Trimethyl((1-phenylvinyl)oxy)silane

Base Information

• Chemical Name: Trimethyl((1-phenylvinyl)oxy)silane
• CAS No.: 13735-81-4
• Deprecated CAS: 1658447-62-1
• Molecular Formula: C11H16OSi
• Molecular Weight: 192.333
• Hs Code.: 2931900090
• European Community (EC) Number: 237-308-1
• DSSTox Substance ID: DTXSID10884636
• Nikkaji Number: J236.395J
• Wikidata: Q82863272
• Mol file: 13735-81-4.mol

Synonyms:13735-81-4;1-Phenyl-1-trimethylsiloxyethylene;Trimethyl((1-phenylvinyl)oxy)silane;Trimethyl[(1-phenylvinyl)oxy]silane;trimethyl(1-phenylethenoxy)silane;1-Phenyl-1-trimethylsilyloxyethylene;1-Phenyl-1-(trimethylsilyloxy)ethylene;EINECS 237-308-1;1-Phenyl-1-(trimethylsiloxy)ethylene;C11H16OSi;Silane, trimethyl[(1-phenylethenyl)oxy]-;Benzene, (1-((trimethylsilyl)oxy)ethenyl)-;trimethyl(1-phenylvinyloxy)silane;MFCD00008582;Silane, trimethyl((1-phenylethenyl)oxy)-;Benzene, [1-[(trimethylsilyl)oxy]ethenyl]-;alpha-trimethylsiloxystyrene;alpha-(Trimethylsiloxy)styrene;SCHEMBL347522;alpha-(Trimethylsilyloxy)styrene;C11-H16-O-Si;.alpha.-(Trimethylsiloxy)styrene;1-Phenyl-1-trimethylsiloxyethene;DTXSID10884636;(1-phenylvinyl)oxy Trimethylsilane;(1-phenylvinyloxy)-trimethylsilane;.alpha.-(Trimethylsilyloxy)styrene;1-phenyl-1-trimethylsilyloxyethene;(1-phenylethenyl)oxytrimethylsilane;Trimethyl(1-phenylethenyloxy)silane;1-Phenylvinyl trimethylsilyl ether #;Phenyl-1-(Trimethylsilyloxy)Ethylene;1-(Trimethylsilyloxy)-1-phenylethene;Trimethyl-(1-phenyl-vinyloxy)-silane;trimethyl[(1-phenylethenyl)oxy]silane;AKOS004907893;Trimethyl-(1 -phenyl-vinyloxy)-silane;Silane, trimethyl[(1-phenylvinyl)oxy]-;[(1-phenyl-1-ethenyl)oxy]trimethylsilane;1-Phenyl-1-trimethylsiloxyethylene, 98%;AS-62136;SY043340;CS-0127818;FT-0608232;P1280;D71013;A886505;J-007010;1-Phenyl-1-trimethylsiloxyethylene, purum, >=98.0% (GC)

Chemical Property of Trimethyl((1-phenylvinyl)oxy)silane

Chemical Property:

• Vapor Pressure: 0.239mmHg at 25°C
• Melting Point: 122-123 °C
• Refractive Index: n20/D 1.502(lit.)
• Boiling Point: 213.452 °C at 760 mmHg
• Flash Point: 76.08 °C
• PSA: 9.23000
• Density: 0.914 g/cm³
• LogP: 3.50880
• Storage Temp.: −20°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: Reacts with water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 192.097041664
• Heavy Atom Count: 13
• Complexity: 175

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-Phenyl-1-trimethylsilyloxyethylene >95.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)OC(=C)C1=CC=CC=C1
• Uses: 1-Phenyl-1-trimethylsiloxyethylene has been used in the synthesis of β-amino ketones in water via Mannich-type reaction and cis-2,6-disubstituted dihydropyrans via three-component, one-pot cascade reaction. It is also used as chemical additives and intermediates. 1-Phenyl-1-trimethylsiloxyethylene has been used in the synthesis of:β-amino ketones in water via Mannich-type reactioncis-2,6-disubstituted dihydropyrans via three-component, one-pot cascade reaction

Technology Process of Trimethyl((1-phenylvinyl)oxy)silane

There total 56 articles about Trimethyl((1-phenylvinyl)oxy)silane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

trimethylsilanyl-acetic acid ethyl ester (4071-88-9) + acetophenone (98-86-2) → 1-styrenyloxytrimethylsilane (13735-81-4)

Guidance literature:

With potassium cyanide; perhydrodibenzo-18-crown-6; In tetrahydrofuran; at 0 ℃; for 0.166667h;

DOI:10.1246/bcsj.54.805

Reference yield: 90.0%

trimethylsilyl iodide (16029-98-4) + 1-chloroacetophenone (532-27-4,108321-66-0,164322-25-2) → 1-styrenyloxytrimethylsilane (13735-81-4) + iodoacetophenone (4636-16-2) + ((Z)-2-Chloro-1-phenyl-vinyloxy)-trimethyl-silane (31151-36-7)

Guidance literature:

With 1,1,1,3,3,3-hexamethyl-disilazane; In tetrachloromethane; at 10 ℃; for 6h; Yields of byproduct given;

Reference yield: 86.0%

3-(trimethylsilyl)-2-oxazolidinone (43112-38-5) + acetophenone (98-86-2) → dimethylenecyclourethane (497-25-6) + 1-styrenyloxytrimethylsilane (13735-81-4)

Guidance literature:

trifluorormethanesulfonic acid; at 0 ℃; for 0.5h;

upstream raw materials:

n-butyllithium

chloro-trimethyl-silane

carbon monoxide

acetophenone

Downstream raw materials:

1-phenylhexane-1,5-dione

diethyl phosphonoacetophenone

benzoyl(dichloroacetyl)methane

4,4,4-trichloro-3-hydroxy-1-phenylbutan-1-one

Refernces

• 1、 Krueger,Rochow. "". . p. 476,479. Retrieved 1964.
• 2、 Dong, Zhaowen,Fadaei-Tirani, Farzaneh,Le Du, Eliott,Muriel, Bastian,Scopelliti, Rosario,Severin, Kay,Suleymanov, Abdusalom A.,Waser, Jér?me. "Triazene-Activated Donor-Acceptor Cyclopropanes: Ring-Opening and (3 + 2) Annulation Reactions". . . Retrieved 2020.
• 3、 House,H.O. et al.. "-". . p. 2324 - 2336. Retrieved 1969.
• 4、 Lee, Thomas V.,Toczek, Judy. "THE REACTION OF CHROMYL CHLORIDE AND O-SILYLATED ENOLATES: A NOVEL REGIOSPECIFIC ROUTE TO α-HYDROXY KETONES.". . p. 2917 - 2920. Retrieved 1982.
• 5、 Lin, Ji-Mao,Liu, Ben-Sheng. "A practical method for the preparation of trimethylsilyl enol ethers". . p. 739 - 749. Retrieved 1997.
• 6、 Gong, Jun,Wan, Qian,Kang, Qiang. "Enantioselective Mukaiyama–Michael Reaction Catalyzed by a Chiral Rhodium Complex Based on Pinene-Modified Pyridine Ligands". . p. 2484 - 2488. Retrieved 2018.
• 7、 Taniguchi, Yoshiyuki,Inanaga, Junji,Yamaguchi, Masaru. "Use of 1,8-Diazabicycloundec-7-ene in Preparation of Trimethylsilyl Enol Ethers and Trimethylsilylacetylenes". . p. 3229 - 3230. Retrieved 1981.
• 8、 Harrowven, David C.,Poon, Hon Suen. "Changing course with an additive: A striking example of the effect of TMSCl on lithium amide reactivity". . p. 4281 - 4282. Retrieved 1996.
• 9、 Itoh, Takashi,Miyazaki, Michiko,Nagata, Kazuhiro,Ohsawa, Akio. "Addition reaction of imidazoles and thiazoles with silyl enol ethers in the presence of alkyl chloroformate". . p. 4383 - 4395. Retrieved 2000.
• 10、 Nakamura, Eiichi,Hashimoto, Koichi,Kuwajima, Isao. "Silylation of Relatively Acidic Compounds with Alkyl Trimethylsilylacetates". . p. 805 - 808. Retrieved 1981.