4-TRIMETHYLSILYL-3-BUTYN-2-OL

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;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 (+/-);4-TRIMETHYLSILYL-3-BUTYN-2-OL: TECH., 90%
CAS:6999-19-5
MF:C7H14OSi
MW:142.27
EINECS:
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
4-TRIMETHYLSILYL-3-BUTYN-2-OL Structure
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
Fp 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.
pka13.78±0.20(Predicted)
form clear liquid
color Colorless to Light orange to Yellow
Specific Gravity0.846
Hydrolytic Sensitivity4: no reaction with water under neutral conditions
BRN 1923632
CAS DataBase Reference6999-19-5(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 Information
ProviderLanguage
SigmaAldrich English
ALFA English
4-TRIMETHYLSILYL-3-BUTYN-2-OL Usage And Synthesis
Chemical PropertiesColorless liquid
Physical propertiesbp 83–85°C (13 mmHg).
UsesMore 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
Preparationracemic 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 materialspropargyl aldehyde
2-METHYL-4-TRIMETHYLSILYL-3-BUTYN-2-OL (+/-),(+/-) 2-METHYL-4-TRIMETHYLSILYL-3-BUTYN-2-OL,2-METHYL-4-TRIMETHYLSILYL-3-BUTYN-2-OL 3-METHYL-1-TRIMETHYLSILYL-1-PENTYN-3-OL (+/-) 1-PHENYL-3-(TERT-BUTYLDIMETHYLSILYL)-2-PROPYN-1-OL 2-HYDROXY-4-(TRIMETHYLSILYL)-3-BUTYNOIC ACID ETHYL ESTER 4-TRIMETHYLSILYL-3-BUTYN-1-OL 5-O-(P-CHLOROBENZOYL)-3-C-(2-TRIMETHYLSILYLETHYNYL)-D-RIBOFURANOSE 1,5-DI(TERT-BUTYLDIMETHYLSILYL)-1,4-PENTADIYN-3-OL 1-ISO-PROPYL-3-(TERT-BUTYLDIMETHYLSILYL)-2-PROPYN-1-OL 1-CYCLOHEXYL-3-(TERT-BUTYLDIMETHYLSILYL)-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-(Trimethylsilyl)-1-butyn-4-ol 1-ISO-PROPYL-3-(1,1,1-TRIMETHYLSILYL)-2-PROPYN-1-OL 1-(TRIMETHYLSILYL)-5-(TRIISOPROPYLSILYL)-1,4-PENTADIYN-3-OL 5-TRIMETHYLSILYL-1-PENTEN-4-YN-3-OL 3-Butyn-2-ol 1,5-DI(TRIISOPROPYLSILYL)-1,4-PENTADIYN-3-OL 1-(TERT-BUTYLDIMETHYLSILYL)-5-(TRIISOPROPYLSILYL)-1,4-PENTADIYN-3-OL

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