2-Hydroxychalcone

Base Information

• Chemical Name: 2-Hydroxychalcone
• CAS No.: 644-78-0
• Molecular Formula: C15H12O2
• Molecular Weight: 224.259
• Hs Code.: 29147000
• European Community (EC) Number: 211-422-1,624-468-6
• NSC Number: 640539,170281,37432
• Nikkaji Number: J400.833B,J95.421G
• Metabolomics Workbench ID: 73727
• ChEMBL ID: CHEMBL147067
• Mol file: 644-78-0.mol

Synonyms:2-Hydroxychalcone;644-78-0;3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one;42224-53-3;(E)-3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one;(2E)-3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one;(E)-2-Hydroxychalcone;Salicylalacetophenone;2-(2-Hydroxybenzal)acetophenone;MLS002608038;2-Hydroxybenzylidene acetophenone;2-Propen-1-one, 3-(2-hydroxyphenyl)-1-phenyl-;EINECS 211-422-1;NSC640539;NSC 640539;AI3-00855;3-(2-hydroxyphenyl)-1-phenyl-2-propen-1-one;(E)-3-(2-hydroxyphenyl)-1-phenyl-prop-2-en-1-one;Chalcone, 1;2-Hydroxychalcone, 95%;SCHEMBL626785;SCHEMBL626787;CHEMBL147067;BDBM86002;6-[(1Z,2Z)-3-Hydroxy-3-phenyl-2-propene-1-ylidene]-2,4-cyclohexadiene-1-one;UDOOPSJCRMKSGL-ZHACJKMWSA-N;HMS3078L22;NSC37432;2-(2-Hydroxybenzylidene)acetophenone;MFCD00016449;NSC-37432;NSC170281;STK093271;AKOS000486194;AKOS025309995;NSC-170281;NSC-640539;MS-10592;SMR001526790;HY-119931;CS-0078796;CS-0311212;H0234;A834764;AB-016/30005051;SR-01000078236;SR-01000078236-1;trans-3-(O-Hydroxyphenyl)-1-phenyl-2-propen-1-one;W-104837;(2E)-3-(2-Hydroxyphenyl)-1-phenyl-2-propen-1-one #

Chemical Property of 2-Hydroxychalcone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 144-150 °C(lit.)
• Refractive Index: 1.654
• Boiling Point: 396.3 °C at 760 mmHg
• PKA: 9.26±0.35(Predicted)
• Flash Point: 169.3 °C
• PSA: 37.30000
• Density: 1.191 g/cm³
• LogP: 3.28830
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 224.083729621
• Heavy Atom Count: 17
• Complexity: 277

Purity/Quality:

97% ^*data from raw suppliers

2-Hydroxychalcone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)C=CC2=CC=CC=C2O
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)/C=C/C2=CC=CC=C2O
• General Description: 2-Hydroxychalcone is a chalcone derivative characterized by an intramolecular hydrogen bond (IHB) between the 2′-hydroxy group and the carbonyl oxygen, which influences its electrochemical and electronic properties. Theoretical and experimental studies suggest that this IHB stabilizes the molecule and its anion radical, impacting redox behavior and electron affinity. The compound's methoxy-substituted analogs exhibit variations in IHB strength and redox potential, which are relevant for designing antitumor agents with optimized electrochemical properties.

Technology Process of 2-Hydroxychalcone

There total 32 articles about 2-Hydroxychalcone 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: 100.0%

salicylaldehyde (90-02-8) + (Benzoylmethylene)triphenylphosphorane (20913-05-7,859-65-4) → 2-hydroxychalcone (644-78-0)

Guidance literature:

In chloroform; for 16h; Reflux;

DOI:10.1039/c6ob01326k

Reference yield: 96.0%

salicylaldehyde (90-02-8) + acetophenone (98-86-2) → 2-hydroxychalcone (644-78-0)

Guidance literature:

With sodium para-toluenesulfonate; In water; at 20 ℃; for 3.5h;

DOI:10.1016/j.tet.2007.06.049

Reference yield: 90.0%

2-methyl-benzyl alcohol (89-95-2) + 3,3-bis(methylthio)-1-phenylprop-2-en-1-one (13636-88-9) → 2-hydroxychalcone (644-78-0)

Guidance literature:

With piperidine; In ethanol; for 10h; Heating;

DOI:10.1021/jo061372e

upstream raw materials:

salicylaldehyde

acetophenone

2-methyl-benzyl alcohol

phenol

Downstream raw materials:

salicylaldehyde

acetophenone

2-(2,6-Diphenyl-8,9-dihydro-7H-imidazo[1,2-b][1,2,4]triazepin-8-yl)-phenol

3-(2-hydroxy-phenyl)-1-phenyl-propan-1-one

Refernces

Correlating experimental electrochemistry and theoretical calculations in 2′-hydroxy chalcones: The role of the intramolecular hydrogen bond

10.1039/c5ra10140a

The study investigates the molecular structure and electrochemical behavior of a series of methoxylated 2'-hydroxychalcones, which are known for their antitumor activity. The research aims to correlate experimental electrochemistry with theoretical calculations, focusing on the role of intramolecular hydrogen bonds (IHBs) in these compounds. Cyclic voltammetry was employed to characterize the formation and stability of anion radicals, while density functional theory (DFT) calculations were used to investigate the molecular structures of the neutral compounds and their anion radicals, particularly the IHBs. The study also calculated adiabatic and vertical electron affinities (AEA, VEA), vertical detachment energy (VDE), and used natural bond orbital (NBO) analysis to gain insights into the electronic characteristics of the IHBs. The purpose of using these chemicals was to understand their redox properties and how the methoxy substitution pattern affects the IHB and redox behavior, which has implications for the design of antitumor chalcones.