1,1-Bis(trimethylsilyloxy)-1,3-butadiene

Base Information

• Chemical Name: 1,1-Bis(trimethylsilyloxy)-1,3-butadiene
• CAS No.: 87121-06-0
• Molecular Formula: C10H22 O2 Si2
• Molecular Weight: 230.454
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID00369947
• Nikkaji Number: J661.400K
• Mol file: 87121-06-0.mol

Synonyms:87121-06-0;1,1-BIS(TRIMETHYLSILYLOXY)-1,3-BUTADIENE;trimethyl(1-trimethylsilyloxybuta-1,3-dienoxy)silane;2,2,6,6-tetramethyl-4-(prop-2-en-1-ylidene)-3,5-dioxa-2,6-disilaheptane;1,1-bis-(Trimethylsilyloxy)-1,3-butadiene;SCHEMBL11096308;DTXSID00369947;4-allylidene-2,2,6,6-tetramethyl-3,5-dioxa-2,6-disilaheptane

Chemical Property of 1,1-Bis(trimethylsilyloxy)-1,3-butadiene

Chemical Property:

• Boiling Point: 80 °C (11 mmHg)
• PSA: 18.46000
• Density: 0.888 (estimate)
• LogP: 3.71680
• Storage Temp.: 0-6°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 230.11583301
• Heavy Atom Count: 14
• Complexity: 203

Purity/Quality:

98%Min ^*data from raw suppliers

1,1-BIS(TRIMETHYLSILYLOXY)-1,3-BUTADIENE 95.00% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)OC(=CC=C)O[Si](C)(C)C

Technology Process of 1,1-Bis(trimethylsilyloxy)-1,3-butadiene

There total 4 articles about 1,1-Bis(trimethylsilyloxy)-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: 76.0%

chloro-trimethyl-silane (75-77-4) + crotonic acid trimethylsilyl ester (18269-64-2,88239-44-5) → 1,1-bis(trimethylsilyloxy)-buta-1,3-diene (87121-06-0)

Guidance literature:

With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; at -70 - 20 ℃; for 2.25h; Product distribution; effect of other reagents;

DOI:10.1016/0022-328X(88)80497-2

Reference yield: 9.0%

chloro-trimethyl-silane (75-77-4) + (crotonoyloxy)trimethylsilane (88239-44-5,18269-64-2) → 1,1-bis(trimethylsilyloxy)-buta-1,3-diene (87121-06-0)

Guidance literature:

With lithium diisopropyl amide; for 2h; Ambient temperature;

Reference yield:

chloro-trimethyl-silane (75-77-4) + 3-butenoictrimethylsilylester (13688-54-5) → 1,1-bis(trimethylsilyloxy)-buta-1,3-diene (87121-06-0)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction; 1.) THF, 0 deg C;

DOI:10.1016/S0022-328X(00)99191-5

upstream raw materials:

chloro-trimethyl-silane

(crotonoyloxy)trimethylsilane

3-butenoictrimethylsilylester

crotonic acid trimethylsilyl ester

Downstream raw materials:

(E)-5-Hydroxy-6-(2-methyl-[1,3]dioxolan-2-yl)-hex-2-enoic acid

6-ethyl-(+/-)-(E)-5-(5-chloro-2-iodo-phenylamino)-hex-2-endioic acid

(E)-4-phenylbut-2-enoic acid

Refernces

• 1、 Bellassoued, M.,Ennigrou, R.,Gaudemar, M.. "Bis(trimethylsiloxy)-1,1 butadiene-1,3 et trimethylsilyl-4 butene-2 oate de trimethylsilyle: preparations et reactions avec benzaldehyde". . p. 149 - 158. Retrieved 2007/10/02.
• 2、 Brady, William T.,Agho, Michael O.. "Halogenated Ketenes. 37. The Synthesis of Pyranones Utilizing the (4 + 2) Cycloaddition of Ketenes and Siloxy Dienes". . p. 501 - 506. Retrieved 2007/10/02.