3-(4-Methylbenzoyl)acrylic acid

Base Information

• Chemical Name: 3-(4-Methylbenzoyl)acrylic acid
• CAS No.: 20972-36-5
• Molecular Formula: C11H10O3
• Molecular Weight: 190.199
• Hs Code.: 2918300090
• European Community (EC) Number: 633-818-7
• DSSTox Substance ID: DTXSID00901326
• Nikkaji Number: J1.003.806E,J1.394.197A
• Wikidata: Q106902674
• ChEMBL ID: CHEMBL44664
• Mol file: 20972-36-5.mol

Synonyms:20972-36-5;3-(4-methylbenzoyl)acrylic acid;(2E)-4-(4-methylphenyl)-4-oxobut-2-enoic acid;(E)-4-Oxo-4-(p-tolyl)but-2-enoic acid;(E)-4-(4-methylphenyl)-4-oxobut-2-enoic acid;MFCD00075338;trans-3-(4-Methylbenzoyl)acrylic acid;3-(4-Methyl benzoyl)acrylic acid;MLS000586683;4-(4-methylphenyl)-4-oxobut-2-enoic acid;2-Butenoic acid, 4-(4-methylphenyl)-4-oxo-, (2E)-;NoName_427;CHEMBL44664;SCHEMBL711570;SCHEMBL711571;REGID_for_CID_691106;DTXSID00901326;CHEBI:167834;VNJMEFZKYZHWEO-VOTSOKGWSA-N;HMS2616K23;AKOS000267605;(E)-4-Oxo-4-(p-tolyl)but-2-enoicacid;SMR000208062;BB 0218775;CS-0215927;EN300-24153;3-(4-Methyl benzoyl)acrylic acid, AldrichCPR;7N-761;EN300-310993;F87228;(E)-4-(4-methylphenyl)-4-oxo-2-butenoic acid;J-013742;2-Butenoic acid,4-(4-methylphenyl)-4-oxo-,(2E)-;Z2768202101;(2E)-4-(4-methylphenyl)-4-oxobut-2-enoic acid compound with quinuclidine (1:1)

Chemical Property of 3-(4-Methylbenzoyl)acrylic acid

Chemical Property:

• Vapor Pressure: 7.24E-06mmHg at 25°C
• Melting Point: 138-140 °C (lit.)
• Refractive Index: 1.569
• Boiling Point: 361.8 °C at 760 mmHg
• PKA: 3.22±0.10(Predicted)
• Flash Point: 186.8 °C
• PSA: 54.37000
• Density: 1.2 g/cm³
• LogP: 1.81850
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 190.062994177
• Heavy Atom Count: 14
• Complexity: 247

Purity/Quality:

99% ^*data from raw suppliers

3-(4-Methyl benzoyl)acrylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 3-(4-Methylbenzoyl)acrylic acid

There total 10 articles about 3-(4-Methylbenzoyl)acrylic 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: 76.0%

→ (E)-4-oxo-4-(p-tolyl)but-2-enoic acid (20972-36-5)

Guidance literature:

With sulfuric acid; acetic acid; at 115 ℃; for 0.5h;

Reference yield: 75.0%

maleic anhydride (108-31-6) + toluene (108-88-3,15644-74-3,16713-13-6) → (E)-4-oxo-4-(p-tolyl)but-2-enoic acid (20972-36-5)

Guidance literature:

maleic anhydride; toluene; With aluminum (III) chloride; In dichloromethane; at 20 ℃;

With hydrogenchloride; In dichloromethane; water; Cooling with ice;

DOI:10.1016/j.ejmech.2011.04.043

Reference yield: 66.0%

para-methylacetophenone (122-00-9) + Glyoxilic acid (298-12-4) → (E)-4-oxo-4-(p-tolyl)but-2-enoic acid (20972-36-5)

Guidance literature:

With toluene-4-sulfonic acid; In 1,4-dioxane; at 160 ℃; for 1h; Microwave irradiation;

DOI:10.1039/d1ra05539a

upstream raw materials:

maleic anhydride

toluene

C₁₃H₁₄O₃

(2-oxo-2-p-tolylethyl)triphenylphosphonium bromide

Downstream raw materials:

2-(4-methyl-phenacyl)-4-oxo-4-p-tolyl-butyric acid

para-methylacetophenone

Glyoxilic acid

2,3-dibromo-4-oxo-4-p-tolyl-butyric acid

Refernces

• 1、 Ying, Jinbiao,Liu, Ting,Liu, Yunyun,Wan, Jie-Ping. "Base-Promoted Annulative Difluoromethylenation of Enaminones with BrCF2CO2Et toward 2,2-Difluorinated 2,3-Dihydrofurans". . p. 2404 - 2408. Retrieved 2022/04/07.
• 2、 Yang, Shanxue,Yao, Lan,Fan, Zhenhua,Han, Jing,Chen, Jie,He, Weimin,Deng, Hongmei,Shao, Min,Zhang, Hui,Cao, Weiguo. "Isocyanide-based MCRs: Diastereoselective cascade synthesis of perfluoroalkylated pyrano[3,4-c]pyrrole derivatives". supporting information. . Retrieved 2021/02/03.