1218-22-0

Usage

Uses

Used in Pharmaceutical Industry:
(E)-1-(5-bromo-2-hydroxy-phenyl)-3-phenyl-prop-2-en-1-one is used as a key intermediate in the synthesis of new drugs due to its chemical versatility and the presence of functional groups that can be further modified for specific therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, (E)-1-(5-bromo-2-hydroxy-phenyl)-3-phenyl-prop-2-en-1-one is used as a building block for the development of novel crop protection agents, leveraging its unique reactivity and structural features to create effective and targeted pest control solutions.
Used in Organic Synthesis:
As a reagent in organic synthesis, (E)-1-(5-bromo-2-hydroxy-phenyl)-3-phenyl-prop-2-en-1-one is used for the preparation of various organic compounds, taking advantage of its bromine substituent to facilitate unique reactions and create a wide range of chemical products.

InChI:InChI=1/C15H11BrO2/c16-12-7-9-15(18)13(10-12)14(17)8-6-11-4-2-1-3-5-11/h1-10,18H/b8-6+

Upstream product

• 100-52-7 benzaldehyde 
• 140-10-3 (E)-3-phenylacrylic acid 
• 1450-75-5 5-Bromo-2-hydroxyacetophenone 
• 39729-11-8 2'-hydroxychalcone dibromides 
• 1927-95-3 4-bromophenyl acetate 
• 106-41-2 4-bromo-phenol 

Downstream Products

• 1220531-63-4 6-bromo-2-phenylchroman-4-one 
• 1393811-60-3 (E)-6-styrylflavone 
• 1393811-61-4 (E)-6-(4-methylstyryl)flavone 
• 1393811-62-5 (E)-6-(4-methoxystyryl)flavone 
• 1393811-63-6 (E)-6-(4-chlorostyryl)flavone 
• 1393811-64-7 (E)-6-(3-hydroxy-3-methylbut-1-enyl)flavone 
• 1393811-65-8 ethyl (E)-6-(2-phenyl-4-oxo-4H-1-benzopyran-3-yl)acrylate 
• 1218-80-0 6-bromoflavone 
• 1393811-72-7 (E)-6-(2-phenyl-4-oxo-4H-1-benzopyran-3-yl)acrylaldehyde 
• 1222-12-4 6-bromo-3-hydroxy-2-phenyl-4H-chromen-4-one 
• 119460-77-4 (+/-)-cis-6-bromoflavan-4-ol 
• 1446340-55-1 C₂₉H₂₂O₄ 
• 1446340-54-0 C₃₁H₂₆O₄ 
• 1446340-53-9 3,6-bis(4-methoxyphenyl)-2-phenyl-4H-chromen-4-one 

Relevant academic research and scientific papers

Chiral Hydroxytetraphenylene-Boron Complex Catalyzed Asymmetric Diels-Alder Cycloaddition of 2′-Hydroxychalcones

(S)-2,15-Cl2-DHTP-boron complex catalyst for the asymmetric Diels-Alder cycloaddition of 2′-hydroxychalcones and dienes was developed and tested. The resulting cyclohexenes with three chiral centers were obtained in high yields (up to 98%) with excellent stereoselectivities (up to >20:1 endo/exo, >99% ee). This catalytic system features high efficiency, broad substrate scopes, and mild reaction conditions. In addition, a DFT study was performed to explain the stereochemical course of the asymmetric induction.

Synthesis of 5-subsituted flavonols via the Algar-Flynn-Oyamada (AFO) reaction: The mechanistic implication

Herein, we report a synthetic method with improved selectivity for 5-substituted flavonols via the Algar-Flynn-Oyamada reaction (AFO), by using of sodium carbonate/hydrogen peroxide A series of 5-substituted flavonols was obtained with moderate to high yields. The mechanism of the AFO reaction was elucidated. LCMS analysis and in situ 1H NMR analysis indicated that the epoxide was involved in the transformation from chalcone to flavonol and/or aurone under alkaline base/peroxide conditions.

Fast and efficient synthesis of flavanones from cinnamic acids

A fast and efficient synthesis of flavanones from cinnamic acids in three steps has been developed. First, the cinnamic acid was converted to cinnamyol chlorides using SOCl2. The acid chlorides were then treated with substituted phenols in BF3· OEt2to furnish corresponding chalcones in 42(75% yields. Base-catalyzed cyclization of the chalcones at room temperature afforded corresponding flavones in 85–95% yields. The conversion of the cinnamic acid derivatives to corresponding chalcones was found to be sensitive to the position and nature of the substituents on the aromatic rings.

COMPOSITION FOR TREATING DIABETES AND METABOLIC DISEASES AND A PREPARATION METHOD THEREOF

Disclosed is a chalcone composition for treating diabetes and metabolic syndromes. In particular, the chalcone compound bound with 2-halogen in ring A significantly decreases the blood glucose level in the in vitro anti-diabetic effect experiment. In the in vivo animal model, the leading chalcone compound can prevent the progression of diabetes and control the blood glucose level, and there is no significant difference in the gains in body weight. Throughout the seven-week administration, there are no hepatic or renal toxicity observed.

NHC-catalyzed reaction of enals with hydroxy chalcones: Diastereoselective synthesis of functionalized coumarins

The N-heterocyclic carbene-catalyzed annulation of enals with 2′-hydroxy chalcones afford cyclopentane-fused coumarin derivatives with an excellent level of diastereocontrol. The reaction tolerates a broad range of functional groups; 25 examples are given, and a preliminary mechanistic investigation is provided.

Ionic liquid mediated Cu-catalyzed cascade oxa-Michael-oxidation: Efficient synthesis of flavones under mild reaction conditions

Flavonoids are a class of natural products, found in a wide range of vascular plants and dietary components. Their low toxicity and extensive biological activities, including anti-cancer and anti-bacterial, have made them attractive candidates to serve as therapeutic agents for many diseases. Herein, we disclose a highly efficient synthetic method of CuI-catalyzed cascade oxa-Michael-oxidation, using chalcones as substrates, mediated by the ionic liquid [bmim][NTf2] at a low temperature. This efficient synthetic method has demonstrated high synthetic utility and can afford flavones in good to high yields (up to 98%).

Reaction of 2'-Hydroxychalcone Dibromides with Me2SO

2'-Hydroxychalcone dibromides on treatment with Me2SO gave 2'-hydroxychalcone, 2'-hydroxy-3'- or 2'-hydroxy-5'-bromochalcone, flavone, monobrominated flavone, 6,8-dibromoflavone, 3-bromoflavone, and 3-, 6-, or 8-dibromoflavone.