2-Hydroxy-6H-benzo(c)chromen-6-one

Base Information

• Chemical Name: 2-Hydroxy-6H-benzo(c)chromen-6-one
• CAS No.: 3525-01-7
• Molecular Formula: C₁₃H₈O₃
• Molecular Weight: 212.205
• NSC Number: 98100
• UNII: 5B7VP6R4DL
• DSSTox Substance ID: DTXSID10188747
• Nikkaji Number: J2.998.167A
• Wikidata: Q83060586
• Mol file: 3525-01-7.mol

Synonyms:2-Hydroxy-6H-benzo(c)chromen-6-one;3525-01-7;5B7VP6R4DL;NSC98100;UNII-5B7VP6R4DL;NSC 98100;NSC-98100;2-Hydroxy-6H-benzo[c]chromen-6-one;2-hydroxybenzo[c]chromen-6-one;NCIOpen2_006200;SCHEMBL7859223;DTXSID10188747;SG-00588;2-HYDROXY-6H-DIBENZO(B,D)PYRAN-6-ONE;6H-DIBENZO(B,D)PYRAN-6-ONE, 2-HYDROXY-;2-BIPHENYLCARBOXYLIC ACID, 2',5'-DIHYDROXY-, .DELTA.-LACTONE

Chemical Property of 2-Hydroxy-6H-benzo(c)chromen-6-one

Chemical Property:

• Vapor Pressure: 4.88E-08mmHg at 25°C
• Boiling Point: 431.1°Cat760mmHg
• Flash Point: 195.9°C
• Density: 1.395g/cm³
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 212.047344113
• Heavy Atom Count: 16
• Complexity: 289

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C3=C(C=CC(=C3)O)OC2=O
• General Description: 2-Hydroxy-6H-benzo[c]chromen-6-one is a fused chromenone derivative synthesized via transition-metal-catalyzed C-H functionalization and cyclization reactions, particularly involving benzoic acids or benzamides with quinones. It is formed through a cascade process involving C-H activation, quinone insertion, and subsequent lactonization. 2-hydroxy-6H-benzo[c]chromen-6-one is accessible under redox-neutral conditions and serves as a key scaffold in synthetic chemistry. Alternative names for this structure may include 2-hydroxybenzo[c]chromen-6-one or related fused chromenone derivatives. **Returned paragraph (conclusion):** 2-Hydroxy-6H-benzo[c]chromen-6-one is a fused chromenone synthesized via transition-metal-catalyzed C-H activation and cyclization of benzoic acids or benzamides with quinones, forming a lactone structure. It is produced through a redox-neutral cascade involving insertion and intramolecular cyclization.

Technology Process of 2-Hydroxy-6H-benzo(c)chromen-6-one

There total 18 articles about 2-Hydroxy-6H-benzo(c)chromen-6-one 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%

4a-hydroxy-5-methoxy-1,4a,5,10b-tetrahydrophenanthridine-2,6-dione → 2-hydroxy-6H-benzo[c]-chromen-6-one (3525-01-7)

Guidance literature:

With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cesium acetate; acetic acid; In 1,2-dichloro-ethane; acetone; at 90 ℃; for 2.5h; chemoselective reaction;

DOI:10.1021/acs.joc.5b02903

Reference yield: 99.0%

N-methoxybenzamide (2446-51-7) + p-benzoquinone (106-51-4) → 2-hydroxy-6H-benzo[c]-chromen-6-one (3525-01-7)

Guidance literature:

With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cesium acetate; acetic acid; In 1,2-dichloro-ethane; acetone; at 90 ℃; for 3h; Mechanism; Sealed tube;

DOI:10.1039/c4cc08260e

Reference yield: 98.0%

N-methoxybenzamide (2446-51-7) + hydroquinone (123-31-9,8027-02-9) → 2-hydroxy-6H-benzo[c]-chromen-6-one (3525-01-7)

Guidance literature:

With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; iodosylbenzene; cesium acetate; acetic acid; In 1,2-dichloro-ethane; acetone; at 90 ℃; for 5h; Solvent; Temperature; Reagent/catalyst; chemoselective reaction; Sealed tube;

DOI:10.1039/c4cc08260e

upstream raw materials:

3′H-spiro[cyclohexane-1,1′-isobenzofuran]-2,5-diene-3′,4-dione

4,4-dimethoxycyclohexa-2,5-dienone

benzoic acid

p-benzoquinone

Downstream raw materials:

6H-benzo[c]chromen-6-one