720-72-9

Basic information

• Product Name: ethyl 2-oxo-3,4-dihydro-2H-chromene-3-carboxylate
• CAS NO: 720-72-9
• Molecular Formula: C₁₂H₁₂O₄
• Molecular Weight: 220.2213
• Mol File: 720-72-9.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 343.8°C at 760 mmHg
• Flash Point: 173.4°C
• Density: 1.237g/cm³
• Vapor Pressure: 6.87E-05mmHg at 25°C
• Refractive Index: 1.539
• CAS DataBase Reference: ethyl 2-oxo-3,4-dihydro-2H-chromene-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-oxo-3,4-dihydro-2H-chromene-3-carboxylate(720-72-9)
• EPA Substance Registry System: ethyl 2-oxo-3,4-dihydro-2H-chromene-3-carboxylate(720-72-9)

Safety Data

• Hazardous Substances Data: 720-72-9(Hazardous Substances Data)

Upstream product

• 1846-76-0 ethyl coumarin-3-carboxylate 
• 91-68-9 3-diethylaminophenol 
• 41175-50-2 8-hydroxyjulolidine 
• 90-02-8 salicylaldehyde 
• 105-53-3 diethyl malonate 
• 3943-94-0 (E)-ethyl 2-hydroxycinnamate 
• 1864-94-4 phenyl formate 
• 74-88-4 methyl iodide 

Downstream Products

• 64261-55-8 3-benzyl-2-oxo-chroman-3-carboxylic acid ethyl ester 
• 2445-82-1 3-methylcoumarine 
• 66898-40-6 3-propyl-2H-chromen-2-one 
• 64261-57-0 rac–3–benzylchroman–2–one 
• 20280-86-8 3-benzyl-2H-chromen-2-one 

Relevant articles and documents

Efficient chemoselective reduction of 3-substituted coumarins utilizing ortho-phenylenediamine and benzaldehyde

2-Phenylbenzimidazoline, generated in situ from ortho-phenylenediamine and benzaldehyde, is an effective reagent to achieve the chemoselective reduction of the styrenic double bond in 3-substituted coumarins, which takes place in high yield.

Substituted coumarins as ambident nucleophiles in one-pot hydrogenation/alkylation reaction

The regioselectivity of a one-pot hydrogenation/alkylation reaction of coumarins 1a and 1b with series of alkyl halides has been elucidated as a complementary work to reaction of acylation with the same coumarins. Reaction conditions have provided formation of only C-alkylation products with good to high yield. The results from the experiments are of significant importance to predict reactivity of 3-substituted coumarins in different reaction conditions.

Construction of 3,4-Dihydrocoumarin Derivatives with Adjacent Quaternary and Tertiary Stereocenters: Organocatalytic Asymmetric Michael Addition of 2-Oxochroman-3-carboxylate Esters to trans-β-Nitroolefins

An asymmetric Michael addition of 2-oxochroman-3-carboxylate esters to trans-β-nitroolefins is described. This strategy can give direct access to dihydrocoumarin derivatives bearing adjacent quaternary and tertiary stereocenters with up to >99% yield, >20:1 dr, and >99% ee. The adduct was further transformed to a spiro-dihydrocoumarin compound in three steps with good yield. (Figure presented.).

Synthesis of 3-arylated 3,4-dihydrocoumarins: Combining continuous flow hydrogenation with laccase-catalysed oxidation

A convenient arylation of diverse 3,4-dihydrocoumarins with a number of catechols is described leading to a new class of compounds. As key step, a laccase-catalysed oxidation/Michael addition sequence is applied using commercially available laccase from Agaricus bisporus. 3,4-Dihydrocoumarins were obtained in a rapid and facile two-step sequence starting from salicylaldehydes: The corresponding coumarins were synthesised through a Knoevenagel condensation in up to 83% yield followed by a quantitative reduction performed in a flow system. Combining the reductive flow reaction with the laccase-catalysed arylation also led to successful consecutive one-pot approaches. Overall, the enzyme-catalysed arylations were carried out with yields ranging from 63 to 94%.