82192-57-2

Basic information

• Product Name: 1-TRIISOPROPYLSILYL-1-PROPYNE
• Synonyms: 1-TRIISOPROPYLSILYL-1-PROPYNE;1-(TRIISOPROPYLSILYL)-PROPYNE;[(CH3)2CH]3SiC≡CCH3;Silane,tris(1-methylethyl)-1-propyn-1-yl-;1-(Triisopropylsilyl)-1-propyne 98%
• CAS NO: 82192-57-2
• Molecular Formula: C₁₂H₂₄Si
• Molecular Weight: 196.4
• Product Categories: Acetylenes;Ethynylsilanes;Functionalized Acetylenes;Si (Classes of Silicon Compounds);Si-(C)4 Compounds;Alkynes;Internal;Organic Building Blocks
• Mol File: 82192-57-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 70 °C / 1mmHg
• Flash Point: 160 °F
• Appearance: /
• Density: 0.82 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.36mmHg at 25°C
• Refractive Index: n20/D 1.4624(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 1-TRIISOPROPYLSILYL-1-PROPYNE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-TRIISOPROPYLSILYL-1-PROPYNE(82192-57-2)
• EPA Substance Registry System: 1-TRIISOPROPYLSILYL-1-PROPYNE(82192-57-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 82192-57-2(Hazardous Substances Data)

Usage

Uses

1-(Triisopropylsilyl)-1-propyne may be used in the synthesis of 1,14-diaza[5]helicene. It may be used in the synthesis of 1- and 2-aza[6]helicene, via [2+2+2] cobalt catalyzed trimerization strategy.

InChI:InChI=1/C12H24Si/c1-8-9-13(10(2)3,11(4)5)12(6)7/h10-12H,1-7H3

Upstream product

• 89343-06-6 tris-iso-propylsilyl acetylene 
• 5633-34-1 (benzoylmethylene)dimethylsulfurane 
• 13154-24-0 triisopropylsilyl chloride 
• 167275-06-1 3-(Triisopropylsilyl)propargyl ethyl carbonate 
• 74-99-7 prop-1-yne 
• 4529-04-8 1-propynyl lithium 
• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 
• 167275-08-3 Tetrahydro-2-<<3-(triisopropylsilyl)-2-propynyl>oxy>-2H-pyran 
• 104493-07-4 3-(triisopropylsilyl)propargyl alcohol 
• 284471-12-1 1-(triisopropylsilyl)-3-bromo-3-fluoropropyne 

Downstream Products

• 566912-07-0 4-bromo-3-[4-(triisopropylsilyl)-3-butynyl]phenyl methyl ether 
• 956103-50-7 [4-(2-iodo-4-methoxyphenyl)-1-butynyl](triisopropyl)silane 
• 1108207-52-8 [4-(2-iodo-3-methoxyphenyl)-1-butynyl](triisopropyl)silane 
• 1414295-75-2 5-methylene-1-phenyl-4-[tris(1-methylethyl)silyl]cyclopenta-1,3-diene 

Relevant articles and documents

Palladium-catalyzed methylation of alkynyl C(sp)-H bonds with dimethyl sulfonium ylides

A novel palladium-catalyzed methylation protocol for the synthesis of methyl-functionalized internal alkynes has been established. This methylation method is achieved through a C(sp)-C(sp3) bond formation process and represents a new synthetic application of sulfonium ylides.

An efficient preparation of TIPS - Halofluoropropyne and its application to the diastereoselective synthesis of propargylic fluorohydrins

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The Hydroboration of Silylacetylenes. The "Silyl-Markovnikov" Hydroboration Route to Pure (Z)-1-(2-Borylvinyl)silanes and β-Keto Silanes

The regiochemistry and stoichiometry of the hydroboration of simple 1-silylacetylenes with 9-borabicyclononane (9-BBN) was examined in detail. (Trimethylsilyl)acetylene (1c) results in only β-mono- and dihydroboration products, behavior common to nonsilylated terminal acetylenes.It is less reactive than its alkyl counterparts toward 9-BBN.It was also demonstrated that (1-trimethylsilyl)alkynes form (α-borylvinyl)silanes, similar to 1-alkynes, but they are much less reactive.Clean monohydroboration of these silylacetylenes is achieved only with a bulky (e.g. t-Bu) group at the C-2 position.However, compared to 1-alkynes, their dihydroboration products differ markedly, with the former giving 1,2-diboryl compounds, while the latter results in 1,1-diboryl adducts. (Triethyl- and tert-butyldimethylsilyl)propynes exhibit similar reactivity to that of the analogous trimethylsilyl derivative.The triisopropylsilyl group was found to not only completely suppress dihydroboration but also gave exclusively (Z)-(β-borylvinyl)silane adducts (9β).Oxidation of 9β produces the corresponding β-keto silanes (12) in excellent yields (i.e. 83-90percent).The bulky (triethyl- and tert-butyldimethylsilyl)propyne hydroboration products were found to be thermally unstable with the initially formed (α-borylvinyl)silanes isomerizing to α/β mixtures through their 1,2-diboryl diadducts (10).Heating 10 produces (3,3-diborylpropyl)silanes (14).Oxidation of the triethylsilyl compound 14b affords the corresponding γ-silylpropanol (15b).The complete characterization of the intermediate organoboranes by 75-MHz 13C NMR was achieved.A detailed discussion of the phenomena involved is presented.The observed results are attributed primarily to the additional steric effects imposed on an unsaturated system by a trialkylsilyl group when compared to a hydrogen atom at that position.