4-Hydroxycoumarin

Base Information

• Chemical Name: 4-Hydroxycoumarin
• CAS No.: 1076-38-6
• Molecular Formula: C9H6O3
• Molecular Weight: 162.145
• Hs Code.: 29322980
• Mol file: 1076-38-6.mol

Synonyms:4-Hydroxy-2H-1-benzopyran-2-one;Benzotetronic acid;2H-1-Benzopyran-2-one,4-hydroxy-;Coumarin, 4-hydroxy-;4-Coumarinol;2-hydroxychromen-4-one;Coumarin, 4-hydroxy- (8CI);2H-1-Benzopyran-2-one, 4-hydroxy-;

Chemical Property of 4-Hydroxycoumarin

Chemical Property:

• Appearance/Colour: Yellow powder or chunks
• Vapor Pressure: 0.02Pa at 25℃
• Melting Point: 210-215 ºC
• Refractive Index: 1.4500 (estimate)
• Boiling Point: 352.41 ºC at 760 mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 165.353 ºC
• PSA: 50.44000
• Density: 1.446 g/cm³
• LogP: 1.49860
• Storage Temp.: Store below +30°C.
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: PRACTICALLY INSOLUBLE

Purity/Quality:

99% ^*data from raw suppliers

4-Hydroxy Coumarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• 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:

• Uses: 4-Hydroxycoumarin is a plant derived antioxidant, protecting against lipid peroxidation, as well as a potential inhibitor of HIV-1 Integrase. 4-Hydroxycoumarins are a very important class of biologically active drugs which are widely used as anticoagulants-Warfarin and Acenocoumarol. 4-Hydroxycoumarin may be regarded as a phenylenetetronic acid , and like tetronic acid forms condensation products with aldehydes. Synthesis of biscoumarin derivatives by the reaction of aldehydes and 4-hydroxycoumarin using ruthenium(III) chloride hydrate as a versatile homogeneous catalyst. 4-Hydroxycoumarin is involved in annulation reactions, due to the relatively high acidity of the C-H bond at the 3-position: a three-component reaction with isocyanides and dialkyl acetylene dicarboxylates affords annulated 4H-pyrans.

Technology Process of 4-Hydroxycoumarin

There total 72 articles about 4-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: 100.0%

carbon monoxide (201230-82-2) + o-hydroxyacetophenone (118-93-4,104809-67-8) → 4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5)

Guidance literature:

With selenium; 1,5-Diazabicyclo[5.4.0]undec-5-ene; In tetrahydrofuran; at 90 ℃;

DOI:10.1039/c39820001283

Reference yield: 99.0%

4-allyloxy-2H-chromen-2-one (31005-07-9) → 4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5)

Guidance literature:

With sodium hydrogen telluride; acetic acid; In ethanol; for 2h; Heating;

Reference yield: 96.0%

ethyl 4-hydroxy-2-oxo-2H-chromene-3-carboxylate (1821-20-1) → 4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5)

Guidance literature:

With potassium hydroxide; In methanol; water;

upstream raw materials:

methyl acetylsalicylate

sodium ethanolate

o-hydroxyacetophenone

Diethyl carbonate

Downstream raw materials:

4-hydroxy-3-[1-(4-hydroxy-3-methoxy-phenyl)-3-oxo-butyl]-coumarin

4-hydroxy-3-(3-oxo-1,3-diphenylpropyl)-2H-chromen-2-one

3-phenylureidomethylene-4-oxo-coumarin

[2,4-Dioxo-chroman-(3Z)-ylidenemethyl]-carbamic acid phenyl ester

Refernces

• 1、 Yang, Feifei,Zhao, Na,Song, Jiali,Zhu, Kongkai,Jiang, Cheng-shi,Shan, Peipei,Zhang, Hua. "Design, synthesis and biological evaluation of novel coumarin-based hydroxamate derivatives as histone deacetylase (HDAC) inhibitors with antitumor activities". . . Retrieved 2019.
• 2、 Revankar, Hrishikesh M.,Kulkarni, Manohar V.. "Cu (I) Catalyzed One Pot SN-Click Reactions of Halogenated Coumarins and 1-aza-coumarins". . p. 537 - 544. Retrieved 2018.
• 3、 Jung,Jung,Park. "A convenient one-pot synthesis of 4-hydroxycoumarin, 4-hydroxythiocoumarin, and 4-hydroxyquinolin-2(1H)-one". . p. 1195 - 1200. Retrieved 2001.
• 4、 Al-Sehemi, Abdullah G.,El-Gogary, Sameh R.. "Synthesis and photooxygenation of furo[3,2-c]coumarin derivatives as antibacterial and DNA intercalating agent". . p. 316 - 320. Retrieved 2012.
• 5、 Ziegler et al.. "-". . p. 386,390. Retrieved 1956.
• 6、 Zhang, Ming-Zhi,Zhang, Rong-Rong,Wang, Jia-Qun,Yu, Xiang,Zhang, Ya-Ling,Wang, Qing-Qing,Zhang, Wei-Hua. "Microwave-assisted synthesis and antifungal activity of novel fused Osthole derivatives". . p. 10 - 16. Retrieved 2016.
• 7、 Zaheer, Zahid,Khan, Firoz A. Kalam,Sangshetti, Jaiprakash N.,Patil, Rajendra H.. "Expeditious synthesis, antileishmanial and antioxidant activities of novel 3-substituted-4-hydroxycoumarin derivatives". . p. 287 - 294. Retrieved 2016.
• 8、 Toan, Vu Ngoc,Thanh, Nguyen Dinh. "Synthesis and antiproliferative activity of hybrid thiosemicarbazone derivatives bearing coumarin and d-galactose moieties with EGFR inhibitory activity and molecular docking study". . p. 1868 - 1885. Retrieved 2021.
• 9、 Hoppe, Heinrich C.,Isaacs, Michelle,Kaye, Perry T.,Krause, Rui W. M.,Manyeruke, Meloddy H.,Seldon, Ronnett,Tshiwawa, Thendamudzimu,Warner, Digby F.. "Synthesis and biological evaluation of bis-N2,N2′-(4-hydroxycoumarin-3-yl)ethylidene]-2,3-dihydroxysuccinodihydrazides". . . Retrieved 2020.
• 10、 Ogawa, Akiya,Kambe, Nobuaki,Murai, Shinji,Sonoda, Noboru. "SELENIUM ASSISTED CARBONYLATION OF ALKYL ARYL KETONES WITH CARBON MONOXIDE". . p. 4813 - 4820. Retrieved 1985.