14595-77-8

Basic information

• Product Name: Silane,(phenylmethylene)bis[trimethyl
• Synonyms: Silane,(phenylmethylene)bis[trimethyl
• CAS NO: 14595-77-8
• Molecular Formula: C₁₃H₂₄Si₂
• Molecular Weight: 236.5
• Mol File: 14595-77-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 247°Cat760mmHg
• Flash Point: 85.3°C
• Appearance: /
• Density: 0.853g/cm³
• Vapor Pressure: 0.0412mmHg at 25°C
• Refractive Index: 1.463
• CAS DataBase Reference: Silane,(phenylmethylene)bis[trimethyl(CAS DataBase Reference)
• NIST Chemistry Reference: Silane,(phenylmethylene)bis[trimethyl(14595-77-8)
• EPA Substance Registry System: Silane,(phenylmethylene)bis[trimethyl(14595-77-8)

Safety Data

• Hazardous Substances Data: 14595-77-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H24Si2/c1-14(2,3)13(15(4,5)6)12-10-8-7-9-11-12/h7-11,13H,1-6H3

Upstream product

• 108-88-3 toluene 
• 14595-76-7 α,α.α-tris(trimethylsilyl)toluene 
• 75-77-4 chloro-trimethyl-silane 
• 98-07-7 Benzotrichlorid 
• 76241-25-3 α-bromo,α,α-bis(trimethylsilyl)toluene 
• 917-54-4 methyllithium 
• 109-72-8 n-butyllithium 
• 140-29-4 phenylacetonitrile 
• 5908-41-8 benzoyltrimethylsilane 
• 17903-41-2 phenyl(trimethylsilyl)methyl bromide 
• 770-09-2 benzyltrimethylsilane 
• 98-87-3 benzylidene dichloride 

Downstream Products

• 538-49-8 (Z)-2-(2-phenylethenyl)pyridine 
• 2039-70-5 (Z)-1-(2-naphthyl)-2-phenylethene 
• 74809-44-2 1,2,3-trimethoxy-5-[(1Z)-2-phenylethenyl]benzene 
• 2039-69-2 (Z)-4-styryl-1,1'-biphenyl 
• 4714-24-3 (Z)-1-(4-bromophenyl)-2-phenylethylene 
• 18138-87-9 cis-1-(2-Furyl)-2-phenylethylene 
• 143207-84-5 (Z)-1-(3,4-dimethoxyphenyl)-2-phenyl-ethene 
• 14301-11-2 (Z)-1-[4-N,N-(dimethylamino)phenyl]-2-phenylethene 
• 124562-04-5 (Z)-1-(2-phenylethenyl)-4-(trifluoromethyl)benzene 
• 1657-53-0 cis-4-methoxystilbene 
• 1657-46-1 cis-4-fluorostilbene 
• 14168-83-3 (Z)-1-(3-methoxyphenyl)-2-phenylethene 
• 19466-30-9 (E)-3-fluorostilbene 
• 19466-30-9 (Z)-1-fluoro-3-styrylbenzene 

Relevant articles and documents

Photochemistry of benzene

Irradiation of benzene (trisylbenzene) (1) gave mainly -p-trimethylsilylbenzene (2) and benzene (3); a free radical mechanism is proposed.

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General Ambient Temperature Benzylic Metalations Using Mixed-Metal Li/K-TMP Amide

Highly regioselective benzylic metalations in hydrocarbon solvent have been achieved at rt and 0 °C using a mixed-metal Li/K-TMP amide comprised of KOtBu, BuLi, and 2,2,6,6,-tetramethylpiperidine (TMP(H)). Mixing of KOtBu, BuLi, and TMP(H) in heptane gave a solution of the base mixture which when used in deuterium labeling experiments confirmed the requirement of the three reagent components for both reactivity and selectivity. The reaction protocol is operationally straightforward and found to be applicable to a broad range of substrates. Upon generation of the metalated products, they are reacted in heptane at ambient temperature in a variety of synthetically useful ways. Illustrated examples include generation of the benzyltrimethylsilanes and α,α-bis(trimethylsilyl)toluenes reagents, which are bench-stable surrogates of benzyl anions and α-silyl carbanions utilized for nucleophilic addition and Peterson olefination reactions. Direct C-C couplings mediated by 1,2-dibromoethane provided entries into bibenzyls and [2.2]metacyclophanes. Comparison of reaction outcomes with the same reactions carried out in THF at -78 °C showed no negative effects for conducting the reactions under these milder more user-friendly conditions.

Ion Pair Carbon Acidities of Some Silanes in Tetrahydrofuran

The relative solvent-separated ion pair (SSIP) lithium acidity (pKLi/THF) and contact ion pair (CIP) cesium acidity (pKCs/THF) were obtained for 9-fluorenyltrimethylsilane (1) (21.3, 21.6, respectively) and 9-fluorenyl-tert-butyldimethylsilane (2) (20.3, 20.6, respectively) in THF.Values for pKCs/THF were determined at 25 deg C for (p-biphenylylmethyl)-tert-butyldimethylsilane (3), 35.4, benzyltrimethylsilane (4), 37.5, α,α-bis(trimethylsilyl)toluene (5), 34.1, 2-(trimethylsilyl)-1,3-dithiane (6), 33.5, (trimethylsilyl)acetonitrile (7), 28.8, and tris(trimethylsilyl)methane (8), 36.8.Some thermodynamic parameters were determined by measurements at other temperatures, and some ionic acidities (pK(FI)) were determined by conductivity studies.Carbanion stabilization by these silyl substituents varies from about 1 to over 3 pK units in different systems. 9,9-Bis(trimethylsilyl)fluorene (9) was found to undergo silyl transfer on treatment with various carbanions, but this reaction is slower than proton transfer.