1,4-Benzodioxane

Base Information

• Chemical Name: 1,4-Benzodioxane
• CAS No.: 493-09-4
• Molecular Formula: C8H8O2
• Molecular Weight: 136.15
• Hs Code.: 29329995
• European Community (EC) Number: 207-775-6
• NSC Number: 406705
• UNII: ZC5YP57PSW
• DSSTox Substance ID: DTXSID8075419
• Nikkaji Number: J147.224K
• Wikipedia: Benzodioxan
• Wikidata: Q15043328
• ChEMBL ID: CHEMBL19452
• Mol file: 493-09-4.mol

Synonyms:1,4-benzodioxane

Chemical Property of 1,4-Benzodioxane

Chemical Property:

• Appearance/Colour: clear colourless to very slightly yellow liquid
• Vapor Pressure: 0.039mmHg at 25°C
• Melting Point: 213-217 °C
• Refractive Index: n20/D 1.549(lit.)
• Boiling Point: 248.138 °C at 760 mmHg
• Flash Point: 87.778 °C
• PSA: 18.46000
• Density: 1.15 g/cm³
• LogP: 1.45780
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: insoluble
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 136.052429494
• Heavy Atom Count: 10
• Complexity: 99.8

Purity/Quality:

99% ^*data from raw suppliers

1,4-Benzodioxan ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COC2=CC=CC=C2O1
• General Description: 1,4-Benzodioxan is a key structural motif in bioactive natural products and pharmaceuticals, characterized by a benzene ring fused to a 1,4-dioxane ring. Its chiral derivatives, such as 1,4-benzodioxanes, can be synthesized enantioselectively via palladium-catalyzed alkene aryloxyarylation reactions, achieving high yields and excellent enantioselectivity when using optimized conditions, including strong bases and chiral monophosphorus ligands. This method highlights 1,4-Benzodioxan's versatility and importance in medicinal chemistry and catalytic synthesis.

Technology Process of 1,4-Benzodioxane

There total 33 articles about 1,4-Benzodioxane 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: 97.0%

2-(2-hydroxy-phenoxy)-ethanol (4792-78-3) → benzo-1,4-dioxane (493-09-4)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; for 3h; Reflux;

DOI:10.1055/s-0037-1611710

Reference yield: 89.0%

benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) + ethylene dibromide (106-93-4) → benzo-1,4-dioxane (493-09-4)

Guidance literature:

With sodium hydroxide; (C₁₆H₃₃CH₃)2NCH₂CH₂N(CH₃)2C₁₆H₃₃)⁽²⁺⁾*Br^(1-)*Br^(1-); In water; Heating;

DOI:10.1007/BF00516441

Reference yield: 88.0%

2-(2-bromophenoxy)ethan-1-ol (34743-89-0) → benzo-1,4-dioxane (493-09-4)

Guidance literature:

With palladium diacetate; 9-di(2-tert-butylphosphinophenyl)phenanthrene; caesium carbonate; In toluene; at 70 ℃; for 40h;

DOI:10.1021/ja012046d

upstream raw materials:

2-(2-hydroxy-phenoxy)-ethanol

2-(2-bromo-ethoxy)-phenol

1-(benzyloxy)-2-(2-bromoethoxy)benzene

benzene-1,2-diol

Downstream raw materials:

3-(6-<1,4>benzodioxanylcarbonyl)propionic acid

hystazarin

1,2-dihydroxy-9,10-anthracenedione

6-(chloromethyl)-2,3-dihydrobenzo[b][1,4]dioxine

Refernces

Synthesis of Chiral 1,4-Benzodioxanes and Chromans by Enantioselective Palladium-Catalyzed Alkene Aryloxyarylation Reactions

10.1002/anie.201600379

The research aims to develop a highly enantioselective method for synthesizing chiral 1,4-benzodioxanes, 1,4-benzooxazines, and chromans, which are important structural units in many bioactive natural products and drugs. The study focuses on using palladium-catalyzed alkene aryloxyarylation reactions, with key chemicals including 2-((2-methylallyl)oxy)phenol (1a), various aryl halides such as bromobenzene (2a), and chiral monophosphorus ligands like L4 and L5. The researchers optimized the reaction conditions, finding that a strong base like NaOtBu and a solvent like hexafluorobenzene (C6F6) enhanced both yield and enantioselectivity. The method demonstrated high yields (up to 90%) and excellent enantioselectivity (up to 95% ee) for a range of substrates, including those with different aryl and heteroaryl groups. The study concludes that the chiral monophosphorus ligands L4 and L5 are crucial for the high reactivity and enantioselectivity of the transformations. The findings not only provide a practical route for synthesizing these chiral compounds but also offer valuable insights into the design of better catalytic systems for similar transformations.

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