(Z)-Tri-n-butyl(1-propenyl)tin

Base Information

• Chemical Name: (Z)-Tri-n-butyl(1-propenyl)tin
• CAS No.: 105494-65-3
• Molecular Formula: C₁₅H₃₂Sn
• Molecular Weight: 331.129
• Hs Code.: 29310099
• European Community (EC) Number: 677-902-1,677-906-3
• Mol file: 105494-65-3.mol

Synonyms:(Z)-Tri-n-butyl(1-propenyl)tin;66680-84-0;(Z)-Tributyl(prop-1-en-1-yl)stannane;CIS-TRI-N-BUTYL(1-PROPENYL)TIN;Tri-n-butyl(1-propenyl)tin, cis + trans;tri-n-butylpropenyltin;tributyl(1Z)-prop-1-en-1-ylstannane;tributyl-propenyl-stannane;tributyl(1-propenyl) tin;cis-2-Methylvinyltributyltin;Z-1-propenyltributyl stannane;(E)-tributyl(1-propenyl)tin;tributyl(prop-1-enyl)stannane;Z-1-propenyl tri-n-butylstannane;Z-1-propenyl-tri-n-butylstannane;cis-1-Propenyltri-n-butylstannane;cis-Tri->N-butyl(1-propenyl)tin;FJXYMVBFBYAWDR-UHFFFAOYSA-N;(E)-tributyl(prop-1-enyl)stannane;(Z)-tributyl(prop-1-enyl)stannane;105494-65-3;MFCD03425868;tributyl-[(Z)-prop-1-enyl]stannane;AKOS015843022;(E)-tributyl(prop-1-en-1-yl)stannane;(Z)-tributyl(prop-1-en-1-yl) stannane;(Z)-tributyl (prop-1-en-1-yl) stannane;cis-Tri-N-butyl(1-propenyl)tin, AldrichCPR;CS-0106370;D76643

Chemical Property of (Z)-Tri-n-butyl(1-propenyl)tin

Chemical Property:

• Vapor Pressure: 0.00087mmHg at 25°C
• Refractive Index: 1.4820
• Boiling Point: 314.3°Cat760mmHg
• Flash Point: 147.8°C
• PSA: 0.00000
• Density: g/cm³
• LogP: 5.95080
• Storage Temp.: Refrigerator (+4°C)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 10
• Exact Mass: 332.152604
• Heavy Atom Count: 16
• Complexity: 151

Purity/Quality:

98%Min ^*data from raw suppliers

Tri-n-butyl(1-propenyl)tin E and Z ^*data from reagent suppliers

Safty Information:

• Hazard Codes: N-T
• Statements: 50/53-48/23/25-36/38-25-21
• Safety Statements: 61-60-45-36/37/39-35

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC[Sn](CCCC)(CCCC)C=CC
• Isomeric SMILES: CCCC[Sn](CCCC)(CCCC)/C=C\C
• Uses: Tri-n-butyl(1-propenyl)tin (E and Z) is a reagent that is used in the synthesis of Englerin A.

Technology Process of (Z)-Tri-n-butyl(1-propenyl)tin

There total 8 articles about (Z)-Tri-n-butyl(1-propenyl)tin 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) + copper(l) cyanide + acetylene (74-86-2,25067-58-7) → (Z)-1-propenyltributyltin (66680-84-0,66680-85-1,105494-65-3)

Guidance literature:

With methyllithium; methyl iodide; 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) + methyllithium (917-54-4) + copper(l) cyanide + acetylene (74-86-2,25067-58-7) + methyl iodide (74-88-4) → (Z)-1-propenyltributyltin (66680-84-0,66680-85-1,105494-65-3)

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 MeI in THF, 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: 61.0%

p-Tolyl chlorothionoformate (937-63-3) + 1-tributylstannyl-propan-1-ol (116064-59-6,117438-45-6,140150-31-8) → (E)-propenyl-tri-n-butylstannane (105494-65-3,66680-85-1,66680-84-0)

Guidance literature:

With sodium hydrogen sulfate; sulfuric acid; water; In pyridine; dichloromethane; byproducts: p-H3CC6H4OH; slow addn. of soln. of CH3PhOC(S)Cl in CH2Cl2 to cold (-20°C) soln. of alcohol in pyridine, 3h/0°C, ice, extd. with CH2Cl2, treatment with H2SO4 (10%), NaHCO3 (10%), H2O; mixt. warmed up to 200°C, then thermolysis at 800°C; in N2, condensation of products in a dewar vessel (liquid N2), warmed up to ambient temp.; first reaction detected by HPLC and IR, purifn. of educt by chromy. (Florisil, pentane), purifn. detected by HPLC or GC, ratio of isomers: cis/trans = 42/58;

DOI:10.1016/0022-328X(87)80020-7

upstream raw materials:

1-bromo-1-propene

tributyltin chloride

tri-n-butyltin lithium

acetylene

Downstream raw materials:

(E)-1-(5,5-dimethyl-1-oxo-cyclohex-2-en-3-yl)-2-buten-1-one

(7R,8R)-7-phenylacetamido-3-[(Z)-propen-1-yl]-3-cephem-4-carboxylic acid p-methoxybenzyl ester

(Z)-1-phenyl-3-penten-1-yne

trans-Crotonaldehyde

Refernces

• 1、 Barbero, Asuncion,Cuadrado, Purificacion,Fleming, Ian,Gonzalez, Ana M.,Pulido, Francisco J.,Rubio, Rosa. "Stannyl-cupration of Acetylenes and the Reaction of the Intermediate Cuprates with Electrophiles as a Synthesis of Substituted Vinylstannanes". . p. 1657 - 1662. Retrieved 2007/10/02.
• 2、 -. "Process for production of ceophalosporins". . . Retrieved 2008/06/13.