77494-35-0

Basic information

• Product Name: 1,3-Dimethyl-1-(trimethylsilyl)allene
• Synonyms: 1,3-Dimethyl-1-(trimethylsilyl)allene;2-(Trimethylsilyl)-2,3-pentadiene
• CAS NO: 77494-35-0
• Molecular Formula: C8H16Si
• Molecular Weight: 140.3
• Mol File: 77494-35-0.mol
• Article Data: 5

Chemical Properties

• Flash Point: -9℃
• Density: 0.746 g/mL at 25 °C
• Refractive Index: n20/D1.444
• CAS DataBase Reference: 1,3-Dimethyl-1-(trimethylsilyl)allene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dimethyl-1-(trimethylsilyl)allene(77494-35-0)
• EPA Substance Registry System: 1,3-Dimethyl-1-(trimethylsilyl)allene(77494-35-0)

Safety Data

• Hazardous Substances Data: 77494-35-0(Hazardous Substances Data)

Usage

Uses

Reactant for:Oxidative cyclization with chlorine to give chloro- and acetoxybenziodoxaboroles and a self-assembled tetrameric macrocyclic structurePreparation of allylic alcohols or enone derivatives using boronic acid as catalystCatalyst for:Preparation of acylsulfoximines via N-acylation of sulfoximines with aliphatic acidsDirect amide bond formationRegioselective preparation of substituted triazole derivatives via dipolar cycloaddition of unsaturated carboxylic acids with azides

Upstream product

• 676-58-4 methylmagnesium chloride 
• 375395-74-7 (S)-4-trimethylsilyl-3-butyn-2-yl mesylate 
• 149002-74-4 (2S)-4-trimethylsilylbut-3-yn-2-yl (1R)-camphorsulfonate 
• 1066-54-2 trimethylsilylacetylene 
• 6999-19-5 (S)-4-trimethylsilyl-3-butyn-2-ol 
• 18000-27-6 trimethylsilyllithium 
• 115884-54-3 pent-3-yn-2-yl N-phenylcarbamate 
• 75-16-1 methylmagnesium bromide 
• 86186-59-6 4-trimethylsilylbut-3-yn-2-yl methanesulphonate 
• 917-54-4 methyllithium 
• 103253-60-7 4-trimethylsilyl-3-butyn-2-ol 
• 57984-70-0 Pent-3-yn-2-ol 

Downstream Products

• 126696-59-1 (trimethylsilyl)(methyl)CCHCH(CH₃)B(C₆H₁₁)2 
• 126696-60-4 (trimethylsilyl)(methyl)CCHCH(CH₃)B(C₆H₁₁)2 
• 56240-42-7 (1E,3E)-2-methyl-1-phenyl-1,3-pentadiene 
• 126696-35-3 (1E,3Z)-2-methyl-1-phenyl-1,3-pentadiene 
• 56240-41-6 (1Z,3E)-2-methyl-1-phenyl-1,3-pentadiene 
• 126696-34-2 (1Z,3Z)-2-methyl-1-phenyl-1,3-pentadiene 
• 100184-52-9 (4R,6R)-2,4,6-Trimethyl-3-trimethylsilanyl-cyclohex-2-enone 
• 100184-52-9 (4R,6S)-2,4,6-Trimethyl-3-trimethylsilanyl-cyclohex-2-enone 

Relevant articles and documents

Crotylation versus propargylation: Two routes for the synthesis of the C13-C18 fragment of the antibiotic branimycin

The C13-C18 fragment 3 of the novel antibiotic branimycin was prepared along two highly stereocontrolled routes. The first one uses a standard Roush crotylation protocol, whereas the second one proceeds via an allenyl silane propargylation with unexpected stereochemical consequences, which are discussed in detail.

Accurate determination of the extent to which the SE2′ reactions of an allenylsilane are stereospecifically anti

The allenylsilane 1 has been prepared in high enantiomeric purity (98% e.e.); its SE2′ reaction with adamantyl chloride and isobutyraldehyde are stereospecifically anti to a very high degree (>99:1).

SCOPE AND STEREOCHEMICAL COURSE OF THE (TRIMETHYLSILYL)CYCLOPENTENE ANNULATION

A new, regiospecific annulation approach to highly substituted 5-membered carbocycles has been developed.The "TMS-cyclopentene annulation" involves the reaction of (trimethylsilyl)allenes with electrondeficient alkenes and alkynes in the presence of titanium tetrachloride to afford, in a single step, a functionalized and highly substituted TMS-cyclopentene derivative.Annulations employing α, β-unsaturated ketones proceed stereoselectively via suprafacial addition to the enone.Some useful transformations of the annulation products are also described; for example, treatment with K2CO3-methanol or HF in acetonitrile effects isomerization and desilylation yielding α, β-unsaturated ketones.