Coumarin-3-carboxylic acid

Base Information

• Chemical Name: Coumarin-3-carboxylic acid
• CAS No.: 531-81-7
• Molecular Formula: C10H6O4
• Molecular Weight: 190.155
• Hs Code.: 29322090
• European Community (EC) Number: 208-518-0
• NSC Number: 53239,44926,14797
• UNII: V85UOV8788
• DSSTox Substance ID: DTXSID70201183
• Nikkaji Number: J1.587C
• Wikidata: Q27291656
• Pharos Ligand ID: 6ZUA9Y74SAT4
• ChEMBL ID: CHEMBL83294
• Mol file: 531-81-7.mol

Synonyms:coumarin-3-carboxylate;coumarin-3-carboxylic acid;potassium coumarin-3-carboxylic acid;sodium coumarin-3-carboxylic acid

Chemical Property of Coumarin-3-carboxylic acid

Chemical Property:

• Appearance/Colour: light brown crystalline powder
• Vapor Pressure: 9.77E-07mmHg at 25°C
• Melting Point: 189-192 ºC(lit.)
• Refractive Index: 1.5380 (estimate)
• Boiling Point: 388.6 °C at 760mmHg
• PKA: 1.84±0.20(Predicted)
• Flash Point: 162.7 °C
• PSA: 67.51000
• Density: 1.493 g/cm³
• LogP: 1.49120
• Storage Temp.: Store below +30°C.
• Solubility.: 13g/l
• Water Solubility.: 13 g/L (37 ºC)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 190.02660867
• Heavy Atom Count: 14
• Complexity: 305

Purity/Quality:

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

Coumarin-3-carboxylic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, Xi
• Hazard Codes: T,Xi
• Statements: 25
• Safety Statements: 36/37/39-45-28A

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(C(=O)O2)C(=O)O
• Uses: Coumarin-3-carboxylic acid is used as pharmaceutical intermediate.

Technology Process of Coumarin-3-carboxylic acid

There total 58 articles about Coumarin-3-carboxylic 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: 100.0%

cycl-isopropylidene malonate (2033-24-1) + 2-methyl-benzyl alcohol (89-95-2) → 2-oxo-2H-chromene-3-carboxylic acid (531-81-7)

Guidance literature:

With piperdinium acetate; In ethanol; for 2h; Heating;

DOI:10.1021/jm0602864

Reference yield: 99.0%

cycl-isopropylidene malonate (2033-24-1) + salicylaldehyde (90-02-8) → 2-oxo-2H-chromene-3-carboxylic acid (531-81-7)

Guidance literature:

With lemon juice; In water; at 20 ℃; for 0.0833333h; Reagent/catalyst; Sonication; Green chemistry;

DOI:10.1016/j.tetlet.2016.09.023

Reference yield: 97.0%

β-Amino-α-cyan-(1,2-dihydro-2-oxo-1-benzopyran-3-yl)-propensaeuremethylester (119689-97-3) → 2-oxo-2H-chromene-3-carboxylic acid (531-81-7)

Guidance literature:

With hydrogenchloride; In ethanol; for 4h; Heating;

DOI:10.1007/BF00809686

upstream raw materials:

pyridine

malonic acid

salicylaldehyde

3-cyanocoumarin

Downstream raw materials:

(E)-3-(2-Hydroxy-phenyl)-1-morpholin-4-yl-propenone

2-oxo-2H-chromene-3-carboxylic acid (6-amino-3-methyl-2,4-dioxo-1-phenyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide

2-oxo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)-2H-chromene

3-[5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]-2H-chromen-2-one

Refernces

• 1、 Avetisyan,Aleksanyan,Alvandzhyan. "Synthesis and some transformations of functionally-substituted coumarins and 2-thioxo-2H-chromenes". . p. 773 - 776. Retrieved 1996.
• 2、 Abyshev et al.. "-". . . Retrieved 1977.
• 3、 Bekircan, Olcay,Dan??, ?zkan,?ahin, Mehmet Eren,?etin, Mert. "Monoamine oxidase A and B inhibitory activities of 3,5-diphenyl-1,2,4-triazole substituted [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives". . . Retrieved 2021/11/24.
• 4、 Mesiti, Francesco,Gaspar, Alexandra,Chavarria, Daniel,Maruca, Annalisa,Rocca, Roberta,Gil Martins, Eva,Barreiro, Sandra,Silva, Renata,Fernandes, Carlos,Gul, Sheraz,Keminer, Oliver,Alcaro, Stefano,Borges, Fernanda. "Mapping Chromone-3-Phenylcarboxamide Pharmacophore: Quid Est Veritas?". . p. 11169 - 11182. Retrieved 2021/08/03.