2-(Trimethylsilylmethyl)allyl acetate

Base Information

• Chemical Name: 2-(Trimethylsilylmethyl)allyl acetate
• CAS No.: 72047-94-0
• Molecular Formula: C9H18O2Si
• Molecular Weight: 186.326
• Hs Code.: 29319090
• European Community (EC) Number: 627-534-2
• DSSTox Substance ID: DTXSID80403196
• Nikkaji Number: J582.191F
• Wikidata: Q72514505
• Mol file: 72047-94-0.mol

Synonyms:72047-94-0;2-(Trimethylsilylmethyl)allyl acetate;2-((Trimethylsilyl)methyl)allyl acetate;2-(trimethylsilylmethyl)prop-2-enyl Acetate;2-(Acetoxymethyl)-3-(trimethylsilyl)propene;2-[(Acetoxymethyl)allyl]trimethylsilane;MFCD00075170;2-[(Trimethylsilyl)methyl]allyl Acetate;2-((trimethylsilyl)methyl)-2-propen-1-yl acetate;2-[(trimethylsilyl)methyl]-2-propen-1-yl acetate;tridecaborondiphosphide;SCHEMBL1561464;DTXSID80403196;IKQWABMHZKGCLX-UHFFFAOYSA-N;2-(acetoxymethyl)allyl-trimethylsilane;2-(trimethyl silylmethyl)allyl acetate;AKOS000283820;FS-5942;AM804277;SY029334;2-(Acetoxymethyl)-2-propenyltrimethylsilane;2-(TRIMETHYLSILYLMETHYL)ALLYLACETATE;CS-0046968;FT-0641390;2-(trimethylsilyl-methyl)-2-propenyl acetate;2-[(Acetoxymethyl)allyl]trimethylsilane, 99%;2-trimethylsilylmethyl-2-propen-1-yl acetate;2-(acetoxymethyl)-3-(trimethylsilyl)-1-propene;2-((trimethylsilyl)methyl)prop-2-en-1-yl acetate;A837402;2-(trimethylsilylmethyl)allyl acetate

Chemical Property of 2-(Trimethylsilylmethyl)allyl acetate

Chemical Property:

• Appearance/Colour: Clear colorless liquid
• Vapor Pressure: 0.074mmHg at 25°C
• Refractive Index: n20/D 1.440(lit.)
• Boiling Point: 228.3 °C at 760 mmHg
• Flash Point: 71.1 °C
• PSA: 26.30000
• Density: 0.882 g/cm³
• LogP: 2.44390
• Storage Temp.: 2-8°C
• Solubility.: Solubility most organic solvents.
• Water Solubility.: reacts
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 186.107606347
• Heavy Atom Count: 12
• Complexity: 180

Purity/Quality:

90.0% ^*data from raw suppliers

2-(Trimethylsilylmethyl)allylAcetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-14
• Safety Statements: 26-36/37/39-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC(=C)C[Si](C)(C)C
• Physical properties: bp 68–70°C/6.5 mmHg;60–61°C/2.5 mmHg.
• Uses: 2-[(Acetoxymethyl)allyl]trimethylsilane was used in the cyclopentane synthesis via Pd(0)-catalyzed reactions with 2π acceptors. precursor for palladium trimethylenemethane cycloaddition reactions.

Technology Process of 2-(Trimethylsilylmethyl)allyl acetate

There total 5 articles about 2-(Trimethylsilylmethyl)allyl acetate 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: 92.0%

2-(trimethylsilylmethyl)prop-2-en-1-ol (81302-80-9) + acetyl chloride (75-36-5) → [2-(acetoxymethyl)prop-2-enyl]trimethylsilane (72047-94-0)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 0.666667h;

DOI:10.1021/ja00346a035

Reference yield: 90.0%

2-chloromethyl-3-trimethylsilyl-1-propene (18388-03-9) + potassium acetate (127-08-2) → [2-(acetoxymethyl)prop-2-enyl]trimethylsilane (72047-94-0)

Guidance literature:

In N,N-dimethyl-formamide; at 55 - 60 ℃; for 48h;

DOI:10.1021/jo00255a048

Reference yield: 74.0%

2-iodoallyl acetate (791845-53-9) + (trimethylsilyl)methylmagnesium chloride (13170-43-9) → [2-(acetoxymethyl)prop-2-enyl]trimethylsilane (72047-94-0)

Guidance literature:

With cobalt(II) chloride; In tetrahydrofuran; diethyl ether; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2018.06.018

upstream raw materials:

2-chloromethyl-3-trimethylsilyl-1-propene

potassium acetate

methyllithium

1-Oxa-2-silacyclopentane

Downstream raw materials:

2-((E)-2-Phenylethenyl)-4-methylenetetrahydrofuran

(E)-2-(acetoxymethyl)-6-phenyl-4-(trimethylsiloxy)-1,5-hexadiene

2-(2-Phenylethyl)-4-methylenetetrahydrofuran

Spiro<<2-(R)-<(benzoyloxy)methyl>-4-(R)-ethoxy-3-oxacyclohexane>-1,2'-(R)-(4'-methylenetetrahydrofuran)>

Refernces

• 1、 Bogen,Journet,Malacria. "Radical cyclization of bromomethyldimethylsilyl propargyl ethers; A general method for the stereoselective synthesis of variously substituted trimethylenemethane (TMM) precursors". . p. 1215 - 1221. Retrieved 1994.
• 2、 Riaz, M. Tariq,Pohorilets, Ivanna,Hernandez, Jackson J.,Rios, Jeovanna,Totah, Nancy I.. "Preparation of 2-(trimethylsilyl)methyl-2-propen-1-ol derivatives by cobalt catalyzed sp2-sp3 coupling". supporting information. p. 2809 - 2812. Retrieved 2018/06/15.