Chemical Properties
Allyl trichhlorosilane is a volatile, corrosive, flammable, colorless liquid. Irritating odor.
Chemical Properties
Clear colorless to slightly yellow liquid
Physical properties
bp 116°C/750 Torr; nD 1.4450; d 1.211.
Uses
Allyltrichlorosilane acts as a reagent that produces homoallylic alcohols upon reaction with aldehydes in DMF. It is used to make silicones and glass fiber fininshes.
Uses
Intermediate for silicones, fiberous glass finishes.
Preparation
allyl trichlorosilane is conveniently prepared
from allyl chloride, Cl3SiH, CuCl, and (i-Pr)2EtN
(or Et3N) in ether at 20°C,or from allyl chloride and coppersilicon
powder at 250°C.Other methods include the reaction
of allyl chloride with SiCl4 in the presence of CuCl and Et3N7 or in the presence of Cp2Ni and HMPA at 90°C,the flash
pyrolysis of allyl chloride with Si2Cl2 in PhCl at 500°C,the
reaction of allylMgBr with SiCl4,coupling of allene with
Cl3SiH, catalyzed by (Ph3P)4Pd (120°C, 5 h),11 and the elimination
of HCl from Cl(CH2)3SiCl3 using, e.g., quinoline as
base.The analogous (E)-crotyl trichlorosilane can be synthesized
from (E)-crotyl chloride, Cl3SiH, CuCl, and (i-Pr)2EtN in
ether at 20°C,or from (E)-crotyl chloride, SiCl4, and
Cp2Ni in HMPA at 90°C.The reaction of (E)-crotyl chloride
with Cl3SiH and Bu4PCl at 150°C has also been reported.
(Z)-crotyl trichlorosilane, on the other hand, was prepared via
the 1,4-addition of Cl3SiH to butadiene, catalyzed by (Ph4P)4Pd
(at 20°Cor78°C)or by (PhCN)2PdCl2;this hydrosilylation
can also be catalyzed by Nior proceed uncatalyzed
at 500–600°C.Analogous trifluoro and tribromo derivatives
C3H5SiX3 (X = F and Br) have also been described.
General Description
A colorless liquid with a pungent odor. Flash point of 95°F. Corrosive to metals and tissue.
Reactivity Profile
Chlorosilanes, such as ALLYLTRICHLOROSILANE, are compounds in which silicon is bonded to from one to four chlorine atoms with other bonds to hydrogen and/or alkyl groups. Chlorosilanes react with water, moist air, or steam to produce heat and toxic, corrosive fumes of hydrogen chloride. They may also produce flammable gaseous H2. They can serve as chlorination agents. Chlorosilanes react vigorously with both organic and inorganic acids and with bases to generate toxic or flammable gases.
Health Hazard
Inhalation of vapor irritates mucous membranes. Liquid causes severe burns of eyes and skin and severe internal burns if ingested.
Safety Profile
Poison by intravenous route. Corrosive. See ALLYL COMPOUNDS. When heated to decomposition it emits toxic Cl-. A dangerous fire hazard. To fight fire, use foam, mist, spray, dry chemical.
Potential Exposure
Used to make silicones and glass fiber finishes.
Shipping
UN1724 Allyltrichlorosilane, stabilized, Hazard class: 8; Labels: 8-Corrosive material, 3-Flammable liquid
Incompatibilities
Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Chlorosilanes react vigorously with bases and both organic and inorganic acids generating toxic and/or flammable gases. Chlorosilanes react with water, moist air, or steam to produce heat and toxic, corrosive fumes of hydrogen chloride gas. They may also produce flammable gaseous hydrogen. Attacks metals in the presence of moisture. Avoid all sources of ignition.
