2-(Trimethylsiloxy)-1,3-butadiene

Base Information

• Chemical Name: 2-(Trimethylsiloxy)-1,3-butadiene
• CAS No.: 38053-91-7
• Molecular Formula: C7H14OSi
• Molecular Weight: 142.273
• Hs Code.: 2931 90 00
• European Community (EC) Number: 609-512-4
• DSSTox Substance ID: DTXSID40339225
• Nikkaji Number: J150.100C
• Wikidata: Q72514415
• Mol file: 38053-91-7.mol

Synonyms:2-(trimethylsiloxy)-1,3-butadiene;38053-91-7;(buta-1,3-dien-2-yloxy)trimethylsilane;2-Trimethylsilyloxy-1,3-butadiene;2-Trimethylsiloxy-1,3-butadiene;buta-1,3-dien-2-yloxy(trimethyl)silane;2-(trimethylsilyloxy)-1,3-butadiene;Silane, trimethyl[(1-methylene-2-propenyl)oxy]-;2-(TRIMETHYLSILOXY)-1 3-BUTADIENE;2-Trimethylsilyloxybutadiene;2-trimethylsilyloxy-butadiene;SCHEMBL27209;LCZC2793;3-trimethylsiloxy-1,3-butadiene;AMY1244;DTXSID40339225;CS-M0480;Trimethyl(1-methyleneallyloxy)silane;MFCD00009852;2-(trimethylsilyl)oxy-1,3-butadiene;2-(Trimethylsilyloxy)buta-1,3-diene;AKOS009157338;2 -(trimethylsilyloxy)-1,3-butadiene;2-Trimethylsiloxy-1,3-butadiene, 98%;AS-19354;(buta-1,3-dien-2-yloxy)(trimethyl)silane;FT-0696756;T1469;1-Methylene-2-propenyl trimethylsilyl ether #;F14908;S18750;A823997;Q-200150;trimethyl[(1-methylideneprop-2-en-1-yl)oxy]silane

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

Chemical Property:

• Vapor Pressure: 14.9mmHg at 25°C
• Melting Point: <0°C
• Refractive Index: 1.4480
• Boiling Point: 125.1 °C at 760 mmHg
• Flash Point: 19.1 °C
• PSA: 9.23000
• Density: 0.808 g/cm³
• LogP: 2.53760
• Storage Temp.: Refrigerator
• 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: 121

Purity/Quality:

98%, ^*data from raw suppliers

2-(Trimethylsiloxy)-1,3-Butadiene ^*data from reagent suppliers

Safty Information:

• Statements: 11-23/24/25
• Safety Statements: 16-23-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)OC(=C)C=C
• General Description: 2-(Trimethylsiloxy)-1,3-butadiene is a reactive organosilicon compound used as a nucleophile in alkylation reactions, such as the synthesis of (σ-alkyl)cobalt(III) porphyrins, where its reactivity is influenced by solvent and porphyrin substituents. It also serves as a key diene component in hetero Diels-Alder reactions, enabling the efficient construction of functionalized piperidine intermediates, as demonstrated in the synthesis of racemic 2-aminomethyl-4-oxo-piperidine derivatives. Its utility lies in facilitating rapid and selective bond formation in complex organic frameworks.

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

There total 1 articles about 2-(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: 58.0%

chloro-trimethyl-silane (75-77-4) + methyl vinyl ketone (78-94-4,25038-87-3) → Hexamethyldisiloxane (107-46-0) + 2-trimethylsilyloxy-1,3-butadiene (38053-91-7)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 80 - 90 ℃; for 18h; Title compound not separated from byproducts;

Reference yield: 100.0%

2-trimethylsilyloxy-1,3-butadiene (38053-91-7) + methyl ethenyl sulphone (3680-02-2) → 4-(methylsulfonyl)cyclohexan-1-one (862129-72-4)

Guidance literature:

2-trimethylsilyloxy-1,3-butadiene; methyl ethenyl sulphone; With hydroquinone; In benzene; at -78 - 105 ℃; for 168h; Sealed tube; Inert atmosphere;

With hydrogenchloride; In acetone; at 0 ℃; for 0.25h;

Reference yield: 97.0%

2-trimethylsilyloxy-1,3-butadiene (38053-91-7) + but-2-enedioic acid tert-butyl ester ethyl ester (107679-25-4,100922-16-5) → 2-tert-butyl 1-ethyl (1,2-trans)-4-[(trimethylsilyl)oxy]cyclohex-4-ene-1,2-dicarboxylate

Guidance literature:

With bis(2,6-di-tert-butyl-4-methylphenoxide)methylaluminum; In dichloromethane; toluene; at -20 ℃; for 70h;

upstream raw materials:

chloro-trimethyl-silane

methyl vinyl ketone

Downstream raw materials:

diethyl cis-4-trimethylsilyloxy-4-cyclohexene-1,2-dicarboxylate

2-Trimethylsiloxy-4,4,5,5-tetracyano-cyclohexen

1-<(Trimethylsilyl)oxy>-4-acetyl-1-cyclohexene

dimethyl trans-4-trimethylsilyloxy-4-cyclohexene-1,2-dicarboxylate

Refernces

Facile alkylation of cobalt(III) porphyrins by organosilicon compounds

10.1021/om970174y

The research focuses on the facile alkylation of cobalt(III) porphyrins using organosilicon compounds as nucleophilic agents. The purpose of this study was to synthesize and isolate stable crystalline (σ-alkyl)cobalt(III) porphyrins by reacting halogenocobalt(III) porphyrins with silyl enol ethers and ketene silyl acetals. The conclusions drawn from the research indicate that the reaction yields and outcomes are influenced by factors such as the solvent used (with CH2Cl2 being more effective than MeOH), the substituents on the porphyrin periphery (meso-tetraphenylporphyrin being more reactive than octaethylporphyrin), and the axial halogeno ligand of cobalt(III) porphyrins (with F > Cl > Br ≈ I ≈ ClO4). The study also observed temperature-dependent dynamic behavior in one of the complexes, which was explained in terms of rotation around the C(R)-C() bond rather than σ-π rearrangement in the 4-oxobut-2-enyl ligand. Key chemicals used in the process include various organosilicon compounds, such as 1-phenyl-1-((trimethylsilyl)oxy)ethene, 1-ethoxy-1((trimethylsilyl)oxy)ethene, 2-((trimethylsilyl)oxy)1,3-butadiene, and 1-methoxy-1-((trimethylsilyl)oxy)-1-propene, as well as cobalt(III) porphyrin derivatives like TPPCoIII-Cl and OEPCoIIICl.

A facile synthesis of racemic 2-aminomethyl-4-oxo-piperidine intermediates

10.1081/SCC-120018941

The research focuses on the facile synthesis of racemic 2-aminomethyl-4-oxo-piperidine intermediates, which are crucial for constructing the piperidine nucleus found in various natural products and drug candidates. The synthesis involves a three-component hetero Diels-Alder reaction using an appropriately functionalized imine and 2-trimethylsiloxy-1,3-butadiene, which allows for the installation of protecting groups for both the piperidine and 2-position side chain nitrogens in a single step, and avoids a reduction step, thus providing rapid entry into the piperidine core structure. The experiments utilized various catalysts to optimize the reaction conditions, with aluminum chloride proving to be the most effective, yielding the desired product in 37%. The synthesized intermediates were then transformed into fully protected 2-aminomethyl-4-oxopiperidine compounds through additional reactions. The analyses included NMR spectroscopy and melting point determination to characterize the compounds, with the final products isolated through flash chromatography.