13688-68-1

Basic information

• Product Name: 9,9-Dimethyl-9-silafluorene
• Synonyms: 9,9-Dimethyl-9-silafluorene;2,2'-(Dimethylsilylene)biphenyl;5,5-Dimethyl-5H-dibenzosilole;9,9-Dimethyl-9-sila-9H-fluorene;5,5-diMethyl-5H-dibenzo[b,d]silole;9,9-Dimethyl-9H-9-silafluorene;9,9-Dimethyldibenzosilole;9,9-Dimethylsilafluorene
• CAS NO: 13688-68-1
• Molecular Formula: C₁₄H₁₄Si
• Molecular Weight: 210.35
• Mol File: 13688-68-1.mol
• Article Data: 39

Chemical Properties

• Melting Point: 60-61℃
• Boiling Point: 298℃
• Flash Point: 120℃
• Appearance: /
• Density: 1.05
• Vapor Pressure: 0.00229mmHg at 25°C
• Refractive Index: 1.591
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 9,9-Dimethyl-9-silafluorene(CAS DataBase Reference)
• NIST Chemistry Reference: 9,9-Dimethyl-9-silafluorene(13688-68-1)
• EPA Substance Registry System: 9,9-Dimethyl-9-silafluorene(13688-68-1)

Safety Data

• Hazardous Substances Data: 13688-68-1(Hazardous Substances Data)

Usage

General Description

9,9-Dimethyl-9-silafluorene is a unique class of aromatic silicon compound that is typically utilized as a semiconductor in the chemical industry. The compound's structure comprises a silicon atom linked to a fluorene molecule, which results in intriguing photophysical characteristics. Its chemical formula is C23H22Si. The introduction of silicon to the organic system significantly enhances the emission intensity due to the lower energy gap than the traditional carbon system. This makes it instrumental in optoelectronics, specifically Organic Light Emitting Diodes (OLEDs). Moreover, 9,9-Dimethyl-9-silafluorene is non-toxic, exhibiting great potential for biocompatible imaging applications.

InChI:InChI=1/C14H14Si/c1-15(2)13-9-5-3-7-11(13)12-8-4-6-10-14(12)15/h3-10H,1-2H3

Upstream product

• 18090-00-1 9-chloro-9-methyl-9-silafluorene 
• 917-54-4 methyllithium 
• 16291-32-0 biphenyl-2,2'-diyl-bis-lithium 
• 563-79-1 2,3-Dimethyl-2-butene 
• 85590-07-4 dibenzo-1,1,2,2-tetramethyl-1,2-disilacyclohexa-3,5-diene 
• 93662-10-3 trisilacycloheptatriene 
• 760-32-7 diethylmethylsilane 
• 75-78-5 dimethylsilicon dichloride 
• 18030-58-5 9,9-dichloro-9-silafluorene 
• 75-16-1 methylmagnesium bromide 
• 178985-68-7 2-bromo-2'-trimethylsilylbiphenyl 
• 4028-23-3 Allylchlorodimethylsilane 
• 13029-09-9 2,2'-dibromobiphenyl 
• 1833-31-4 benzyl(chloro)dimethylsilane 

Downstream Products

• 602-15-3 9,10-diphenylphenanthrene 
• 21015-56-5 9,10-bis(4-chlorolphenyl)phenanthrene 
• 1274702-35-0 9-(4-bromophenyl)-10-phenylphenanthrene 
• 176955-47-8 9,10-bis-(4-bromophenyl)phenanthrene 
• 1288982-13-7 10,10'-diphenyl-9,9'-biphenanthrene 
• 92-52-4 biphenyl 
• 1013428-43-7 5-(2,4,6-tri-t-butylphenyl)dibenzo[b,d]borole 

Relevant articles and documents

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THE CHEMISTRY OF SILOLES. SYNTHESIS AND REACTIONS OF η6-CHROMIUM TRICARBONYL

η6-chromium tricarbonyl (II) was prepared by the reaction of 1-methyl-1-(trimethylsilyl)dibenzosilole with chromium hexacarbonyl.The reaction of II with methyllithium in THF gave η6-(1,1-dimethyldibenzosilacyclopentadiene)chromium tricarbonyl.Similar reaction of II with butyllithium, followed by oxidation, gave 1-butyl-1-methyldibenzosilole and 1,1-dibutyldibenzosilole, while reaction with (methyldiphenylsilyl)lithium under similar conditions afforded 1-methyl-4-(methyldiphenylsilyl)-1-(trimethylsilyl)dibenzosilole.

Synthesis and characterization of dibenzannulated silole dianions. The 1,1-dilithiosilafluorene and 1,1'-dilithiobis(silafluorene) dianions

Stirring of 1,1-dichloro-SiFl (1), (SiFl, silafluorene) in THF with excess lithium for 1 h gave a dark green solution of 1,1-dilithio-SiFl (2) in high yield. The dark red solution of the intermediate 1,1'-dilithio-(SiFl)2 (3) was also observed from this reaction within 10 min. Treatment of 2 with excess trimethylchlorosilane gave the 1,1-bis(trimethylsilyl)-SiFl derivative (4) in 95% yield. Treatment of the dark red solution of 3 and 2 with excess methyliodide gave the 1,1'-dimethyl-bis(SiFl) (5) and 1,1-dimethyl-SiFl (6) derivatives in a 4:1 ratio. The upfield locations of the 29Si resonances of dianions 2 and 3 (-1.09 ppm and -39.25 ppm, respectively) are consistent with π-electron localization on the silicon atoms. (C) 2000 Elsevier Science Ltd.

UNEXPECTED BEHAVIOR OF SILOLES TOWARD ORGANOLITHIUM REAGENTS

The reaction of 5-trimethylsilyl-5-methyldibenzosilole (I) with an excess of methyllithium in THF afforded 5,5-dimethyldibenzosilole (II) in quantitative yield.Treatment of I with an excess of butyllithium gave 5,5-dibutyldibenzosilole (III) quantitatively.Similar treatment of II with butyllithium in THF at room temperature gave III in almost quantitative yield, while treatment of III with methyllithium at reflux temperature gave II and 5-butyl-5-methyldibenzosilole in 10 and 40percent yield, in addition to 37percent of the starting III. 1,2,5-Tris(trimethylsilyl)-1-methyl-3,4-diphenylsilole also reacted with methyllithium to give 1,1-dimethyl-2,2,5-tris(trimethylsilyl)-3,4-diphenyl-1-silacyclopent-3-ene and 1,1-dimethyl-2,5-bis(trimethylsilyl)-3,4-diphenylsilole in 70 and 7percent yield.A five-coordinate silicon compound is proposed as an intermediate.

A Catalytic SEAr Approach to Dibenzosiloles Functionalized at Both Benzene Cores

A general procedure for the catalytic preparation of dibenzosiloles functionalized at one or both benzene rings starting from readily available ortho-silylated biphenyls is reported. This method provides rapid access to silole building blocks substituted with chlorine atoms at both phenylene groups, thereby allowing catalytic access to directly polymerizable dibenzosiloles. Moreover, it is shown that, despite the involvement of highly electrophilic intermediates, a considerable range of Lewis-basic, for example, oxygen- and nitrogen-containing, functional groups is tolerated. The mechanism of this intramolecular electrophilic aromatic substitution (SEAr) proceeds through a sulfur-stabilized silicon cation, generated catalytically from the hydrosilane precursor.

Synthesis of Dibenzosiloles through Electrocatalytic Sila-Friedel-Crafts Reaction

A novel electrocatalyzed method for the preparation of dibenzosiloles was developed through intramolecular C?H/Si?H dehydrogenative coupling strategy starting from biarylhydrosilanes. Both electro-donating and electro-withdrawing substitution groups were tolerated for this transformation, and the desired dibenzosilole products could be obtained in moderate to excellent yields. A sila-Friedel-Crafts reaction mechanism was proposed on the basis of previous literature and our controlled experiments. (Figure presented.).

Aromatic Metamorphosis of Thiophenes by Means of Desulfurative Dilithiation

A new mode of aromatic metamorphosis has been developed, which allows thiophenes and their benzo-fused derivatives to be converted to a variety of exotic heteroles. This transformation involves 1) the efficient generation of key 1,4-dianions by means of desulfurative dilithiation with lithium powder and 2) the subsequent trapping of the dianions with heteroatom electrophiles in a one-pot manner. Via the desulfurative dilithiation, the sulfur atoms of thiophenes are replaced also with a carbon–carbon double bond or a 1,2-phenylene for the construction of benzene rings.