4-TRIMETHYLSILYL-3-BUTYN-2-OL

4-TRIMETHYLSILYL-3-BUTYN-2-OL
  • CAS No.:6999-19-5

Important Notice

  1. This product is a chemical product/pharmaceutical intermediate. It is not a drug, an active pharmaceutical ingredient (API), or a pharmaceutical-grade material. It has not been granted a drug approval number or a Chemical Drug Substance Approval Notice, has not passed drug-related review and approval, and is not manufactured, tested, or released in accordance with pharmaceutical GMP.
  2. This product is intended solely for non-clinical research, process development, quality studies, further chemical processing, or chemical synthesis. It must not be used in drug-product manufacturing, clinical trials, clinical diagnosis, or administration to humans or animals, or be sold, used as an input, submitted for regulatory filing, or released as an API or pharmaceutical material.
  3. The purchaser must not use this product, or supply it to another party, for personal consumption, sports or fitness, weight loss, health supplements, food, or animal feed.
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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
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 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).
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

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