Allyltrimethylsilane

Base Information

• Chemical Name: Allyltrimethylsilane
• CAS No.: 762-72-1
• Deprecated CAS: 255878-58-1
• Molecular Formula: C6H14Si
• Molecular Weight: 114.263
• Hs Code.: 29310095
• European Community (EC) Number: 212-104-5
• UNII: 8B84C337VF
• DSSTox Substance ID: DTXSID5061089
• Nikkaji Number: J129.396F
• Wikipedia: Allyltrimethylsilane
• Wikidata: Q2838752
• Mol file: 762-72-1.mol

Synonyms:allyltrimethylsilane

Chemical Property of Allyltrimethylsilane

Chemical Property:

• Appearance/Colour: clear, colorless liquid
• Vapor Pressure: 79.2mmHg at 25°C
• Refractive Index: n20/D 1.407(lit.)
• Boiling Point: 84.9 °C at 760 mmHg
• Flash Point: 7.2 °C
• PSA: 0.00000
• Density: 0.721 g/cm³
• LogP: 2.51060
• Storage Temp.: 0-6°C
• Solubility.: freely sol all organic solvents.
• Water Solubility.: insoluble
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 114.086476981
• Heavy Atom Count: 7
• Complexity: 59.1

Purity/Quality:

99% ^*data from raw suppliers

Allyltrimethylsilane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36-23-33-7/9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[Si](C)(C)CC=C
• Uses: Allyltrimethylsilane is a general reagent to introduce allyl groups across acid chlorides, aldehydes, ketones, iminium ions, enones, and for cross-coupling with other carbon electrophiles. It is used as a reagent in Hosomi?Sakurai reaction.

Technology Process of Allyltrimethylsilane

There total 45 articles about Allyltrimethylsilane 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%

1,1,1,2,2,2-hexamethyldisilane (1450-14-2) + Allyl acetate (591-87-7) → propene (187737-37-7,13987-01-4,15220-87-8,9003-07-0,676-63-1,25085-53-4) + trimethylsilyl acetate (2754-27-0) + allyl-trimethyl-silane (762-72-1) + (E)-trimethyl(prop-1-en-1-yl)silane (4964-03-8)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; at 180 ℃; for 2h; high pressure, under nitrogen;

DOI:10.1246/bcsj.57.607

Reference yield: 92.0%

cis-[Pd(1,3,4,5-tetramethylimidazol-2-ylidene)2(SiMe3)2] + allyl bromide (106-95-6) → trans-[Pd(1,3,4,5-tetramethylimidazol-2-ylidene)2(SiMe3)(Br)] + allyl-trimethyl-silane (762-72-1)

Guidance literature:

at 20 ℃; for 1.5h;

DOI:10.3390/molecules26092460

Reference yield: 90.0%

chloro-trimethyl-silane (75-77-4) + 3-chloroprop-1-ene (107-05-1) → allyl-trimethyl-silane (762-72-1)

Guidance literature:

3-chloroprop-1-ene; With naphthalene; sodium; In tetrahydrofuran; at -78 ℃; for 1h;

chloro-trimethyl-silane; In tetrahydrofuran; at -78 - 20 ℃; Further stages.;

DOI:10.1039/b710308e

upstream raw materials:

allyltrichlorosilane

methylmagnesium bromide

allyltriethoxysilane

chloro-trimethyl-silane

Downstream raw materials:

1,3-diphenylhex-5-en-1-one

5-Hexen-1-ol

dimethyl 4-phenyl-2,6-dimethyl-3,5-pyridinedicarboxylate

dimethyl 1α,3-dimethyl-5β-phenyl-8-<(trimethylsilyl)methyl>-2-azabicyclo<2.2.2>oct-2-ene-4,6α-dicarboxylate

Refernces

• 1、 Mal'tsev et al.. "". . . Retrieved 1979.
• 2、 Maeda, Hajime,Nishitsuji, Nana,Mizuno, Kazuhiko. "Diastereoselective protonation on a radical anion in the photoallylation and photoreduction of 1,1-dicyano-2-methyl-3-phenyl-1-butene by allyltrimethylsilane". experimental part. p. 577 - 585. Retrieved 2011/11/30.