3-Acetylcoumarin

Base Information

• Chemical Name: 3-Acetylcoumarin
• CAS No.: 3949-36-8
• Molecular Formula: C11H8O3
• Molecular Weight: 188.183
• Hs Code.: 29322090
• European Community (EC) Number: 223-541-6
• NSC Number: 31678
• UNII: ID71XJ0D40
• DSSTox Substance ID: DTXSID10192627
• Nikkaji Number: J79.887H
• Wikipedia: 3-Acetylcoumarin
• Wikidata: Q27167088
• Pharos Ligand ID: 6VYKK7LPWSQN
• Metabolomics Workbench ID: 73949
• ChEMBL ID: CHEMBL149463
• Mol file: 3949-36-8.mol

Synonyms:3-acetylcoumarin

Chemical Property of 3-Acetylcoumarin

Chemical Property:

• Appearance/Colour: yellow crystalline powder
• Vapor Pressure: 2.43E-06mmHg at 25°C
• Melting Point: 119-122 °C(lit.)
• Refractive Index: 1.583
• Boiling Point: 391.6 °C at 760 mmHg
• Flash Point: 179 °C
• PSA: 47.28000
• Density: 1.286 g/cm³
• LogP: 1.99560
• Storage Temp.: 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 188.047344113
• Heavy Atom Count: 14
• Complexity: 304

Purity/Quality:

98% ^*data from raw suppliers

3-Acetylcoumarin ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)C1=CC2=CC=CC=C2OC1=O

Technology Process of 3-Acetylcoumarin

There total 49 articles about 3-Acetylcoumarin 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%

2-methyl-benzyl alcohol (89-95-2) + ethyl acetoacetate (141-97-9) → 3-acetylcoumarin (3949-36-8)

Guidance literature:

With piperidine; at 20 ℃; for 0.0833333h;

DOI:10.1246/cl.2001.110

Reference yield: 99.0%

O-Merrifield resin-bound 4-(2-acetoacetylethyl)phenol + 2-methyl-benzyl alcohol (89-95-2) → 3-acetylcoumarin (3949-36-8)

Guidance literature:

With piperidine; In ethanol; for 2h; Heating;

DOI:10.1055/s-2005-872142

Reference yield: 90.0%

salicylaldehyde (90-02-8) + N-phenylacetoacetamide (102-01-2,98624-45-4) → 3-acetylcoumarin (3949-36-8)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutylammomium bromide; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1039/c7nj00980a

upstream raw materials:

piperidine

ethyl acetoacetate

salicylaldehyde

4-methyleneoxetan-2-one

Downstream raw materials:

3a-acetyl-1ξ-benzoyl-(3ar,9bc)-3a,9b-dihydro-1H-chromeno[3,4-c]pyrazol-4-one

4-Methyl-5-oxo-2-thioxo-1,5-dihydro-2H-chromeno[3,4-c]pyridine-1-carbonitrile

C₁₉H₁₇N₃O₃S

C₁₉H₁₇N₃O₃S

Refernces

• 1、 Al-Radha, Nabeel A.A.,Jaber, Qassim A.H.. "Synthesis of some substituted pyrimidines derived from 3-acetyl coumarin". . p. 3687 - 3691. Retrieved 2015.
• 2、 Cui, Yali,Jiang, Yingxia,Sun, Xiaodong,Wang, Ruijie,Yan, Fanyong,Zhang, Yuyang. "Dual-function fluorescent probe with red emission for sensing viscosity and OCl? and its applications in bioimaging". . . Retrieved 2020.
• 3、 Hussain, Habib,Gilani, Syeda Rubina,Jabeen, Farkhanda,Ali, Zulfiqar,Rehman, Hajira,Hussain, Imdad. "Synthesis and antibacterial activity of Zn(II) Schiff base complexes derived from 3-acetyl-2H-chromen-2-one". . p. 3440 - 3444. Retrieved 2015.
• 4、 Upadhyay, Kaushal Kumar,Mishra, Rakesh Kumar. "Zn2+ specific colorimetric receptor based on coumarin". . p. 1211 - 1215. Retrieved 2010.
• 5、 Lalitha, Krishnamoorthy,Nagarajan, Subbiah. "Strongly fluorescent organogels and self-assembled nanostructures from pyrene coupled coumarin derivatives: Application in cell imaging". . p. 5690 - 5701. Retrieved 2015.
• 6、 Zhou, Zi-chun,Zheng, An-na,Cui, Yan-hong,Lin, Zhang-qi,Niu, Wen-jie,Zhang, Yong-jian,Gao, Jian-rong,Li, Yu-jin. "Rational design and synthesis of 3-heteroaromatics coumarin molecules with unusual solution and solid dual efficient luminescence". . p. 2958 - 2964. Retrieved 2019.
• 7、 Basavarajappa,Nayaka, Y. Arthoba,Yathisha,Manjunatha. "Synthesis, Characterization, Optical, Electrochemical and Current-Voltage Characteristics of Coumarin Dyes". . p. 1201 - 1211. Retrieved 2019.
• 8、 Alotaibi, Saad H.. "Spectroscopic and biophysical studies on chalcones and schiff bases derived from chromen-2-one and quinoline-2(1h)-one derivatives as antibacterial agents". . p. 1719 - 1727. Retrieved 2020.
• 9、 Al-Sehemi, Abdullah G.,Pannipara, Mehboobali,Kalam, Abul,Asiri, Abdullah M.. "A Combined Experimental and Computational Investigation on Spectroscopic and Photophysical Properties of a Coumarinyl Chalcone". . p. 1357 - 1365. Retrieved 2016.
• 10、 Upadhyay,Mishra, Rakesh K.,Kumar, Ajit,Zhao, Jianzhang,Prasad, Rajendra. "Self assembled pseudo double helix architecture and anion sensing behavior of a coumarin based ICT probe". . p. 228 - 233. Retrieved 2010.