4-HYDROXY-3-NITROCOUMARIN

Base Information

• Chemical Name: 4-HYDROXY-3-NITROCOUMARIN
• CAS No.: 20261-31-8
• Molecular Formula: C9H5 N O5
• Molecular Weight: 207.142
• Mol file: 20261-31-8.mol

Synonyms:Coumarin,4-hydroxy-3-nitro- (6CI,7CI,8CI); 3-Nitro-4-hydroxycoumarin;4-Hydroxy-3-nitro-2H-chromen-2-one; 4-Hydroxy-3-nitrocoumarin; NSC 519722

Chemical Property of 4-HYDROXY-3-NITROCOUMARIN

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 172 °C (dec.) (lit.)
• Boiling Point: 288.4°Cat760mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 128.2°C
• Density: 1.63g/cm³

Purity/Quality:

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

4-Hydroxy-3-nitrocoumarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 1247343
• Hazard Codes: T
• Statements: 25
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-Hydroxy-3-nitrocoumarin (cas# 20261-31-8) is a compound useful in organic synthesis. 4-Hydroxy-3-nitrocoumarin may be used as starting reagent for the synthesis of following compounds:4-chloro-3-nitrocoumarin2-unsubstituted 3-nitrochromone4-amino-3-nitrocoumarins

Technology Process of 4-HYDROXY-3-NITROCOUMARIN

There total 8 articles about 4-HYDROXY-3-NITROCOUMARIN 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: 95.0%

4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5) → 4-hydroxy-3-nitrocoumarin (20261-31-8)

Guidance literature:

With oxygen; nitrogen(II) oxide; In dichloromethane; for 1.5h;

DOI:10.1081/SCC-120028628

Reference yield: 88.0%

4-chloro-3-nitro-chromen-2-one (38464-20-9) → 4-hydroxy-3-nitrocoumarin (20261-31-8)

Guidance literature:

With sodium sulfide; sodium acetate; In ethanol; dimethyl sulfoxide; at 18 - 20 ℃; for 0.416667h;

DOI:10.1007/BF00472278

Reference yield: 80.0%

3-(ethylthio)-4-hydroxy-2H-chromen-2-one (86931-22-8) → 4-hydroxy-3-nitrocoumarin (20261-31-8)

Guidance literature:

With nitric acid; Ambient temperature;

upstream raw materials:

potassium ethyleneglycolate

4-chloro-3-nitro-chromen-2-one

3-(ethylthio)-4-hydroxy-2H-chromen-2-one

nitric acid

Downstream raw materials:

2'-Hydroxy-ω-nitroacetophenone

2-amino-1-(2-hydroxy-phenyl)-ethanone

2-(benzyl(3-nitro-2-oxo-2H-chromen-4-yl)amino)-N-(tert-butyl)-2-phenylacetamide

N⁽¹⁾-(4-hydroxy-2-oxo-2H-chromen-3-yl)-N⁽¹⁰⁾-phenyldecanediamide

Refernces

• 1、 Sen, Bhaskar,Sheet, Sanjoy Kumar,Thounaojam, Romita,Jamatia, Ramen,Pal, Amarta Kumar,Aguan, Kripamoy,Khatua, Snehadrinarayan. "A coumarin based Schiff base probe for selective fluorescence detection of Al3?+ and its application in live cell imaging". . p. 537 - 543. Retrieved 2017.
• 2、 Radulovi?, Niko S.,Bogdanovi?, Goran A.,Blagojevi?, Polina D.,Deki?, Vidosav S.,Vuki?evi?, Rastko D.. "Could X-ray analysis explain for the differing antimicrobial and antioxidant activity of two 2-arylamino-3-nitro-coumarins?". . p. 545 - 551. Retrieved 2011.
• 3、 Radulovi, Niko S.,Stojanovi-Radi, Zorica,Stojanovi, Predrag,Stojanovi, Nikola,Deki, Vidoslav,Deki, Biljana. "A small library of 4-(alkylamino)-3-nitrocoumarin derivatives with potent antimicrobial activity against gastrointestinal pathogens". . . Retrieved 2014.
• 4、 Ganguly, Nemai C.,Datta, Mrityunjoy,De, Prithwiraj,Chakravarty, Romaprosad. "Studies on regioselectivity of nitration of coumarins with cerium(IV) ammonium nitrate: Solid-state nitration of 6-hydroxy-coumarins on montmorillonite K-10 clay support under microwave irradiation". . p. 647 - 659. Retrieved 2003.