ethyl 6-bromo-2-oxo-2H-chromene-3-carboxylate

Base Information

• Chemical Name: ethyl 6-bromo-2-oxo-2H-chromene-3-carboxylate
• CAS No.: 2199-90-8
• Molecular Formula: C12H9 Br O4
• Molecular Weight: 297.105
• Hs Code.: 2932209090
• DSSTox Substance ID: DTXSID40351124
• Nikkaji Number: J2.189.469I
• Wikidata: Q82127288
• ChEMBL ID: CHEMBL1650557
• Mol file: 2199-90-8.mol

Synonyms:ethyl 6-bromo-2-oxo-2H-chromene-3-carboxylate;ethyl 6-bromo-OCC

Chemical Property of ethyl 6-bromo-2-oxo-2H-chromene-3-carboxylate

Chemical Property:

• Vapor Pressure: 1.77E-07mmHg at 25°C
• Melting Point: 164 °C
• Refractive Index: 1.595
• Boiling Point: 426.4°C at 760 mmHg
• Flash Point: 211.7°C
• PSA: 56.51000
• Density: 1.602g/cm³
• LogP: 2.73220
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 295.96842
• Heavy Atom Count: 17
• Complexity: 364

Purity/Quality:

97% ^*data from raw suppliers

Ethyl 6-Bromocoumarin-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC2=C(C=CC(=C2)Br)OC1=O

Technology Process of ethyl 6-bromo-2-oxo-2H-chromene-3-carboxylate

There total 11 articles about ethyl 6-bromo-2-oxo-2H-chromene-3-carboxylate 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: 98.0%

ethyl 6-bromo-2-hydroxy-2H-chromene-3-carboxylate → ethyl 6-bromo-2-oxo-2H-chromene-3-carboxylate (2199-90-8)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; Reflux;

DOI:10.1002/ejoc.201500616

Reference yield: 95.0%

diethyl malonate (105-53-3) + 5-bromosalicyclaldehyde (1761-61-1) → ethyl 6-bromo-2-oxo-2H-chromene-3-carboxylate (2199-90-8)

Guidance literature:

With piperidine; In ethanol; for 4h; Reflux;

DOI:10.3987/COM-20-14300

Reference yield: 90.0%

cycl-isopropylidene malonate (2033-24-1) + ethanol (64-17-5) + 5-bromosalicyclaldehyde (1761-61-1) → ethyl 6-bromo-2-oxo-2H-chromene-3-carboxylate (2199-90-8)

Guidance literature:

With iron(III) chloride; at 70 ℃; for 8h;

DOI:10.1016/j.tet.2014.12.042

upstream raw materials:

diethyl malonate

5-bromosalicyclaldehyde

ethyl 2-cyanoacetate

salicylaldehyde

Downstream raw materials:

6-bromocoumarin-3-carboxylic acid

2-oxo-6-bromo-2H-chromene-3-carbonitrile

6-bromo-2-oxo-2H-chromene-3-carbohydrazide

C₁₉H₁₄BrNO₅