9,9-Dimethyl-9-silafluorene

Base Information

• Chemical Name: 9,9-Dimethyl-9-silafluorene
• CAS No.: 13688-68-1
• Molecular Formula: C14H14 Si
• Molecular Weight: 210.351
• NSC Number: 131592
• DSSTox Substance ID: DTXSID50159991
• Nikkaji Number: J47.161E
• Wikidata: Q63396251
• Mol file: 13688-68-1.mol

Synonyms:13688-68-1;9,9-Dimethyl-9-silafluorene;9,9-Dimethyl-9H-9-silafluorene;5,5-dimethylbenzo[b][1]benzosilole;5,5-Dimethyl-5H-dibenzo[b,d]silole;5H-Dibenzosilole, 5,5-dimethyl-;9,9-dimethyl-9H-dibenzo[b,d]silol;NSC131592;C14H14Si;DTXSID50159991;9,9-dimethyl-9H,9-silafluorene;9,9-dimethyl-9 h-9-silafluorene;9H-9-Silafluorene, 9,9-dimethyl-;MFCD00093801;AKOS016038621;5,5-dimethyl-5H-d ibenzo[b,d]silole;NSC 131592;NSC-131592;5,5-Dimethyl-5H-dibenzo[b,d]silole #;AS-60839;CS-0158127;D4308;T70232;Q63396251;8,8-DIMETHYL-8-SILATRICYCLO[7.4.0.0(2),?]TRIDECA-1(9),2,4,6,10,12-HEXAENE

Chemical Property of 9,9-Dimethyl-9-silafluorene

Chemical Property:

• Vapor Pressure: 0.00229mmHg at 25°C
• Melting Point: 60-61℃
• Boiling Point: 298.2°Cat760mmHg
• Flash Point: 120°C
• PSA: 0.00000
• Density: 1.05g/cm³
• LogP: 2.48960
• Storage Temp.: Sealed in dry,Room Temperature
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 210.086476981
• Heavy Atom Count: 15
• Complexity: 222

Purity/Quality:

98% ^*data from raw suppliers

9,9-Dimethyl-9H-9-silafluorene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si]1(C2=CC=CC=C2C3=CC=CC=C31)C

Technology Process of 9,9-Dimethyl-9-silafluorene

There total 58 articles about 9,9-Dimethyl-9-silafluorene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

2’-(trimethylsilyl)biphenyl-2-ylboronic acid (1160757-29-8) → 9,9-dimethyl-9-silafluorene (13688-68-1)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; chloro(1,5-cyclooctadiene)rhodium(I) dimer; In 1,4-dioxane; water; at 100 ℃; for 15h; oilbath; Inert atmosphere;

Reference yield: 94.1%

2,2'-dibromobiphenyl (13029-09-9) + dimethylsilicon dichloride (75-78-5,30107-43-8) → 9,9-dimethyl-9-silafluorene (13688-68-1)

Guidance literature:

2,2'-dibromobiphenyl; With n-butyllithium; In diethyl ether; hexane; at -78 - 20 ℃;

dimethylsilicon dichloride; In diethyl ether; hexane; at -78 - 20 ℃; Further stages.;

DOI:10.1021/ja011821m

Reference yield: 94.0%

1,1’-biphenyl-2-yl-dimethylsilane (31101-71-0) → 9,9-dimethyl-9-silafluorene (13688-68-1)

Guidance literature:

With norborn-2-ene; [Rh(coe)₂OH]₂; 3,4,5-MeO-MeO-BIPHEP; In tetrahydrofuran; at 80 ℃; for 1h;

upstream raw materials:

9-chloro-9-methyl-9-silafluorene

methyllithium

biphenyl-2,2'-diyl-bis-lithium

2,3-Dimethyl-2-butene

Downstream raw materials:

biphenyl

5-(2,4,6-tri-t-butylphenyl)dibenzo[b,d]borole

10,10'-diphenyl-9,9'-biphenanthrene

Refernces

• 1、 Chauvin, Yves,Marchal, Nathalie,Olivier, Helene,Saussine, Lucien. "Synthesis and characterization of novel covalent biphenyldiyl Sm(II) and Yb(II) complexes". . p. 93 - 97. Retrieved 1993.
• 2、 Sasaki, Hiroshi,Akioka, Ippei,Imoto, Hiroaki,Naka, Kensuke. "Arsenic-Bridged Silafluorene and Germafluorene as a Novel Class of Mixed-Heteroatom-Bridged Heterofluorenes". . p. 1390 - 1395. Retrieved 2021.
• 3、 Corey, Joyce Y.,Jonh, Christy S.,Ohmsted, Martha C.,Chang, Lihsueh S.. "TRICYCLIC HETEROCYCLES WITH BIFUNCTIONAL SILICON CENTERS". . p. 93 - 106. Retrieved 1986.
• 4、 Murai, Masahito,Matsumoto, Koji,Takeuchi, Yutaro,Takai, Kazuhiko. "Rhodium-Catalyzed Synthesis of Benzosilolometallocenes via the Dehydrogenative Silylation of C(sp2)-H Bonds". . p. 3102 - 3105. Retrieved 2015.
• 5、 Lillo, Victor J.,Gómez, Cecilia,Yus, Miguel. "2,2′-Dilithiobiphenyl by direct lithiation of biphenylene". . p. 2266 - 2269. Retrieved 2009.
• 6、 Xu, Yankun,Xu, Weiwei,Chen, Xinyang,Luo, Xiai,Lu, Haiyan,Zhang, Minghao,Yang, Xiumei,Deng, Guobo,Liang, Yun,Yang, Yuan. "Me3SiSiMe2(OnBu): a disilane reagent for the synthesis of diverse silacyclesviaBrook- And retro-Brook-type rearrangement". . p. 11756 - 11761. Retrieved 2021/09/22.