2-(Trimethylsiloxy)-1,3-cyclohexadiene

Base Information

• Chemical Name: 2-(Trimethylsiloxy)-1,3-cyclohexadiene
• CAS No.: 54781-19-0
• Molecular Formula: C9H16OSi
• Molecular Weight: 168.311
• Hs Code.: 2931900090
• European Community (EC) Number: 627-751-2
• DSSTox Substance ID: DTXSID30399257
• Nikkaji Number: J46.587I
• Wikidata: Q63395632
• Mol file: 54781-19-0.mol

Synonyms:54781-19-0;2-(Trimethylsiloxy)-1,3-cyclohexadiene;2-(Trimethylsilyloxy)-1,3-cyclohexadiene;cyclohexa-1,5-dien-1-yloxy(trimethyl)silane;(cyclohexa-1,5-dien-1-yloxy)trimethylsilane;Silane, (1,5-cyclohexadien-1-yloxy)trimethyl-;2-trimethylsiloxy-1,3-cyclohexadiene;1-(Trimethylsilyloxy)-3,4-dihydrobenzene;2-[(trimethylsilyl)oxy]-1,3-cyclohexadiene;SCHEMBL449127;DTXSID30399257;WPIRVUXAMPRMAY-UHFFFAOYSA-N;MFCD00274202;AKOS015839977;2-(Trimethylsiloxy)1,3-cyclohexadiene;2-trimethylsilyloxy-1,3-cyclohexadiene;(cyclohexa-1,5-dienyloxy)trimethylsilane;2-(trimethylsilyoxy)-1,3-cyclohexadiene;BS-22771;CS-0182166;FT-0746385;T2630;2-(Trimethylsiloxy)-1,3-cyclohexadiene, 95%;D92628;Q63395632;InChI=1/C9H16OSi/c1-11(2,3)10-9-7-5-4-6-8-9/h5,7-8H,4,6H2,1-3H

Chemical Property of 2-(Trimethylsiloxy)-1,3-cyclohexadiene

Chemical Property:

• Vapor Pressure: 0.862mmHg at 25°C
• Melting Point: 242-246 °C
• Refractive Index: n20/D 1.462(lit.)
• Boiling Point: 65 °C7 mm Hg(lit.)
• Flash Point: 117 °F
• PSA: 9.23000
• Density: 0.899 g/mL at 25 °C(lit.)
• LogP: 3.07180
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 168.097041664
• Heavy Atom Count: 11
• Complexity: 186

Purity/Quality:

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

2-(Trimethylsilyloxy)-1,3-cyclohexadiene >94.0%(GC) ^*data from reagent suppliers

Safty Information:

• Statements: 10
• Safety Statements: 16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[Si](C)(C)OC1=CCCC=C1
• Uses: 2-(Trimethylsiloxy)-1,3-cyclohexadiene may be used as a diene in the synthesis of isoquinuclidinone 2-aza[2.2.2]octa-3,5-dione by reacting with p-toluenesulfonyl cyanide.

Technology Process of 2-(Trimethylsiloxy)-1,3-cyclohexadiene

There total 7 articles about 2-(Trimethylsiloxy)-1,3-cyclohexadiene 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: 93.0%

chloro-trimethyl-silane (75-77-4) + cyclohexenone (930-68-7) → 2-(trimethylsiloxy)cyclohexa-1,3-diene (54781-19-0)

Guidance literature:

cyclohexenone; With lithium hexamethyldisilazane; In tetrahydrofuran; at 4 ℃; for 0.5h;

chloro-trimethyl-silane; In tetrahydrofuran; at 4 ℃; for 0.75h;

DOI:10.1021/ja055301t

Reference yield: 48.0%

cyclohexenone (930-68-7) + N,O-bis-(trimethylsilyl)-acetamide (10416-59-8) → 2-(trimethylsiloxy)cyclohexa-1,3-diene (54781-19-0)

Guidance literature:

With polystyrene-bound 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine; In neat (no solvent); at 60 ℃; for 12h;

DOI:10.1055/s-0036-1590876

Reference yield:

cyclohexenone (930-68-7) + diisopropylamine (108-18-9) → 2-(trimethylsiloxy)cyclohexa-1,3-diene (54781-19-0)

Guidance literature:

With n-butyllithium; N₂; In tetrahydrofuran; hexane;

upstream raw materials:

chloro-trimethyl-silane

cyclohexenone

trimethylsilyl trifluoromethanesulfonate

diisopropylamine

Downstream raw materials:

Bicyclo<2.2.2>octane-2,4-dione

(1S,4R,5S,6S)-5,6-Bis-benzenesulfonyl-bicyclo[2.2.2]octan-2-one

(1S,3S,4S)-5-Oxo-2-(toluene-4-sulfonyl)-2-aza-bicyclo[2.2.2]octane-3-carboxylic acid methyl ester

phenyltrimethylsilyl ether