2H-Chromene

Base Information

• Chemical Name: 2H-Chromene
• CAS No.: 254-04-6
• Molecular Formula: C9H8 O
• Molecular Weight: 132.162
• Hs Code.: 2901299090
• UNII: 7U3W6XRV5U
• DSSTox Substance ID: DTXSID80180051
• Nikkaji Number: J5.443G
• Wikipedia: Benzopyran
• Wikidata: Q421311
• Metabolomics Workbench ID: 55156
• Mol file: 254-04-6.mol

Synonyms:2H-chromene;5,7-dimethoxy-2-methyl-2H-benzopyran;chromene I

Chemical Property of 2H-Chromene

Chemical Property:

• Vapor Pressure: 0.169mmHg at 25°C
• Melting Point: <25 °C
• Refractive Index: 1.5869
• Boiling Point: 220.2°Cat760mmHg
• Flash Point: 79.7°C
• PSA: 9.23000
• Density: 1.095g/cm³
• LogP: 2.09220
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 132.057514874
• Heavy Atom Count: 10
• Complexity: 140

Purity/Quality:

97% ^*data from raw suppliers

2H-chromene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=CC2=CC=CC=C2O1
• General Description: 2H-Chromene, also known as 1,2-benzopyran or 2H-1-benzopyran, is an oxygen-containing heterocyclic compound with a benzene ring fused to a pyran ring. It serves as a core structure for synthesizing biologically active derivatives, such as TGF-β receptor inhibitors, and can be functionalized at the 2-position using methods like the reaction of potassium vinyltrifluoroborates with salicylaldehydes. The resulting 2-substituted 2H-chromenes exhibit diverse potential applications in medicinal chemistry.

Technology Process of 2H-Chromene

There total 15 articles about 2H-Chromene 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: 53.0%

4-bromo-3,4-dihydro-2H-chromene + 4-flourophenylmagnesium bromide (352-13-6) → 2H-chromene (254-04-6) + 4-(4-fluorophenyl)-3,4-dihydro-2H-chromene (1192278-62-8)

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; acetonitrile; at 20 ℃; for 14h; Inert atmosphere;

DOI:10.1021/ol902335c

Reference yield: 45.0%

1-phenoxy-2-propyne (13610-02-1) + anthranil (271-58-9) → 2H-chromene (254-04-6) + 6H-chromeno[3,4-b]quinoline (66129-51-9) + 2-((2H-chromen-3-yl)amino)benzaldehyde

Guidance literature:

With silver hexafluoroantimonate; 2-(di-tert-butylphosphino)-1,1'-biphenylgold(I) chloride; zinc trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 80 ℃; for 48h; Overall yield = 65 %; Inert atmosphere; Molecular sieve;

DOI:10.1039/c9ob00468h

Reference yield:

4H-1-benzopyran (254-03-5) → styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 1-benzofurane (271-89-6) + 2H-chromene (254-04-6) + chromane (493-08-3) + ethylbenzene (100-41-4,27536-89-6) + inden-1-one (83-33-0)

Guidance literature:

at 413 ℃; for 20.5h; under 1 - 1.5 Torr; Product distribution; Mechanism; other reaction time;

DOI:10.1021/jo00071a013

upstream raw materials:

4H-1-benzopyran

3-bromo-2H-chromene

acetic anhydride

3-Phenyl-1-propanol

Downstream raw materials:

trans-4-methoxy-3-phenylchroman

3-phenyl-2H-benzopyran

4-Phenyl-4H-1-benzopyran

(6aS,11aS)-9-Methoxy-6a,11a-dihydro-6H-benzo[4,5]furo[3,2-c]chromen-8-ol

Refernces

Synthesis of 2-substituted 2H-chromenes using potassium vinyltrifluoroborates

10.1016/j.tetlet.2008.01.008

The research focuses on the synthesis of 2-substituted 2H-chromenes, which are important oxygenated heterocyclic compounds with potential applications as inhibitors for TGF-b receptors. The synthesis is achieved using potassium vinyltrifluoroborates and salicylaldehyde in the presence of secondary amines, specifically dibenzylamine, at 80°C in dimethylformamide (DMF). The reactants include various substituted salicylaldehydes and potassium vinylboronic acids. The products, 2-substituted 2H-chromene derivatives, are obtained with yields ranging from 51% to 90%. The analyses used to characterize the synthesized compounds include thin layer chromatography, 1H NMR, 13C NMR, and high-resolution mass spectrometry, which confirm the purity and structure of the products.

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