8-Hydroxycoumarin

Base Information

• Chemical Name: 8-Hydroxycoumarin
• CAS No.: 2442-31-1
• Molecular Formula: C9H6O3
• Molecular Weight: 162.145
• Hs Code.: 2932209090
• UNII: 854P936B10
• DSSTox Substance ID: DTXSID50873761
• Nikkaji Number: J419.094G
• Wikidata: Q27269592
• Metabolomics Workbench ID: 133383
• ChEMBL ID: CHEMBL389988
• Mol file: 2442-31-1.mol

Synonyms:8-hydroxycoumarin

Chemical Property of 8-Hydroxycoumarin

Chemical Property:

• Vapor Pressure: 9.86E-06mmHg at 25°C
• Refractive Index: 1.64
• Boiling Point: 361.573 °C at 760 mmHg
• Flash Point: 170.279 °C
• PSA: 50.44000
• Density: 1.403 g/cm³
• LogP: 1.49860
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 162.031694049
• Heavy Atom Count: 12
• Complexity: 222

Purity/Quality:

99%, ^*data from raw suppliers

8-Hydroxycoumarin 98.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 8-Hydroxycoumarin

There total 21 articles about 8-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: 93.0%

3-(3-Acetoxy-2-hydroxy-phenyl)-3-(2-methoxycarbonyl-ethylsulfanyl)-propionic acid methyl ester (114106-30-8) → 8-hydroxycoumarin (2442-31-1)

Guidance literature:

With potassium carbonate; In acetone; for 1.5h; Heating;

Reference yield: 87.0%

(E)-3-(2,3-Dimethoxy-phenyl)-acrylic acid methyl ester → 8-hydroxycoumarin (2442-31-1)

Guidance literature:

With boron tribromide; In dichloromethane; for 3h; Heating;

DOI:10.1080/00397919908086054

Reference yield: 72.0%

2,3-dihydroxybenzaldehyde (24677-78-9) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → 8-hydroxycoumarin (2442-31-1)

Guidance literature:

In toluene; at 220 ℃; for 1h; Inert atmosphere; Microwave irradiation; Sealed tube;

DOI:10.1002/ejoc.201701021

upstream raw materials:

8-methoxycoumarine

8-methoxy-2-oxo-2H-chromene-3-carboxylic acid

2-cyano-3t-(2,3-dimethoxy-phenyl)-acrylic acid

3-(3-Acetoxy-2-hydroxy-phenyl)-3-(2-methoxycarbonyl-ethylsulfanyl)-propionic acid methyl ester

Downstream raw materials:

Carbonic acid 2-oxo-2H-chromen-8-yl ester 3,4,4-trimethyl-[1,2]dioxetan-3-ylmethyl ester

6-<(E)-3-(4,5-dihydro-5,5-dimethyl-4-oxo-2-furanyl)-2-butenyloxy>-coumarin

8-allyloxycoumarin

8-(7-methoxy-6,6-dimethyl-2-oxo-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-chromen-2-one

Refernces

• 1、 Cerqueira, Nuno M. F. S. A.,Oliveira-Campos, Ana M. F.,Coelho, Paulo J.,Melo De Carvalho, Luis H.,Samat, Andre,Guglielmetti, Robert. "Synthesis of photochromic dyes based on annulated coumarin systems". . p. 442 - 450. Retrieved 2002.
• 2、 Symeonidis, Theodoros,Chamilos, Michael,Hadjipavlou-Litina, Dimitra J.,Kallitsakis, Michael,Litinas, Konstantinos E.. "Synthesis of hydroxycoumarins and hydroxybenzo[f]- or [h]coumarins as lipid peroxidation inhibitors". . p. 1139 - 1142. Retrieved 2009.
• 3、 Konrádová, Daniela,Kozubíková, Hana,Dole?al, Karel,Pospí?il, Ji?í. "Microwave-Assisted Synthesis of Phenylpropanoids and Coumarins: Total Synthesis of Osthol". supporting information. p. 5204 - 5213. Retrieved 2017/09/29.
• 4、 Pisani, Leonardo,Catto, Marco,Giangreco, Ilenia,Leonetti, Francesco,Nicolotti, Orazio,Stefanachi, Angela,Cellamare, Saverio,Carotti, Angelo. "Design, synthesis, and biological evaluation of coumarin derivatives tethered to an edrophonium-like fragment as highly potent and selective dual binding site acetylcholinesterase inhibitors". experimental part. p. 1616 - 1630. Retrieved 2011/11/29.