5,5-dimethyl-5H-dibenzo[b,d]stannole

Base Information

• Chemical Name: 5,5-dimethyl-5H-dibenzo[b,d]stannole
• CAS No.: 5565-85-5
• Molecular Formula: C₁₄H₁₄Sn
• Molecular Weight: 300.975
• Mol file: 5565-85-5.mol

Synonyms:5,5-dimethyl-5H-dibenzo[b,d]stannole

Chemical Property of 5,5-dimethyl-5H-dibenzo[b,d]stannole

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5,5-dimethyl-5H-dibenzo[b,d]stannole

There total 3 articles about 5,5-dimethyl-5H-dibenzo[b,d]stannole 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: 58.0%

bis(2-bromo-2'-biphenyl)dimethylstannane (1236140-30-9) → (CH3)3Sn(C6H4C6H5) (14275-65-1) + 9-(2-biphenyl)-9-methyl-9-stannafluorene + 5,5-dimethyl-5H-dibenzo[b,d]stannole (5565-85-5)

Guidance literature:

With t-BuLi; In tetrahydrofuran; pentane; byproducts: LiBr, Me2CCH2; Ar; pentane soln. of BuLi (0.57 mmol) added to THF soln. of Sn compd. (0.14 mmol) at -78°C, mixt. warmed to room temp.; evapd., WCC(hexane/ethyl acetate=5/1), NMR;

DOI:10.1002/ejic.201000089

Reference yield: 12.0%

2-bromo-2'-(trimethylstannyl)biphenyl (436850-51-0) + magnesium (7439-95-4) → 2-bromomagnesio-2'-(trimethylstannyl)biphenyl (436850-57-6) + tetramethylstannane (594-27-4) + 5,5-dimethyl-5H-dibenzo[b,d]stannole (5565-85-5)

Guidance literature:

In tetrahydrofuran-d8; byproducts: 2,2'-bis(bromomagnesio)biphenyl, CH3MgBr; mixt. stirred in NMR tube at room temp.; after 1 h monitored by NMR; not isolated;

DOI:10.1021/om011083a

Reference yield:

dimethyltin dichloride (753-73-1) + biphenyl-2,2'-diyl-bis-lithium (16291-32-0) → dimethyltin oxide (2273-45-2) + 5,5-dimethyl-5H-dibenzo[b,d]stannole (5565-85-5)

Guidance literature:

In diethyl ether; under Ar, (C6H4Li)2 dissolved in abs. ether, slowly treated with Cl2SnMe2 portionwise at -20°C, stirred for 2 h at room temp., hydrolysed; filtered, product isolated by sublimation; elem. anal.;

DOI:10.1016/S0022-328X(00)87089-8

upstream raw materials:

dimethyltin dichloride

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

2-bromo-2'-(trimethylstannyl)biphenyl

magnesium

Downstream raw materials:

dibenzo[f,h]quinoline

9-benzhydrylidenefluorene

diphenanthro[9,10-b:9',10'-d]thiophene

triphenylene

Refernces

• 1、 Van Klink, Gerard P.M.,De Boer, Henricus J.R.,Schat, Gerrit,Akkerman, Otto S.,Bickelhaupt, Friedrich,Spek, Anthony L.. "Carbanions as intermediates in the formation of Grignard reagents". . p. 2119 - 2135. Retrieved 2008/10/08.