ChemicalBook > CAS DataBase List > 1-(2,4-bis (benzyloxy)-6-hydroxyphenyl) ethanone

1-(2,4-bis (benzyloxy)-6-hydroxyphenyl) ethanone

Product Name: 1-(2,4-bis (benzyloxy)-6-hydroxyphenyl) ethanone
CAS No.: 18065-05-9
Chemical Name: 1-(2,4-bis (benzyloxy)-6-hydroxyphenyl) ethanone
Synonyms: 2-Acetyl-3,5-bis(benzyloxy)phenol;1-(2,4-bis (benzyloxy)-6-hydroxyphenyl) ethanone;1-[2-hydroxy-4,6-bis(phenylmethoxy)phenyl]ethanone;Ethanone, 1-[2-hydroxy-4,6-bis(phenylmethoxy)phenyl]-
CBNumber: CB01564400
Molecular Formula: C22H20O4
Formula Weight: 348.39
MOL File: 18065-05-9.mol

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1-(2,4-bis (benzyloxy)-6-hydroxyphenyl) ethanone Property

Melting point:: 108-109 °C(Solv: methanol (67-56-1))
Boiling point:: 550.4±45.0 °C(Predicted)
Density: 1.206±0.06 g/cm3(Predicted)
pka: 9.41±0.15(Predicted)
InChI: InChI=1S/C22H20O4/c1-16(23)22-20(24)12-19(25-14-17-8-4-2-5-9-17)13-21(22)26-15-18-10-6-3-7-11-18/h2-13,24H,14-15H2,1H3
InChIKey: HEHTYXOPJQUNOF-UHFFFAOYSA-N
SMILES: C(=O)(C1=C(OCC2=CC=CC=C2)C=C(OCC2=CC=CC=C2)C=C1O)C

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC

Product number: B591878
Product name: 1-(2,4-bis(Benzyloxy)-6-hydroxyphenyl)ethanone
Packaging: 500mg
Price: $110
Updated: 2021/12/16

TRC

Product number: B591878
Product name: 1-(2,4-bis(Benzyloxy)-6-hydroxyphenyl)ethanone
Packaging: 100mg
Price: $60
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: CHM0386641
Product name: 1-(2,4-BIS(BENZYLOXY)-6-HYDROXYPHENYL)ETHANONE
Purity: 95.00%
Packaging: 5MG
Price: $502.08
Updated: 2021/12/16

Ambeed

Product number: A746836
Product name: 2-Acetyl-3,5-bis(benzyloxy)phenol
Purity: 98%
Packaging: 25g
Price: $757
Updated: 2021/12/16

Ambeed

Product number: A746836
Product name: 2-Acetyl-3,5-bis(benzyloxy)phenol
Purity: 98%
Packaging: 1g
Price: $106
Updated: 2021/12/16

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1-(2,4-bis (benzyloxy)-6-hydroxyphenyl) ethanone Chemical Properties,Usage,Production

Uses

1-(2,4-bis(Benzyloxy)-6-hydroxyphenyl)ethanone is a useful reactant for the synthesis of fluorine-containing chalcone derivatives that have antiproliferative activity.

Preparation

Preparation by reaction of benzyl chloride on phloroacetophenone with potassium carbonate in refluxing acetone (29%), (20%), in DMF at 100° (54%) and at 150–153° (26%) or in HMPA at 90–93° (80%).

Synthesis

480-66-0

100-44-7

18065-05-9

The general procedure for the synthesis of 2-acetyl-3,5-bis(benzyloxy)phenol from 2',4',6'-trihydroxyacetophenone and benzyl chloride was as follows: to a solution of hexamethylphosphoramidite (HMPA, 300 mL) of 1-(2,4,6-trihydroxyphenyl)acetophenone (60 g, 0.36 mol) was added potassium carbonate (K2CO3, 148 g, 1.07 mol) and benzyl chloride (BnCl, 86.3 mL, 0.75 mol). The reaction suspension was stirred at 90 °C for 3 hours. After completion of the reaction, the solids were removed by filtration and the filtrate was poured into ice water. The pH of the mixture was adjusted to 2 by dropwise addition of dilute hydrochloric acid.Subsequently, the precipitated solid was collected by filtration and recrystallized in a solvent mixture of dichloromethane (CH2Cl2) and methanol (MeOH) to afford 1-(2,4-bis(benzyloxy)-6-hydroxyphenyl)ethanone. The product yield was 75%; 1H NMR (CDCl3, 300 MHz) δ: 2.56 (3H, s), 5.06 (4H, s), 6.11 (1H, s), 6.17 (1H, s), 7.41 (10H, m), 14.04 (1H, s).

References

[1] Journal of Chemical Research - Part S, 1999, # 2, p. 148 - 149
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 488 - 490
[3] Synthesis, 2010, # 16, p. 2776 - 2786
[4] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 8, p. 2864 - 2871
[5] Biochemical Pharmacology, 2014, vol. 92, # 2, p. 358 - 368

1-(2,4-bis (benzyloxy)-6-hydroxyphenyl) ethanone Preparation Products And Raw materials

Raw materials

Preparation Products

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18065-05-9, 1-(2,4-bis (benzyloxy)-6-hydroxyphenyl) ethanoneRelated Search:

1-(2,4-bis (benzyloxy)-6-hydroxyphenyl) ethanone

2-Acetyl-3,5-bis(benzyloxy)phenol

Ethanone, 1-[2-hydroxy-4,6-bis(phenylmethoxy)phenyl]-

1-[2-hydroxy-4,6-bis(phenylmethoxy)phenyl]ethanone

18065-05-9