3-Cyano-6-fluoro-4-methylcoumarin

Base Information

• Chemical Name: 3-Cyano-6-fluoro-4-methylcoumarin
• CAS No.: 288399-90-6
• Molecular Formula: C11H6 F N O2
• Molecular Weight: 203.1692432
• Hs Code.: 2932209088
• DSSTox Substance ID: DTXSID80380998
• Nikkaji Number: J3.096.092K
• Wikidata: Q82171547
• Mol file: 288399-90-6.mol

Synonyms:288399-90-6;3-Cyano-6-fluoro-4-methylcoumarin;6-Fluoro-4-methyl-2-oxo-2H-chromene-3-carbonitrile;6-Fluoro-4-methylcoumarin-3-carbonitrile;6-fluoro-4-methyl-2-oxochromene-3-carbonitrile;6-FLUORO-4-METHYLCOUMARIN-3-CARBONITRIL&;SCHEMBL3078189;DTXSID80380998;MFCD03094005;AKOS024015179;6-Fluoro-4-methylcoumarin-3-carbonitrile, 97%;A899566;J-017288;2-Oxo-4-methyl-6-fluoro-2H-1-benzopyran-3-carbonitrile

Chemical Property of 3-Cyano-6-fluoro-4-methylcoumarin

Chemical Property:

• Vapor Pressure: 3.39E-05mmHg at 25°C
• Melting Point: 164-168 °C(lit.)
• Refractive Index: 1.579
• Boiling Point: 354.3°C at 760 mmHg
• Flash Point: 168.1°C
• PSA: 54.00000
• Density: 1.37g/cm³
• LogP: 2.11218
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 203.03825660
• Heavy Atom Count: 15
• Complexity: 379

Purity/Quality:

98%min ^*data from raw suppliers

6-Fluoro-4-methylcoumarin-3-carbonitrile 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)OC2=C1C=C(C=C2)F)C#N

Technology Process of 3-Cyano-6-fluoro-4-methylcoumarin

There total 2 articles about 3-Cyano-6-fluoro-4-methylcoumarin 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: 92.0%

1-(5-fluoro-2-hydroxyphenyl)ethan-1-one (394-32-1) + cyanoacetic acid (372-09-8) → C11H6FNO2 (288399-90-6)

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:

1-(5-fluoro-2-hydroxyphenyl)ethan-1-one (394-32-1) + ethyl 2-cyanoacetate (105-56-6) → C11H6FNO2 (288399-90-6)

Guidance literature:

With ammonium acetate; In neat (no solvent); at 155 ℃; for 5h;

DOI:10.1039/c8cc07249c

Reference yield: 95.0%

tert-butyl (1-benzyl-2-oxoindolin-3-ylidene)carbamate (1373942-84-7) + C11H6FNO2 (288399-90-6) → C31H26FN3O5

Guidance literature:

With C₃₃H₃₁F₆NOP⁽¹⁺⁾*Br^(1-); potassium carbonate; In toluene; at -10 ℃; for 4h; enantioselective reaction;

DOI:10.1002/cctc.201901677

upstream raw materials:

1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

cyanoacetic acid

ethyl 2-cyanoacetate

Refernces

• 1、 Augustine, John Kallikat,Bombrun, Agnes,Ramappa, Balakrishna,Boodappa, Chandrakantha. "An efficient one-pot synthesis of coumarins mediated by propylphosphonic anhydride (T3P) via the Perkin condensation". experimental part. p. 4422 - 4425. Retrieved 2012/09/25.