4H-1,3-Benzodioxin-4-one, 5-hydroxy-2,2-dimethyl-

Base Information

• Chemical Name: 4H-1,3-Benzodioxin-4-one, 5-hydroxy-2,2-dimethyl-
• CAS No.: 154714-19-9
• Molecular Formula: C10H10O4
• Molecular Weight: 194.187
• DSSTox Substance ID: DTXSID00453416
• Nikkaji Number: J580.410H
• Wikidata: Q82274555
• Mol file: 154714-19-9.mol

Synonyms:154714-19-9;4H-1,3-Benzodioxin-4-one, 5-hydroxy-2,2-dimethyl-;5-HYDROXY-2,2-DIMETHYL-1,3-BENZODIOXIN-4-ONE;5-hydroxy-2,2-dimethyl-4H-1,3-benzodioxin-4-one;5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one;5-hydroxy-2,2-dimethyl-2,4-dihydro-1,3-benzodioxin-4-one;starbld0005242;SCHEMBL620203;DTXSID00453416;GCOZFWFNEBPOJF-UHFFFAOYSA-N;AKOS006288844;F72900;2,2-dimethyl-5-hydroxy-4-oxobenzo-1,3-dioxin;2,2-dimethyl-5-hydroxy-4-oxo-benzo-1,3-dioxin;5-hydroxy-2,2-dimethyl-4H-(1,3)benzodioxin-4-one;5-HYDROXY-2,2-DIMETHYL-BENZO[1,3]DIOXIN-4-ONE

Chemical Property of 4H-1,3-Benzodioxin-4-one, 5-hydroxy-2,2-dimethyl-

Chemical Property:

• Melting Point: 64-65 °C(Solv: cyclohexane (110-82-7))
• Boiling Point: 382.1±42.0 °C(Predicted)
• PKA: 9.39±0.40(Predicted)
• PSA: 55.76000
• Density: 1.280±0.06 g/cm3(Predicted)
• LogP: 1.67750
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 194.05790880
• Heavy Atom Count: 14
• Complexity: 249

Purity/Quality:

99% ^*data from raw suppliers

5-Hydroxy-2,2-dimethyl-4H-1,3-benzodioxin-4-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2=CC=CC(=C2C(=O)O1)O)C
• Uses: 5-Hydroxy-2,2-dimethyl-4H-1,3-benzodioxin-4-one, is an intermediate in the synthesis of H946280. This complex is also an activator of 5-lipoxygenase (5-LOX) from compounds derived from anacardic acid.

Technology Process of 4H-1,3-Benzodioxin-4-one, 5-hydroxy-2,2-dimethyl-

There total 9 articles about 4H-1,3-Benzodioxin-4-one, 5-hydroxy-2,2-dimethyl- 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: 96.0%

2,6-Dihydroxybenzoic acid (303-07-1) + acetone (67-64-1) → 5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (154714-19-9)

Guidance literature:

With dmap; thionyl chloride; In 1,2-dimethoxyethane;

DOI:10.1021/ol006646d

Reference yield: 76.0%

(E)-4-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)but-3-enoic acid (1646145-64-3) → 5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (154714-19-9)

Guidance literature:

With triphenylphosphine; In tetrachloromethane; dichloromethane; for 3h; Reagent/catalyst; Solvent; Inert atmosphere; Reflux;

DOI:10.1002/ejoc.201402473

Reference yield: 62.0%

5-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-benzo[1,3]dioxin-4-one (888958-29-0) → 2,6-dihydroxybenzaldehyde (387-46-2) + 5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (154714-19-9)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 2h;

DOI:10.1021/jo0601664

upstream raw materials:

2,6-Dihydroxybenzoic acid

acetone

5-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-benzo[1,3]dioxin-4-one

2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one

Downstream raw materials:

2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one

5-(benzyloxy)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one

2,6-dihydroxybenzaldehyde

5-[3,4-bis(tert-butyldimethylsilanyloxy)phenylethynyl]-2,2-dimethyl-1,3-benzodioxin-4-one

Refernces

• 1、 Patel, Sahishnu,Pongkulapa, Thanapat,Yin, Perry T.,Pandian, Ganesh N.,Rathnam, Christopher,Bando, Toshikazu,Vaijayanthi, Thangavel,Sugiyama, Hiroshi,Lee, Ki-Bum. "Integrating Epigenetic Modulators into NanoScript for Enhanced Chondrogenesis of Stem Cells". . p. 4598 - 4601. Retrieved 2015.
• 2、 Del Bel, Matthew,Abela, Alexander R.,Ng, Jeffrey D.,Guerrero, Carlos A.. "Enantioselective Chemical Syntheses of the Furanosteroids (-)-Viridin and (-)-Viridiol". . p. 6819 - 6822. Retrieved 2017.
• 3、 Brackett, Christopher M.,García-Casas, Ana,Castillo-Lluva, Sonia,Blagg, Brian S. J.. "Synthesis and Evaluation of Ginkgolic Acid Derivatives as SUMOylation Inhibitors". supporting information. p. 2221 - 2226. Retrieved 2020/12/17.