779-30-6

Basic information

• Product Name: 3-ACETAMIDOCOUMARIN
• Synonyms: 3-(AcetylaMino)couMarin;N-(2-Oxo-2H-1-benzopyran-3-yl)acetaMide;NSC 65873;3-ACETAMIDOCOUMARIN;ACETAMIDOCOUMARIN, 3-;N-(2-Oxo-2H-chromen-3-yl)acetamide;3-ACETAMIDOCOUMARIN 99%;PALMATINE CHLORIDE(P)
• CAS NO: 779-30-6
• Molecular Formula: C₁₁H₉NO₃
• Molecular Weight: 203.19
• EINECS: 125-784-9
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Coumarin;Building Blocks;Coumarins;Heterocyclic Building Blocks;Amines
• Mol File: 779-30-6.mol
• Article Data: 28

Chemical Properties

• Melting Point: 205-207 °C(lit.)
• Boiling Point: 482 °C at 760 mmHg
• Flash Point: 245.3 °C
• Appearance: /
• Density: 1.31 g/cm³
• Vapor Pressure: 1.89E-09mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: 3-ACETAMIDOCOUMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ACETAMIDOCOUMARIN(779-30-6)
• EPA Substance Registry System: 3-ACETAMIDOCOUMARIN(779-30-6)

Safety Data

• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.
• WGK Germany: 3
• Hazardous Substances Data: 779-30-6(Hazardous Substances Data)

Usage

Uses

3-ACETAMIDOCOUMARIN is a 3-substituted couramin derivative with antioxidant activity. It is used as a matrix in MALDI TOF-MS analysis of polyethylene glycol samples.

InChI:InChI=1/C11H9NO3/c1-7(13)12-9-6-8-4-2-3-5-10(8)15-11(9)14/h2-6H,1H3,(H,12,13)

Upstream product

• 24474-93-9 2-methyl-4H-oxazol-5-one 
• 90-02-8 salicylaldehyde 
• 91137-46-1 3-(1-hydroxyimino-ethyl)-coumarin 
• 10026-13-8 phosphorus pentachloride 
• 7719-12-2 phosphorus trichloride 
• 1635-31-0 aminocoumarine 
• 75-36-5 acetyl chloride 
• 1906-82-7 ethyl acetamidoacetate 
• 3949-36-8 3-acetylcoumarin 
• 60-35-5 acetamide 
• 939-18-4 3-bromo-2H-chromen-2-one 
• 543-24-8 N-acetylglycine 

Downstream Products

• 1635-31-0 aminocoumarine 
• 5818-89-3 Chromannedione-2,3 
• 6803-09-4 3-(2'-hydroxyphenyl)-2-hydroxypropanoic acid 
• 709-16-0 2-hydroxy-phenylalanine 
• 76461-89-7 N-(2-oxo-2H-chromen-3-yl)-3-phenylacrylamide 
• 330662-51-6 3-(4-chlorophenyl)-N-(2-oxo-2H-chromen-3-yl)acrylamide 
• 1310689-43-0 3-(4-nitrophenyl)-N-(2-oxo-2H-chromen-3-yl)acrylamide 
• 1310689-44-1 3-(4-methoxyphenyl)-N-(2-oxo-2H-chromen-3-yl)acrylamide 
• 1310689-38-3 3-(2-oxo-2-phenylethylamino)chromen-2-one 
• 1310689-41-8 1-phenylchromeno[3,4-b]pyrrole-4(3H)-one 
• 1414381-84-2 3-(4-chlorophenyl)-1-phenyl-5H-chromeno[3,4-b]pyridin-5-one 
• 1414381-86-4 3-(4-fluorophenyl)-1-phenyl-5H-chromeno[3,4-b]pyridin-5-one 
• 1414381-88-6 1-phenyl-3-(p-tolyl)-5H-chromeno[3,4-b]pyridin-5-one 
• 1414381-83-1 1,3-diphenyl-5H-chromeno[3,4-b]pyridin-5-one 

Relevant articles and documents

A convenient and expeditious synthesis of 3-(N-substituted) aminocoumarins via palladium-catalyzed Buchwald-Hartwig coupling reaction

A convenient protocol for the rapid and efficient synthesis of 3-(N-substituted) aminocoumarins is described. The synthetic route developed involves the Pd-catalyzed C-N coupling reaction from readily available 3-bromocoumarin derivatives in the presence of the catalytic system Pd(OAc)2/Xantphos. Under these conditions, a series of nucleophiles including amides, sulfonamides, carbamates and functionalized amines, have been successfully reacted to afford the coupling products in fair to good yields.

Mild and highly efficient deacetylation of acetamido and acetoxy coumarins: A convenient and expeditious synthesis of substituted 3-aminocoumarins

A convenient protocol for efficient and cost-effective method for synthesis of substituted 3-aminocoumarins has been developed. The synthetic route involves expeditious and fast quantitative deacetylation of readily available acetamido derivative under anhydrous acidic conditions, employing thionyl chloride in methanol, without formation of undesired substituted 3-hydroxycoumarins. The method is suitable for derivatives bearing electron-donating as well as electron-withdrawing groups at position 7 of the coumarin scaffold. Under these conditions, a series of acetoxy substituted 3-dialkylaminocoumarins has been also successfully deacetylated to afford easily isolable corresponding hydroxy derivatives in high yields.

Beckmann rearrangement: Thiamine hydrochloride as a remarkable catalyst for one-pot synthesis of amides from ketones

Thiamine hydrochloride catalyzed synthesis of amides from ketones including 3-acetyl coumarin via Beckmann rearrangement has been reported. The reaction is believed to involve oxime formation, cleavage of C[sbnd]C bond followed by C[sbnd]N bond formation in one-pot. Thiamine hydrochloride is stable, cheap, easy to handle and environmentally friendly.