107-37-9

Basic information

• Product Name: ALLYLTRICHLOROSILANE
• Synonyms: 3-TRICHLOROSILYLPROPENE;ALLYLTRICHLOROSILANE;TRICHLOROALLYLSILANE;Allyl trichlorosilane, stabilized;allylsilicone;allylsiliconetrichloride;allyltrichloro-silan;allyltrichlorosilane,stabilized
• CAS NO: 107-37-9
• Molecular Formula: C₃H₅Cl₃Si
• Molecular Weight: 175.52
• EINECS: 203-485-9
• Product Categories: Functional Materials;Si (Classes of Silicon Compounds);Si-Cl Compounds;Silane Coupling Agents;Trichlorosilanes;Vinyl Silanes (Silane Coupling Agents);Vinylsilanes, Allylsilanes;Protecting and Derivatizing Reagents;Self Assembly&Contact Printing;Self-Assembly Materials;SilanesProtection and Derivatization;Silicon-Based;Protection and Derivatization
• Mol File: 107-37-9.mol

Chemical Properties

• Melting Point: 35℃
• Boiling Point: 116 °C750 mm Hg(lit.)
• Flash Point: 88 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.211 g/mL at 25 °C(lit.)
• Vapor Density: >1 (vs air)
• Vapor Pressure: 10 mm Hg ( 16.1 °C)
• Refractive Index: n20/D 1.443(lit.)
• Storage Temp.: Flammables area
• Solubility: soluble in MeCN, THF, CH2Cl2, toluene, benzene, etc.; not compatible with protic solvents, acetone, and other ketones. Dipolar aprotic solvents (DMF, DMSO, HMPA, etc.) coordinate Si, thereby increasing the reactivity of C3H5SiCl3 with electrophiles.
• Water Solubility: Soluble in THF, toluene, benzene. Reacts with water.
• Sensitive: Moisture Sensitive
• BRN: 1743449
• CAS DataBase Reference: ALLYLTRICHLOROSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: ALLYLTRICHLOROSILANE(107-37-9)
• EPA Substance Registry System: ALLYLTRICHLOROSILANE(107-37-9)

Safety Data

• Hazard Codes: F,C
• Statements: 11-34
• Safety Statements: 16-26-33-36/37/39-43-45
• RIDADR: UN 1724 8/PG 2
• WGK Germany: 1
• RTECS: VV1530000
• F: 10-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 107-37-9(Hazardous Substances Data)

Usage

Chemical Description

Allyltrichlorosilane is an organosilicon compound used as a reagent.

Uses

Used in Silicone Industry:
ALLYLTRICHLOROSILANE is used as an intermediate for the production of silicones, which are versatile materials with a wide range of applications, including sealants, adhesives, and coatings.
Used in Fiber Glass Industry:
ALLYLTRICHLOROSILANE is used as a component in the production of fiberous glass finishes, which are used to enhance the strength and durability of fiber glass products.
Used in Chemical Synthesis:
ALLYLTRICHLOROSILANE acts as a reagent that produces homoallylic alcohols upon reaction with aldehydes in DMF (dimethylformamide). This reaction is useful in the synthesis of various organic compounds and pharmaceuticals.

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°Cor?78°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.

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.

InChI:InChI=1/C3H5Cl3Si/c1-2-3-7(4,5)6/h2H,1,3H2

Upstream product

• 119-65-3 isoquinoline 
• 2550-06-3 3-chloropropyltrichlorosilane 
• 542-75-6 E/Z-1,3-Dichloropropene 
• 7787-88-4 (n-pr-1-Cl)SiCl₃ 
• 107-05-1 3-chloroprop-1-ene 
• 1730-25-2 allylmagnesium bromide 
• 674-82-8 4-methyleneoxetan-2-one 
• 75-94-5 trichlorovinylsilane 
• 463-49-0 1,2-propanediene 
• 3937-28-8 allyldichlorosilane 
• 624-65-7 2-propynyl chloride 
• 78-88-6 2,3-Dichloroprop-1-ene 
• 26198-63-0 1,2-Dichloropropane 
• 4873-09-0 allyl tosylate 

Downstream Products

• 4028-23-3 Allylchlorodimethylsilane 
• 1873-92-3 allyldichloromethylsilane 
• 2550-04-1 allyltriethoxysilane 
• 762-72-1 allyl-trimethyl-silane 
• 5929-71-5 triacetoxyallylsilane 
• 7719-03-1 allyl (phenyl)-dichlorosilane 
• 18191-59-8 allylsilane 
• 13883-39-1 (3-bromopropyl)trichlorosilane 
• 18171-50-1 1,3-bis(trichlorosilyl)propane 
• 17861-30-2 all(ph-4-Cl)SiCl₂ 
• 17478-03-4 all(be)SiCl₂ 
• 2551-83-9 allyltrimethoxysilane 
• 85551-57-1 (R)-1-Phenylbut-3-en-1-ol 
• 60340-28-5 1-phenylhex-5-en-3-ol 

Relevant articles and documents

SOME PRACTICAL USES OF THE DISILANE RESIDUE FROM THE DIRECT SYNTHESIS OF METHYLCHLOROSILANES

Some practical uses for the disilane residue from the direct synthesis of methylchlorosilanes have been proposed.This residue can be converted into organochloro-(Me2SiCl2, MeSiCl3, Me3SiCl) or organohydrochloro-monosilanes (HMeSiCl2, HMe2SiCl).These disilanes can also be used for the synthesis of alkyl (haloalkyl, alkenyl, aryl, etc.) methyldichlorosilanes or alkyl (haloalkyl, alkenyl, aryl, etc.) trichlorosilanes.The reductive properties of the Si-Si bond of these species have been utilized (e.g. in the reduction of phosphine oxides into the corresponding phosphines).Polysilanes resulting from the disproportionation of this residue are precursors of polycarbosilanes.

METHOD FOR THE DEHYDROGENATION OF DICHLOROSILANE

Dichlorosilane and trichlorosilane are dehydrogenated at elevated temperature in the presence of an ammonium or phosphonium salt as a catalyst, and a halogenated hydrocarbon or hydrogen halide. The method may be used to synthesize organochlorosilane.

METHOD OF PREPARING ALLYLCHLOROSILANE DERIVATIVE

Provided is a method of preparing allylchlorosilane, and more particularly, a method of preparing allylchlorosilane with high yield by Si—C coupling reaction of an allyl chloride derivativce with a hydrosilane derivative under specific reaction conditions without using a catalyst.

PRODUCTION METHOD FOR LINEAR AND CYCLIC TRISILAALKANE

The present invention relates to a preparation method for a linear or cyclic trisilaalkane which is a substance useful in the preparation of polycarbosilane and silicon carbide precursors. Linear or cyclic trisilaalkane and organic trichlorosilane derivatives can be synthesized simultaneously and in high yield by reacting bis(chlorosily)methane having a Si—H bond, either alone or together with an organic chloride, using a quaternary organic phosphonium salt compound as a catalyst. Further, since the catalyst can be recovered after use, the present invention is very economical and is thus effective for mass-producing precursors for organic/inorganic hybrid substances.

Controlled introduction of allylic group to chlorosilanes

Allylation of chlorosilanes has been achieved with allylsamarium bromide, especially in a controlled manner. Thus allylation of trisubstituted chlorosilanes (R3SiCl) afforded a variety of aryl, aralkyl, and alkenyl substituted allylsilanes. Dichlorosilanes (R2SiCl2) can either afford monoallylated silanes or diallylated silanes depending on the amount of allylsamarium bromide used. Similarly, trichlorosilanes (RSiCl3) can selectively afford mono-, di-, and tri-allylation products. Finally, perchlorosilane (SiCl4) was allylated stepwise and the corresponding silanes containing one, two, three or four allylic groups, respectively, were obtained in satisfactory yields.

Processes for manufacturing organochlorosilanes and dipodal silanes and silanes made thereby

Processes are provided for producing organchlorosilanes and dipodal silanes in which an organic halide or alkene or chloralkene is reacted with a hydridochlorosilane in the presence of a quarternary phosphonium salt catalyst by providing sufficient heat to effect a dehydrohalogenative coupling reaction and/or a hydrosilylation reaction and venting the reaction to control reaction pressure and to remove gaseous byproducts from the reaction. The processes are preferably continuous using a catalyst in fluid form at reaction pressures not exceeding about 600 psi. The reactions may be carried out substantially isothermally and/or isobarically, for example in a plug flow reactor or continuous stirred tank reactor. The processes may produce novel silylated compounds including 1,2-bis(trichlorosilyl)decane or 1,2-bis(trimethoxysilyl)decane.

PROCESS FOR PREPARING ORGANOCHLOROSILANES BY DEHYDROHALOGENATIVE COUPLING REACTION OF ALKYL HALIDES WITH CHLOROSILANES

The present invention relates to a process for preparing organochlorosilanes and more particularly, to the process for preparing organochlorosilanes of formula I by a dehydrohalogenative coupling of hydrochlorosilanes of formula II with organic halides of formula III in the presence of quaternary phosphonium salt as a catalyst to provide better economical matter and yield compared with conventional methods, because only catalytic amount of phosphonium chloride is required and the catalyst can be separated from the reaction mixture and recycled easily, wherein R1 represents hydrogen, chloro, or methyl; X represents chloro or bromo; R2 is selected from the group consisting of C1-17 alkyl, C1-10 fluorinated alkyl with partial or full fluorination, C2-5 alkenyl, silyl containing alkyl group represented by (CH2)nSiMe3-mClm wherein n is an integer of 0 to 2 and m is an integer of 0 to 3, aromatic group represented by Ar(R′)q wherein Ar is C6-14 aromatic hydrocarbon, R′ is C1-4 alkyl, halogen, alkoxy, or vinyl, and q is an integer of 0 to 5, haloalkyl group represented by (CH2)pX wherein p is an integer of 1 to 9 and X is chloro or bromo, and aromatic hydrocarbon represented by ArCH2X wherein Ar is C6-14 aromatic hydrocarbons and X is a chloro or bromo; R3 is hydrogen, C1-6 alkyl, aromatic group represented by Ar(R′)q wherein Ar is C6-14 aromatic hydrocarbon, R′ is C1-4 alkyl, halogen, alkoxy, or vinyl, and q is an integer of 0 to 5; and R4 in formula I is the same as R2 in formula III and further, R4 can also be (CH2)pSiR1Cl2 or ArCH2SiR1Cl2, when R2 in formula III is (CH2)pX or ArCH2X, which is formed from the coupling reaction of X—(CH2)p+1—X or XCH2ArCH2X with the compounds of formula II; or when R2 and R3 are covalently bonded to each other to form a cyclic compounds of cyclopentyl or cyclohexyl group, R3 and R4 are also covalently bonded to each other in the same fashion.

Process for preparing organochlorosilanes by dehydrohalogenative coupling reaction of alkyl halides with chlorosilanes

The present invention relates to a process for preparing organochlorosilanes and more particularly, to the process for preparing organochlorosilanes of R4R3CHSiR1Cl2(I) by a dehydrohalogenative coupling of hydrochlorosilanes of HSiR1Cl2(II) with organic halides of R2R3CHX (III) in the presence of quaternary phosphonium salt as a catalyst to provide better economical matter and yield compared with conventional methods, because only a catalytic amount of phosphonium chloride is required and the catalyst can be separated from the reaction mixture and recycled easily.

Dehydrohalogenative coupling reaction of organic halides with silanes

The present invention relates to methods for making the compounds of formula I which is a dehydrohalogenative coupling of hydrochlorosilanes of formula II with organic halides of formula III in the presence of a Lewis base catalyst. R3CH2SiR1Cl2??(I) HSiR1Cl2??(II) R2CH2X??(III) In formulas I and II, R1represents a hydrogen, chloro, or methyl; in formula III, X represents a chloro or bromo; in formula III, R2can be selected from the group consisting of a C1-17alkyl, a C1-10fluorinated alkyl with partial or full fluorination, a C1-5alkenyl groups, a silyl group containing alkyls, (CH2)nSiMe3-mClmwherein n is 0 to 2 and m is 0 to 3, aromatic groups, Ar(R′)1wherein Ar is C6-14aromatic hydrocarbon, R′ is a C1-4alkyl, halogen, alkoxy, or vinyl, and q is 0 to 5, a haloalkyl group, (CH2)pX wherein p is 1 to 9 and X is a chloro or bromo; or an aromatic hydrocarbon, Ar CH2X wherein Ar is C6-14aromatic hydrocarbon and X is a chloro or bromo. in formula I, R3is the same as R2in formula III and further, R3can also be (CH2)pSiR1Cl2or ArCH2SiR1Cl2when R2in formula III is (CH2)pX or ArCH2X, because of the coupling reaction of X with the compound of formula II.

One-pot enantioselective synthesis of optically active homoallylic alcohols from allyl halides

A one-pot, convenient method for the preparation of optically active homoallylic alcohols from allyl halides was developed. Allyltrichlorosilanes were generated in situ from allyl halides and trichlorosilane in the presence of cuprous chloride and tertiary amine. Without isolation of the allyltrichlorosilanes, benzaldehyde and chiral biquinoline N,N'-dioxide were introduced into the same flask, producing the corresponding homoallylic alcohols with good to high enantioselectivities.