17891-65-5

Basic information

• Product Name: 2,3-BIS(TRIMETHYLSILYL)-1-PROPENE
• Synonyms: 2,3-BIS(TRIMETHYLSILYL)-1-PROPENE
• CAS NO: 17891-65-5
• Molecular Formula: C₉H₂₂Si₂
• Molecular Weight: 186.44
• Product Categories: Acyclic;Alkenes;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 17891-65-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 63 °C30 mm Hg(lit.)
• Flash Point: 99 °F
• Appearance: /
• Density: 0.779 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.439(lit.)
• CAS DataBase Reference: 2,3-BIS(TRIMETHYLSILYL)-1-PROPENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-BIS(TRIMETHYLSILYL)-1-PROPENE(17891-65-5)
• EPA Substance Registry System: 2,3-BIS(TRIMETHYLSILYL)-1-PROPENE(17891-65-5)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 17891-65-5(Hazardous Substances Data)

Usage

General Description

2,3-Bis(trimethylsilyl)-1-propene, also known as BTMSPE, is a chemical compound containing trimethylsilyl groups attached to a propene molecule. It is commonly used as a reagent in organic synthesis and in the production of silicon-containing materials. BTMSPE is a versatile compound that can participate in a variety of chemical reactions, including cross-coupling reactions and olefin metathesis. It is known for its stability and ability to undergo selective transformations, making it a valuable tool in the development of new synthetic pathways. Additionally, the trimethylsilyl groups provide protection for reactive functional groups, allowing for controlled manipulation of the molecule’s reactivity. Overall, 2,3-Bis(trimethylsilyl)-1-propene is an important building block in organic chemistry with potential applications in various fields.

Upstream product

• 18083-57-3 2,3-bis-trichlorosilanyl-propene 
• 56699-68-4 1,1-Bis(trimethylsilyl)cyclopropan 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 463-49-0 1,2-propanediene 
• 119649-70-6 1-[2-(tributylstannyl)allyl]phenoxide 
• 17955-46-3 trimethylsilyltributyltin 
• 75-77-4 chloro-trimethyl-silane 
• 81790-10-5 (2-bromoallyl)trimethylsilane 

Downstream Products

• 125315-71-1 (E)-1-Phenyl-5-trimethylsilanyl-hexa-1,5-dien-3-ol 
• 94225-18-0 1-Phenyl-3-trimethylsilanyl-but-3-en-1-one 
• 94225-11-3 1-phenyl-3-(trimethylsilyl)-3-buten-1-ol 
• 125315-78-8 3-Phenyl-5-trimethylsilanyl-hex-5-enoic acid methyl ester 
• 125315-77-7 2-(1-Phenyl-3-trimethylsilanyl-but-3-enyl)-malonic acid dimethyl ester 

Relevant articles and documents

GROUP VIII METAL PHOSPHINE COMPLEXES-CATALYZED ADDITION OF DISILANES TO ALLENIC COMPOUNDS. FORMATION OF NEW ORGANOSILICON COMPOUNDS CONTAINING BOTH VINYLSILANE AND ALLYLSILANE UNITS

Addition of chloromethyl- and methoxymethyldisilanes, X3-mMeMSiSiMenX3-n (X = Cl and OMe; m, n=0-2), as well as hexamethyldisilane, to allene and 1,2-butadiene in the presence of Pd(PPd3)4 catalyst gave regioselectively new functionalized organosilicon compounds, 2,3-bis(organosilyl)prop-1-enes and 2,3-bis(organosilyl)but-1-enes, respectively.Other Group VIII metal-phosphine complexes also affected the reaction, but results were found to be less satisfactory.Also, the reaction of an unsymmetrical disilane with an allenic compound gave only a single product; e.g., the addition of chloropentamethyldisilane to 1,2-butadiene in the presence of Pd(PPh3)4 gave CH2=C(SiMe3)CH(SiMe2Cl)Me in 93percent yield.

Double Silylation of Allene and Buta-1,2-diene: Formation of New Organosilicon Compounds containing both Vinylsilane and Allylsilane Units

Addition of chloromethyl- and methoxymethyldisilanes, as well as hexamethyldisilane, to allene and buta-1,2-diene in the presence of a Pd(PPh3)4 catalyst gave, regioselectively, new functionalized organosilicon compounds, 2,3-bis(organosilyl)prop-1-enes and 2,3-bis(organosilyl)but-1-enes, respectively.

Distannylations and silastannylations of in situ generated allenes

(Chemical Equation Presented) Propargylic ethers and acetates can be converted into distannylated alkenes in the presence of Bu3SnH and a Pd catalyst. The reaction proceeds via a stannylated allyl alcohol derivative, which undergoes elimination and subsequent dimetalation. If a molybdenum catalyst is used in the hydrostannylation step, and the stannylated intermediates can be reacted with other dimetallic compounds.