4-TRIMETHYLSILYL-3-BUTYN-2-OL

CAS NO.：6999-19-5
Empirical Formula: C7H14OSi
Molecular Weight: 142.27
MDL number: MFCD00190213
SAFETY DATA SHEET (SDS)
Update Date: 2023-04-23 13:52:06

What is 4-TRIMETHYLSILYL-3-BUTYN-2-OL?

Chemical properties

Colorless liquid

Physical properties

bp 83–85°C (13 mmHg).

The Uses of 4-TRIMETHYLSILYL-3-BUTYN-2-OL

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). Reactions of 4-TriMethylsilyl-3-butyn-2-ol

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.

Properties of 4-TRIMETHYLSILYL-3-BUTYN-2-OL

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)
Specific Gravity	0.846
color	Colorless to Light orange to Yellow
Hydrolytic Sensitivity	4: no reaction with water under neutral conditions
BRN	1923632
CAS DataBase Reference	6999-19-5(CAS DataBase Reference)

Safety information for 4-TRIMETHYLSILYL-3-BUTYN-2-OL

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.