8-Acetyl-7-hydroxycoumarin

Base Information

• Chemical Name: 8-Acetyl-7-hydroxycoumarin
• CAS No.: 6748-68-1
• Molecular Formula: C11H8O4
• Molecular Weight: 204.182
• Hs Code.: 2932209090
• European Community (EC) Number: 623-154-6
• UNII: QD6QWL7EQR
• DSSTox Substance ID: DTXSID40419935
• Nikkaji Number: J1.382.704D
• Wikidata: Q82231162
• Pharos Ligand ID: 5U1RB7Z4G9CF
• Metabolomics Workbench ID: 73952
• ChEMBL ID: CHEMBL446518
• Mol file: 6748-68-1.mol

Synonyms:8-acetyl-7-hydroxycoumarin

Chemical Property of 8-Acetyl-7-hydroxycoumarin

Chemical Property:

• Vapor Pressure: 6.63E-08mmHg at 25°C
• Melting Point: 167-171 °C(lit.)
• Refractive Index: 1.62
• Boiling Point: 427.3oC at 760 mmHg
• PKA: 8.10±0.20(Predicted)
• Flash Point: 175.4oC
• PSA: 67.51000
• Density: 1.388g/cm3
• LogP: 1.70120
• Storage Temp.: 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 204.04225873
• Heavy Atom Count: 15
• Complexity: 321

Purity/Quality:

98%,99%, ^*data from raw suppliers

8-Acetyl-7-hydroxycoumarin 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)C1=C(C=CC2=C1OC(=O)C=C2)O

Technology Process of 8-Acetyl-7-hydroxycoumarin

There total 4 articles about 8-Acetyl-7-hydroxycoumarin 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: 21.0%

(S)-3,3-dimethyloxirane-2-carboxaldehyde (121571-31-1) + 7-acetyloxy-8-iodo-2H-1-benzopyran-2-one (112699-36-2) → 7-hydroxy-8-(1-hydroxy-1,2-dimethylpropyl)-2H-1-benzopyran-2-one + trans-8,9-dihydro-9-hydroxy-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]-1-benzopyran-2-one + cis-8,9-dihydro-9-hydroxy-8-(1-hydroxy-1-methylethyl)-2H-furo[2,3-h]-1-benzopyran-2-one (26992-52-9,46954-39-6,56815-93-1,62624-87-7,86851-58-3) + 8-acetyl-7-hydroxycoumarin (6748-68-1)

Guidance literature:

7-acetyloxy-8-iodo-2H-1-benzopyran-2-one; With isopropylmagnesium chloride; In tetrahydrofuran; at -100 ℃; for 1h;

(S)-3,3-dimethyloxirane-2-carboxaldehyde; In tetrahydrofuran; at -100 - 20 ℃; for 1h;

DOI:10.1021/jo047974k

Reference yield:

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) + 7-acetyloxycoumarin (10387-49-2) → 7-hydroxy-2H-chromen-2-one (93-35-6) + 8-acetyl-7-hydroxycoumarin (6748-68-1) + 8-acetyl-7-hydroxy-4-methyl-2H-chromen-2-one (2555-29-5)

Guidance literature:

With aluminium trichloride; at 140 ℃; for 1h;

Reference yield:

7-acetyloxycoumarin (10387-49-2) + 7-(phenylcarbonyl)oxy-4-methyl-2H-1-benzopyran-2-one (66185-72-6) → 8-acetyl-7-hydroxycoumarin (6748-68-1) + 8-acetyl-7-hydroxy-4-methyl-2H-chromen-2-one (2555-29-5) + 8-Benzoyl-7-hydroxycoumarin (90104-85-1) + 8-Benzoyl-7-hydroxy-4-methylcoumarin (20312-83-8)

Guidance literature:

With aluminium trichloride; at 140 ℃; for 1h;

upstream raw materials:

7-hydroxy-4-methyl-chromen-2-one

7-acetyloxycoumarin

7-(phenylcarbonyl)oxy-4-methyl-2H-1-benzopyran-2-one

4-methylumbelliferyl acetate

Downstream raw materials:

8-benzyloxy-7-hydroxycoumarin

daphneticin

7-benzyloxy-8-methoxymethoxycoumarin

8-benzyloxy-7-methanesulfonyloxycoumarin

Refernces

• 1、 Kravchenko,Chibisova,Traven'. "Intermolecular character of the Fris rearrangement in the series of acyloxycoumarins". . p. 899 - 909. Retrieved 2007/10/03.