77086-38-5

Basic information

• Product Name: 1-(TERT-BUTYLDIMETHYLSILYLOXY)-1-
• Synonyms: 1-(TERT-BUTYLDIMETHYLSILYLOXY)-1-;Silane, (1,1-diMethylethyl)[(1-Methoxyethenyl)oxy]diMethyl-;1-(tert-ButyldiMethylsilyloxy)-1-Methoxyethane;1-(tert-ButyldiMethylsilyloxy)-1-Methoxyethene 97%;1-Methoxy-1-[(tert-butyldimethylsilyl)oxy]ethylene;Ketene methyl t-butyldimethylsilyl acetal;tert-Butyl[(1-methoxyvinyl)oxy]dimethylsilane;tert-butyl-(1-methoxyethenoxy)-dimethylsilane
• CAS NO: 77086-38-5
• Molecular Formula: C₉H₂₀O₂Si
• Molecular Weight: 188.341
• Product Categories: Enol Ethers;Organic Building Blocks;Oxygen Compounds
• Mol File: 77086-38-5.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 62 °C9 mm Hg(lit.)
• Flash Point: 125 °F
• Appearance: /
• Density: 0.863 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.01mmHg at 25°C
• Refractive Index: n20/D 1.429(lit.)
• CAS DataBase Reference: 1-(TERT-BUTYLDIMETHYLSILYLOXY)-1-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(TERT-BUTYLDIMETHYLSILYLOXY)-1-(77086-38-5)
• EPA Substance Registry System: 1-(TERT-BUTYLDIMETHYLSILYLOXY)-1-(77086-38-5)

Safety Data

• Statements: 10
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 77086-38-5(Hazardous Substances Data)

Usage

General Description

1-(tert-butyldimethylsilyloxy)-1-propene is a chemical compound that contains a tert-butyldimethylsilyloxy group and a propene group. It is commonly used as a building block in organic synthesis and serves as a protecting group for alcohols in chemical reactions. The tert-butyldimethylsilyloxy group provides steric hindrance and stability to the alcohol, allowing for selective manipulation of other functional groups within the molecule. 1-(TERT-BUTYLDIMETHYLSILYLOXY)-1- is often employed in the synthesis of complex organic molecules and pharmaceutical intermediates due to its versatile reactivity and ease of removal under mild conditions. Its use in synthetic chemistry has led to advancements in the development of new drugs and materials.

InChI:InChI=1/C9H20O2Si/c1-8(10-5)11-12(6,7)9(2,3)4/h1H2,2-7H3

Upstream product

• 125606-54-4 (2S)-2-(phenylsulfinylmethyl)butanamide 
• 109-72-8 n-butyllithium 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 108-18-9 diisopropylamine 
• 79-20-9 acetic acid methyl ester 

Downstream Products

• 84784-61-2 2-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-3-phenylselanyl-propionitrile 
• 144293-60-7 (3-Methyl-cyclohex-2-enyl)-acetic acid methyl ester 
• 144293-61-8 (1-Methyl-cyclohex-2-enyl)-acetic acid methyl ester 
• 5661-55-2 4-phenylazetidin-2-one 
• 113107-70-3 1-tert-butyldimethylsiloxy-2-propynyl phenyl sulfide 
• 113107-71-4 methyl 3-(phenylthio)-4-pentynoate 
• 94718-56-6 2-tert-butyldimethylsiloxy-2-(phenylthio)cyclohexanone 
• 113107-67-8 1-tert-butyldimethylsiloxy-3-methoxycarbonylmethyl-3-(phenylsulfinyl)cyclohexene 
• 94718-55-5 2-tert-butyldimethylsiloxy-2-(phenylthio)acetophenone 
• 56631-64-2 2-(phenylsulfanyl)-2-cyclooctanene 
• 94718-57-7 2-tert-butyldimethylsiloxy-2-(phenylthio)cyclooctanone 
• 90696-17-6 3-Methyl-4-phenylsulfanyl-butyric acid ethyl ester 
• 137528-08-6 (3S)-3-<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-1-(2,4-dimethoxybenzyl)-4-(phenylthio)azetidin-2-one 
• 148409-86-3 methyl (3S,4S)-4-benzyloxy-3-(tert-butyldimethylsilyloxy)pentanoate 

Relevant articles and documents

Nucleophilic Addition to Nitrones Using a Flow Microreactor

Nucleophilic addition reactions of soft carbon nucleophiles to nitrones in a flow microreactor are reported for the first time. Under microflow conditions at 30 to 0 °C, a range of nitrones can be efficiently transformed into the corresponding oxyiminium ions by reaction with either acyl halides or trialkylsilyl triflates. These can subsequently undergo the addition of nucleophiles including allyltributylstannane, ketene methyl tert-butyldimethylsilyl acetal, and N-silyl ketene imines to afford the corresponding adducts in high yields; such reactions at a similar temperature under batch conditions resulted in lower yields because of undesired side reactions.

Triflimide: An Overlooked High-Performance Catalyst of the Mukaiyama Aldol Reaction of Silyl Ketene Acetals with Ketones

The Mukaiyama aldol reaction is a widely applied carbon–carbon bond forming reaction. However, despite numerous well-established methods using aldehydes as acceptors, only few examples exist with ketones. Here we report a highly practical catalytic approach to this transformation, namely, the triflimide catalyzed Mukaiyama aldol reaction of silyl ketene acetals with ketones. This method exhibits a broad substrate scope, is very rapid, tolerates functionalized substrates, and requires only parts-per-million catalyst loadings with preparative scale reactions up to hundreds of grams in excellent purity (>99 %).

Chiral helical oligotriazoles: New class of anion-binding catalysts for the asymmetric dearomatization of electron-deficient N -heteroarenes

Helical chirality and selective anion-binding processes are key strategies used in nature to promote highly enantioselective chemical reactions. Although enormous efforts have been made to develop simple helical chiral systems and thus open new possibilities in asymmetric catalysis and synthesis, the efficient use of synthetic oligo- and polymeric helical chiral catalysts is still very challenging and rather unusual. In this work, structural unique chiral oligotriazoles have been developed as C-H bond-based anion-binding catalysts for the asymmetric dearomatization of N-heteroarenes. These rotational flexible catalysts adopt a reinforced chiral helical conformation upon binding to a chloride anion, allowing high levels of chirality transfer via a close chiral anion-pair complex with a preformed ionic substrate. This methodology offers a straightforward and potent entry to the synthesis of chiral (bioactive)heterocycles with added synthetic value from simple and abundant heteroarenes.