Isocoumarin

Base Information

• Chemical Name: Isocoumarin
• CAS No.: 491-31-6
• Molecular Formula: C9H6O2
• Molecular Weight: 146.145
• European Community (EC) Number: 835-104-2
• UNII: SR89982S3E
• DSSTox Substance ID: DTXSID8060080
• Nikkaji Number: J6.053D
• Wikipedia: Isocoumarin
• Wikidata: Q412756
• Metabolomics Workbench ID: 55998
• ChEMBL ID: CHEMBL457811
• Mol file: 491-31-6.mol

Synonyms:1-Isochromen-1-ones;1H-2-Benzopyran-1-ones;Isocoumarin;Isocoumarins

Chemical Property of Isocoumarin

Chemical Property:

• Vapor Pressure: 0.0111mmHg at 25°C
• Melting Point: 47°C
• Refractive Index: 1.5100 (estimate)
• Boiling Point: 262.1°Cat760mmHg
• Flash Point: 103.5°C
• PSA: 30.21000
• Density: 1.248g/cm³
• LogP: 1.79300
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 146.036779430
• Heavy Atom Count: 11
• Complexity: 196

Purity/Quality:

98%Min ^*data from raw suppliers

1H-Isochromen-1-one 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=COC2=O

Technology Process of Isocoumarin

There total 14 articles about Isocoumarin 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: 50.0%

3-phenyl-1-{2-{[triethyl(methyl)-l5-silyl]ethynyl}phenyl}prop-2-yn-1-one → isocoumarin (491-31-6) + 4-(phenylethynyl)-3-[2-(3-phenylpropioloyl)phenyl]-1-naphthaldehyde + 3-phenyl-1-{2-[1-(phenylethynyl)naphthalen-2-yl]phenyl}prop-2-yn-1-one

Guidance literature:

With silver trifluoromethanesulfonate; In toluene; at 20 ℃; for 7h;

DOI:10.1039/d1ob02229f

Reference yield: 34.0%

1,2-naphthoquinone (524-42-5) → isocoumarin (491-31-6) + coumarin (91-64-5)

Guidance literature:

With chloro(1,5-cyclooctadiene)rhodium(I) dimer; oxygen; 1,4-di(diphenylphosphino)-butane; In chlorobenzene; at 100 ℃; for 60h; regioselective reaction; Schlenk technique;

DOI:10.1021/acs.orglett.7b03837

Reference yield: 15.0%

vinyl propionate (105-38-4) + 2-vinylbenzoic acid (27326-43-8) → isocoumarin (491-31-6) + vinyl 2-vinylbenzoate

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In toluene; at 80 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.joc.0c02135

upstream raw materials:

α-naphthol

1-diazo-(1H)-indene

4-Methoxymethylen-3,4-dihydro-1H-2-benzopyran-1,3-dion

ethene

Downstream raw materials:

15,16,17,18,19,20-hexahydroyohimban-21-one

2-Hydroxyisocarbostyril

1-hydroxyisoquinoline

(2-hydroxymethyl-phenyl)-acetaldehyde

Refernces

• 1、 Brodzka, Anna,Koszelewski, Dominik,Ostaszewski, Ryszard,Brodzka, Anna,Ostaszewski, Ryszard. "Dual Activity of Grubbs-Type Catalyst in the Transvinylation of Carboxylic Acids and Ring-Closing Metathesis Reactions". . p. 15305 - 15313. Retrieved 2020/12/01.
• 2、 Batanero, Belen,Barba, Fructuoso,Barba, Isidoro,Elinson, Michail N.. "Reductive electrochemical formation of 6H-dibenzo[b,d]pyran-6-one and 2-benzopyran-1(1H)-one". . p. 82 - 85. Retrieved 2014/01/06.