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% ^*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
• General Description: 2-Coumaranone, also known as 2(3H)-Benzofuranone or Isophthalide, is a heterocyclic compound with a benzofuranone core structure. It serves as a key intermediate in synthetic chemistry, particularly in the formation of pharmacologically active compounds, including potential anti-neoplastic agents. The compound can undergo catalytic transformations, such as oxygen-to-carbon ester migration, facilitated by DMAP, highlighting its reactivity and utility in regioselective acylation reactions. Additionally, its derivatives, such as α-quaternary allylated benzofuran-2-ones, are synthesized via dual Rh(II)/Pd(0) relay catalysis, demonstrating its versatility in constructing bioactive heterocycles.

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

Dual Rh(II)/Pd(0) Relay Catalysis for One-Pot Synthesis of α-Quaternary Allylated Indolin-2-ones and Benzofuran-2-ones

10.1002/bkcs.12211

The study presents a dual Rh(II)/Pd(0) relay catalytic method for the one-pot synthesis of α-quaternary allylated indolin-2-ones and benzofuran-2-ones. Key chemicals used include α-diazo carbonyl compounds as substrates, Rh(II) and Pd(0) catalysts for the catalysis process, and allyl carbonates for the allylic alkylation step. The Rh(II) catalyst initiates the intramolecular aromatic C(sp2)-H bond functionalization, while the Pd(0) catalyst facilitates the subsequent allylic alkylation, leading to the formation of the desired heterocyclic compounds with high yields. This dual catalytic system showcases good functional group tolerance and provides an efficient route to synthesize compounds that are prevalent in bioactive natural products and pharmaceuticals.

A Novel Oxygen-to-Carbon Ester Migration catalysed by 4-(N,N-Dimethylamino)pyridine in the Benzofuranone Ring System

10.1039/c39860001524

The research details a novel method for oxygen-to-carbon ester migration in the benzofuranone ring system, catalyzed by 4-(N,N-dimethylamino)pyridine (DMAP). The purpose of this study was to address the challenge in synthetic chemistry of regioselective carbon acylation of enolates, particularly those that are highly delocalized, as the kinetically-formed oxygen-acylated products usually predominate. The researchers reported a method that quantitatively rearranges the initially-formed enol carbonate to its carbon-acylated isomer, using DMAP as a catalyst. The benzofuranones, which have a wide spectrum of pharmacological activity, were the focus of this study due to their importance in the synthesis of potential anti-neoplastic agents. Key chemicals used in the process included sodium hydride in dimethylformamide (DMF) for deprotonating 3-phenyl-2(3H)-benzofuranone, ethyl chloroformate for the formation of enol carbonate, and DMAP for catalyzing the rearrangement to the C-acylated ester. The study concluded that DMAP could effectively catalyze the carbon acylation, leading to the desired C-acylated ester, and that this reaction was general for several alkyl chloroformates.