6-Hydroxy-chroman-4-one

Base Information

• Chemical Name: 6-Hydroxy-chroman-4-one
• CAS No.: 80096-64-6
• Molecular Formula: C9H8O3
• Molecular Weight: 164.161
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID70427765
• Nikkaji Number: J1.185.755H
• Wikidata: Q82240457
• Mol file: 80096-64-6.mol

Synonyms:6-HYDROXY-CHROMAN-4-ONE;80096-64-6;6-hydroxychroman-4-one;6-hydroxy-2,3-dihydrochromen-4-one;6-hydroxy-3,4-dihydro-2H-1-benzopyran-4-one;4H-1-Benzopyran-4-one, 2,3-dihydro-6-hydroxy-;6-hydroxy-2,3-dihydro-4H-chromen-4-one;6-hydroxy-4-chromanone;6-hydroxy chroman-4-one;2,3-Dihydro-6-hydroxy-4H-1-benzopyran-4-one;SCHEMBL2981516;DTXSID70427765;HTKPIKIGEYFNBY-UHFFFAOYSA-N;AM9451;MFCD02113988;AKOS006277993;CS-W006471;2,3-dihydro-6-hydroxy benzopyran-4-one;DS-16591;FT-0709799;W17780;F2147-8399

Chemical Property of 6-Hydroxy-chroman-4-one

Chemical Property:

• Melting Point: 129-131 °C(Solv: benzene (71-43-2); ligroine (8032-32-4))
• Boiling Point: 372.4±42.0 °C(Predicted)
• PKA: 9.58±0.20(Predicted)
• PSA: 46.53000
• Density: 1.343±0.06 g/cm3(Predicted)
• LogP: 1.35740
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 164.047344113
• Heavy Atom Count: 12
• Complexity: 190

Purity/Quality:

98% ^*data from raw suppliers

6-Hydroxy-chroman-4-one 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COC2=C(C1=O)C=C(C=C2)O
• Uses: 6-Hydroxy-chroman-4-one is used in the preparation of novels parasite transmission blocking antimalarials targeting male gametes

Technology Process of 6-Hydroxy-chroman-4-one

There total 14 articles about 6-Hydroxy-chroman-4-one 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: 93.0%

6-methoxychroman-4-one (5802-17-5) → 6-hydroxy-2,3-dihydro-4H-chromen-4-one (80096-64-6)

Guidance literature:

With hydrogen bromide; acetic acid; Heating;

DOI:10.1016/S0960-894X(99)00461-8

Reference yield: 88.0%

6-hydroxy-4H-1-benzopyran-4-one (38445-24-8) → 6-hydroxy-2,3-dihydro-4H-chromen-4-one (80096-64-6)

Guidance literature:

With triethylsilane; 1,1,1,3',3',3'-hexafluoro-propanol; tris(pentafluorophenyl)borate; at 40 ℃; for 1h; chemoselective reaction;

DOI:10.1021/acs.joc.0c00568

Reference yield: 45.0%

6-bromochroman-4-one (49660-57-3) → 6-hydroxy-2,3-dihydro-4H-chromen-4-one (80096-64-6)

Guidance literature:

With tris(6,6'-diamino-2,2'-bipyridine); 4,4-diphenyl-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene; Br₂Ni*3H₂O; water; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; acetonitrile; at 20 ℃; for 24h; Glovebox; Irradiation; Inert atmosphere;

DOI:10.1002/anie.201710698

upstream raw materials:

3-(4-hydroxy-phenoxy)-propionic acid

4-methoxyphenyl 3-chloropropionate

6-methoxychroman-4-one

2-chloropropionyl chloride

Downstream raw materials:

6-tert-butyldiphenylsilyloxy-2,3-dihydro-4H-chromen-4-one

6-hydroxyflavanone

6-[(4-chlorobenzyl)oxy]-4H-chromen-4-one

6-[(4-fluorobenzyl)oxy]-4H-chromen-4-one

Refernces

• 1、 -. "POLYMERIZABLE ABSORBERS OF UV AND HIGH ENERGY VISIBLE LIGHT". . . Retrieved 2020/04/10.
• 2、 Cho, Yang Yil,Jang, Hyu Jeong,Kim, Dong Hwan,Kim, Nam Yong,Kim, Nam-Jung,Kim, Young Min,Lee, Soo Jin,Lee, Yong Sup,Park, Boyoung Y.,Son, Seung Hwan,Yoo, Hyung-Seok. "Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids". supporting information. p. 10012 - 10023. Retrieved 2019/08/30.