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4-TRIMETHYLSILYL-3-BUTYN-2-OL

CAS No.
6999-19-5
Chemical Name:
4-TRIMETHYLSILYL-3-BUTYN-2-OL
Synonyms
DK369;TIMTEC-BB SBB009027;4-TRIMETHYLSILYL-3-BUTYN-2-OL;4-(Trimethysilyl)-3-butyn-2-ol;1-TRIMETHYLSILYLBUT-1-YNE-3-OL;4-Trimethylsilyl-3-butynol, t;4-(triMethylsilyl)but-3-yn-2-ol;3-Butyn-2-ol, 4-(trimethylsilyl)-;(+/-) 4-TRIMETHYLSILYL-3-BUTYN-2-OL;4-TRIMETHYLSILYL-3-BUTYN-2-OL (+/-)
CBNumber:
CB5676325
Molecular Formula:
C7H14OSi
Molecular Weight:
142.27
MDL Number:
MFCD00190213
MOL File:
6999-19-5.mol
MSDS File:
SDS
Last updated:2023-04-23 13:52:06

4-TRIMETHYLSILYL-3-BUTYN-2-OL 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.
pka 13.78±0.20(Predicted)
form clear liquid
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

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P264-P271-P280-P302+P352-P305+P351+P338
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
NFPA 704
2
0 0

4-TRIMETHYLSILYL-3-BUTYN-2-OL price More Price(15)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 666955 4-(Trimethylsilyl)-3-butyn-2-ol 97% 6999-19-5 5g $45.3 2023-06-20 Buy
Sigma-Aldrich 666955 4-(Trimethylsilyl)-3-butyn-2-ol 97% 6999-19-5 25g $225 2023-01-07 Buy
TCI Chemical T1926 4-Trimethylsilyl-3-butyn-2-ol >97.0%(GC) 6999-19-5 5g $66 2024-03-01 Buy
Alfa Aesar L14815 4-Trimethylsilyl-3-butyn-2-ol, 97% 6999-19-5 5g $62.65 2024-03-01 Buy
Alfa Aesar L14815 4-Trimethylsilyl-3-butyn-2-ol, 97% 6999-19-5 25g $207.65 2024-03-01 Buy
Product number Packaging Price Buy
666955 5g $45.3 Buy
666955 25g $225 Buy
T1926 5g $66 Buy
L14815 5g $62.65 Buy
L14815 25g $207.65 Buy

4-TRIMETHYLSILYL-3-BUTYN-2-OL Chemical Properties,Uses,Production

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).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.

4-TRIMETHYLSILYL-3-BUTYN-2-OL Preparation Products And Raw materials

Raw materials

Preparation Products

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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% 4-(Trimethysilyl)-3-butyn-2-ol 4-Trimethylsilyl-3-butynol, tech. 90% 4-TRIMETHYLSILYL-3-BUTYN-2-OL, (+/-), 98%4-TRIMETHYLSILYL-3-BUTYN-2-OL, (+/-), 98%4-TRIMETHYLSILYL-3-BUTYN-2-OL, (+/-), 98% 3-Butyn-2-ol, 4-(trimethylsilyl)- DK369 6999-19-5 CH33SiCCCHOHCH3 Building Blocks Alkynes Organic Building Blocks Internal Ethynylsilanes Si-(C)4 Compounds Si (Classes of Silicon Compounds) Acetylenes Acetylenic Alcohols & Their Derivatives Acetylenes Acetylenic Alcohols & Their Derivatives Ethynylsilanes Si (Classes of Silicon Compounds) Si-(C)4 Compounds Alkynes Building Blocks Chemical Synthesis Internal Organic Building Blocks