tert-Butyl trimethylsilylacetate

Base Information

• Chemical Name: tert-Butyl trimethylsilylacetate
• CAS No.: 41108-81-0
• Molecular Formula: C9H20O2Si
• Molecular Weight: 188.342
• Hs Code.: 2931900090
• European Community (EC) Number: 255-222-2
• NSC Number: 237636
• DSSTox Substance ID: DTXSID00194054
• Nikkaji Number: J267.305C
• Wikidata: Q83066792
• Mol file: 41108-81-0.mol

Synonyms:41108-81-0;tert-Butyl trimethylsilylacetate;tert-butyl 2-trimethylsilylacetate;TERT-BUTYL (TRIMETHYLSILYL)ACETATE;TERT-BUTYL 2-(TRIMETHYLSILYL)ACETATE;1,1-Dimethylethyl trimethylsilylacetate;EINECS 255-222-2;C9H20O2Si;tert-butyl(trimethylsilyl)acetate;NSC237636;t-butyltrimethylsilylacetate;t-butyl trimethylsilylacetate;SCHEMBL9019859;tert-Butyl=trimethylsilylacetate;C9-H20-O2-Si;Acetic acid, (trimethylsilyl)-, 1,1-dimethylethyl ester;DTXSID00194054;TERT-BUTYLTRIMETHYLSILYLACETATE;NSC 237636;NSC-237636;FT-0719923;tert-Butyl trimethylsilylacetate, >=95.0% (GC)

Chemical Property of tert-Butyl trimethylsilylacetate

Chemical Property:

• Vapor Pressure: 1.06mmHg at 25°C
• Refractive Index: n20/D 1.417
• Boiling Point: 177 °C at 760 mmHg
• Flash Point: 54.2 °C
• PSA: 26.30000
• Density: 0.87 g/cm³
• LogP: 2.66630
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 188.123256411
• Heavy Atom Count: 12
• Complexity: 162

Purity/Quality:

tert-Butyl trimethylsilylacetate ^*data from reagent suppliers

Safty Information:

• Statements: 10
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C[Si](C)(C)C
• 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.

Technology Process of tert-Butyl trimethylsilylacetate

There total 4 articles about tert-Butyl trimethylsilylacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

chloro-trimethyl-silane (75-77-4) + acetic acid tert-butyl ester (540-88-5) → tert-butyl (trimethylsilyl)acetate (41108-81-0) + 1-tert-butoxy-1-(trimethylsiloxy)ethylene (93215-51-1)

Guidance literature:

acetic acid tert-butyl ester; With n-butyllithium; diisopropylamine; In tetrahydrofuran; at -78 ℃; for 3h; Inert atmosphere;

chloro-trimethyl-silane; at -35 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ja107314p

Reference yield:

trimetylsilylketene (4071-85-6) + tert-butyl alcohol (75-65-0) → tert-butyl (trimethylsilyl)acetate (41108-81-0)

Guidance literature:

With boron trifluoride diethyl etherate;

DOI:10.1021/jo00938a041

Reference yield:

chloro-trimethyl-silane (75-77-4) + acetic acid tert-butyl ester (540-88-5) → tert-butyl (trimethylsilyl)acetate (41108-81-0)

Guidance literature:

Multistep reaction; (i) cyclohexyl-isopropyl-amine

, (ii) /BRN= 1209232/;

upstream raw materials:

chloro-trimethyl-silane

acetic acid tert-butyl ester

trimetylsilylketene

tert-butyl alcohol

Downstream raw materials:

tert-butyl cinnamate

tert-butyl 5-phenylpenta-2,4-dienoate

3-Oxo-5-phenyl-penten-⁽⁴⁾-saeure-⁽¹⁾-tert.-butylester

tert-butyl 3-methyl-2-butenoate