic by
inhalation and skin contact. Human
mutation data reported. A skin and severe
eye irritant. An experimental teratogen.
Other experimental reproductive effects.
When heated to decomposition or in
reaction with water, steam, acid, or acid
fumes it produces toxic fumes of CN-, Cl-,
and NOx. Used as an insecticide. See also
NITRILES and CYANIDE. |
| | Trichloroacetonitrile Preparation Products And Raw materials |
| Raw materials | Phosphorus pentoxide-->2,2,2-Trichloroacetamide | | Preparation Products | Trifluoroacetic acid-->2,5-DIHYDROXYBENZONITRILE-->2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSYL TRICHLOROACETIMIDATE-->Tetramethoxymethane-->2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl 2,2,2-Trichloroacetimidate-->2-Propynenitrile, 3-phenyl- (9CI)-->BENZYL 2,2,2-TRICHLOROACETIMIDATE-->DIMETHYL PHOSPHOROCHLORIDATE |
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