Stannane, 1,3-phenylenebis[trimethyl-

Base Information

• Chemical Name: Stannane, 1,3-phenylenebis[trimethyl-
• CAS No.: 65844-89-5
• Molecular Formula: C12H22Sn2
• Molecular Weight: 403.727
• Mol file: 65844-89-5.mol

Synonyms:

Chemical Property of Stannane, 1,3-phenylenebis[trimethyl-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Stannane, 1,3-phenylenebis[trimethyl-

There total 9 articles about Stannane, 1,3-phenylenebis[trimethyl- 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: 89.0%

trimethylstannylsodium (16643-09-7) + 1,3,5-trisbromobenzene (626-39-1) → 1,3,5-tris(trimethylstannyl)benzene (197141-36-9) + 1,3-bis-(trimethylstannyl)benzene (65844-89-5)

Guidance literature:

In further solvent(s); (N2); solvent tetraglyme; soln. of Me3SnNa added dropwise (1.5 h, 0°C); stirred (4 h, 0°C); warmed to room temp. overnight; satd. NH4Cl soln. added; extd. (diethyl ether); washed (water); dried (MgSO4); evapd. (vac.); recrystd. (CH3OH); sublimed (95°C, 4 mm Hg); elem. anal.;

DOI:10.1016/S0022-328X(99)00471-4

Reference yield: 69.0%

1,3,5-trisbromobenzene (626-39-1) + trimethyltin(IV)chloride (1066-45-1) → trimethyl(phenyl)stannane (934-56-5) + 1,3,5-tris(trimethylstannyl)benzene (197141-36-9) + 1,3-bis-(trimethylstannyl)benzene (65844-89-5)

Guidance literature:

With lithium 4,4′-di-tert-butylbiphenylide; In tetrahydrofuran; diethyl ether; Ar-atmosphere; addn. of LiDBB (THF, 7 equivs.) to Et2O soln. of tribromobenzene at -75°C, warming to -40°C within 5 min, addn. of excess Me3SnCl, stirring for 15 min, addn of MeOD, warming to room temp.; addn. of hexamethylbenzene, extn. (H2O:Et2O), sepn. of org. layer, washing (H2O, brine), drying (MgSO4), filtration, evapn.; GC/MS;

DOI:10.1021/om9705620

Reference yield: 49.0%

1,3-dibromobenzene (108-36-1) + trimethyltin(IV)chloride (1066-45-1) → trimethyl(phenyl)stannane (934-56-5) + 1,3-bis-(trimethylstannyl)benzene (65844-89-5)

Guidance literature:

With magnesium; ethylene dibromide; In tetrahydrofuran; inert atmosphere, activation of Mg with ethylene bromide in THF, addn. of THF and a further portion of ethylene bromide, reflux, addn. of soln. of dibromobenzene and soln. of (CH3)3SnCl to the boiling soln., reflux (6 h); saturated aq. NH4Cl, extn. (Et2O), washing of extracts (water), drying (Na2SO4), concn. (reduced pressure), distillation (92-95°C, 0.1 Torr);

DOI:10.1002/(SICI)1099-0682(199806)1998:6<761::AID-EJIC761>3.0.CO;2-1

upstream raw materials:

trimethyltin(IV)chloride

1,3-dilithiobenzene

1,3-dibromobenzene

trimethylstannylsodium

Downstream raw materials:

1,3-diphenylbenzene

1,3-bis(diethylgallyl)benzene

1,3-bis(chloromercurio)benzene

1-chloroadamantane

Refernces

• 1、 Rot, Nicolette,De Kanter, Frans J.J.,Bickelhaupt, Friedrich,Smeets, Wilberth J.J.,Spek, Anthony L.. "Synthesis of 1,3,5-tri- and 1,2,4,5-tetrasubstituted tin and mercury derivatives of benzene. Crystal structure of 1,3,5-tris(chloromercurio)benzene". . p. 369 - 379. Retrieved 2007/10/03.
• 2、 Rot, Nicolette,Bickelhaupt, Friedrich. "Formation of 1,3,5-trilithiobenzene and its conversion to the corresponding magnesium, mercury, and tin derivatives". . p. 5027 - 5031. Retrieved 2008/10/08.