(Z)-2-naphthalen-1-yl-3-phenylprop-2-enoic acid

Base Information

• Chemical Name: (Z)-2-naphthalen-1-yl-3-phenylprop-2-enoic acid
• CAS No.: 71432-05-8
• Molecular Formula: C19H14O2
• Molecular Weight: 274.3133
• NSC Number: 180620
• DSSTox Substance ID: DTXSID70421420
• Wikidata: Q82232912
• Mol file: 71432-05-8.mol

Synonyms:NSC180620;71432-05-8;DTXSID70421420;NSC-180620

Chemical Property of (Z)-2-naphthalen-1-yl-3-phenylprop-2-enoic acid

Chemical Property:

• Vapor Pressure: 3.58E-08mmHg at 25°C
• Boiling Point: 430.4°Cat760mmHg
• Flash Point: 323.1°C
• Density: 1.239g/cm³
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 274.099379685
• Heavy Atom Count: 21
• Complexity: 392

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=C(C2=CC=CC3=CC=CC=C32)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)/C=C(/C2=CC=CC3=CC=CC=C32)\C(=O)O

Technology Process of (Z)-2-naphthalen-1-yl-3-phenylprop-2-enoic acid

There total 6 articles about (Z)-2-naphthalen-1-yl-3-phenylprop-2-enoic 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: 90.0%

naphth-1-yl acetic acid (86-87-3) + benzaldehyde (100-52-7) → 2-(1-naphthyl)-3-phenylpropenoic acid (71432-05-8)

Guidance literature:

With acetic anhydride; triethylamine; at 120 ℃; for 24h;

DOI:10.1080/00304949709355210

Reference yield:

(E)-2-(naphthalen-1-yl)-3-phenylacrylaldehyde → 2-(1-Naphthyl)-3-phenylpropenoic acid (71432-05-8)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 20 ℃; for 4h;

DOI:10.1021/acs.orglett.1c02692

Reference yield:

carbon monoxide (201230-82-2) + 1-phenylethynyl-naphthalene (4044-57-9) → 2-(1-naphthyl)-3-phenylpropenoic acid (71432-05-8) + C19H14O2

Guidance literature:

With water; palladium diacetate; 4,5-bis(diphenylphosphanyl)-9,9-dimethyl-9H-xanthene-2,7-disulfonic acid; at 100 ℃; for 24h; under 2250.23 Torr; Overall yield = 73 percent; regioselective reaction;

DOI:10.1039/d1cy00699a

upstream raw materials:

α-bromocinnamaldehyde

naphth-1-yl acetic acid

benzaldehyde

carbon monoxide

Refernces

• 1、 Gao, Mingjie,Jia, Xiaofei,Lv, Jinhe,Ren, Xinyi,Song, Jiaxin,Xie, Congxia,Zhang, Jinrong,Zhang, Kai,Zhao, Jinyu,Zhou, Ziqin,Zong, Lingbo. "Access to α,β-unsaturated carboxylic acids through water-soluble palladium catalyzed hydroxycarbonylation of alkynes using water as the solvent". . p. 4708 - 4713. Retrieved 2021/07/26.
• 2、 Dai, Wei,Harvey, Ronald G.. "Synthesis of 4H-cyclopenta[def]chrysene and other methylene-bridged polycyclic hydrocarbons". . p. 347 - 352. Retrieved 2007/10/03.