1-(Trimethylsiloxy)-1,3-butadiene

Base Information

• Chemical Name: 1-(Trimethylsiloxy)-1,3-butadiene
• CAS No.: 6651-43-0
• Molecular Formula: C7H14 O Si
• Molecular Weight: 142.273
• Hs Code.: 2931900090
• European Community (EC) Number: 628-678-9
• Nikkaji Number: J283.505C,J370.814D
• Mol file: 6651-43-0.mol

Synonyms:1-(Trimethylsiloxy)-1,3-butadiene;6651-43-0;1-trimethylsiloxy-1,3-butadiene;1-trimethylsilyloxy-1,3-butadiene;Silane, (1,3-butadienyloxy)trimethyl-;[(1E)-buta-1,3-dienoxy]-trimethylsilane;SCHEMBL771486;4-(Trimethylsiloxy)-1,3-butadiene;AKOS015902923;(e)-(buta-1,3-dienyloxy)trimethylsilane;(E)-1-(Trimethylsiloxy)-1,3-butadiene;1-(Trimethylsiloxy)-1,3-butadiene, 98%;[(1E)-BUTA-1,3-DIEN-1-YLOXY]TRIMETHYLSILANE

Chemical Property of 1-(Trimethylsiloxy)-1,3-butadiene

Chemical Property:

• Vapor Pressure: 9.43mmHg at 25°C
• Refractive Index: n20/D 1.448(lit.)
• Boiling Point: 131 °C(lit.)
• Flash Point: 77 °F
• PSA: 9.23000
• Density: 0.811 g/mL at 25 °C(lit.)
• LogP: 2.53760
• Storage Temp.: 2-8°C
• Solubility.: Sol most standard organic solvents.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 142.081391600
• Heavy Atom Count: 9
• Complexity: 111

Purity/Quality:

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

1-(Trimethylsiloxy)-1,3-butadiene 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[Si](C)(C)OC=CC=C
• Isomeric SMILES: C[Si](C)(C)O/C=C/C=C
• Physical properties: bp 131 °C, bp 49.5 °C/25 mmHg; d 0.811 g cm?3.
• Uses: 1-Trimethylsilyloxy-1,3-butadiene is an easily prepared reactive diene for Diels–Alder reactions and other cycloadditions; reactive silyl enol ether for aldol and Michael reactions, and electrophilic additions. 1-Trimethylsiloxy-1,3-butadiene is a diene used in the Diels-Alder reaction. 1-(Trimethylsiloxy)-1,3-butadiene is commonly employed as diene in the Diels-Alder reaction.

Technology Process of 1-(Trimethylsiloxy)-1,3-butadiene

There total 8 articles about 1-(Trimethylsiloxy)-1,3-butadiene 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: 65.0%

chloro-trimethyl-silane (75-77-4) + trans-Crotonaldehyde (123-73-9,4170-30-3) → 1-(trimethylsiloxy)-1,3-butadiene (6651-43-0)

Guidance literature:

With triethylamine; zinc(II) chloride; In benzene;

DOI:10.1021/jo00008a006 DOI:10.1016/S0040-4039(00)93538-X

Reference yield:

chloro-trimethyl-silane (75-77-4) + crotonaldehyde (123-73-9,4170-30-3) → 1-(trimethylsiloxy)-1,3-butadiene (6651-43-0)

Guidance literature:

With triethylamine; zinc(II) chloride; In diethyl ether; for 25h; Reflux; Inert atmosphere;

DOI:10.1002/anie.200804777

Reference yield:

1,2-epoxy-1-trimethylsilyl-but-3-ene (163161-73-7) → 1-(trimethylsiloxy)-1,3-butadiene (6651-43-0)

Guidance literature:

With palladium diacetate; triisopropyl phosphite; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/0040-4039(95)00084-P

upstream raw materials:

chloro-trimethyl-silane

trans-Crotonaldehyde

3-butenal

1,2-epoxy-1-trimethylsilyl-but-3-ene

Downstream raw materials:

(E)-6-oxohept-2-enal

C₂₂H₂₆O₂Si

(1S,2R,3S)-3-hydroxycyclohex-4-ene-1,2-dicarbonyl diazide

(5R,2E)-5-phenyl-5-(2-thienylsulfonyl)amino-2-pentenal

Refernces

• 1、 Bideau, Franck Le,Gilloir, Fabienne,Nilsson, Ylva,Aubert, Corinne,Malacria, Max. "Stereoselective Addition of Nucleophiles on α-Trialkylsilyl-β,γ-Unsaturated Aldehydes". . p. 1641 - 1644. Retrieved 1995.
• 2、 Yamatsugu, Kenzo,Yin, Liang,Kamijo, Shin,Kimura, Yasuaki,Kanai, Motomu,Shibasaki, Masakatsu. "A synthesis of tamiflu by using a barium-catalyzed asymmetric diels-alder-type reaction". supporting information; experimental part. p. 1070 - 1076. Retrieved 2009/06/20.