6-Chloro-3-cyano-4-methylcoumarin

Base Information

• Chemical Name: 6-Chloro-3-cyano-4-methylcoumarin
• CAS No.: 56394-24-2
• Molecular Formula: C11H6ClNO2
• Molecular Weight: 219.627
• DSSTox Substance ID: DTXSID60351005
• Nikkaji Number: J2.903.184C
• Wikidata: Q82127093
• Metabolomics Workbench ID: 74085
• Mol file: 56394-24-2.mol

Synonyms:6-chloro-3-cyano-4-methylcoumarin;56394-24-2;6-chloro-4-methyl-2-oxochromene-3-carbonitrile;6-CHLORO-4-METHYL-2-OXO-2H-CHROMENE-3-CARBONITRILE;SCHEMBL3079524;DTXSID60351005;JYTVXFGXASPMRG-UHFFFAOYSA-N;6-Chloro-3-cyano-4-methyl coumarin;6-Chloro-3-cyano-4-methylcoumarin, AldrichCPR

Chemical Property of 6-Chloro-3-cyano-4-methylcoumarin

Chemical Property:

• PSA: 54.00000
• LogP: 2.62648
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 219.0087061
• Heavy Atom Count: 15
• Complexity: 379

Purity/Quality:

98%Min ^*data from raw suppliers

6-Chloro-4-methyl-2-oxo-2H-chromene-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)Cl)C#N

Technology Process of 6-Chloro-3-cyano-4-methylcoumarin

There total 3 articles about 6-Chloro-3-cyano-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: 87.0%

5-chloro-2-hydroxyacetophenone (1450-74-4) + ethyl 2-cyanoacetate (105-56-6) → 6-chloro-4-methyl-2-oxo-2H-chromene-3-carbonitrile (56394-24-2)

Guidance literature:

With piperidine; for 1h; Ambient temperature;

Reference yield:

4-chlorophenyl acetate (876-27-7) → 6-chloro-4-methyl-2-oxo-2H-chromene-3-carbonitrile (56394-24-2)

Guidance literature:

Multi-step reaction with 2 steps

1: aluminum (III) chloride / 120 - 160 °C

2: sodium ethanolate / ethanol / 2 h / Reflux

With aluminum (III) chloride; sodium ethanolate; In ethanol; 1: Fries rearrangement / 2: Claisen condensation;

DOI:10.1016/j.bmcl.2011.02.016

Reference yield:

4-chloro-phenol (106-48-9,82344-39-6) → 6-chloro-4-methyl-2-oxo-2H-chromene-3-carbonitrile (56394-24-2)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuric acid / 2 h / Reflux

2: aluminum (III) chloride / 120 - 160 °C

3: sodium ethanolate / ethanol / 2 h / Reflux

With aluminum (III) chloride; sulfuric acid; sodium ethanolate; In ethanol; 2: Fries rearrangement / 3: Claisen condensation;

DOI:10.1016/j.bmcl.2011.02.016

upstream raw materials:

5-chloro-2-hydroxyacetophenone

ethyl 2-cyanoacetate

4-chlorophenyl acetate

4-chloro-phenol

Downstream raw materials:

6-chloro-2-oxo-4-[2-(4-chlorophenyl)ethenyl]-2H-chromene-3-carbonitrile

4-[(Z)-2-(4-Bromo-phenyl)-vinyl]-6-chloro-2-oxo-2H-chromene-3-carbonitrile

6-chloro-2-oxo-4-[2-(3-bromophenyl)ethenyl]-2H-chromene-3-carbonitrile

6-chloro2-oxo-4-[2-(4-fluorophenyl)ethenyl]-2H-chromene-3-carbonitrile

Refernces

• 1、 Shi, Chang-Yun,Xiao, Jun-Zhao,Yin, Liang. "Iridium-catalyzed direct asymmetric vinylogous allylic alkylation". supporting information. p. 11957 - 11960. Retrieved 2018/11/02.
• 2、 Madkour, Hassan M. F.. "SYNTHESIS AND REACTIONS OF SOME 3-CYANO-4-METHYLCOUMARINS". . p. 947 - 959. Retrieved 2007/10/02.