3-Benzoylcoumarin

Base Information

• Chemical Name: 3-Benzoylcoumarin
• CAS No.: 1846-74-8
• Molecular Formula: C16H10O3
• Molecular Weight: 250.254
• Hs Code.: 2932209090
• NSC Number: 11862
• UNII: XF9P5UO8IN
• DSSTox Substance ID: DTXSID6075144
• Nikkaji Number: J48.482B
• Wikidata: Q82003174
• ChEMBL ID: CHEMBL591522
• Mol file: 1846-74-8.mol

Synonyms:3-Benzoylcoumarin;1846-74-8;3-benzoyl-2H-chromen-2-one;3-benzoylchromen-2-one;COUMARIN, 3-BENZOYL-;2H-1-Benzopyran-2-one, 3-benzoyl-;3-Benzoyl-chromen-2-one;3-Benzoyl-2H-1-benzopyran-2-one;NSC 11862;XF9P5UO8IN;BRN 0190875;NSC-11862;5-17-11-00557 (Beilstein Handbook Reference);NSC11862;UNII-XF9P5UO8IN;ChemDiv3_012376;Oprea1_857667;SCHEMBL51507;MLS001201222;CHEMBL591522;DTXSID6075144;HMS1508C12;HMS2850G06;MFCD00233579;STL145336;3-(phenylcarbonyl)-2H-chromen-2-one;AKOS002087789;NCGC00245922-01;LS-55119;SMR000564143;CS-0359755;EU-0027162;2H-1-Benzopyran-2-one, 3-benzoyl- (9CI);SR-01000143218;SR-01000143218-1;BRD-K16706387-001-01-0;F0916-3926

Chemical Property of 3-Benzoylcoumarin

Chemical Property:

• Vapor Pressure: 3.29E-08mmHg at 25°C
• Melting Point: 138 °C
• Boiling Point: 447.7°C at 760 mmHg
• Flash Point: 202°C
• PSA: 47.28000
• Density: 1.302g/cm³
• LogP: 3.02400
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 250.062994177
• Heavy Atom Count: 19
• Complexity: 404

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Benzoylcoumarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)C2=CC3=CC=CC=C3OC2=O
• Uses: 3-Benzoylcoumarin is a useful intermediate used in the synthesis of coumarin-chalcone derivatives with antibacterial properties for the treatment of tenacibaculosis.

Technology Process of 3-Benzoylcoumarin

There total 32 articles about 3-Benzoylcoumarin 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: 97.0%

ethyl 3-oxo-3-phenylpropionate (94-02-0) + salicylaldehyde (90-02-8) → 3-benzoyl-chromen-2-one (1846-74-8)

Guidance literature:

With 1,3-dimethylimidazolium sulfate monomethyl ester; L-proline; In water; at 90 ℃; for 6h;

DOI:10.3390/molecules16064379

Reference yield: 97.0%

2-methyl-benzyl alcohol (89-95-2) + ethyl 3-oxo-3-phenylpropionate (94-02-0) → 3-benzoyl-chromen-2-one (1846-74-8)

Guidance literature:

With piperidine; at 20 ℃; for 0.0833333h;

DOI:10.1246/cl.2001.110

Reference yield: 95.0%

perchlorate de carbomethoxy-3 flavylium → 3-benzoyl-chromen-2-one (1846-74-8)

Guidance literature:

With water; In pyridine; Heating;

upstream raw materials:

piperidine

ethyl 3-oxo-3-phenylpropionate

salicylaldehyde

2-hydroxyphenyl-bis-1,1-piperidinomethane

Downstream raw materials:

salicylaldehyde

2-oxo-2H-1-benzopyran<3,4-c>-6,6-dimethoxy-2-phenyl-1-(phenylsulfonyl)-1,4,5,6-tetrahydropyridine

(6S^*)-2-oxo-2H-1-benzopyran<3,4-c>-6-ethoxy-2-phenyl-1-(phenylsulfonyl)-1,4,5,6-tetrahydropyridine

Refernces

• 1、 Niu, Ben,Zhao, Wannian,Ding, Yingcai,Bian, Zhaogang,Pittman, Charles U.,Zhou, Aihua,Ge, Haibo. "Regioselective Cross-Couplings of Coumarins and Flavones with Ethers via C(sp3)-H Functionalization". . p. 7251 - 7257. Retrieved 2015.
• 2、 Arthoba Nayaka, Y.,Basavarajappa, K. V.,Manjunatha, K. B.,Purushothama, H. T.,Rudresha, B. J.,Vinay, M. M.,Yathisha, R. O.. "Optical, electrochemical and current?voltage characteristics of novel coumarin based 2,4-dinitrophenylhydrazone derivatives". . . Retrieved 2020.
• 3、 Jafarpour, Farnaz,Abbasnia, Masoumeh. "A Regioselective Metal-Free Construction of 3-Aroyl Coumarins by Csp2-H Functionalization". . p. 11982 - 11986. Retrieved 2016.
• 4、 ?ubari?, Domagoj,Agi?, Dejan,Be?lo, Drago,Kara?i?, Zrinka,Karna?, Maja,Lisjak, Miroslav,Lon?ari?, Melita,Molnar, Maja,Popovi?, Boris M.,Rastija, Vesna,Tomi?, Sanja. "Coumarin derivatives act as novel inhibitors of human dipeptidyl peptidase III: Combined in vitro and in silico study". . . Retrieved 2021/06/22.
• 5、 Salar, Uzma,Mohammed Khan, Khalid,Jabeen, Almas,Faheem, Aisha,Naqvi, Farwa,Ahmed, Shakil,Iqbal, Erum,Ali, Farman,Kanwal,Perveen, Shahnaz. "Ros inhibitory activity and cytotoxicity evaluation of benzoyl, acetyl, alkyl ester, and sulfonate ester substituted coumarin derivatives". . p. 1099 - 1111. Retrieved 2020/11/09.