2-Coumaranone

Base Information

• Chemical Name: 2-Coumaranone
• CAS No.: 553-86-6
• Molecular Formula: C8H6O2
• Molecular Weight: 134.134
• Hs Code.: 29322090
• European Community (EC) Number: 209-052-0
• NSC Number: 227414
• UNII: 4K47Z4Q1E7
• DSSTox Substance ID: DTXSID70203829
• Nikkaji Number: J11.370K
• Wikidata: Q27259814
• ChEMBL ID: CHEMBL284584
• Mol file: 553-86-6.mol

Synonyms:2-coumaranone

Chemical Property of 2-Coumaranone

Chemical Property:

• Appearance/Colour: white to light yellow crystalline powder
• Vapor Pressure: 0.0235mmHg at 25°C
• Melting Point: 49-51 °C(lit.)
• Refractive Index: 1.585
• Boiling Point: 249 °C at 760 mmHg
• Flash Point: 96.9 °C
• PSA: 26.30000
• Density: 1.264 g/cm³
• LogP: 1.14810
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: H2O: soluble3.8g/L at 30°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 134.036779430
• Heavy Atom Count: 10
• Complexity: 153

Purity/Quality:

99.9% ^*data from raw suppliers

2(3H)-Benzofuranone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-43-36/38
• Safety Statements: 24/25-36-26-36/37

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C2=CC=CC=C2OC1=O
• Description: 2-Coumaranone (also named as Isophthalide, 3H-benzofuran-2-one) belongs to a class of organic compounds named as benzofuranones which exhibits mutagenic and carcinogenic activity. 2-Coumaranone has been used to study the effects of coumarins on 7,12-dimethyibenz(a)anthracene induced neoplasia of the rat mammary gland and as probe for detecting enzymes which hydrolyze 2-hydroxybenzofuran structures.
• Uses: 2-Coumaranone has been used to study the effects of coumarins on 7,12-dimethyibenz(a)anthracene induced neoplasia of the rat mammary gland. It was employed as probe for detecting enzymes which hydrolyze 2-hydroxybenzofuran structures.

Technology Process of 2-Coumaranone

There total 73 articles about 2-Coumaranone 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%

2-Hydroxyphenylacetic acid (614-75-5) → benzofuran-2(3H)-one (553-86-6)

Guidance literature:

With pyrophosphoryl chloride; at 35 ℃; for 0.333333h;

DOI:10.3390/60300279

Reference yield: 98.0%

butyl o-acetoxyphenylacetate → benzofuran-2(3H)-one (553-86-6)

Guidance literature:

With tin(IV) oxide; at 140 ℃; for 5h; Inert atmosphere;

Reference yield: 97.0%

ethyl o-acetoxyphenylacetate → benzofuran-2(3H)-one (553-86-6)

Guidance literature:

With magnesium oxide; at 120 ℃; for 2h; Temperature; Reagent/catalyst;

upstream raw materials:

acetic anhydride

2-Hydroxyphenylacetic acid

acetyl chloride

2-chlorophenyl acetate

Downstream raw materials:

3-morpholino-3H-benzofuran-2-one

[1]benzopyrano[4,3-c][1]benzopyran-5,11-dione

2-(2-hydroxyphenyl)-1-phenylethan-1-one

2-(2-hydroxy-phenyl)-1-(2-oxo-2,3-dihydro-benzofuran-3-yl)-ethanone

Refernces

• 1、 Goncalo, Paulo,Roussel, Christophe,Melot, Jean Marie,Vebrel, Joel. "Contribution of microwaves in organic synthesis: Statement of a methodology for the microwave-induced preparation of benzofuran-2(3H)-one and its comparison with classical heating". . p. 2111 - 2115. Retrieved 1999.
• 2、 Li, Hao-Peng,Ai, Han-Jun,Qi, Xinxin,Peng, Jin-Bao,Wu, Xiao-Feng. "Palladium-catalyzed carbonylative synthesis of benzofuran-2(3H)-ones from 2-hydroxybenzyl alcohols using formic acid as the CO source". . p. 1343 - 1345. Retrieved 2017.
• 3、 Ibrahim, Nagham,Moussallem, Chady,Allain, Magali,Segut, Olivier,Gohier, Frédéric,Frère, Pierre. "Exploring the Electronic Properties of Extended Benzofuran-Cyanovinyl Derivatives Obtained from Lignocellulosic and Carbohydrate Platforms Raw Materials". . p. 475 - 482. Retrieved 2021/03/31.
• 4、 Zhang, Xiaojie,Beaudry, Christopher M.. "Regioselective Synthesis of Benzofuranones and Benzofurans". supporting information. p. 6931 - 6936. Retrieved 2021/05/06.