1777-03-3

Basic information

• Product Name: (TRIETHYLSILYL)ACETYLENE
• Synonyms: Triethylsilylacetylene, min. 97%;(Triethylsilyl)acetylene,97%;Ethynyltriethylsilane Triethylethynylsilane;Triethylsilyl)acetylen;TRIETHYLETHYNYLSILANE;(TRIETHYLSILYL)ACETYLENE;ETHYNYLTRIETHYLSILANE;Triethylsilylacetylene,min.97%
• CAS NO: 1777-03-3
• Molecular Formula: C₈H₁₆Si
• Molecular Weight: 140.3
• EINECS: 1308068-626-2
• Product Categories: Si (Classes of Silicon Compounds);Si-(C)4 Compounds;organosilicon compound;Acetylenes;Ethynylsilanes;Functionalized Acetylenes
• Mol File: 1777-03-3.mol

Chemical Properties

• Melting Point: 95-97 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• Boiling Point: 136 °C
• Flash Point: 63 °F
• Appearance: colorless/liquid
• Density: 0.783 g/mL at 25 °C(lit.)
• Vapor Pressure: 7.75mmHg at 25°C
• Refractive Index: n20/D 1.433(lit.)
• Storage Temp.: Flammables area
• BRN: 1743814
• CAS DataBase Reference: (TRIETHYLSILYL)ACETYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: (TRIETHYLSILYL)ACETYLENE(1777-03-3)
• EPA Substance Registry System: (TRIETHYLSILYL)ACETYLENE(1777-03-3)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36/37/39
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• TSCA: No
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 1777-03-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(Triethylsilyl)acetylene is used as a synthetic building block for the creation of various organic compounds, particularly in the synthesis of triethylsilylethynyl anthradithiophenes (ADTs). These compounds have potential applications in the development of advanced materials and technologies.
Used in the Synthesis of Triethylsilylethynyl Anthradithiophenes:
(Triethylsilyl)acetylene is used as a key component in the synthesis of triethylsilylethynyl anthradithiophenes, such as:
1. 2,8-dimethyl-5,11-bis(triethylsilylethynyl)ADT
2. 2,8-diethyl-5,11-bis(triethylsilylethynyl)ADT
3. 2,8-dipropyl-5,11-bis(triethylsilylethynyl)ADT
These specific ADT compounds can be utilized in different industries, such as in the development of electronic devices, photovoltaic materials, or as components in the pharmaceutical industry. The use of (triethylsilyl)acetylene in these syntheses is crucial due to its unique chemical properties and reactivity, which enable the formation of complex molecular structures with potential applications in various fields.

InChI:InChI=1/C8H16Si/c1-5-9(6-2,7-3)8-4/h1H,6-8H2,2-4H3

Upstream product

• 1112-48-7 triethyl-bromo-silane 
• 4301-14-8 acetylenemagnesium bromide 
• 994-30-9 triethylsilyl chloride 
• 79-01-6 Trichloroethylene 
• 51283-55-7 2-Diethylamino-1-triethylsilanylethynyl-cyclohexanol 
• 74-86-2 acetylene 
• 14579-57-8 phosphoric acid tris-triethylsilanyl ester 
• 21692-58-0 [(1,2-epoxy-cyclohexyl)-ethynyl]-triethyl-silane 
• 461695-84-1 (hydrotris(3,5-diisopropylpyrazolyl)borato)CoCCSi(CH₂CH₃)3 
• 7732-18-5 water 
• 1066-26-8 sodium acetylide 

Downstream Products

• 38002-30-1 1,2,4,5-Tetrafluoro-3,6-bis-triethylsilanylethynyl-benzene 
• 39755-80-1 1-Triaethylsilyl-6-mesityl-hexa-1,3,5-triin 
• 39231-45-3 1-Triaethylsilyl-8-mesityl-octa-1,3,5,7-tetrain 
• 39231-47-5 1-Triaethylsilyl-10-mesityl-deca-1,3,5,7,9-pentain 
• 39230-02-9 1,4-Bis-[methyl-phenyl-((E)-2-triethylsilanyl-vinyl)-silanyl]-benzene 
• 17947-98-7 bis(triethylsilyl)acetylene 
• 32117-61-6 1-Triaethylsilyl-4-(p-nitrophenyl)-buta-1,3-diin 
• 155623-70-4 1-(phenylseleno)-2-(triethylsilyl)ethene 
• 191529-11-0 2,4,6-Tris-triethylsilanylethynyl-benzene-1,3,5-tricarbaldehyde 
• 188636-72-8 [4-Bromo-2-propoxy-5-(tetrahydro-pyran-2-yloxy)-phenylethynyl]-triethyl-silane 
• 223637-97-6 1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(3-hydroxy-prop-1-ynyl)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxymethyl)-5-triethylsilanylethynyl-1H-pyrimidine-2,4-dione 
• 191351-72-1 (R)-5-benzyloxy-4-hydroxy-1-triethylsilyl-1-pentyne 
• 2652-46-2 3-(triethylsilyl)prop-2-yn-1-ol 

Relevant articles and documents

Synthesis method for ethynyltriethylsilane

The invention relates to a synthesis method for ethynyltriethylsilane. The synthesis method comprises the steps that triethyl halogenosilane and acetylene metallide serve as raw materials, triethyl halogenosilane is added into an organic solution of the acetylene metallide, the mixture is heated to be subjected to a reflux reaction for 6-13 hours and then cooled to room temperature, ice water is added to carry out a quenching reaction, then pressure-reducing distillation is carried out, and fraction at the temperature of 42 DEG C-48 DEG C is collected and washed with water to remove inorganic salt, so that ethynyltriethylsilane is obtained. Compared with the prior art, the synthesis steps are simple, conditions are mild, the raw materials are wide in source, economic cost is low, controllability and repeatability are good, the yield can be up to 75% or more, and the method has a good application prospect.

Bulky trialkylsilyl acetylenes in the Cadiot-Chodkiewicz cross-coupling reaction

Bulky trialkylsilyl-protected alkynes such as triethylsilyl (TES), tert-butyldimethylsilyl (TBS), and tri-isopropylsilyl (TIPS) acetylenes underwent the Cadiot-Chodkiewicz cross-coupling reaction with different bromoalkynes to form a variety of synthetically useful unsymmetrical diynes in good yields. The diyne alcohol 10 was transformed regio- and stereoselectively into enynes by hydrotelluration, carbometalation, and reduction reactions.

Synthesis and characterization of coordinatively unsaturated alkynyl- and aryl-cobalt complexes with 15 valence electrons, TpiPr2Co-R, bearing the hydrotris(3,5-diisopropylpyrazolyl)borato ligand (TpiPr2)

Coordinatively unsaturated 15e alkynyl- (TpiPr2Co-C≡C-R) and aryl-cobalt complexes (TpiPr2Co-aryl) bearing the hydrotris(3,5-diisopropylpyrazolyl)borato ligand (TpiPr2) are prepared by dehydrative condensation of the hydroxo complex [TpiPr2Co(μ-OH)2]2 with 1-alkyne and arylation of the chloro complex TpiPr2Co-Cl with Grignard reagents, respectively. Spectroscopic and crystallographic analyses reveal the apparent C3-symmetrical tetrahedral structures with high-spin electronic configuration (S = 3/2), which should result from the property of the TpiPr2 ligand as a tetrahedral enforcer. The TpiPr2Co and hydrocarbyl fragments, are connected dominantly through σ-bonding interaction, and π-interaction including back-donation is not significant as revealed by EHMO calculations. The Co-C bonds are so polarized as to be readily protonated even by moisture to give the corresponding hydrocarbons, but the reactivity toward unsaturated hydrocarbons turns out to be sluggish. TpiPr2Co-C≡C-COOMe is found to catalyze a rare example of specific linear trimerization of methyl propiolate to give (E,E)-MeOOC(H)C=CH-CH=C(COOMe)-C≡C-COOMe.