(2E)-2-(phenylmethylidene)butanoic acid

Base Information

• Chemical Name: (2E)-2-(phenylmethylidene)butanoic acid
• CAS No.: 26197-64-8
• Molecular Formula: C11H12O2
• Molecular Weight: 176.215
• European Community (EC) Number: 636-387-3,842-073-9
• Nikkaji Number: J139.263H,J875.648A
• Mol file: 26197-64-8.mol

Synonyms:(2E)-2-(phenylmethylidene)butanoic acid;26197-64-8;(e)-2-benzylidenebutanoic acid;(2E)-2-benzylidenebutanoic acid;Butanoic acid, 2-(phenylmethylene)-;620-78-0;(2E)-2-(phenylmethylidene)butanoicacid;(2E)-2-ethyl-3-phenyl-2-propenoic acid;alpha-Ethylbenzeneacrylic acid;2-ethyl-3-phenylacrylic acid;BBA19764;(E)-2-Ethyl-3-phenylpropenoic acid;MFCD00136914;AKOS006274150;NS-01472;CS-0450488;EN300-391563;AS-871/43475214

Chemical Property of (2E)-2-(phenylmethylidene)butanoic acid

Chemical Property:

• Melting Point: 104.3 - 105.8 °C
• PSA: 37.30000
• LogP: 2.56460
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 176.083729621
• Heavy Atom Count: 13
• Complexity: 200

Purity/Quality:

99% ^*data from raw suppliers

(2E)-2-(Phenylmethylidene)butanoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC(=CC1=CC=CC=C1)C(=O)O
• Isomeric SMILES: CC/C(=C\C1=CC=CC=C1)/C(=O)O

Technology Process of (2E)-2-(phenylmethylidene)butanoic acid

There total 26 articles about (2E)-2-(phenylmethylidene)butanoic 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: 99.0%

(E)-ethyl 2-benzylidenebutanoate (60754-33-8) → (E)-2-benzylidenebutanoic acid (26197-64-8)

Guidance literature:

With water; potassium hydroxide; In ethanol; Inert atmosphere; Reflux;

DOI:10.1021/acs.orglett.0c02894

Reference yield: 84.0%

carbon dioxide (124-38-9,18923-20-1) + 1-phenyl-1-butyne (622-76-4,83585-27-7) → (E)-2-benzylidenebutanoic acid (26197-64-8)

Guidance literature:

With manganese; (1,2-dimethoxyethane)dichloronickel(II); Bathocuproine; tert-butyl alcohol; In N,N-dimethyl-formamide; at 60 ℃; for 36h; regioselective reaction; Schlenk technique;

DOI:10.1021/jacs.5b05513

Reference yield: 78.0%

triethyl borane (97-94-9) + carbon dioxide (124-38-9,18923-20-1) + phenylacetylene (536-74-3) → (E)-2-benzylidenebutanoic acid (26197-64-8)

Guidance literature:

With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); potassium methanolate; In tetrahydrofuran; 1,4-dioxane; at 20 ℃; for 24h; under 760.051 Torr; Reagent/catalyst; Solvent; stereoselective reaction; Catalytic behavior;

DOI:10.1021/acs.orglett.6b03860

upstream raw materials:

piperidine

benzaldehyde

ethylmalonic acid

(E)-3-ethyl-4-phenyl-3-buten-2-one

Downstream raw materials:

2-ethyl-3t-phenyl-acrylic acid-(2-diethylamino-ethyl ester)

(Z)-2-benzylidenebutanoic acid

(E)-2-benzylidenebutanoyl chloride

(S)-2-(phenylmethyl)butyric acid

Refernces

• 1、 -. "Method for preparing alpha, beta-unsaturated carboxylic acid compound". Paragraph 0103-0110; 0519-0526. . Retrieved 2021/05/05.
• 2、 Shao, Peng,Wang, Sheng,Du, Gaixia,Xi, Chanjuan. "Cp2TiCl2-catalyzed hydrocarboxylation of alkynes with CO2: formation of α,β-unsaturated carboxylic acids". . p. 3534 - 3539. Retrieved 2017/01/25.