2916-76-9

Basic information

• Product Name: METHYL (TRIMETHYLSILYL)ACETATE
• Synonyms: METHYLTRIMETHYLSILICATE;METHYL (TRIMETHYLSILYL)ACETATE;2-(Trimethylsilyl)acetic acid methyl ester;2-[Dimethyl(methyl)silyl]acetic acid methyl ester;Trimethylsilylacetic acid methyl ester;Methyl (trimethylsilyl)acetate,98%;Methyl 2-(triMethylsilyl)acetate
• CAS NO: 2916-76-9
• Molecular Formula: C₆H₁₄O₂Si
• Molecular Weight: 146.26
• EINECS: 220-845-0
• Product Categories: C6 to C7;Carbonyl Compounds;Esters
• Mol File: 2916-76-9.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 38-39 °C13 mm Hg(lit.)
• Flash Point: 91 °F
• Appearance: clear colourless liquid
• Density: 0.891 g/mL at 25 °C(lit.)
• Vapor Pressure: 6.02mmHg at 25°C
• Refractive Index: n20/D 1.414(lit.)
• Storage Temp.: Flammables area
• BRN: 1098961
• CAS DataBase Reference: METHYL (TRIMETHYLSILYL)ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL (TRIMETHYLSILYL)ACETATE(2916-76-9)
• EPA Substance Registry System: METHYL (TRIMETHYLSILYL)ACETATE(2916-76-9)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 3
• F: 10-21
• TSCA: No
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 2916-76-9(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

Methyl 2-(Trimethylsilyl)acetate is a useful compound in the organic synthesis.

General Description

Methyl trimethylsilylacetate on reaction with lithium diisopropylamide in THF at -78°C yields methyl lithiotrimethylsilylacetate. It also undergoes Peterson olefination to yield mainly Z-isomers of steroid 17β-side chain methyl acrylates.

Purification Methods

Methyl trimethylsilylacetate [2916-76-9] M 146.3, b 65-68o/50mm, d 4 0.89. Dissolve it in Et2O, shaken with 1M HCl, wash with H2O, aqueous saturated NaHCO3, H2O again, and dry it (a precipitate may be formed in the NaHCO3 solution and should be drawn off and discarded). The solvent is distilled off, and the residue is fractionated through a good column. IR (CHCl3) max 1728cm
1 . [Fessenden & Fessenden J Org Chem 32 3535 1967, Matsuda et al. J Org Chem 45 237 1980, Beilstein 4 III 1855, 4 IV 3974 for Et ester.]

InChI:InChI=1/C6H14O2Si/c1-8-6(7)5-9(2,3)4/h5H2,1-4H3

Upstream product

• 67-56-1 methanol 
• 4071-85-6 trimetylsilylketene 
• 79-20-9 acetic acid methyl ester 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 94363-48-1 (dibromoboryl)(trimethylsily)ketene 
• 6990-27-8 bromobis(dimethylamino)borane 
• 32278-79-8 (ethoxyethynyl)trimethylgermane 
• 36850-80-3 [(1-methoxyvinyl)oxy]trimethylsilane 
• 1000-62-0 trimethylsilylethoxyacetylene 
• 155402-41-8 dimethoxyboryl trimethylsilyl ketene 
• 75-77-4 chloro-trimethyl-silane 
• 96-32-2 bromoacetic acid methyl ester 
• 922-69-0 1,1-dimethoxyethylene 
• 16029-98-4 trimethylsilyl iodide 

Downstream Products

• 74080-58-3 methyl 3α-hydroxy-2β-(benzyloxymethyl)-5-(carbomethoxymethylene)cyclopentane-1α-acetate 3-tetrahydropyran-2-yl ether 
• 82259-28-7 [(4S,5R)-4-Benzyloxymethyl-2-oxo-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-6a-yl]-trimethylsilanyl-acetic acid methyl ester 
• 118533-11-2 benzyl 2-deoxy-3,4-O-isopropylidene-2C<(E)-methoxycarbonylmethylene>-β-L-erythro-pentopyranoside 
• 118533-09-8 benzyl 2-deoxy-3,4-O-isopropylidene-2C<(Z)-methoxycarbonylmethylene>-β-L-erythro-pentopyranoside 
• 97522-09-3 methyl 2-(2-chloro-6-nitrophenyl)acetate 
• 177956-75-1 Methyl (Z)-2-(carboxyethyl)cyclohexylideneacetate 
• 6717-72-2 17β-((Trimethysilyl)oxy)estr-4-en-3-one 
• 139042-23-2 17β-((Trimethylsilyl)oxy)estr-1-en-3-one 
• 72049-87-7 ((S)-3-Oxo-cyclohexyl)-trimethylsilanyl-acetic acid methyl ester 
• 135253-30-4 Methyl <(R),(Z)-2-(t-butyldiphenylsiloxy)methyl-1-cyclobutylidene>acetate 
• 463-51-4 Ketene 
• 1825-61-2 Trimethylmethoxysilane 
• 3219-63-4 (trimethylsilyl)methanol 
• 2945-08-6 methyl (4-nitrophenyl)acetate 

Relevant articles and documents

Novel tocopherol compounds XI. Synthesis, bromination and oxidation reactions of 3-(5-tocopheryl)propionic acid

3-(5-Tocopheryl)propionic acid (γ-tocopherol-5-propionic acid, 13) has been synthesized by a multi-step sequence involving the hetero-Diels-Alder reaction between O-methyl-C,O-bis-(trimethylsilyl)ketene acetal (10) and the ortho-quinone methide of α-tocopherol (5) as the key step. The title compound is the first 5a-substituted tocopherol that shows an oxidation behavior largely similar to α-tocopherol.

Regio- and stereoselective generation of alkenylindium compounds from indium tribromide, alkynes, and ketene silyl acetals

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Preparation and reactivity of persistent and stable silyl-substituted bisketenes

2,3-Bis(trimethylsilyl)-1,3-butadiene-1,4-dione (1) is formed as the only product on thermolysis of 3,4-bis(trimethylsilyl)cyclobut-3-ene-1,2-dione (2), and the rate of ring opening of 2 is comparable to that of substituted cyclobutenes and cyclobutenones. Photolysis of 2 also forms 1, which reacts with ethanol in a stepwise fashion with faster addition of one ethanol molecule to give an isolable monoketene 18, which reacts in a further slower step to give succinate diesters, accompanied by desilylation. 2,3-Bis(tert-butyldimethylsilyl)-1,3-butadiene-1,4-dione (3), prepared analogously to 1, similarly adds one molecule of methanol to give the isolable monoketene 20, which then reacts to give dimethyl 2,3-bis(tert-butyldimethylsilyl)succinate (21) as the major product. The reaction of 1 with H2O is faster than with alcohols and forms (E)- and (Z)-2,3-bis(trimethylsilyl)succinic anhydrides (13) as the first observed products. The reactivity of 1 with different nucleophilic solvents is correlated by the Winstein-Grunwald equation and increases with both solvent ionizing power and solvent nucleophilicity.