4-PHENYLETHYNYL-BENZOIC ACID

Base Information

• Chemical Name: 4-PHENYLETHYNYL-BENZOIC ACID
• CAS No.: 25739-23-5
• Molecular Formula: C15H10 O2
• Molecular Weight: 222.243
• Hs Code.: 2916399090
• European Community (EC) Number: 801-532-3
• DSSTox Substance ID: DTXSID80401793
• Nikkaji Number: J706.836K
• Wikidata: Q72501864
• ChEMBL ID: CHEMBL3548948
• Mol file: 25739-23-5.mol

Synonyms:Benzoicacid, 4-(phenylethynyl)- (9CI);Benzoic acid, p-(phenylethynyl)- (6CI,7CI,8CI);(p-Carboxyphenyl)phenylacetylene;4-(Phenylethynyl)benzoic acid;Tolan-4-carboxylic acid;p-(Phenylethynyl)benzoic acid;

Chemical Property of 4-PHENYLETHYNYL-BENZOIC ACID

Chemical Property:

• Vapor Pressure: 2.3E-07mmHg at 25°C
• Melting Point: 220.5-221.0 °C(Solv: ethanol (64-17-5))
• Refractive Index: 1.655
• Boiling Point: 407.3 °C at 760 mmHg
• PKA: 4.08±0.10(Predicted)
• Flash Point: 185.6°C
• PSA: 37.30000
• Density: 1.25 g/cm³
• LogP: 2.78460
• Storage Temp.: 2-8°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 222.068079557
• Heavy Atom Count: 17
• Complexity: 319

Purity/Quality:

98%min ^*data from raw suppliers

4-?(Phenylethynyl)?benzoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C#CC2=CC=C(C=C2)C(=O)O
• Uses: 4-?(Phenylethynyl)?benzoic Acid is a reagent in the preparation og hGPR54 agonists which may be used in the modulation of testosterone levels in male mammals.

Technology Process of 4-PHENYLETHYNYL-BENZOIC ACID

There total 18 articles about 4-PHENYLETHYNYL-BENZOIC 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: 100.0%

methyl 4-(phenylethynyl)benzoate (42497-80-3) → 4-(phenylethynyl)benzoic acid (25739-23-5)

Guidance literature:

With water; sodium hydroxide; In methanol; at 70 ℃; for 1h;

Reference yield: 99.0%

4-(phenylethynyl)benzaldehyde (57341-98-7) → 4-(phenylethynyl)benzoic acid (25739-23-5)

Guidance literature:

With sodium chlorite; potassium dihydrogenphosphate; 2-methyl-but-2-ene; tert-butyl alcohol; In tetrahydrofuran; water; at 20 ℃; for 1.5h;

DOI:10.1016/j.bmcl.2009.04.095

Reference yield: 97.0%

4-iodobenzoic acid (619-58-9) + phenylacetylene (536-74-3) → 4-(phenylethynyl)benzoic acid (25739-23-5)

Guidance literature:

With Cu(II)IL/Schiff base complex decorated on γ-Fe2O3; In dimethyl sulfoxide; at 90 ℃; for 3h;

DOI:10.1007/s13738-019-01732-0

upstream raw materials:

Stilben-aldehyd-⁽⁴⁾-dibromid

4-iodobenzoic acid

phenylacetylene

4-(phenylethynyl)benzaldehyde

Downstream raw materials:

methyl 4-(phenylethynyl)benzoate

4-[oxo(phenyl)acetyl]benzoic acid

3-hydroxy-2-(4-phenylethynylbenzoylamino)butyric acid methyl ester

N-(2-hydroxy-1-hydroxycarbamoylpropyl)-4-phenylethynylbenzamide

Refernces

• 1、 Allahresani, Ali,Kazemnejadi, Milad,Nasseri, Mohammad Ali,Rezazadeh, Zinat. "A Co-Cu bimetallic magnetic nanocatalyst with synergistic and bifunctional performance for the base-free Suzuki, Sonogashira, and C-N cross-coupling reactions in water". . p. 10645 - 10660. Retrieved 2020/09/18.
• 2、 Nasseri, Mohammad Ali,Rezazadeh, Zinat,Kazemnejadi, Milad,Allahresani, Ali. "Magnetic Cu–Schiff base complex with an ionic tail as a recyclable bifunctional catalyst for base/Pd-free Sonogashira coupling reaction". . p. 2693 - 2705. Retrieved 2019/07/23.