6-Hydroxycoumarin

Base Information

• Chemical Name: 6-Hydroxycoumarin
• CAS No.: 6093-68-1
• Molecular Formula: C9H6 O3
• Molecular Weight: 162.145
• Hs Code.: 2932209090
• European Community (EC) Number: 628-689-9
• NSC Number: 677227,226192
• UNII: 7FS6H939K6
• DSSTox Substance ID: DTXSID70209760
• Nikkaji Number: J419.093I
• Wikidata: Q83084178
• Pharos Ligand ID: LL7SBC48542R
• Metabolomics Workbench ID: 129283
• ChEMBL ID: CHEMBL243263
• Mol file: 6093-68-1.mol

Synonyms:6-Hydroxycoumarin;6093-68-1;6-Hydroxy-2H-chromen-2-one;6-hydroxychromen-2-one;2H-1-Benzopyran-2-one, 6-hydroxy-;6-hydroxy coumarin;6-Hydroxycoumaran;2H-1-Benzopyran-2-one,6-hydroxy-;6-Hydroxy-2H-1-benzopyran-2-one;CHEMBL243263;7FS6H939K6;NSC677227;NSC-226192;NSC-677227;NSC226192;6-Hydroxycoumarin, 96%;6-hydroxy-chromene-2-one;SCHEMBL187709;UNII-7FS6H939K6;6-Hydroxy-2H-chromen-2-one #;DTXSID70209760;HY-N6656;BDBM50327651;MFCD00630040;s9364;AKOS005258623;CCG-266293;NSC 226192;AC-34657;AS-17834;PD087275;CS-0083182;FT-0635972;H1327;N12041;J-518781;InChI=1/C9H6O3/c10-7-2-3-8-6(5-7)1-4-9(11)12-8/h1-5,10

Chemical Property of 6-Hydroxycoumarin

Chemical Property:

• Melting Point: 249-253 °C(lit.)
• Refractive Index: 1.5380 (estimate)
• Boiling Point: 398.2 °C at 760 mmHg
• PKA: 8.92±0.20(Predicted)
• Flash Point: 189.6 °C
• PSA: 50.44000
• Density: 1.403 g/cm³
• LogP: 1.49860
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1
• 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:

99.5% ^*data from raw suppliers

6-Hydroxycoumarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C=CC(=O)O2)C=C1O
• Description: 6-Hydroxycoumarin is a coumarin which has anti-inflammatory, anti-pyretic, anti-oxidant, vasodilator, anti-amoebic, anti-bacterial, anti-fungal, bacteriostatic and antitumor activity.
• Uses: 6-Hydroxycoumarin (cas# 6093-68-1) is a compound useful in organic synthesis.

Technology Process of 6-Hydroxycoumarin

There total 3 articles about 6-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:

coumarin (91-64-5) → 7-hydroxy-2H-chromen-2-one (93-35-6) + 6-hydroxycoumarin (6093-68-1) + 8-hydroxycoumarin (2442-31-1) + o-Hydroxyphenylacetaldehyde (7451-95-8)

Guidance literature:

With human CYP₂A₁₃; NADP; glucose 6-phosphate dehydrogenase; D-glucose 6-phosphate; In water; at 37 ℃; pH=7.4; Enzyme kinetics; Product distribution;

DOI:10.1080/0049825021000022302

Reference yield:

coumarin (91-64-5) → 7-hydroxy-2H-chromen-2-one (93-35-6) + 6-hydroxycoumarin (6093-68-1)

Guidance literature:

With titanium(IV) dioxide; Reagent/catalyst; Kinetics; UV-irradiation;

DOI:10.1016/j.apcata.2020.117566

Reference yield:

2-formyl-1,4-phenylene diacetate (3524-69-4) + ethyl diphenylphosphonoacetate (16139-79-0) → 6-hydroxycoumarin (6093-68-1) + ethyl 2,5-dihydroxycinnamate (40931-15-5)

Guidance literature:

2-formyl-1,4-phenylene diacetate; ethyl diphenylphosphonoacetate; With 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; In tetrahydrofuran; at -78 ℃;

With potassium hydroxide; In methanol; at 20 ℃; for 0.25h;

DOI:10.3987/COM-02-S23

upstream raw materials:

2-formyl-1,4-phenylene diacetate

ethyl diphenylphosphonoacetate

coumarin

Downstream raw materials:

6-methoxycoumarin

2,5-dimethoxy-cis-cinnamic acid

6-cyclohex-2-enyloxycoumarin

coumarin-6-carboxaldehyde

Refernces

• 1、 Takeuchi, Yasuo,Ueda, Norihiro,Uesugi, Koji,Abe, Hitoshi,Nishioka, Hiromi,Harayama, Takashi. "Convenient synthesis of a simple coumarin from salicylaldehyde and wittig reagent. IV: Improved synthetic method of substituted coumarins". . p. 217 - 224. Retrieved 2007/10/03.