Methyl 4-(tributylstannyl)benzoate

Base Information

• Chemical Name: Methyl 4-(tributylstannyl)benzoate
• CAS No.: 91734-76-8
• Molecular Formula: C20H34O2Sn
• Molecular Weight: 425.199
• DSSTox Substance ID: DTXSID80532334
• Mol file: 91734-76-8.mol

Synonyms:91734-76-8;Methyl 4-(tributylstannyl)benzoate;SCHEMBL5952565;DTXSID80532334;LBHLJZPUIYTSKK-UHFFFAOYSA-N;methyl 4-tri-n-butylstannylbenzoate

Chemical Property of Methyl 4-(tributylstannyl)benzoate

Chemical Property:

• PSA: 26.30000
• LogP: 4.96060
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 12
• Exact Mass: 426.158083
• Heavy Atom Count: 23
• Complexity: 300

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC[Sn](CCCC)(CCCC)C1=CC=C(C=C1)C(=O)OC

Technology Process of Methyl 4-(tributylstannyl)benzoate

There total 11 articles about Methyl 4-(tributylstannyl)benzoate 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: 92.0%

methyl 4-iodobenzoate (619-44-3) + bis(tri-n-butyltin) (813-19-4) → tributyltin iodide (7342-47-4) + methyl 4-tri-n-butylstannylbenzoate (91734-76-8)

Guidance literature:

dichloro bis(acetonitrile) palladium(II); In N,N,N,N,N,N-hexamethylphosphoric triamide; 20°C, molar ratio distannane/halide 1.3:1, 10 min;

DOI:10.1007/BF01141722

Reference yield: 88.0%

4-methoxycarbonylphenyl bromide (619-42-1) + bis(tri-n-butyltin) (813-19-4) → methyl 4-tri-n-butylstannylbenzoate (91734-76-8)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; the methyl ester was dissolved in anhydrous toluene, the soln. was degassed by bubbling nitrogen, an excess hexabutylditin was added followed by addn. of Pd-compd., the soln. was refluxed for 24 h; removal of the solvent under reduced pressure, the product was applied to a silica gel chromatographic column, elution with 10% ethyl acetate/90% hexane;

DOI:10.1016/0022-328X(89)87048-2

Reference yield: 87.0%

methyl 4-iodobenzoate (619-44-3) + bis(tri-n-butyltin) (813-19-4) → methyl 4-tri-n-butylstannylbenzoate (91734-76-8)

Guidance literature:

With potassium fluoride; tetraethylene glycol monododecyl ether; tetrabutyl-ammonium chloride; C₃₄H₃₄NO₃PPdS; In tetrahydrofuran; water; at 65 ℃; for 4h; Inert atmosphere;

DOI:10.1002/anie.202014141

upstream raw materials:

methyl 4-iodobenzoate

bis(tri-n-butyltin)

4-methoxycarbonylphenyl bromide

tributyltin chloride

Downstream raw materials:

methyl 4’-(trifluoromethyl)-[1,1’-biphenyl]-4-carboxylate

NO₂(C₆H₄)C(C₄H₂(CH₃OOCC₆H₄)N)2BF₂

Br(C₆H₄)C(C₄H₂(SC₄H₉)N)(C₄H₂(C₆H₄OOCCH₃)N)BF₂

Br(C₆H₄)C(C₄H₂(C₆H₄OOCCH₃)N)2BF₂

Refernces

• 1、 Chen, Chuan-Xin,Chen, Xiao-Qu,Lu, Heng,Shi, Chang-Yun,Wang, Dong-Yu,Zeng, Ruoqing,Zhang, Ao. "Palladium-Catalyzed gem-Difluoroallylation Reaction between Aryltributyltin and Bromodifluoromethylated Alkenes". supporting information. . Retrieved 2022/02/10.
• 2、 Yue, Huifeng,Zhu, Chen,Rueping, Magnus. "Catalytic Ester to Stannane Functional Group Interconversion via Decarbonylative Cross-Coupling of Methyl Esters". supporting information. p. 385 - 388. Retrieved 2018/01/27.