Dihydrochalcone

Base Information

• Chemical Name: Dihydrochalcone
• CAS No.: 1083-30-3
• Molecular Formula: C15H14O
• Molecular Weight: 210.276
• Hs Code.: 2914399090
• European Community (EC) Number: 621-467-2
• NSC Number: 12245
• UNII: H5W525SX7Q
• DSSTox Substance ID: DTXSID7061481
• Nikkaji Number: J254.530F
• Wikipedia: Dihydrochalcone
• Wikidata: Q2357209
• Metabolomics Workbench ID: 26939
• ChEMBL ID: CHEMBL490512
• Mol file: 1083-30-3.mol

Synonyms:2',4-dihydroxy-alpha,beta-dihydrochalcone;dihydrochalcone

Chemical Property of Dihydrochalcone

Chemical Property:

• Vapor Pressure: 3.78E-05mmHg at 25°C
• Melting Point: 70-72 °C
• Refractive Index: 1.574
• Boiling Point: 352.7 °C at 760 mmHg
• Flash Point: 152.9 °C
• PSA: 17.07000
• Density: 1.061 g/cm³
• LogP: 3.50210
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Toluene
• Water Solubility.: Insoluble in water.
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 210.104465066
• Heavy Atom Count: 16
• Complexity: 210

Purity/Quality:

99% ^*data from raw suppliers

3-?Phenylpropiophenone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CCC(=O)C2=CC=CC=C2
• Uses: 3-Phenylpropiophenone is a potential antioxidant, found in fruit extracts, and is synthesized as a part of last stage applications to natural products and pharmaceuticals.

Technology Process of Dihydrochalcone

There total 496 articles about Dihydrochalcone 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: 97.0%

(E)-3-phenylpropenal (14371-10-9) + phenyllithium (591-51-5) → dihydrochalcone (1083-30-3) + 1,3-diphenyl-propen-3-one (614-47-1)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 7h;

DOI:10.1021/jo980769i

Reference yield: 92.7%

benzalacetophenone (94-41-7) + benzyl alcohol (100-51-6,185532-71-2) → dihydrochalcone (1083-30-3) + benzaldehyde (100-52-7)

Guidance literature:

With potassium hydroxide; In water; at 60 ℃; for 6h; under 750.075 Torr; Reagent/catalyst; Sealed tube; Green chemistry;

DOI:10.1016/S1872-2067(16)62511-1

Reference yield: 80.0%

acetophenone (98-86-2) + benzyl alcohol (100-51-6,185532-71-2) → 1-Phenylethanol (98-85-1,13323-81-4) + dihydrochalcone (1083-30-3) + 1,3-diphenylpropan-1-ol (14097-24-6)

Guidance literature:

With potassium hydroxide; dichlorotetrakis(dimethyl sulfoxide)ruthenium(II); In 1,4-dioxane; at 80 ℃; for 24h;

DOI:10.1016/j.tet.2006.07.013

upstream raw materials:

3-Bromopropionic acid

ethyl bromide

2-benzyl-1-phenylbutane-1,3-dione

sodium ethanolate

Downstream raw materials:

1-fluoren-9-ylidene-1,3-diphenyl-propane

(1,3-diphenylpropyl)amine

1-phenyl-3-(p-nitrophenyl)-1-propanone

3-(2-nitrobenzene)-1-phenylpropan-1-one

Refernces

• 1、 Allen, Laura J.,Crabtree, Robert H.. "Green alcohol couplings without transition metal catalysts: Base-mediated β-alkylation of alcohols in aerobic conditions". . p. 1362 - 1364. Retrieved 2010.
• 2、 Yasui, Shinro,Fujii, Masayuki,Nakamura, Kaoru,Ohno, Atsuyoshi. "NAD(P)+-NAD(P)H Model. 62. The Mechanism of the Silica Gel-Catalyzed Reduction with an NAD(P)H Model". . p. 963 - 968. Retrieved 1987.
• 3、 Nitta, Makoto,Iino, Yukio. "Metal Carbonyl-Induced N-O Bond Cleavage of the Oxime Group". . p. 2365 - 2367. Retrieved 1986.
• 4、 Wang, Rongzhou,Ma, Juan,Li, Feng. "Synthesis of a-Alkylated Ketones via Tandem Acceptorless Dehydrogenation/a-Alkylation from Secondary and Primary Alcohols Catalyzed by Metal-Ligand Bifunctional Iridium Complex [CpIr(2,2′-bpyO)(H2O)]". . p. 10769 - 10776. Retrieved 2015.
• 5、 Yasui, Shinro,Fujii, Masayuki,Ohno, Atsuyoshi. "NAD(P)+-NAD(P)H Models. 64. The Quantitative Elucidation of the Mechanistic Aspects in the Silica Gel-Catalyzed Reduction of α,β-Unsaturated Carbonyl Compounds by a Model of NAD(P)H". . p. 4019 - 4026. Retrieved 1987.
• 6、 Barman, Milan K.,Jana, Akash,Maji, Biplab. "Phosphine-Free NNN-Manganese Complex Catalyzed α-Alkylation of Ketones with Primary Alcohols and Friedl?nder Quinoline Synthesis". . p. 3233 - 3238. Retrieved 2018.
• 7、 Li, Nan,Li, Tianyu,Wu, Botao,Xi, Zhenfeng,Yu, Chao,Zhang, Wen-Xiong. "Trishomoaromatic (B3N3Ph6) Dianion: Characterization and Two-Electron Reduction". . p. 8868 - 8872. Retrieved 2020.
• 8、 Hasegawa, Eietsu,Izumiya, Norihiro,Miura, Tomoaki,Ikoma, Tadaaki,Iwamoto, Hajime,Takizawa, Shin-Ya,Murata, Shigeru. "Benzimidazolium Naphthoxide Betaine Is a Visible Light Promoted Organic Photoredox Catalyst". . p. 3921 - 3927. Retrieved 2018.
• 9、 Silva, Vanessa Dutra,Stambuk, Boris Ugarte,Nascimento, Maria da Graca. "Efficient chemoselective biohydrogenation of 1,3-diaryl-2-propen-1-ones catalyzed by Saccharomyces cerevisiae yeasts in biphasic system". . p. 157 - 163. Retrieved 2010.
• 10、 Stompor, Monika,Potaniec, Bartomiej,Szumny, Antoni,Zielinski, Pawe,Zonierczyk, Anna Katarzyna,Aniol, Miroslaw. "Microbial synthesis of dihydrochalcones using Rhodococcus and Gordonia species". . p. 283 - 288. Retrieved 2013.