4-TRIMETHYLSILYL-3-BUTYN-2-OL
- Product Name
- 4-TRIMETHYLSILYL-3-BUTYN-2-OL
- CAS No.
- 6999-19-5
- Chemical Name
- 4-TRIMETHYLSILYL-3-BUTYN-2-OL
- Synonyms
- DK369;TIMTEC-BB SBB009027;4-TRIMETHYLSILYL-3-BUTYN-2-OL;4-(Trimethysilyl)-3-butyn-2-ol;1-TRIMETHYLSILYLBUT-1-YNE-3-OL;4-Trimethylsilyl-3-butynol, t;4-(triMethylsilyl)but-3-yn-2-ol;3-Butyn-2-ol, 4-(trimethylsilyl)-;4-TRIMETHYLSILYL-3-BUTYN-2-OL (+/-);(+/-) 4-TRIMETHYLSILYL-3-BUTYN-2-OL
- CBNumber
- CB5676325
- Molecular Formula
- C7H14OSi
- Formula Weight
- 142.27
- MOL File
- 6999-19-5.mol
4-TRIMETHYLSILYL-3-BUTYN-2-OL Property
- Boiling point:
- 76 °C
- Density
- 0.847 g/mL at 25 °C
- refractive index
- n 20/D 1.446
- Flash point:
- 143 °F
- storage temp.
- 2-8°C
- solubility
- highly soluble in all standard organic solvents (hexanes, toluene, CH2Cl2, EtOAc, alcohols, ethers). Partially soluble in water.
- form
- clear liquid
- pka
- 13.78±0.20(Predicted)
- color
- Colorless to Light orange to Yellow
- Specific Gravity
- 0.846
- Hydrolytic Sensitivity
- 4: no reaction with water under neutral conditions
- BRN
- 1923632
- CAS DataBase Reference
- 6999-19-5(CAS DataBase Reference)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 666955
- Product name
- 4-(Trimethylsilyl)-3-butyn-2-ol
- Purity
- 97%
- Packaging
- 5g
- Price
- $45.3
- Updated
- 2023/06/20
- Product number
- 666955
- Product name
- 4-(Trimethylsilyl)-3-butyn-2-ol
- Purity
- 97%
- Packaging
- 25g
- Price
- $225
- Updated
- 2023/01/07
- Product number
- T1926
- Product name
- 4-Trimethylsilyl-3-butyn-2-ol
- Purity
- >97.0%(GC)
- Packaging
- 5g
- Price
- $66
- Updated
- 2024/03/01
- Product number
- L14815
- Product name
- 4-Trimethylsilyl-3-butyn-2-ol, 97%
- Packaging
- 5g
- Price
- $62.65
- Updated
- 2024/03/01
- Product number
- L14815
- Product name
- 4-Trimethylsilyl-3-butyn-2-ol, 97%
- Packaging
- 25g
- Price
- $207.65
- Updated
- 2024/03/01
4-TRIMETHYLSILYL-3-BUTYN-2-OL Chemical Properties,Usage,Production
Chemical Properties
Colorless liquid
Physical properties
bp 83–85°C (13 mmHg).
Uses
More recently, Mulzer has reported use of the corresponding
allenylsilane derived from 4-TMS-3-butyn-2-ol for use in the synthesis
of the C13–C18 fragment of branimycin (eq 2).
Preparation
racemic 4-trimethylsilyl-3-butyn-2-ol can
be prepared by deprotonation with strong bases (BuLi, LDA,
Grignards reagents) of trimethylsilylacetylene followed
by addition to acetaldehyde.Deprotonation of 3-butyn-2-
ol followed by quenching with excess trimethylsilyl chloride
followed by concomitant hydrolysis of the trimethylsilyl ether
is generally the most straightforward route.Enzymatic reduction
of 4-TMS-3-butyn-2-one has also been used to prepare the
reagent using alcohol dehydrogenase.
Preparation of nonracemic 4-TMS-3-butyn-2-ol has been
accomplished by asymmetric addition of dimethylzinc to
acetaldehyde promoted by TADDOL or addition of a
trimethylsilylvinylsulfoxide to acetaldehyde followed by thermal
elimination of the sulfoxide.Asymmetric reduction of 4-
TMS-3-butyn-2-one using stoichiometric reducing reagents,
catalytic transfer hydrodrogenation,and enzymatic reduction
with isolated protein or whole cells afford the 4-TMS-3-butyn-
2-ol with varying degrees of enantioenrichment.Enzymatic resolution by esterification of the racemic alcohol is the method
of choice for the large-scale preparation.