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4-TRIMETHYLSILYL-3-BUTYN-2-OL

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4-TRIMETHYLSILYL-3-BUTYN-2-OL Basic information

Product Name:
4-TRIMETHYLSILYL-3-BUTYN-2-OL
Synonyms:
  • 4-Trimethylsilyl-3-butynol, t
  • 4-(triMethylsilyl)but-3-yn-2-ol
  • 4-TRIMETHYLSILYL-3-BUTYN-2-OL, (+/-), 98%4-TRIMETHYLSILYL-3-BUTYN-2-OL, (+/-), 98%4-TRIMETHYLSILYL-3-BUTYN-2-OL, (+/-), 98%
  • TIMTEC-BB SBB009027
  • 1-TRIMETHYLSILYLBUT-1-YNE-3-OL
  • (+/-) 4-TRIMETHYLSILYL-3-BUTYN-2-OL
  • 4-TRIMETHYLSILYL-3-BUTYN-2-OL
  • 4-TRIMETHYLSILYL-3-BUTYN-2-OL (+/-)
CAS:
6999-19-5
MF:
C7H14OSi
MW:
142.27
Product Categories:
  • Acetylenes
  • Acetylenic Alcohols & Their Derivatives
  • Ethynylsilanes
  • Si (Classes of Silicon Compounds)
  • Si-(C)4 Compounds
  • Alkynes
  • Building Blocks
  • Chemical Synthesis
  • Internal
  • Organic Building Blocks
Mol File:
6999-19-5.mol
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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)
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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

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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 Preparation Products And Raw materials

Raw materials

4-TRIMETHYLSILYL-3-BUTYN-2-OLSupplier

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