41108-81-0

Basic information

• Product Name: TERT-BUTYL TRIMETHYLSILYLACETATE
• Synonyms: TERT-BUTYL TRIMETHYLSILYLACETATE;1,1-dimethylethyl trimethylsilylacetate;(Trimethylsilyl)acetic acid 1,1-dimethylethyl ester;Einecs 255-222-2;t-Butyl Trimethylsilylacetate
• CAS NO: 41108-81-0
• Molecular Formula: C₉H₂₀O₂Si
• Molecular Weight: 188.34
• EINECS: 255-222-2
• Product Categories: C8 to C9;Carbonyl Compounds;Esters
• Mol File: 41108-81-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 67 °C13 mm Hg(lit.)
• Flash Point: 42 °C
• Appearance: /
• Density: 0.86 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.06mmHg at 25°C
• Refractive Index: n20/D 1.417
• BRN: 1930256
• CAS DataBase Reference: TERT-BUTYL TRIMETHYLSILYLACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL TRIMETHYLSILYLACETATE(41108-81-0)
• EPA Substance Registry System: TERT-BUTYL TRIMETHYLSILYLACETATE(41108-81-0)

Safety Data

• Statements: 10
• Safety Statements: 23-24/25
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 3
• F: 10-21
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 41108-81-0(Hazardous Substances Data)

Usage

Physical properties

air stable, colorless liquid; bp 67°C/13 mmHg; n20 D 1.4184; 1H NMR (CDCl3, 90 MHz) 0.13 (s, 9H), 1.45 (s, 9H), 1.80 (s, 2H); IR 1710 cm?1.

Uses

t-Butyl Trimethylsilylacetate is used to prepare lithium enolates which can be alkylated;can be alkenated with aldehydes and ketones;can be acylated;can be reacted with Group 14 halides.Most applications require initial formation of the enolate (1) (eq 1), which is obtained as a white solid suspended in THF, stable indefinitely at ?78°C.

Preparation

an advantage of t-butyl trimethylsilylacetate over its methyl and ethyl ester analogs is that it can be prepared by C-silylation of the lithium enolate of t-butyl acetate at ?78°C in THF (85–90% yield). Under the same conditions the enolates of methyl and ethyl acetate give primarily O-silylated products.The reagent has also been prepared by a rapid boron trifluoride etherate catalyzed reaction of trimethylsilylketene with t-butyl alcohol.

InChI:InChI=1/C9H20O2Si/c1-9(2,3)11-8(10)7-12(4,5)6/h7H2,1-6H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 540-88-5 acetic acid tert-butyl ester 
• 4071-85-6 trimetylsilylketene 
• 75-65-0 tert-butyl alcohol 

Downstream Products

• 53138-75-3 tert-butyl cyclohexylideneacetate 
• 14990-09-1 tert-butyl cinnamate 
• 120823-67-8 tert-butyl 5-phenylpenta-2,4-dienoate 
• 101054-40-4 tert-butyl 3-(2-methylphenyl)-4-methyl-2-pentenoate 
• 100994-05-6 (E)-3-o-Tolyl-pent-2-enoic acid tert-butyl ester 
• 119880-46-5 tert-butyl trans-1-(trimethylsilyl)-4-tert-butylcyclohexanecarboxylate 
• 119880-47-6 tert-butyl cis-1-(trimethylsilyl)-4-tert-butylcyclohexanecarboxylate 
• 78816-29-2 (Z)-3-Dimethoxymethyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-pent-2-enoic acid tert-butyl ester 
• 105426-86-6 (2E,6E)-3-Dimethoxymethyl-7-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6-dienoic acid tert-butyl ester 
• 105426-86-6 (2Z,6E)-3-Dimethoxymethyl-7-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6-dienoic acid tert-butyl ester 
• 208582-31-4 t-butyl 3-methyl-4-phenylthiohept-2(Z)-enoate 
• 208582-32-5 t-butyl 3-methyl-4-phenylthiohept-2(E)-enoate 
• 1361407-77-3 tert-butyl (Z)-3-[(4R,5R)-N-(tert-butoxycarbonyl)-4-(4-methoxybenzyl)-5-methyl-1,3-oxazolidin-2-on-5-yl]but-2-enoate 
• 1361407-66-0 tert-butyl (E)-3-[(4R,5R)-N-(tert-butoxycarbonyl)-4-(4-methoxybenzyl)-5-methyl-1,3-oxazolidin-2-on-5-yl]but-2-enoate 

Relevant articles and documents

Synthesis of phototrappable shape-shifting molecules for adaptive guest binding

We have designed and synthesized oligosubstituted bullvalenes 1 and 2 as adaptive molecules that can change their shapes in order to bind tightly to a suitable guest. By incorporation of a photolabile o-nitroveratryloxycarbonate (NVOC) group into bullvalenes 1 and 2, tightly binding species can be selectively isolated from a population of hundreds of interconverting structural isomers. Spontaneous strain-assisted Cope rearrangements allow these shape-shifting molecules to exist in a dynamic equilibrium of configurationally distinct valence isomers, as revealed by dynamic NMR and HPLC studies. When NVOC bullvalenes 1 and 2 were exposed to UV light, the cleavage of the NVOC group resulted in a mixture of static isomers of the corresponding bullvalone. Binding studies of NVOC bisporphyrin bullvalene 1 demonstrated that the dynamic isomeric equilibrium shifted in the presence of C60, favoring configurations with more favorable binding affinities. Irradiation of a mixture of 1 and C60 with UV light and isolation of the major static isomer yielded an isomer of bisporphyrin bullvalone with a binding affinity for C 60 that was ～2 times larger than that of the nonadapted isomer bisporphyrin bullvalone 41.