24238-62-8

Basic information

• Product Name: 3-(bromoacetyl)-4-hydroxy-2H-chromen-2-one
• Synonyms: 2H-1-benzopyran-2-one, 3-(2-bromoacetyl)-4-hydroxy-; 3-(Bromoacetyl)-4-hydroxy-2H-chromen-2-one
• CAS NO: 24238-62-8
• Molecular Formula: C₁₁H₇BrO₄
• Molecular Weight: 283.0749
• Mol File: 24238-62-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 453.253°C at 760 mmHg
• Flash Point: 227.919°C
• Density: 1.832g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.679
• CAS DataBase Reference: 3-(bromoacetyl)-4-hydroxy-2H-chromen-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(bromoacetyl)-4-hydroxy-2H-chromen-2-one(24238-62-8)
• EPA Substance Registry System: 3-(bromoacetyl)-4-hydroxy-2H-chromen-2-one(24238-62-8)

Safety Data

• Hazardous Substances Data: 24238-62-8(Hazardous Substances Data)

Upstream product

• 2555-37-5 3-acetyl-4-hydroxychromen-2-one 
• 1076-38-6 4-hydroxy[1]benzopyran-2-one 

Downstream Products

• 1383922-95-9 (2Z)-2-(3,4,5-trimethoxybenzylidene)-4H-furo[3,2-c]chromene-3,4(2H)-dione 
• 1383922-99-3 (2Z)-2-(2-hydroxy-3-methoxybenzylidene)-4H-furo[3,2-c]chromene-3,4(2H)-dione 
• 1383923-03-2 (2Z)-2-(6-chloro-2,4-dimethoxybenzylidene)-4H-furo[3,2-c]chromene-3,4(2H)-dione 
• 1383923-07-6 (2Z)-2-(5-bromo-2-methoxybenzylidene)-4H-furo[3,2-c]chromene-3,4(2H)-dione 
• 1383923-10-1 (2Z)-2-[4-(dimethylamino)benzylidene]-4H-furo[3,2-c]chromene-3,4(2H)-dione 
• 1383923-13-4 (2Z)-2-(3-chlorobenzylidene)-4H-furo[3,2-c]chromene3,4(2H)-dione 
• 1383923-16-7 (2Z)-2-(2,4-dimethoxybenzylidene)-4H-furo[3,2-c]chromene-3,4(2H)-dione 
• 1383923-27-0 (2E,2'Z)-2'-(5'-bromo-2'-hydroxybenzylidene)-4H,4'H-2,3'-bifuro[3,2-c]chromenylidene-3,4,4'-trione 
• 1383922-72-2 (2Z)-2-benzylidene-4H-furo[3,2-c]chromene-3,4(2H)-dione 
• 1383922-79-9 (2Z)-2-(2-chlorobenzylidene)-4H-furo[3,2-c]chromene-3,4(2H)-dione 
• 1383922-83-5 (2Z)-2-(4-nitrobenzylidene)-4H-furo[3,2-c]chromene-3,4(2H)-dione 
• 1383922-87-9 (2Z)-2-(4-methoxybenzylidene)-4H-furo[3,2-c]chromene-3,4(2H)-dione 
• 1383922-91-5 (2Z)-2-(3-bromo-4-methoxybenzylidene)-4H-furo[3,2-c]chromene-3,4(2H)-dione 
• 944548-93-0 2-hydroxy-4-[4-(4-hydroxy-2-oxo-2H-chromen-3-yl)thiazol-2-ylamino]benzoic acid 

Relevant articles and documents

Hantzsch reaction of 3-(2-bromoacetyl)-4-hydroxy-chromen-2-one. Synthesis of 3-(thiazol-4-yl)-4-hydroxy coumarines

3-Acetyl-4-hydroxy-chromen-2-one (1) was brominated with phenyltrimethylammonium tribromide to afford 3-(2-bromoacetyl)-4-hydroxy- chromen-2-one (2) whose reactions with thiourea, thioacetamide and ammonium dithiocarbamate gave respectively 3-(2-amino-thiazol-4-yl)-4-hydroxy-, 4-hydroxy-3-(2-phenyl-thiazol-4-yl)- and 4-hydroxy-3-(2-mercapto-thiazol-4-yl) chromen-2-one. In a similar manner, compound 2 was treated with four 1-substituted-2-thioureas and thiobenzamide to give the corresponding 4-hydroxy-3-(thiazol-4-yl)-chromen-2-one derivatives.

Structure and condensation reactions of 2,3-dihydrofuro[3,2-c]coumarin-3- one

2,3-Dihydrofuro[3,2-c]coumarin-3-one was synthesized in quantitative yield from 3-(ffl-bromoacetyl)-4-hydroxycoumarin in the presence of nucleophiles (including solvents). This compound undergoes keto-enol tautomerization and easily reacts with aromatic and hetero-aromatic aldehydes to form crotonization products having a Z configuration and exhibiting strong fluorescence.