58107-33-8

Basic information

• Product Name: 2-(trimethylsilyl)prop-2-enal
• Synonyms: 2-(Trimethylsilyl)acrylaldehyde; 2-Propenal, 2-(trimethylsilyl)-
• CAS NO: 58107-33-8
• Molecular Formula: C₆H₁₂OSi
• Molecular Weight: 128.2444
• Mol File: 58107-33-8.mol

Chemical Properties

• Boiling Point: 147.2°C at 760 mmHg
• Flash Point: 42.8°C
• Density: 0.824g/cm³
• Vapor Pressure: 4.47mmHg at 25°C
• Refractive Index: 1.407
• CAS DataBase Reference: 2-(trimethylsilyl)prop-2-enal(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(trimethylsilyl)prop-2-enal(58107-33-8)
• EPA Substance Registry System: 2-(trimethylsilyl)prop-2-enal(58107-33-8)

Safety Data

• Hazardous Substances Data: 58107-33-8(Hazardous Substances Data)

Usage

Type of compound

Aldehyde derivative

Functional group

Trimethylsilyl group attached to prop-2-enal (acrolein) molecule

Usage

Versatile intermediate in organic synthesis for the preparation of various organic compounds

Reactivity

Can undergo addition, condensation, and reduction reactions to form different functional groups and compounds

Application in medicinal chemistry

Synthesis of pharmaceuticals and bioactive molecules due to its reactivity and functional group transformations.

Upstream product

• 754-05-2 ethenyltrimethylsilane 
• 993-07-7 trimethylsilan 
• 5582-62-7 1-trimethylsilyloxy-2-propyne 
• 13683-41-5 1-bromo-1-(trimethylsilyl)ethene 
• 55287-89-3 2-(trimethylsilyl)prop-2-en-1-ol 
• 69519-67-1 2-trimethylsilyl-3,3-diethoxypropene 

Downstream Products

• 43209-86-5 3-trimethylsilyl-3-buten-2-one 
• 221299-15-6 C₂₅H₄₃NO₄Si₂ 
• 51666-96-7 1-phenyl-2-(trimethylsilyl)-2-propen-1-ol 
• 66374-47-8 3-trimethylsilanyl-but-3-en-2-ol 

Relevant articles and documents

Preparation and double Michael addition reactions of a synthetic equivalent of the Nazarov reagent

A synthetic equivalent of the Nazarov reagent, the silyl derivative 2, able to undergo base-catalyzed double Michael addition reactions with α,β-unsaturated carbonyl compounds has been developed. The new reagent satisfactorily reacts with unsaturated indo

An efficient synthesis of 2-trimethylsilyl-2-propenal, a useful three- carbon synthon

A formal efficient synthesis of 2-trimethylsilyl-2-propenal (2), a potentially useful synthetic reagent, is hereby described. The readily available α-bromovinyltrimethylsilane can be converted into 2- trimethylsilyl-2-propen-1-ol (1) via Grignard formation followed by addition of paraformaldehyde. The alcohol 1 can be oxidized using Jones reagent or PCC to yield the desired aldehyde 2.

1-Bromo-2-ethoxycyclolithium: A Synthetic Equivalent of 2-Lithio or 3-Lithiopropenal. Application to the Synthesis of Juvenile Hormone (JH-II), β-Sinensal, and Jasmonoids.

The ethyl vinyl ether-dibromocarbene adduct was lithiated with butyllithium at -95 deg C in tetrahydrofuran.The resulting lithium carbenoid 3 was allowed to react with various electrophiles to give 1-substituted trans-1-bromo-2-ethoxycyclopropanes (1) in good yields.The trans relationship of Br and OEt groups was found particularly pertinent to the ethanolysis of 1 producing 2-substituted propenal diethyl acetal derivatives.The reaction has been applied to 1-methoxycyclohexene-dibromocarbene adducts, giving rise hereby 2-substituted 2-cyclohepten-1-one dimethyl acetals under ring enlargement.T he transformation has been utilized in the synthesis of a homoterpenoid (JH-II) or a terpenoid (β-sinensal) structure by SN2' substitution of allylic acetates with lithium dimethylcuprate(I) or iron pentacarbonyl respectively.The reaction products of 3 with aldehydes are oxidized with dimethyl sulfoxide to give cyclopropyl ketones whose ethanolysis in the presence of boron trifluoride ether complex gives β-bromo γ-keto aldehyde acetals.Debromination followed by acidic hydrolysis produces γ-keto aldehydes serving as precursors of dihydrojasmone and cis-jasmone.

A CONVENIENT SYNTHETIC METHOD FOR 3-TRIMETHYLSILYLBUTENONE

Convenient synthetic method for 2-trimethylsilylbutenone from acrolein is presented.