6651-43-0

Basic information

• Product Name: 1-TRIMETHYLSILOXY-1,3-BUTADIENE
• Synonyms: 1-TRIMETHYLSILYLOXY-1,3-BUTADIENE;1-TRIMETHYLSILOXY-1,3-BUTADIENE;1-(TRIMETHYLSILYLOXY)-1,3-BUTADIENE, 98% , MIXTURE OF ISOMERS;1-(Trimethylsilyloxy)-1,3-butadiene, mixture of isomers, 98%;Silane, (1,3-butadienyloxy)trimethyl-;(1,3-Butadienyloxy)trimethylsilane;1,3-Butadienyl(trimethylsilyl) ether;4-(Trimethylsiloxy)-1,3-butadiene
• CAS NO: 6651-43-0
• Molecular Formula: C₇H₁₄OSi
• Molecular Weight: 142.27
• Product Categories: Enol Ethers;Organic Building Blocks;Oxygen Compounds;Building Blocks;Chemical Synthesis;Enol Ethers;Organic Building Blocks;Oxygen Compounds
• Mol File: 6651-43-0.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 131 °C(lit.)
• Flash Point: 77 °F
• Appearance: /
• Density: 0.811 g/mL at 25 °C(lit.)
• Vapor Pressure: 9.43mmHg at 25°C
• Refractive Index: n20/D 1.448(lit.)
• Storage Temp.: 2-8°C
• Solubility: Sol most standard organic solvents.
• BRN: 1902024
• CAS DataBase Reference: 1-TRIMETHYLSILOXY-1,3-BUTADIENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-TRIMETHYLSILOXY-1,3-BUTADIENE(6651-43-0)
• EPA Substance Registry System: 1-TRIMETHYLSILOXY-1,3-BUTADIENE(6651-43-0)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 10-21
• TSCA: No
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 6651-43-0(Hazardous Substances Data)

Usage

Chemical Properties

clear light yellow liquid

Physical properties

bp 131 °C, bp 49.5 °C/25 mmHg; d 0.811 g cm?3.

Uses

Different sources of media describe the Uses of 6651-43-0 differently. You can refer to the following data:
1. 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.
2. 1-Trimethylsiloxy-1,3-butadiene is a diene used in the Diels-Alder reaction.
3. 1-(Trimethylsiloxy)-1,3-butadiene is commonly employed as diene in the Diels-Alder reaction.

General Description

Mechanism of Diels-Alder reaction between 1-(trimethylsiloxy)-1,3-butadiene and 4,6-dinitrobenzofuroxan has been studied using state-of-the-art computational methods.

Purification Methods

Purify it by fractional distillation and collect the fractions with the required 1H NMR. Store it under N2 — it is a flammable and moisture-sensitive liquid. [Caseau et al. Bull Soc Chim Fr 16658 1972, Belge Patent 670,769, Chem Abstr 65 5487d 1966.]

InChI:InChI=1/C7H14OSi/c1-5-6-7-8-9(2,3)4/h5-7H,1H2,2-4H3/b7-6+

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 123-73-9 trans-Crotonaldehyde 
• 123-73-9 crotonaldehyde 
• 646058-55-1 2,3-epoxy-3-trimethylsilyl-propan-1-ol 
• 163161-73-7 1,2-epoxy-1-trimethylsilyl-but-3-ene 
• 7319-38-2 3-butenal 

Downstream Products

• 4748-86-1 6-methylcyclohexa-1,3-diene-1-carbaldehyde 
• 89553-29-7 (E)-5-ethoxy-7-(p-methoxyphenyl)-2,6-heptadienal 
• 1121-54-6 1,3-Cyclohexadiene-1-carbaldehyde 
• 86778-39-4 2-<(trimethylsilyl)oxy>-3-cyclohexene-1-carboxaldehyde 
• 1137726-94-3 C₂₂H₂₆O₂Si 
• 1018454-69-7 (1S,2R,3S)-3-hydroxycyclohex-4-ene-1,2-dicarbonyl diazide 
• 89553-28-6 (E)-5-ethoxy-5-(p-methyoxyphenyl)-2-pentenal 

Relevant articles and documents

RAPID SYNTHESIS OF 2',3'-DIDEOXYCYTIDINE (ddC) FROM A SIMPLE ACHIRAL PRECURSOR

The antiviral nucleoside analogue, 2',3'-dideoxycytidine (ddC) 1, has been synthesized in nine steps and good overall yield from crotonaldehyde 2 via the chiral epoxy alcohol 4 prepared by a Sharpless oxidation.

Influence of the acetylenic substituent on the intramolecular carbolithiation of alkynes

The intramolecular carbolithiation of a series of propargylic ethers has been performed to evaluate the influence of the terminal substituent on the efficiency and the stereochemical outcome of the cyclization. Our results show that only 5-exo-dig cyclizations are observed, and dihydrobenzofurans are obtained exclusively. Depending on the nature of the terminal substituent, two cases can be considered. If the terminal substituent carried by the acetylenic carbon atom is itself a carbon atom, the cyclization can occur provided the terminal propargylic position bears a coordinating element and is at least disubstituted. When the cyclization occurs, it follows an anti-carbolithiation pathway and thus leads to the E isomer of the exocyclic double bond. Only in one case (Ph) was a mixture of the E and Z isomers of the resulting olefin recovered. The cyclization can also take place if the alkyne is directly substituted by S or Si, provided the cyclization conditions are tuned. In the case of the trimethylsilyl substituent, a syn-carbolithiation was observed. If the double bond is recovered, in most cases, in the exocyclic position, the products can aromatize directly for SPh-substituted substrate 24. Furthermore, in the two latter cases, when alkylation of the vinyllithium intermediate is performed, isomerization of the double bond seems instantaneous. Copyright

Stereocontrolled synthesis of α-trialkylsilyl-β,γ-unsaturated aldehydes via palladium (0) catalysis synthetic usefulness

The reaction of silicon substituted vinyloxiranes in the presence of catalytic amount of palladium (0) catalyst affords the title compounds. This new reaction proceeds smoothly, under very mild conditions and with complete chirality transfer. One-pot addition of selected organometallic nucleophiles to these aldehydes at very low temperature led to a highly selective preparation of the corresponding alcohols in very good yields. Influence of substituents on the silicon atom and of the ligands of palladium have been studied.