8-Acetyl-7-hydroxy-4-methylcoumarin

Base Information

• Chemical Name: 8-Acetyl-7-hydroxy-4-methylcoumarin
• CAS No.: 2555-29-5
• Molecular Formula: C12H10 O4
• Molecular Weight: 218.209
• Hs Code.: 2932209088
• European Community (EC) Number: 631-036-0
• NSC Number: 19027
• UNII: 0084XV5Z4C
• DSSTox Substance ID: DTXSID30180243
• Nikkaji Number: J187.043B
• Wikidata: Q63395748
• Metabolomics Workbench ID: 73954
• ChEMBL ID: CHEMBL1784035
• Mol file: 2555-29-5.mol

Synonyms:8-acetyl-7-hydroxy-4-methylcoumarin

Chemical Property of 8-Acetyl-7-hydroxy-4-methylcoumarin

Chemical Property:

• Vapor Pressure: 7.3E-08mmHg at 25°C
• Melting Point: 174-178°C
• Boiling Point: 426.1°Cat760mmHg
• PKA: 8.21±0.20(Predicted)
• Flash Point: 170.7°C
• PSA: 67.51000
• Density: 1.322g/cm³
• LogP: 2.00960
• Solubility.: soluble in Methanol
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 218.05790880
• Heavy Atom Count: 16
• Complexity: 358

Purity/Quality:

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

8-Acetyl-7-hydroxy-4-methylcoumarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)OC2=C1C=CC(=C2C(=O)C)O
• Uses: 8-Acetyl-7-hydroxy-4-methylcoumarin is a coumarin with fungicidal and herbicidal activities.

Technology Process of 8-Acetyl-7-hydroxy-4-methylcoumarin

There total 18 articles about 8-Acetyl-7-hydroxy-4-methylcoumarin 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: 86.69%

4-methylumbelliferyl acetate (2747-05-9) → 8-acetyl-7-hydroxy-4-methyl-2H-chromen-2-one (2555-29-5)

Guidance literature:

With Aluminum Chloride; at 170 ℃; for 6.08333h;

DOI:10.1016/j.bmcl.2009.09.031

Reference yield: 86.0%

8-acetyl-7-<(β-chloroallyl)oxy>-4-methylcoumarin (86290-51-9) → 8-acetyl-7-hydroxy-4-methyl-2H-chromen-2-one (2555-29-5) + 8-(β-chloroallyl)-7-hydroxy-4-methylcoumarin (86290-43-9) + 8-acetyl-6-(β-chloroallyl)-7-hydroxy-4-methylcoumarin (86290-53-1) + 6-Acetyl-8-(2-chloro-allyl)-7-hydroxy-4-methyl-chromen-2-one (86290-61-1)

Guidance literature:

With 1,4-bis(1-methylethyl)benzene; for 8h; Heating;

DOI:10.1021/jo00164a015

Reference yield: 80.0%

2,6-dihydroxylacetophenone (699-83-2) + ethyl acetoacetate (141-97-9) → 8-acetyl-7-hydroxy-4-methyl-2H-chromen-2-one (2555-29-5)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 8h; Reflux;

DOI:10.1007/s00706-008-0931-3

upstream raw materials:

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

acetic anhydride

4-methylumbelliferyl acetate

2,6-dihydroxylacetophenone

Downstream raw materials:

2,6-dihydroxylacetophenone

8-acetyl-7-hydroxy-4-methyl-2-oxo-2H-chromene-3,6-disulfonic acid

8,8'-diacetyl-7,7'-dihydroxy-4,4'-dimethyl-2,2'-dioxo-2H,2'H-bis-chromene-6-sulfonic acid-6=>7';6'=>7-dilactone

4-Methyl-9-(4-o-tolyl-piperazin-1-ylmethyl)-8,9-dihydro-pyrano[2,3-f]chromene-2,10-dione

Refernces

• 1、 Ostrowska, Kinga,Grzeszczuk, Dawid,G?uch-Lutwin, Monika,Grybo?, Anna,Siwek, Agata,Le?niak, Anna,Sacharczuk, Mariusz,Trzaskowski, Bartosz. "5-HT1A and 5-HT2A receptors affinity, docking studies and pharmacological evaluation of a series of 8-acetyl-7-hydroxy-4-methylcoumarin derivatives". . p. 527 - 535. Retrieved 2018.
• 2、 -. "(E)-4 - methyl -7 - hydroxyl -8 - (3 - (ferrocenyl) acryloyl) coumarin as well as preparation method and application thereof". Paragraph 0025; 0037; 0058; 0061; 0063; 0066. . Retrieved 2021/10/20.
• 3、 Zhang, Qiang,Ma, Ruifang,Li, Zhuying,Liu, Zizhong. "A multi-responsive crown ether-based colorimetric/fluorescent chemosensor for highly selective detection of Al3+, Cu2+ and Mg2+". . . Retrieved 2019/12/09.