trans-1,2-Bis(tributylstannyl)ethene

Base Information

• Chemical Name: trans-1,2-Bis(tributylstannyl)ethene
• CAS No.: 14275-61-7
• Molecular Formula: C₂₆H₅₆Sn₂
• Molecular Weight: 606.151
• Hs Code.: 29312000
• European Community (EC) Number: 664-439-5
• DSSTox Substance ID: DTXSID00418823
• Mol file: 14275-61-7.mol

Synonyms:14275-61-7;trans-1,2-Bis(tributylstannyl)ethene;trans-1,2-bis(tri-n-butylstannyl)ethylene;(E)-1,2-Bis(tributylstannyl)ethene;tributyl-[(E)-2-tributylstannylethenyl]stannane;trans-1,2-Bis(tributylstannyl)ethylene;Stannane, (1E)-1,2-ethenediylbis[tributyl-;tributyl-[(Z)-2-tributylstannylethenyl]stannane;C26H56Sn2;Stannane, 1,2-ethenediylbis[tributyl-;PROSTAGLANDINF3ALPHA;Tributyl[(E)-2-(tributylstannyl)ethenyl]stannane;DTXSID00418823;MFCD01631299;AKOS015843032;GS-6197;trans-1,2-bis(tri-n-butylstannyl) ethylene;(E)-1,2-bis-(tri-n-butylstannyl)-ethylene;B1975;trans-1,2-Bis(tributylstannyl)ethene, 97%;F11312;tributyl[(1E)-2-(tributylstannyl)ethenyl]stannane;J-524981;Tributyl[(E)-2-(tributylstannyl)ethenyl]stannane #

Chemical Property of trans-1,2-Bis(tributylstannyl)ethene

Chemical Property:

• Vapor Pressure: 1.89E-09mmHg at 25°C
• Melting Point: 180-182℃
• Refractive Index: 1.5030
• Boiling Point: 494.8°Cat760mmHg
• Flash Point: 252.8°C
• PSA: 0.00000
• Density: g/cm³
• LogP: 10.31920
• Storage Temp.: Refrigerator
• Sensitive.: Air & Moisture Sensitive
• Water Solubility.: Miscible with terahydrofuran and dimethyl formamide. Slightly miscible with water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 20
• Exact Mass: 606.24201
• Heavy Atom Count: 28
• Complexity: 284

Purity/Quality:

98% ^*data from raw suppliers

trans-1,2-Bis(tributylstannyl)ethylene ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T,N
• Statements: 21-25-36/38-48/23/25-50/53
• Safety Statements: 36/37/39-45-61-60

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC[Sn](CCCC)(CCCC)C=C[Sn](CCCC)(CCCC)CCCC
• Isomeric SMILES: CCCC[Sn](CCCC)(CCCC)/C=C/[Sn](CCCC)(CCCC)CCCC
• Uses: trans-1,2-Bis(tri-n-butylstannyl)ethylene is used as an intermediate in organic synthesis. It is also employed in the synthesis of gamma, delta-alkynones.

Technology Process of trans-1,2-Bis(tributylstannyl)ethene

There total 10 articles about trans-1,2-Bis(tributylstannyl)ethene 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: 98.0%

tri-n-butyltin lithium (4226-01-1) + tributyltin chloride (1461-22-9) + copper(l) cyanide + acetylene (74-86-2,25067-58-7) → trans-1,2-bis-(tri-n-butylstannyl)ethylene (14275-61-7,15979-38-1,118855-16-6)

Guidance literature:

With methyllithium; In tetrahydrofuran; diethyl ether; at -20°C addn. of MeLi in Et2O to Bu3SnLi in THF, addn. of this mixt. to a suspn. of CuCN in THF, stirring for 15 min, cooling to -78°C, addn. of acetylene, after 30 min addn. of electrophile, after 15 to 30 min. warming to 0°C; after 1 h quenching of mixt. with NH4Cl;

DOI:10.1039/c39920000351

Reference yield: 98.0%

tri-n-butyltin lithium (4226-01-1) + tributyltin chloride (1461-22-9) + methyllithium (917-54-4) + copper(l) cyanide + acetylene (74-86-2,25067-58-7) → trans-1,2-bis-(tri-n-butylstannyl)ethylene (14275-61-7,15979-38-1,118855-16-6)

Guidance literature:

In tetrahydrofuran; hexane; a soln. of stannyllithium in THF and MeLi in hexane and CuCN is stirred at -78°C for 30 min, dropwise addn. of acetylene and tributyltin chloridee, the mixt. is stirred at this temp. for 1 h and then at 0°C for 3 h (under nitrogen); saturated aq. NH4Cl is added, extn. with Et2O, drying (MgSO4) and chromy., elem. anal.;

Reference yield: 90.0%

tributylethynyltin (994-89-8) + tri-n-butyl-tin hydride (688-73-3) → 1,2-bis(tributylstannyl)ethylene (14275-61-7,15979-38-1,118855-16-6)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); In toluene; at 90 ℃; for 17h; Inert atmosphere;

upstream raw materials:

tributylethynyltin

tri-n-butyl-tin hydride

dibutylstannane

tributylstannylethynylbenzene

Downstream raw materials:

(E)-1-[2-bromovinyl]-4-nitrobenzene

isopropyl (2E,4E)-13-iodo-11-hydroxy-3,7,11-trimethyl-2,4,12-tridecatrienoate

(2R,4E)-5-bromo-2-methoxy-1-(triphenylmethoxy)pent-4-ene

2,2'-diaminostilbene

Refernces

• 1、 -. "NOVEL HETEROCYCLIC COMPOUND, METHOD FOR PRODUCING INTERMEDIATE THEREFOR, AND USE THEREOF". Paragraph 0174. . Retrieved 2014/01/17.
• 2、 Barbero, Asuncion,Cuadrado, Purificacion,Fleming, Ian,Gonzalez, Ana M.,Pulido, Francisco J.. "The Stannyl-Cupration of Acetylenes and the Reaction of the Intermediate Cuprates with Electrophiles as a Synthesis of Substituted Vinylstannanes". . p. 351 - 353. Retrieved 2007/10/02.