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

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)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

RIDADR 

1993

WGK Germany 

3

TSCA 

No

HazardClass 

3

PackingGroup 

III

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-TRIMETHYLSILYL-3-BUTYN-2-OL Usage And Synthesis

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.

4-TRIMETHYLSILYL-3-BUTYN-2-OL(6999-19-5)Related Product Information

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• 4-TRIMETHYLSILYL-3-BUTYN-2-OL
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• 1-PHENYL-3-(TRIMETHYLSILYL)-2-PROPYN-1-&
• 5-TRIMETHYLSILYL-1-PENTEN-4-YN-3-OL
• 1-CYCLOHEXYL-3-(TERT-BUTYLDIMETHYLSILYL)-2-PROPYN-1-OL
• 2-HYDROXY-4-(TRIMETHYLSILYL)-3-BUTYNOIC ACID ETHYL ESTER
• 3-METHYL-1-TRIMETHYLSILYL-1-PENTYN-3-OL (+/-)
• 4-TRIMETHYLSILYL-3-BUTYN-1-OL
• 5-O-(P-CHLOROBENZOYL)-3-C-(2-TRIMETHYLSILYLETHYNYL)-D-RIBOFURANOSE
• 1-(Trimethylsilyl)-1-butyn-4-ol
• 1-ISO-PROPYL-3-(1,1,1-TRIMETHYLSILYL)-2-PROPYN-1-OL
• 1-CYCLOPROPYL-3-TRIMETHYLSILANYL-PROP-2-YN-1-OL
• 3-(1-CYCLOPROPYL-3-TRIMETHYLSILANYL-PROP-2-YNYLOXY)-4,5-DIMETHOXY-BENZALDEHYDE
• 1-PHENYL-3-(TERT-BUTYLDIMETHYLSILYL)-2-PROPYN-1-OL
• 1,5-DI(TERT-BUTYLDIMETHYLSILYL)-1,4-PENTADIYN-3-OL
• 1-(TERT-BUTYLDIMETHYLSILYL)-5-(TRIISOPROPYLSILYL)-1,4-PENTADIYN-3-OL