17869-76-0

Basic information

• Product Name: 2-TRIMETHYLSILYLOXY-3-BUTYNE
• Synonyms: 3-(TRIMETHYLSILOXY)-1-BUTYNE;3-(TRIMETHYLSILYLOXY)-1-BUTYNE;2-TRIMETHYLSILOXY-3-BUTYNE;2-TRIMETHYLSILYLOXY-3-BUTYNE;TIMTEC-BB SBB009059;(1-Methyl-2-propynyl)(trimethylsilyl) ether;(1-Methyl-2-propynyloxy)trimethylsilane;3-(Trimethylsiloxy)-3-methyl-1-propyne
• CAS NO: 17869-76-0
• Molecular Formula: C₇H₁₄OSi
• Molecular Weight: 142.27
• Mol File: 17869-76-0.mol

Chemical Properties

• Melting Point: 127-131 °C(lit.)
• Boiling Point: 116 °C
• Flash Point: 42 °F
• Appearance: clear pale yellow liquid
• Density: 0.818 g/mL at 25 °C(lit.)
• Vapor Pressure: 23.5mmHg at 25°C
• Refractive Index: n20/D 1.405(lit.)
• Storage Temp.: Refrigerator (+4°C)
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: 2-TRIMETHYLSILYLOXY-3-BUTYNE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-TRIMETHYLSILYLOXY-3-BUTYNE(17869-76-0)
• EPA Substance Registry System: 2-TRIMETHYLSILYLOXY-3-BUTYNE(17869-76-0)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• TSCA: No
• HazardClass: 3
• Hazardous Substances Data: 17869-76-0(Hazardous Substances Data)

Usage

Chemical Properties

Clear pale yellow liquid

InChI:InChI=1/C7H14OSi/c1-6-7(2)8-9(3,4)5/h1,7H,2-5H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 1067-35-2 triethyl-(1-methyl-prop-2-ynyloxy)-stannane 
• 2028-63-9 but-3-yn-2-ol 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 

Downstream Products

• 1345828-52-5 1,3,5-tris(1-(trimethylsilyloxy)ethyl)benzene 
• 1345828-54-7 1,2,4-tris(1-(trimethylsilyloxy)ethyl)benzene 
• 205172-19-6 (1R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-1-((E)-3-trimethylsilanyloxy-but-1-enyl)-cyclohexanol 
• 205172-20-9 (1S,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-1-((E)-3-trimethylsilanyloxy-but-1-enyl)-cyclohexanol 
• 103253-60-7 4-trimethylsilyl-3-butyn-2-ol 

Relevant articles and documents

[3,3]-Sigmatropic rearrangement of boronated allylcyanates: A new route to α-aminoboronate derivatives and trisubstituted tetrahydrofurans

[3,3]-Sigmatropic cyanate-isocyanate rearrangement provides a powerful tool for the preparation of α-isocyanato allylboronic esters, which can be further trapped with a variety of nucleophiles. Hydrogenation gave the corresponding α-aminoboronates derivatives while addition of aldehydes afforded homoallylic alcohols, (tetrahydrofuran-2-yl)carbamate, ether, or urea derivatives.

SN2′ boron-mediated Mitsunobu reactions - A new one-pot three-component synthesis of substituted enamides and enol benzoates

The conversion of (3-hydroxy-1-propen-1-yl)boronates to substituted enamides and enol benzoates is readily achieved in a one-pot procedure consisting of a regiocontrolled Mitsunobu reaction with convenient nucleophiles, followed by allylboration of aldehydes. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.

Nafion SAC-13: heterogeneous and reusable catalyst for the activation of HMDS for efficient and selective O-silylation reactions under solvent-free condition

Nafion SAC-13 effectively activates hexamethyldisilazane (HMDS) for the efficient and selective silylation of alcohols. Primary, secondary, and tertiary alcohols and phenols are efficiently converted to their corresponding silylethers in short reaction ti

Mild and efficient silylation of alcohols and phenols with HMDS using Bi(OTf)3 under solvent-free condition

A very efficient and mild silylation of alcohols and phenols with hexamethyldisilazane (HMDS) at rt is developed using Bi(OTf)3 as the catalyst. Primary, secondary and tertiary alcohols as well as phenols are excellently converted into correspo

Silylation of hydroxy groups with HMDS under microwave irradiation and solvent-free conditions

Phenols and alcohols are silylated with hexamethyldisilazane (HMDS) under microwave irradiation in solvent-free condition in good to excellent yields.

Total synthesis and biological activities of (+)- and (-)-boscialin and their 1'-epimers

Natural (-)-boscialin [(-)-1] has recently been described as one of the constituents of various medicinal plants. To obtain more material for investigations of its biological activities, we carried out the synthesis of (-)-1 and its isomers. Starting from the chiral building block 2, the key steps of the synthesis involved a regioselective reduction and a nucleophilic addition. The enantiomer of the natural product, (+)-boscialin [(+)-1], could be obtained via acid-catalyzed epimerization of hydroxyketone 4 to (+)-3. Starting the synthesis with (-)-3 led to (-)-boscialin [(-)-1] with the natural absolute configuration. In addition to (+)- and (-)-boscialin, the corresponding 1'-epimers (+)- and (-)-epiboscialin were also obtained. In vitro assays with (-)-boscialin [(-)-1] and its three stereoisomers were carried out to test for activity against microbes, parasites, and human fibroblasts. The investigations revealed activity against various microbes and against Trypanosoma brucei rhodesiense and also revealed cytotoxicity against human cancer cells.

Universal method for trimethylsilylation of acetylenic alcohols and glycols

A highly convenient universal method for trimethylsilylation of acetylenic alcohols and glycols via treatment by hexamethyldisilazane in the presence of benzoic acid sulphimide as a catalyst has been developed. The rate of trimethylsilylation of acetylenic alcohols is reduced from primary to secondary and to tertiary alcohols accordingly, as well as with the decreasing of hydroxyl nucleophylicity. The toxicity of trimethylsilyl acetylenic ethers, except 2-trimethylsiloxy-3-butyne, is much lower than that of original compounds.

TRIMETHYLSILYLATION OF ACETYLENIC ALCOHOLS AND GLYCOLS

A universal method for trimethylsilylation of acetylenic alcohols and glycols based on reaction with hexamethyldisilazane in the presence of catalytic quantities of saccharin was developed.The rate of trimethylsilylation of acetylenic alcohols decreases in the series primary-secondary-tertiary acetylenic alcohols.Trimethylsilylation of acetylenic alcohols, except dimethylethynylcarbinol, reduces their toxicity.

Preparation of 3-Substituted (E)-1-Alkenylboronic Esters

The conversion of functionalized 1-alkynes into E-1-alkenylboronic esters is achieved in a one-pot procedure consisting of hydroboration with dicyclohexylborane followed by oxidation with trimethylamine oxide.