3-Cyanocoumarin

Base Information

• Chemical Name: 3-Cyanocoumarin
• CAS No.: 15119-34-3
• Molecular Formula: C10H5NO2
• Molecular Weight: 171.155
• Hs Code.: 2932209090
• European Community (EC) Number: 681-439-0
• DSSTox Substance ID: DTXSID10164728
• Nikkaji Number: J736.548I
• Wikidata: Q83033800
• Metabolomics Workbench ID: 74175
• ChEMBL ID: CHEMBL1767304
• Mol file: 15119-34-3.mol

Synonyms:3-cyanocoumarin

Chemical Property of 3-Cyanocoumarin

Chemical Property:

• Vapor Pressure: 4.32E-05mmHg at 25°C
• Melting Point: 184-188 °C(lit.)
• Refractive Index: 1.621
• Boiling Point: 350.7 °C at 760 mmHg
• Flash Point: 167.2 °C
• PSA: 54.00000
• Density: 1.34 g/cm³
• LogP: 1.66468
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 171.032028402
• Heavy Atom Count: 13
• Complexity: 310

Purity/Quality:

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

3-Cyanocoumarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(C(=O)O2)C#N

Technology Process of 3-Cyanocoumarin

There total 40 articles about 3-Cyanocoumarin 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: 98.0%

salicylaldehyde (90-02-8) + ethyl 2-cyanoacetate (105-56-6) → 3-cyanocoumarin (15119-34-3)

Guidance literature:

With zirconyl chloride octahydrate; sodium amide; In tetrahydrofuran; at 25 ℃; for 0.5h; Green chemistry;

DOI:10.14233/ajchem.2020.22849

Reference yield: 97.0%

salicylaldehyde (90-02-8) + cyanoacetic acid (372-09-8) → 3-cyanocoumarin (15119-34-3)

Guidance literature:

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In acetic acid butyl ester; ethyl acetate; at 120 ℃;

DOI:10.1016/j.tetlet.2012.06.037

Reference yield: 96.0%

salicylaldehyde (90-02-8) + malononitrile (109-77-3) → 3-cyanocoumarin (15119-34-3)

Guidance literature:

salicylaldehyde; malononitrile; With silicium tetrachloride; In ethanol; at 20 ℃; for 0.25h;

With water monomer; In ethanol; Cooling with ice;

DOI:10.3998/ark.5550190.0013.921

upstream raw materials:

3-cyano-2-iminocoumarin

salicylaldehyde

ethyl 2-cyanoacetate

2-imino-2H-1-benzopyran-3-carboxamide

Refernces

• 1、 Valizadeh, Hassan,Gholipour, Hamid. "Imidazolium-based phosphinite ionic liquid (IL-OPPh2) as reusable catalyst and solvent for the knoevenagel condensation reaction". . p. 1477 - 1485. Retrieved 2010.
• 2、 Nemeryuk,Dimitrova,Sedov,Traven'. "Unusual "replacement" of carbonyl containing functions at position 3 of coumarin by a cyano group". . p. 1234 - 1235. Retrieved 1997.
• 3、 Valizadeh, Hassan,Shockravi, Abbas,Gholipur. "Microwave assisted synthesis of coumarins via potassium carbonate catalyzed knoevenagel condensation in 1-n-butyl-3-methylimidazolium bromide ionic liquid". . p. 867 - 870. Retrieved 2007.
• 4、 Kiyani, Hamzeh,Daroonkala, Masoumeh Darzi. "A cost-effective and green aqueous synthesis of 3-substituted coumarins catalyzed by potassium phthalimide". . p. 449 - 456. Retrieved 2015.
• 5、 Keshavarzipour, Fariba,Tavakol, Hossein. "The synthesis of coumarin derivatives using choline chloride/zinc chloride as a deep eutectic solvent". . p. 149 - 153. Retrieved 2016.
• 6、 Tanaka, Takanori,Yamashita, Kohei,Hayashi, Masahiko. "Titanium tetraisopropoxide promoted rreactions for the synthesis of substituted coumarins". . p. 631 - 636. Retrieved 2010.
• 7、 Cao, Jing,Fu, Fubin,Li, Jiangmin,Rao, Yanzhao,Shi, Wei,Wu, Lei,Yu, Jiajia,Zhang, Xueyan,Zhou, Shengquan. "Non-salen coumarin Schiff base chiral fluorescent probe turn on circularly polarized luminescence by Mg2+ and Zn2+". . p. 5034 - 5042. Retrieved 2022/04/07.
• 8、 ?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.