763-13-3

Basic information

• Product Name: 3-Butenyltrimethylsilane
• Synonyms: 3-BUTENYLTRIMETHYLSILANE;4-(TRIMETHYLSILYL)BUT-1-ENE;4-(Trimethylsilyl)but-1-ene 97%;4-(Trimethylsilyl)-1-butene;4-Trimethylsilyl-1-butene
• CAS NO: 763-13-3
• Molecular Formula: C₇H₁₆Si
• Molecular Weight: 128.29
• Product Categories: Aliphatics
• Mol File: 763-13-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: <0°C
• Boiling Point: 112 °C
• Flash Point: 11.8 °C
• Appearance: /
• Density: 0.73
• Vapor Pressure: 25.9mmHg at 25°C
• Refractive Index: 1.4102
• CAS DataBase Reference: 3-Butenyltrimethylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Butenyltrimethylsilane(763-13-3)
• EPA Substance Registry System: 3-Butenyltrimethylsilane(763-13-3)

Safety Data

• Statements: 11
• Safety Statements: 9-16-33
• RIDADR: 1993
• TSCA: No
• Hazardous Substances Data: 763-13-3(Hazardous Substances Data)

Usage

General Description

3-Butenyltrimethylsilane is an organosilicon compound with the chemical formula C7H16Si. It is a colorless, flammable liquid with a pungent odor, and it is commonly used as a reagent in organic chemistry reactions. This chemical is known for its ability to undergo a variety of chemical transformations, such as hydrogenation, addition reactions, and cross-coupling reactions. It is commonly used as a reagent in the synthesis of various organic compounds and is often used in the production of pharmaceuticals, agrochemicals, and a variety of other fine chemicals. Additionally, 3-Butenyltrimethylsilane is also used as a building block in the synthesis of complex molecules and functionalized organosilicon compounds.

InChI:InChI=1/C7H16Si/c1-5-6-7-8(2,3)4/h5H,1,6-7H2,2-4H3

Upstream product

• 33558-80-4 (but-3-enyl)(chloromethyl)dimethylsilane 
• 16054-35-6 (E)-1,4-bis(trimethylsilyl)but-2-ene 

Downstream Products

• 6739-22-6 2-cyclopropyl-1-phenylethanone 
• 66557-23-1 3-Chlor-5-phenyl-pentan-5-on 
• 3240-29-7 1-Phenylpent-4-en-1-one 
• 75-77-4 chloro-trimethyl-silane 
• 87640-84-4 trans-1-(phenylsulfonyl)-4-(trimethylsilyl)-1-butene 
• 106-98-9 1-butylene 
• 34557-54-5 methane 
• 41866-81-3 trimethylsiloxide anion 
• 1627-98-1 1,1,3,3-tetramethyl-1,3-disiletane 
• 75-76-3 tetramethylsilane 
• 3439-38-1 trimethylsilylethane 
• 762-72-1 allyl-trimethyl-silane 
• 754-05-2 ethenyltrimethylsilane 
• 31594-49-7 1-Cyclopropyl-4-penten-1-one 

Relevant articles and documents

(E)-1-(Phenylsulfonyl)-4-(trimethylsilyl)-1-butene: An Advantageous Synthetic Equivalent for the 1-(1,3-Butadienyl) Anion and the 1,1-(1,3-Butadienyl) Dianion

The (E)-1-(arylsulfonyl)-4-(trimethylsilyl)-1-butenes 9, 25, and 26 are prepared by CuCl2-promoted and by photolytic additions of their precursor 1-arylsulfonyl chlorides and bromides to 4-(trimethylsilyl)-1-butene (14) and then dehydrohalogenation of the resulting 1-(arylsulfonyl)-2-halo-4-(trimethylsilyl)butanes 15a, 15b, 23a, and 23b with KOH, LDA, or n-BuLi. Silylbutene 14 is obtained from reaction of [(trimethylsilyl)methyl]magnesium chloride (16, X = Cl) and allyl bromide (17) and better by protiodesilylations of (E)- and (Z)-1,4-bis(trimethylsilyl)-2-butenes (20) with sulfuric or trifluoroacetic acids. (Arylsulfonyl)(trimethylsilyl)-1-butenes 9, 25, and 26 are converted efficiently by LDA or n-BuLi at -78°C to 1-(arylsulfonyl)-1-lithio-4-(trimethylsilyl)-1-butenes 10, 27a, and 27b, respectively. Reactions of 27a and 27b with deuterium oxide yield (E)-1-(4-chlorophenylsulfonyl)-1-deuterio-4-(trimethylsilyl)-1-butene (28a, 83%) and (E)-1-deuterio-1-(4-methylphenylsulfonyl)-4-(trimethylsilyl)-1-butene (28b, 89%), respectively. 1-Lithio derivatives 10, 27a, and 27b undergo benzylations by benzyl bromide in THF/HMPA with retention of the positions of their olefinic double bonds to give the (E)-2-(arylsulfonyl)-1-phenyl-5-(trimethylsilyl)-2-pentenes 29a, 29b, and 29c, respectively, in 84-90% yields. Of particular interest is that 29a-c are isomerized to their corresponding 2-(arylsulfonyl)-1-phenyl-5-(trimethylsilyl)-3-pentenes 30a-c, respectively, which then undergo conjugative eliminations of their arylsulfonyl and their trimethylsilyl groups to give (E)-5-phenyl-1,3-pentadiene (33) in 56-63% yields upon reactions with TBAF in THF at 25°C. Further, 27b reacts with 1,3-dichloropropane to form 1-chloro-4-(4-methylphenylsulfonyl)-7-(trimethylsilyl)-4-heptene (35) which is cyclized by n-BuLi to 1-(4-methylphenylsulfonyl)-1-(3-(trimethylsilyl)-1-propenyl)cyclobutane (37, 67%). Elimination of 37 by TBAF then gives allylenecyclobutane (34, n = 3, 84%) simply. This study thus reveals that 9, 25, and 26 have outstanding potential as 1-(1,3-butadienyl) anion (7) and 1,1-(1,3-butadienyl) dianion (8) synthons.

Effect of the Silicon Site on the Cyclization of Sila-5-hexen-1-yl Radicals. The Unusual Effect of α-Silicon

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