4H-1,3-Benzodioxin-6-carboxaldehyde

Base Information

• Chemical Name: 4H-1,3-Benzodioxin-6-carboxaldehyde
• CAS No.: 29668-44-8
• Molecular Formula: C9H8O3
• Molecular Weight: 164.161
• Hs Code.: 29329990
• Mol file: 29668-44-8.mol

Synonyms:4H-1,3-benzodioxine-6-carbaldehyde;4H-1,3-Benzodioxin-6-carboxaldehyde;UNII-92TK3MD2XP;SCHEMBL10843574;NSC 64681;AKOS006371255

Chemical Property of 4H-1,3-Benzodioxin-6-carboxaldehyde

Chemical Property:

• Appearance/Colour: Yellowish-beige powder and chunks
• Vapor Pressure: 0.000238mmHg at 25°C
• Melting Point: 50-52 °C(lit.)
• Refractive Index: 1.588
• Boiling Point: 221.2 °C at 760 mmHg
• Flash Point: 116 °C
• PSA: 35.53000
• Density: 1.262 g/cm³
• LogP: 1.27030
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Solubility in methanol is almost transparent.
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 164.047344113
• Heavy Atom Count: 12
• Complexity: 169

Purity/Quality:

99%, ^*data from raw suppliers

3,4-Ethylenedioxybenzaldehyde >98.0%(GC) ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2=C(C=CC(=C2)C=O)OCO1
• Description: 1,4-benodioxan-6-carboxaldehyde is a kind of aldehyde derivative. It is a useful intermediate in organic synthesis. It can be used as the building bock of the manufacturing tetrahydroisoquinoliones and benzofuran analog (a inhibitor of cAMP-specific phosphodiesterase type IV). It can also be used as an intermediate during the manufacturing of some novel Dopamine D3 and D4 receptor antagonists. It can also be used as the initial material for the manufacturing of some novel chalcone analogues that exhibit strong anti-tumor activity and low toxic side effects.
• Uses: 1,4-Benzodioxane-6-carboxaldehyde was screened as a fragment for inhibitors of PDEA using enthalpy arrays and X-ray crystallography. 1,4-Benzodioxane-6-carboxaldehyde have also been used as an interme diate in the synthesis of a new class of Dopamine D3 and D4 receptor antagonists. 1,4-Benzodioxan-6-carboxaldehyde finds its uses as building block in the synthesis of tetrahydroisoquinolinones, in the preparation of benzofuran analog, a potential inhibitor of CAMP-specific phosphodiesterase type IV, in the synthesis of (5Z)-5-(2,3-dihydro-1,4-benzodioxan-6-ylmethylene)-1-methyl-2-thioxoimidazolidin-4-one. It was screened as a fragment for inhibitors of PDEA using enthalpy arrays and X-ray crystallography. 1,4-Benzodioxane-6-carboxaldehyde have also been used as an intermediate in the synthesis of a new class of Dopamine D3 and D4 receptor antagonists.

Technology Process of 4H-1,3-Benzodioxin-6-carboxaldehyde

There total 18 articles about 4H-1,3-Benzodioxin-6-carboxaldehyde 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%

ethylene dibromide (106-93-4) + 3,4-dihydroxybenzaldehyde (139-85-5) → 2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde (29668-44-8)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 70 ℃; for 16h;

DOI:10.1021/jm070315q

Reference yield: 90.0%

1,2-dichloro-ethane (107-06-2,52399-93-6) + 3,4-dihydroxybenzaldehyde (139-85-5) → 2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde (29668-44-8)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 105 ℃; for 4h;

DOI:10.1021/acs.jafc.8b03690

Reference yield: 81.0%

9-methyl-9H-fluorene-9-carbonyl chloride (82102-37-2) + 6-bromo-1,4-benzodioxane (52287-51-1) → 2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde (29668-44-8)

Guidance literature:

With dichloro(1,5-cyclooctadiene)palladium(II); N-Methyldicyclohexylamine; potassium formate; tetra-(n-butyl)ammonium iodide; tricyclohexylphosphine tetrafluoroborate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; tri tert-butylphosphoniumtetrafluoroborate; at 100 ℃; for 18h; Reagent/catalyst; Solvent; Sealed tube; Glovebox; Inert atmosphere;

DOI:10.1021/jo400741t

upstream raw materials:

benzo-1,4-dioxane

hydrogen cyanide

ethylene dibromide

3,4-dihydroxybenzaldehyde

Downstream raw materials:

4-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethylene)-2-phenyl-4H-oxazol-5-one

1-(2-hydroxy-5-methoxyphenyl)-3-(6-benzodioxan-1,4-yl)propenone

(E)-1-(4-Benzyloxy-2-hydroxy-phenyl)-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-propenone

1-(2-hydroxy-4-methoxyphenyl)-3-(6-benzodioxan-1,4-yl)propenone

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