3-Benzoylacrylic acid

Base Information

• Chemical Name: 3-Benzoylacrylic acid
• CAS No.: 17812-07-6
• Molecular Formula: C10H8O3
• Molecular Weight: 176.172
• European Community (EC) Number: 209-496-5,605-817-1
• NSC Number: 143
• DSSTox Substance ID: DTXSID1060392,DTXSID30901612
• Nikkaji Number: J188.447F,J193.323J
• ChEMBL ID: CHEMBL16365
• Mol file: 17812-07-6.mol

Synonyms:benzoylacrylic acid;beta-benzoylacrylic acid

Chemical Property of 3-Benzoylacrylic acid

Chemical Property:

• Melting Point: 94-97 °C(lit.)
• PSA: 54.37000
• Density: 1.238
• LogP: 1.51010
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 176.047344113
• Heavy Atom Count: 13
• Complexity: 224

Purity/Quality:

98%Min ^*data from raw suppliers

4-Oxo-4-phenyl-but-2-enoicacid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C1=CC=C(C=C1)C(=O)C=CC(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)/C=C/C(=O)O

Technology Process of 3-Benzoylacrylic acid

There total 20 articles about 3-Benzoylacrylic 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: 84.0%

maleic anhydride (108-31-6) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → Benzoylacrylic acid (17812-07-6)

Guidance literature:

With aluminium trichloride; In 1,2-dichloro-ethane; Ambient temperature;

DOI:10.1016/0223-5234(88)90166-3

Reference yield: 79.0%

4,4-diethoxy-1-phenylbut-2-yn-1-one (53366-80-6) → Benzoylacrylic acid (17812-07-6)

Guidance literature:

With hydrogen bromide; In 1,4-dioxane; at 50 ℃; for 12h;

DOI:10.1002/hlca.19890720115

Reference yield: 78.0%

2-(Dimethoxy-phosphoryl)-4-oxo-4-phenyl-butyric acid (124658-40-8) → Benzoylacrylic acid (17812-07-6)

Guidance literature:

at 220 ℃; for 0.5h; under 10 Torr;

upstream raw materials:

maleic anhydride

diethyl ether

phenylzinc chloride

benzene

Downstream raw materials:

4-oxo-2,4-diphenylbutanoic acid

4-methyl-5-oxo-3-phenyl-cyclohex-3-enecarboxylic acid

3-benzoyl-2-propenoic acid

4-hydroxy-4-phenylbut-2-enoic acid

Refernces

• 1、 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.
• 2、 Bao, Jia-Xin,Fu, Jiang-Yan,Han, Hong-Wei,Lin, Hong-Yan,Lu, Gui-Hua,Lu, Yun-Ting,Qi, Jin-Liang,Sun, Wen-Xue,Wang, Ming-Yue,Wang, Xiao-Ming,Wang, Yin-Song,Wen, Zhong-Ling,Yang, Min-Kai,Yang, Yong-Hua. "Design, synthesis and biological evaluation of benzoylacrylic acid shikonin ester derivatives as irreversible dual inhibitors of tubulin and EGFR". . . Retrieved 2019/11/03.