|
|
| | TERT-BUTYL TRIMETHYLSILYLACETATE Basic information |
| Product Name: | TERT-BUTYL TRIMETHYLSILYLACETATE | | Synonyms: | TERT-BUTYL TRIMETHYLSILYLACETATE;1,1-dimethylethyl trimethylsilylacetate;t-Butyl Trimethylsilylacetate;(Trimethylsilyl)acetic acid 1,1-dimethylethyl ester;Einecs 255-222-2;tert-butyl 2-trimethylsilylacetate;Acetic acid, 2-(trimethylsilyl)-, 1,1-dimethylethyl ester | | CAS: | 41108-81-0 | | MF: | C9H20O2Si | | MW: | 188.34 | | EINECS: | 255-222-2 | | Product Categories: | C8 to C9;Carbonyl Compounds;Esters | | Mol File: | 41108-81-0.mol |  |
| | TERT-BUTYL TRIMETHYLSILYLACETATE Chemical Properties |
| Boiling point | 67 °C13 mm Hg(lit.) | | density | 0.86 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.417 | | Fp | 42 °C | | solubility | Chloroform (Soluble), Methanol (Soluble) | | form | Oil | | color | Colourless | | BRN | 1930256 |
| Risk Statements | 10 | | Safety Statements | 23-24/25 | | RIDADR | UN 3272 3/PG 3 | | WGK Germany | 3 | | F | 10-21 | | HazardClass | 3.2 | | PackingGroup | III |
| | TERT-BUTYL TRIMETHYLSILYLACETATE Usage And Synthesis |
| 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. |
| | TERT-BUTYL TRIMETHYLSILYLACETATE Preparation Products And Raw materials |
|