Diethyl 4,4'-(ethyne-1,2-diyl)dibenzoate

Base Information

• Chemical Name: Diethyl 4,4'-(ethyne-1,2-diyl)dibenzoate
• CAS No.: 83536-13-4
• Molecular Formula: C20H18O4
• Molecular Weight: 322.361
• DSSTox Substance ID: DTXSID60573083
• Nikkaji Number: J1.080.531G
• Wikidata: Q82461668
• Mol file: 83536-13-4.mol

Synonyms:83536-13-4;Diethyl 4,4'-(ethyne-1,2-diyl)dibenzoate;Bis[4-(ethoxycarbonyl)phenyl]ethyne;ethyl 4-[2-(4-ethoxycarbonylphenyl)ethynyl]benzoate;Benzoic acid, 4,4'-(1,2-ethynediyl)bis-, diethyl ester;SCHEMBL6365625;YSCK0195;DTXSID60573083;MFCD34563613;Bis[4-(ethoxycarbonyl)phenyl]acetylene;BS-45996;E85560

Chemical Property of Diethyl 4,4'-(ethyne-1,2-diyl)dibenzoate

Chemical Property:

• Melting Point: 143-145 °C
• Boiling Point: 462.9±30.0 °C(Predicted)
• PSA: 52.60000
• Density: 1.19±0.1 g/cm3(Predicted)
• LogP: 3.43980
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 322.12050905
• Heavy Atom Count: 24
• Complexity: 440

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC=C(C=C1)C#CC2=CC=C(C=C2)C(=O)OCC

Technology Process of Diethyl 4,4'-(ethyne-1,2-diyl)dibenzoate

There total 10 articles about Diethyl 4,4'-(ethyne-1,2-diyl)dibenzoate 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: 90.0%

4-iodobenzoic acid ethyl ester (51934-41-9) + ethyl 4-ethynylbenzoate (10602-03-6) → bis(4-ethoxycarbonylphenyl)acetylene (83536-13-4)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; Inert atmosphere;

DOI:10.1002/chem.202004140

Reference yield: 88.0%

Ethyl 4-bromobenzoate (5798-75-4) + bis-pivaloyloxyzinc acetylide → bis(4-ethoxycarbonylphenyl)acetylene (83536-13-4)

Guidance literature:

With 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In dimethyl sulfoxide; at 25 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.8b01892

Reference yield: 72.0%

4-iodobenzoic acid ethyl ester (51934-41-9) + trimethylsilylacetylene (1066-54-2) → bis(4-ethoxycarbonylphenyl)acetylene (83536-13-4)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; water; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1021/ja104305s

upstream raw materials:

Ethyl 4-bromobenzoate

4-iodobenzoic acid ethyl ester

trimethylsilylacetylene

1,2-bis(methylthio)acetylene

Downstream raw materials:

C₂₇H₂₇NO₇

(3E)-1,1,2-tris[4-(ethoxycarbonyl)phenyl]-4-(4-hydroxy-3-methoxyphenyl)buta-1,3-diene

diethyl 4,4'-(6-nitropyrazolo[5,1-a]isoquinoline-3,4-diyl)dibenzoate

ethyl 4-(2-phenyl-2H-indazol-3-yl)benzoate

Refernces

• 1、 Kim, Hyun Tae,Kang, Eunsu,Kim, Minkyu,Joo, Jung Min. "Synthesis of Bidentate Nitrogen Ligands by Rh-Catalyzed C-H Annulation and Their Application to Pd-Catalyzed Aerobic C-H Alkenylation". supporting information. p. 3657 - 3662. Retrieved 2021/05/10.
• 2、 Qian, Lei-Lei,Min, Xiang-Ting,Hu, Yan-Cheng,Shen, Bing-Xue,Yang, Sa-Na,Wan, Boshun,Chen, Qing-An. "Ruthenium(ii)-catalyzed intermolecular annulation of alkenyl sulfonamides with alkynes: Access to bicyclic sultams". supporting information. p. 2614 - 2617. Retrieved 2020/03/10.