4,4'-(ethyne-1,2-diyl)dibenzoic acid

Base Information

• Chemical Name: 4,4'-(ethyne-1,2-diyl)dibenzoic acid
• CAS No.: 16819-43-5
• Molecular Formula: C16H10O4
• Molecular Weight: 266.253
• Hs Code.: 2916399090
• Mol file: 16819-43-5.mol

Synonyms:4-[2-(4-carboxyphenyl)ethynyl]benzoic acid;

Chemical Property of 4,4'-(ethyne-1,2-diyl)dibenzoic acid

Chemical Property:

• Melting Point: > 163°C
• PSA: 74.60000
• LogP: 2.48280
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Sparingly, Heated)

Purity/Quality:

99%, ^*data from raw suppliers

4,4'-(1,2-Ethynediyl)dibenzoicAcid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4,4'-(ethyne-1,2-diyl)dibenzoic acid

There total 7 articles about 4,4'-(ethyne-1,2-diyl)dibenzoic acid 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: 97.0%

bis(4-(methoxycarbonyl)phenyl)acetylene (16882-08-9) → 4,4'-(1,2-ethynediyl)bisbenzoic acid (16819-43-5)

Guidance literature:

bis(4-(methoxycarbonyl)phenyl)acetylene; With sodium hydroxide; In ethanol; for 6h; Reflux;

With hydrogenchloride; In water; pH=1;

DOI:10.1007/s11172-019-2416-4

Reference yield:

methyl 4-iodobenzoate (619-44-3) → 4,4'-(1,2-ethynediyl)bisbenzoic acid (16819-43-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / Pd(PPh₃)2Cl₂; CuI; triethylamine / 2 h / 20 °C

2: 81 percent / sodium carbonate / methanol / 3 h / 20 °C

3: 91 percent / Pd(PPh₃)2Cl₂; CuI; triethylamine / 2 h / 20 °C

4: 0.48 g / NaOH / methanol / 24 h / Heating

With bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; copper(l) iodide; sodium carbonate; triethylamine; In methanol; 1: Sonogashira cross-coupling reaction / 3: Sonogashira cross-coupling reaction;

DOI:10.1039/b413514h

Reference yield:

4-ethynylbenzoic acid methyl ester (3034-86-4) → 4,4'-(1,2-ethynediyl)bisbenzoic acid (16819-43-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / Pd(PPh₃)2Cl₂; CuI; triethylamine / 2 h / 20 °C

2: 0.48 g / NaOH / methanol / 24 h / Heating

With bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; copper(l) iodide; triethylamine; In methanol; 1: Sonogashira cross-coupling reaction;

DOI:10.1039/b413514h

upstream raw materials:

4-iodobenzoic acid

4-Ethynyl-benzoic acid

bis(4-(methoxycarbonyl)phenyl)acetylene

methyl 4-iodobenzoate

Refernces

• 1、 Fasina, Tolulope M.,Collings, Jonathan C.,Burke, Jacqueline M.,Batsanov, Andrei S.,Ward, Richard M.,Albesa-Jove, David,Porres, Laurent,Beeby, Andrew,Howard, Judith A. K.,Scott, Andrew J.,Clegg, William,Watt, Stephen W.,Viney, Christopher,Marder, Todd B.. "Synthesis, optical properties, crystal structures and phase behaviour of symmetric, conjugated ethynylarene-based rigid rods with terminal carboxylate groups". . p. 690 - 697. Retrieved 2005.
• 2、 Lozanova,Stepanov,Mel′nik,Zlokazov,Veselovsky. "Synthesis of functionalized 1,2-diphenylacetylene derivatives". . p. 64 - 67. Retrieved 2019/04/25.