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

Base Information

• Chemical Name: 1,1-Bis(trimethylsilyloxy)-3-methyl-1,3-butadiene
• CAS No.: 87121-05-9
• Molecular Formula: C₁₁H₂₄O₂Si₂
• Molecular Weight: 244.481
• DSSTox Substance ID: DTXSID40369941
• Nikkaji Number: J1.251.001B
• Mol file: 87121-05-9.mol

Synonyms:1,1-BIS(TRIMETHYLSILYLOXY)-3-METHYL-1,3-BUTADIENE;DTXSID40369941;Isopropenylketene di(trimethylsilyl)acetal;1,1-bis-(Trimethylsilyloxy)-3-methyl-1,3-butadiene;2,2,6,6-TETRAMETHYL-4-(2-METHYLPROP-2-EN-1-YLIDENE)-3,5-DIOXA-2,6-DISILAHEPTANE

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

Chemical Property:

• Boiling Point: 92-96 °C (13 mmHg)
• Storage Temp.: 0-6°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 244.13148307
• Heavy Atom Count: 15
• Complexity: 239

Purity/Quality:

98%min ^*data from raw suppliers

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

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Useful:

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

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

There total 4 articles about 1,1-Bis(trimethylsilyloxy)-3-methyl-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: 74.0%

chloro-trimethyl-silane (75-77-4) + trimethylsilyl 3,3-dimethylacrylate (25436-25-3) → bis(trimethylsilyl) vinyl ketene acetal (87121-05-9)

Guidance literature:

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

Reference yield:

chloro-trimethyl-silane (75-77-4) + 3-Methylbutenoic acid (541-47-9) → bis(trimethylsilyl) vinyl ketene acetal (87121-05-9)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; hexane; 1.) -78 deg C to RT, 2.) RT, 1.5 h;

DOI:10.1016/S0040-4020(01)81434-4

Reference yield:

3-Methylbutenoic acid (541-47-9) → bis(trimethylsilyl) vinyl ketene acetal (87121-05-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / hexamethyldisilazan/pyridine / tetrahydrofuran / 17 h / Ambient temperature

2: 74 percent / LDA / 2 h / Ambient temperature

With pyridine; 1,1,1,3,3,3-hexamethyl-disilazane; lithium diisopropyl amide; In tetrahydrofuran;

upstream raw materials:

chloro-trimethyl-silane

3-Methylbutenoic acid

lithium hexamethyldisilazane

trimethylsilyl 3,3-dimethylacrylate

Downstream raw materials:

4-chloro-3',6'-dihydro-4'-methylspiro-1,6'-dione

6-Benzhydrylidene-4-methyl-5,6-dihydro-pyran-2-one

3-methyl-2-phenl-but-3-enoic acid

6-Benzhydryl-4-methyl-pyran-2-one