Chalcone

Base Information

• Chemical Name: Chalcone
• CAS No.: 94-41-7
• Deprecated CAS: 1801869-81-7
• Molecular Formula: C15H12O
• Molecular Weight: 208.26
• Hs Code.: 29143900
• DSSTox Substance ID: DTXSID8022531
• Wikidata: Q97974701
• ChEMBL ID: CHEMBL4777263
• Mol file: 94-41-7.mol

Synonyms:1,3 Diphenyl 2 Propen 1 One;1,3-Diphenyl-2-Propen-1-One;Benzalacetophenone;Benzylideneacetophenone;Chalcone;Chalkone

Chemical Property of Chalcone

Chemical Property:

• Appearance/Colour: light yellow powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 55-59 °C
• Refractive Index: 1.625
• Boiling Point: 346.61 °C at 760 mmHg
• Flash Point: 150.062 °C
• PSA: 17.07000
• Density: 1.097 g/cm³
• LogP: 3.58270
• Storage Temp.: Storage temperature: no restrictions.
• Solubility.: dioxane: soluble1g/10 mL, clear, colorless
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 208.088815002
• Heavy Atom Count: 16
• Complexity: 242

Purity/Quality:

Chalcone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37
• Safety Statements: 22-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=CC(=O)C2=CC=CC=C2
• Description: Chalcone is the organic compound C6H5C(O)CH=CHC6H5. It is an α,β-unsaturated ketone. A variety of important biological compounds are known collectively as chalcones or chalconoids.They show antibacterial, antifungal, antitumor and anti-inflammatory properties. They are also intermediates in the biosynthesis of flavonoids, which are substances widespread in plants and with an array of biological activities. Chalcones are also intermediates in the Auwers synthesis of flavones.
• Uses: 1,3-Diphenyl-2-propenone was used in the preparation of pharmacologically-interesting heterocyclic systems like pyrazolines and pyrimidines. Chalcone is used in the preparation of pharmacologically-interesting heterocyclic systems like pyrazolines and pyrimidines. It also inhibits the proliferation of human breast cancer cell lines, MCF-7 and MDA-MB-231 by inducing apoptosis and blocking cell cycle progression in the G2/M phase.

Technology Process of Chalcone

There total 323 articles about Chalcone 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: 44.0%

acetophenone (98-86-2) + benzyl alcohol (100-51-6,185532-71-2) → 1-Phenylethanol (98-85-1,13323-81-4) + dihydrochalcone (1083-30-3) + benzalacetophenone (94-41-7)

Guidance literature:

With ceria; In para-xylene; at 150 ℃; for 24h; under 760.051 Torr; Reagent/catalyst; Solvent; Temperature; Time; chemoselective reaction; Mechanism; Kinetics;

DOI:10.1039/c5cy01607j

Reference yield: 44.0%

acetophenone (98-86-2) + benzyl alcohol (100-51-6,185532-71-2) → 1-Phenylethanol (98-85-1,13323-81-4) + benzalacetophenone (94-41-7)

Guidance literature:

With yttrium(III) oxide; In para-xylene; at 150 ℃; for 24h; under 760.051 Torr;

DOI:10.1039/c5cy01607j

Reference yield: 43.0%

1,3-diphenyl-2-propynone (7338-94-5) → (Z)-chalcone (94-41-7) + 1,3-diphenyl-propen-3-one (614-47-1)

Guidance literature:

With silver hexafluoroantimonate; chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); triphenylphosphine; tert-butyl alcohol; In acetonitrile; at 60 ℃; for 24h; diastereoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1055/s-0040-1707395

upstream raw materials:

1,3,5-triphenyl-1,5-pentanedione

cinnamonitrile

2-bromo-1,3-diphenyl-2-propen-1-one

ethanol

Downstream raw materials:

(3-oxo-1,3-diphenyl-propyl)-phenyl-phosphinic acid

5-hydroxy-2,3,5-triphenyl-valeric acid

3-ethoxycarbonyl-4,6-diphenyl-2,6-hexanedione

ethyl 2-oxo-4,6-diphenylcyclohex-3-enecarboxylate

Refernces

• 1、 Gao, Jian-Rong,Li, Chao-Dong,Li, Yu-Jin,Lin, Zhang-Qi,Xue, Shuai,Ye, Qing,Zhou, Zi-Chun. "Copper(II)-Promoted Oxidation/[3+2]Cycloaddition/Aromatization Cascade: Efficient Synthesis of Tetrasubstituted NH -Pyrrole from Chalcones and Iminodiacetates". . p. 1442 - 1446. Retrieved 2019.
• 2、 Wu, Songhai,Ma, Xin,Ran, Jingyu,Zhang, Yanfei,Qin, Fengxiang,Liu, Yong. "Application of basic isoreticular nanoporous metal-organic framework: IRMOF-3 as a suitable and efficient catalyst for the synthesis of chalcone". . p. 14221 - 14227. Retrieved 2015.
• 3、 Varma, Manju,Stirling, Charles J. M.. "Ranks of Carbon Leaving Groups in Alkene-forming Elimination". . p. 553 - 554. Retrieved 1981.
• 4、 Lutz,Jordan. "-". . p. 4090. Retrieved 1950.
• 5、 Zhu, Guanxin,Duan, Zheng-Chao,Zhu, Haiyan,Ye, Dongdong,Wang, Dawei. "Selective C-C bonds formation, N-alkylation and benzo[d]imidazoles synthesis by a recyclable zinc composite". supporting information. p. 266 - 270. Retrieved 2021/08/06.
• 6、 Ahmed, Eman A.,Soliman, Ahmed M.M.,Ali, Ali M.,Ali El-Remaily, Mahmoud Abd El Aleem Ali. "Boosting the catalytic performance of zinc linked amino acid complex as an eco-friendly for synthesis of novel pyrimidines in aqueous medium". . . Retrieved 2021/02/26.