4-Hydroxycoumarin
- CasNo:1076-38-6
Product Description
4-Hydroxycoumarin GMP Manufacturer Global Trade 1076-38-6 with Fast Delivery
- Molecular Formula: C9H6O3
- Molecular Weight: 162.145
- 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
4-Hydroxycoumarin(Cas 1076-38-6) Usage
|
Synthesis Reference(s) |
The Journal of Organic Chemistry, 25, p. 677, 1960 DOI: 10.1021/jo01074a630 |
|
Flammability and Explosibility |
Notclassified |
|
Purification Methods |
Crystallise 4-hydroxycoumarin from water and dry it in a vacuum desiccator over pKEst Sicapent. [Beilstein 18/1 V 378.] |
|
General Description |
4-Hydroxycoumarin is a versatile chemical scaffold widely used in organic synthesis, particularly in the construction of pharmacologically active compounds such as furocoumarins, warfarin analogues, and benzopyranopyridine derivatives. It serves as a key reactant in multicomponent reactions, asymmetric syntheses, and the formation of heterocyclic systems, often under green chemistry conditions. Its derivatives exhibit significant biological activities, including anticoagulant and antibacterial properties, making it a valuable intermediate in medicinal chemistry. |
|
Definition |
ChEBI: 4-hydroxycoumarin is a hydroxycoumarin that is coumarin in which the hydrogen at position 4 is replaced by a hydroxy group. It is a conjugate acid of a 4-hydroxycoumarin(1-). |
InChI:InChI:1S/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,10H
1076-38-6 Relevant articles
CONTROLLING EFFECT OF SUBSTITUENTS ON THE REDUCTION OF 4-SUBSTITUTED 3-NITROCOUMARINS BY SODIUM HYDROSULFITE
Parfenov, E. A.,Savel'ev, V. L.,Smirnov, L. D.
, p. 356 (1989)
-
Design, synthesis and biological evaluation of novel coumarin-based hydroxamate derivatives as histone deacetylase (HDAC) inhibitors with antitumor activities
Yang, Feifei,Zhao, Na,Song, Jiali,Zhu, Kongkai,Jiang, Cheng-shi,Shan, Peipei,Zhang, Hua
, (2019)
A series of novel coumarin-based hydroxa...
Coumarin derivatives as potential inhibitors of acetylcholinesterase: Synthesis, molecular docking and biological studies
Singla, Shaffali,Piplani, Poonam
, p. 4587 - 4599 (2016)
A series of novel hybrids has been synth...
Cu (I) Catalyzed One Pot SN-Click Reactions of Halogenated Coumarins and 1-aza-coumarins
Revankar, Hrishikesh M.,Kulkarni, Manohar V.
, p. 537 - 544 (2018)
A one pot three component, copper cataly...
-
Shah et al.
, p. 677,678 (1960)
-
A convenient one-pot synthesis of 4-hydroxycoumarin, 4-hydroxythiocoumarin, and 4-hydroxyquinolin-2(1H)-one
Jung,Jung,Park
, p. 1195 - 1200 (2001)
An improved one-pot synthesis of 4-hydro...
Synthesis of substituted 4-(4-((3-Nitro-2-oxo-2H-chromene-4-yl)amino)phenyl)morpholine-3-one coumarin derivatives
Sanghani, Yogesh J.,Koradiya, Suresh B.,Patel, Anilkumar S.
, p. 1461 - 1464 (2019)
A series of novel 4-(4-amino phenyl) mor...
Synthesis and photooxygenation of furo[3,2-c]coumarin derivatives as antibacterial and DNA intercalating agent
Al-Sehemi, Abdullah G.,El-Gogary, Sameh R.
, p. 316 - 320 (2012)
Syntheses of 2,3-dimethyl-4H-furo[3,2-c]...
Synthesis and biological evaluation of 4 arylcoumarin analogues as tubulin-targeting antitumor agents
Mutai, Peggoty,Breuzard, Gilles,Pagano, Alessandra,Allegro, Diane,Peyrot, Vincent,Chibale, Kelly
, p. 1652 - 1665 (2017)
The synthesis of twenty-six 4-arylcoumar...
-
Ziegler et al.
, p. 386,390 (1956)
-
Chromenone derivatives as a versatile scaffold with dual mode of inhibition of HIV-1 reverse transcriptase-associated Ribonuclease H function and integrase activity
Esposito, Francesca,Ambrosio, Francesca Alessandra,Maleddu, Rita,Costa, Giosuè,Rocca, Roberta,Maccioni, Elias,Catalano, Raffaella,Romeo, Isabella,Eleftheriou, Phaedra,Karia, Denish C.,Tsirides, Petros,Godvani, Nilesh,Pandya, Hetal,Corona, Angela,Alcaro, Stefano,Artese, Anna,Geronikaki, Athina,Tramontano, Enzo
, (2019)
A number of compounds targeting differen...
Microwave-assisted synthesis and antifungal activity of novel fused Osthole derivatives
Zhang, Ming-Zhi,Zhang, Rong-Rong,Wang, Jia-Qun,Yu, Xiang,Zhang, Ya-Ling,Wang, Qing-Qing,Zhang, Wei-Hua
, p. 10 - 16 (2016)
Based on the microwave-assisted syntheti...
One-pot two-step synthesis of 3-iodo-4-aryloxy coumarins and their Pd/C-catalyzed annulation to coumestans
Panda, Niranjan,Mattan, Irshad
, p. 7716 - 7725 (2018)
An efficient protocol for the synthesis ...
Expeditious synthesis, antileishmanial and antioxidant activities of novel 3-substituted-4-hydroxycoumarin derivatives
Zaheer, Zahid,Khan, Firoz A. Kalam,Sangshetti, Jaiprakash N.,Patil, Rajendra H.
, p. 287 - 294 (2016)
A series of novel 3-substituted-4-hydrox...
-
Merchant et al.
, p. 2061 (1972)
-
Synthesis and antiproliferative activity of hybrid thiosemicarbazone derivatives bearing coumarin and d-galactose moieties with EGFR inhibitory activity and molecular docking study
Toan, Vu Ngoc,Thanh, Nguyen Dinh
, p. 1868 - 1885 (2021)
A series of substituted N-(2,3,4,6-tetra...
Combined Claisen Rearrangement and Oxidative Cyclization as a Route to Hydroxymethyl Dihydrofuran-Annulated Coumarins
Jayaprakash, Rao Y.,Chakravarthula, Venu
, p. 1014 - 1018 (2015)
A convenient and simple method for the s...
Synthesis and biological evaluation of bis-N2,N2′-(4-hydroxycoumarin-3-yl)ethylidene]-2,3-dihydroxysuccinodihydrazides
Hoppe, Heinrich C.,Isaacs, Michelle,Kaye, Perry T.,Krause, Rui W. M.,Manyeruke, Meloddy H.,Seldon, Ronnett,Tshiwawa, Thendamudzimu,Warner, Digby F.
, (2020)
A series of N2,N2′-bis[4-hydroxycoumarin...
Combining silver catalysis and organocatalysis: A sequential michael addition/hydroalkoxylation one-pot approach to annulated coumarins
Hack, Daniel,Chauhan, Pankaj,Deckers, Kristina,Hermann, Gary N.,Mertens, Lucas,Raabe, Gerhard,Enders, Dieter
, p. 5188 - 5191 (2014)
A highly stereoselective one-pot procedu...
SELENIUM ASSISTED CARBONYLATION OF ALKYL ARYL KETONES WITH CARBON MONOXIDE
Ogawa, Akiya,Kambe, Nobuaki,Murai, Shinji,Sonoda, Noboru
, p. 4813 - 4820 (1985)
Selenium assisted carbonylation of alkyl...
Facile Synthesis of 4-Hydroxycoumarins by Sulfur-Assisted Carbonylation of 2'-Hydroxyacetophenones with Carbon Monoxide
Mizuno, Takumi,Nishiguchi, Ikuzo,Hirashima, Tsuneaki,Ogawa, Akiya,Kambe, Nobuaki,Sonoda, Noboru
, p. 257 - 259 (1988)
4-Hydroxycoumarins (4-hydroxy-2-oxo-2H-1...
Synthesis of furo[3,2-c]coumarins via I2/TBHP-mediated reaction of 4-hydroxycoumarins with terminal alkynes
Chu, Xianglong,Tang, Ziqiang,Ma, Jiangshan,He, Libowen,Feng, Lei,Ma, Chen
, p. 970 - 974 (2018)
An efficient I2/TBHP-mediated process fo...
Synthesis and reactivity of boron difluoride complexes of N,N-dimethylsalicylacetamide
Morris,Fang,Wishka,Han
, p. 3817 - 3820 (1993)
The synthesis and reactivity of a series...
Selenium-assisted Carbonylation of o-Hydroxyacetophenone with Carbon Monoxide
Ogawa, Akiya,Kondo, Kiyoshi,Murai, Shinji,Sonoda, Noboru
, p. 1283 - 1284 (1982)
Selenium-assisted carbonylation of o-hyd...
Sulfonamides containing coumarin moieties selectively and potently inhibit carbonic anhydrases II and IX: Design, synthesis, inhibitory activity and 3D-QSAR analysis
Wang, Zhong-Chang,Qin, Ya-Juan,Wang, Peng-Fei,Yang, Yong-An,Wen, Qing,Zhang, Xin,Qiu, Han-Yue,Duan, Yong-Tao,Wang, Yan-Ting,Sang, Ya-Li,Zhu, Hai-Liang
, p. 1 - 11 (2013)
A series of sulfonamides containing coum...
Design, Synthesis, and Evaluation of in Vitro and in Vivo Anticancer Activity of 4-Substituted Coumarins: A Novel Class of Potent Tubulin Polymerization Inhibitors
Cao, Dong,Liu, Yibin,Yan, Wei,Wang, Chunyu,Bai, Peng,Wang, Taijin,Tang, Minghai,Wang, Xiaoyan,Yang, Zhuang,Ma, Buyun,Ma, Liang,Lei, Lei,Wang, Fang,Xu, Bixue,Zhou, Yuanyuan,Yang, Tao,Chen, Lijuan
, p. 5721 - 5739 (2016)
In this paper, a series of novel 4-subst...
Novel conjugates of podophyllotoxin and coumarin: Synthesis, cytotoxicities, cell cycle arrest, binding CT DNA and inhibition of Topo IIβ
Hao, Shu-Yi,Feng, Shi-Liang,Wang, Xing-Rong,Wang, Zhichao,Chen, Shi-Wu,Hui, Ling
, p. 2129 - 2135 (2019)
A series of conjugates of podophyllotoxi...
Photooxygenation of chromone-2-carboxylic acid: Identification of ketohydroperoxide using a chemiluminescence technique
Kawata, Hiroki,Kumagai, Tsutomu,Niizuma, Shigeya
, p. 985 - 986 (1999)
Irradiation of chromone-2-carboxylic aci...
Energy transfer in coumarin-sensitised lanthanide luminescence: Investigation of the nature of the sensitiser and its distance to the lanthanide ion
Andres, Julien,Chauvin, Anne-Sophie
, p. 15981 - 15994 (2013)
A series of lanthanide complexes [Ln(dpx...
Design, synthesis, and mechanism of dihydroartemisinin-coumarin hybrids as potential anti-neuroinflammatory agents
Yu, Haonan,Hou, Zhuang,Yang, Xiaoguang,Mou, Yanhua,Guo, Chun
, (2019)
Cancer patients frequently suffer from c...
Copper(II)-Catalyzed Tandem Reaction: Synthesis of Furo[3,2- c]coumarin Derivatives and Evaluation for Photophysical Properties
Feng, Xi,Qin, Zhen,Cheng, Xinying,Liu, Dongyu,Peng, Yinghe,Huang, Huidan,Song, Bin,Bian, Jinlei,Li, Zhiyu
supporting information, p. 12537 - 12548 (2021/09/20)
An efficient protocol for synthesizing f...
TRICYCLIC COMPOUNDS ACTING ON CRBN PROTEINS
-
Paragraph 0155-0156, (2021/07/17)
The present invention discloses a series...
Nickel-catalyzed deallylation of aryl allyl ethers with hydrosilanes
Ding, Guangni,Fan, Sijie,Wang, Jingyang,Wang, Yu,Wu, Xiaoyu,Xie, Xiaomin,Yang, Liqun,Zhang, Zhaoguo
supporting information, (2021/09/28)
An efficient and mild catalytic deallyla...
1076-38-6 Process route
-
-
119-84-6,1341-36-2
C6 H4 (CH2 CH2 C(O)O)
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![4-hydroxy[1]benzopyran-2-one](/upload/2026/8/8adb677ee05941f9891ea2ce367dd212_56a05eac-38db-4f11-b3e4-fa8c713308cd.png)
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1076-38-6,92395-12-5
4-hydroxy[1]benzopyran-2-one
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-
2669-94-5
6-hydroxy-3,4-dihydrocoumarin
-
-
495-78-3
3-(2-hydroxyphenyl)propionic acid
-
-
1318928-52-7
2-(3-hydroxypropyl)phenyl acetate
-
-
1481-92-1
2-(3-hydroxypropyl)phenol
-
-
20349-89-7
methyl 3-(2-hydroxyphenyl)propionate
| Conditions | Yield |
|---|---|
|
With
sodium nitrate; dipotassium hydrogenphosphate; magnesium sulfate heptahydrate; potassium chloride; iron(II) sulfate; Sucrose;
In
water; dimethyl sulfoxide;
at 28 ℃;
for 96h;
pH=5;
Reagent/catalyst;
Time;
Kinetics;
Microbiological reaction;
|
15 %Chromat.
8.4 %Chromat. 38 %Chromat. 4.6 %Chromat. 24 %Chromat. 10 %Chromat. |
-
-
118-93-4,104809-67-8
o-hydroxyacetophenone
-
-
105-58-8,76619-83-5
Diethyl carbonate
-
-
1076-38-6,92395-12-5
4-hydroxy[1]benzopyran-2-one
| Conditions | Yield |
|---|---|
|
With
sodium hydride;
In
toluene;
at 0 ℃;
for 4.5h;
Reflux;
|
95%
|
|
With
sodium hydride;
In
toluene;
at 100 ℃;
for 3h;
|
85%
|
|
o-hydroxyacetophenone;
With
sodium hydride;
In
toluene; mineral oil;
Diethyl carbonate;
In
toluene; mineral oil;
Reflux;
With
hydrogenchloride;
In
water;
|
85%
|
|
o-hydroxyacetophenone;
With
sodium hydride;
In
toluene;
at 0 ℃;
for 0.333333h;
Inert atmosphere;
Diethyl carbonate;
at 110 ℃;
for 4h;
Inert atmosphere;
|
81%
|
|
o-hydroxyacetophenone;
With
sodium hydride;
In
toluene; mineral oil;
at 20 ℃;
for 0.5h;
Inert atmosphere;
Diethyl carbonate;
In
toluene; mineral oil;
for 3h;
Reflux;
|
68%
|
|
o-hydroxyacetophenone;
With
sodium hydride;
In
toluene;
at 20 ℃;
for 0.5h;
Cooling with ice;
Diethyl carbonate;
In
toluene;
for 4h;
Reflux;
|
65%
|
|
With
sodium hydroxide;
In
benzene;
|
50%
|
|
With
sodium;
for 1.16667h;
Heating;
Inert atmosphere;
|
45%
|
|
With
sodium hydride;
|
|
|
With
sodium hydride;
In
toluene;
at 110 ℃;
|
|
|
With
sodium hydride;
In
toluene;
at 105 ℃;
for 3h;
Inert atmosphere;
|
|
|
With
sodium hydride;
In
toluene; mineral oil;
at 0 - 80 ℃;
for 2h;
|
|
|
With
sodium hydride;
In
mineral oil;
at 0 ℃;
for 5h;
Reflux;
|
|
|
o-hydroxyacetophenone;
With
sodium hydride;
In
toluene;
for 0.25h;
Inert atmosphere;
Cooling with ice;
Diethyl carbonate;
In
toluene;
at 20 ℃;
for 5.5h;
Inert atmosphere;
Reflux;
|
|
|
With
sodium hydride;
at 100 ℃;
for 3h;
|
|
|
o-hydroxyacetophenone;
With
sodium hydride;
In
toluene; mineral oil;
for 0.166667h;
Inert atmosphere;
Diethyl carbonate;
In
toluene; mineral oil;
for 3.5h;
Reflux;
|
|
|
With
sodium hydride;
In
toluene;
|
|
|
With
sodium hydride;
|
|
|
With
sodium hydride;
at 0 - 200 ℃;
for 2.5h;
|
|
|
With
sodium hydride;
In
toluene;
Inert atmosphere;
Reflux;
|
|
|
o-hydroxyacetophenone;
With
sodium hydride;
In
toluene;
at 0 ℃;
for 0.25h;
Inert atmosphere;
Diethyl carbonate;
In
toluene;
Inert atmosphere;
|
|
|
With
sodium hydride;
In
toluene;
at 100 ℃;
for 3h;
|
|
|
o-hydroxyacetophenone;
With
sodium hydride;
In
toluene;
at 0 ℃;
for 0.25h;
Diethyl carbonate;
In
toluene;
at 0 - 120 ℃;
|
|
|
With
sodium;
Yield given. Multistep reaction;
1.) reflux, 4 h;
|
|
|
With
sodium hydride;
at 0 ℃;
Cooling with ice;
|
|
|
With
sodium hydride;
In
toluene;
at 0 - 100 ℃;
Inert atmosphere;
|
|
|
With
sodium hydride;
In
toluene;
|
|
|
With
sodium methylate;
In
diethyl ether;
for 5h;
Heating;
|
|
|
With
sodium hydride;
at 0 - 110 ℃;
for 4h;
|
|
|
With
sodium hydride;
In
toluene;
at 0 - 120 ℃;
for 12h;
|
1076-38-6 Upstream products
-
580-02-9
methyl acetylsalicylate
-
141-52-6
sodium ethanolate
-
118-93-4
o-hydroxyacetophenone
-
105-58-8
Diethyl carbonate
1076-38-6 Downstream products
-
84245-27-2
4-hydroxy-3-[1-(4-hydroxy-3-methoxy-phenyl)-3-oxo-butyl]-coumarin
-
10475-15-7
4-hydroxy-3-(3-oxo-1,3-diphenylpropyl)-2H-chromen-2-one
-
114695-02-2
(3-ethoxy-4-hydroxy-phenyl)-bis-(4-hydroxy-2-oxo-2H -chromen-3-yl)-methane
-
112222-66-9
(4,7-dihydroxy-2-oxo-2H -chromen-3-yl)-(4-hydroxy-2-oxo-2H -chromen-3-yl)-acetic acid ethyl ester