1833-53-0

Basic information

• Product Name: ISOPROPENYLOXYTRIMETHYLSILANE
• Synonyms: (CH3)3SiOC(CH3)=CH2;Silane, trimethyl[(1-methylethenyl)oxy]-;trimethyl[(1-methylethenyl)oxy]-silan;trimethyl[(1-methylethenyl)oxy]-Silane;TRIMETHYLISOPROPENYLOXYSILANE;ACETONE ENOL TRIMETHYLSILYL ETHER;2-(TRIMETHYLSILYLOXY)PROPENE;2-(TRIMETHYLSILOXY)PROPENE
• CAS NO: 1833-53-0
• Molecular Formula: C₆H₁₄OSi
• Molecular Weight: 130.26
• EINECS: 217-393-1
• Product Categories: Monoalkoxysilanes;Si (Classes of Silicon Compounds);Silicon Compounds (for Synthesis);Si-O Compounds;Synthetic Organic Chemistry;Vinylsilanes, Allylsilanes;Building Blocks;Chemical Synthesis;Enol Ethers;Organic Building Blocks;Oxygen Compounds
• Mol File: 1833-53-0.mol
• Article Data: 17

Chemical Properties

• Melting Point: 40-45 °C
• Boiling Point: 93-95 °C
• Flash Point: 45 °F
• Appearance: clear colorless liquid
• Density: 0.78 g/mL at 25 °C(lit.)
• Vapor Pressure: 57.4mmHg at 25°C
• Refractive Index: n20/D 1.395(lit.)
• Storage Temp.: −20°C
• BRN: 1849023
• CAS DataBase Reference: ISOPROPENYLOXYTRIMETHYLSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: ISOPROPENYLOXYTRIMETHYLSILANE(1833-53-0)
• EPA Substance Registry System: ISOPROPENYLOXYTRIMETHYLSILANE(1833-53-0)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36-37/39
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• F: 10-21
• TSCA: Yes
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 1833-53-0(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

General Description

(Isopropenyloxy)trimethylsilane is an enol silyl ether. It participates as nucleophile in Lewis acid-promoted C3-nucleophile substitution of tetracyclic bromide. It is reported to participate in the total synthesis of (±)-powelline. It is reported to participate in dityltin bis(triflate) catalyzed Michael addition reaction of enol silyl ethers.

Purification Methods

Purify it by fractional distillation using a very efficient column at atmospheric pressure. It usually contains 5% of hexamethyldisiloxalane which boils at 99-101o, but is generally non-reactive and need not be removed. [Hauser & Hance J Am Chem Soc 71 5091 1952.] It has been distilled under N2 through a 15cm column packed with glass helices. Fraction b 99-104o is further purified by gas chromatography through a Carbowax column (Autoprep A 700) at a column temperature of 87o, and has a retention time of 9.5minutes. [Krüger & Rochow J Organomet Chem 1 476 1963-4.]

InChI:InChI=1/C6H14OSi/c1-6(2)7-8(3,4)5/h1H2,2-5H3

Upstream product

• 2295-12-7 1,1-dimethylsilacyclobutane 
• 67-64-1 acetone 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 75-77-4 chloro-trimethyl-silane 
• 16029-98-4 trimethylsilyl iodide 
• 28483-52-5 tripropylstannyl-acetone 
• 75-36-5 acetyl chloride 
• 1450-18-6 1,1,1-trimethyl-2,2,2-triphenyldisilane 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 17955-46-3 trimethylsilyltributyltin 
• 598-31-2 1-bromoacetone 
• 78-93-3 butanone 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 63698-90-8 C₁₅H₄₂N₃OPSi₄ 

Downstream Products

• 26205-43-6 O-trimethylsilylacetol 
• 109-09-1 2-chloropyridine 
• 6302-02-9 2-acetonylpyridine 
• 372-48-5 2-fluoropyridine 
• 82959-19-1 α-heptadeca-fluorooctylacetone 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 84796-82-7 methyl 4-oxo-2-(phenylthio)pentanoate 
• 10542-87-7 (E)-4-(2-methoxyphenyl)but-3-en-2-one 
• 110080-20-1 4,4-bis-(4-dimethylamino-phenyl)-butan-2-one 
• 205679-08-9 2-Oxo-propane-1-sulfonic acid ((R)-1-phenyl-ethyl)-amide 

Relevant articles and documents

Tandem 1,4-addition reactions with benzene and alkylated benzenes promoted by pentaammineosmium(II)

Electrophiles such as dimethoxymethane and 3-penten-2-one react with the complex [Os(NH3)5-(η2-benzene)]2+ in the presence of triflic acid to form metastable benzenium intermediates. These benzenium intermediates further react with carbon nucleophiles including silyl ketene acetals, (silyloxy)alkenes, and phenyllithium in an overall tandem 1,4-addition sequence. The metal fragment controls the relative stereo- and regiochemistry for both electrophilic and nucleophilic addition steps. Upon oxidative demetalation with silver triflate, cis-1,4 cyclohexadienes are formed in yields ranging from 16 to 82%. This methodology can also be used to dearomatize toluene and ortho- and meta-xylene with unexpectedly high regio- and stereocontrol.

Three-Component Coupling of Acyl Fluorides, Silyl Enol Ethers, and Alkynes by P(III)/P(V) Catalysis

We report herein on the phosphine-catalyzed hydrovinylation reaction by three-component coupling of acyl fluorides, silyl enol ethers, and alkynoates. The key to the success of the reaction is the formal transmetalation between pentacoordinate P(V) species (i.e., fluorophosphorane) and a silyl enol ether, which allows for C-C bond formation between the polarity-mismatched sites. The bond formation that cannot be attained even by transition metal catalysis is accomplished by a P(III)/P(V) manifold.

Enantioselective N-Heterocyclic Carbene Catalyzed Synthesis of Functionalized Indenes

An enantioselective NHC (N-heterocyclic carbene) catalyzed synthesis of indenes from bifunctional α,β-unsaturated acyl fluorides and TMS enol ethers has been discovered. The reaction has broad generality (31 examples) and proceeds with high levels of enantioselectivity (most >92:8 er). Mechanistically the reaction likely occurs via a Michael/β-lactonization/decarboxylation sequence. Derivatization studies and limitations are discussed.