1218-22-0

Basic information

• Product Name: (E)-1-(5-bromo-2-hydroxy-phenyl)-3-phenyl-prop-2-en-1-one
• Synonyms: (E)-1-(5-bromo-2-hydroxy-phenyl)-3-phenyl-prop-2-en-1-one
• CAS NO: 1218-22-0
• Molecular Formula: C₁₅H₁₁BrO₂
• Molecular Weight: 303.1506
• Mol File: 1218-22-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 445.9°Cat760mmHg
• Flash Point: 223.5°C
• Appearance: /
• Density: 1.482g/cm³
• Vapor Pressure: 1.45E-08mmHg at 25°C
• Refractive Index: 1.673
• CAS DataBase Reference: (E)-1-(5-bromo-2-hydroxy-phenyl)-3-phenyl-prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-(5-bromo-2-hydroxy-phenyl)-3-phenyl-prop-2-en-1-one(1218-22-0)
• EPA Substance Registry System: (E)-1-(5-bromo-2-hydroxy-phenyl)-3-phenyl-prop-2-en-1-one(1218-22-0)

Safety Data

• Hazardous Substances Data: 1218-22-0(Hazardous Substances Data)

Usage

Description

(E)-1-(5-bromo-2-hydroxy-phenyl)-3-phenyl-prop-2-en-1-one, an organic compound with the molecular formula C15H11BrO2, is a yellow solid known for its versatile chemical structure and potential applications across various industries. It is commonly utilized as a reagent in organic synthesis, and its unique features, such as the presence of a phenolic and enone group along with a bromine substituent, make it a promising candidate for the development of new drugs and crop protection agents.

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

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

Downstream Products

• 1220531-63-4 6-bromo-2-phenylchroman-4-one 
• 119460-77-4 (+/-)-cis-6-bromoflavan-4-ol 
• 86882-49-7 4-Bromo-2-(1,1-dioxo-2-phenyl-2,3-dihydro-1H-1λ⁶-benzo[b][1,4]thiazepin-4-yl)-phenol 
• 1218-80-0 6-bromoflavone 
• 58554-76-0 2,6-Diphenyl-4H-chromen-4-one 
• 1222-12-4 6-bromo-3-hydroxy-2-phenyl-4H-chromen-4-one 
• 1446340-56-2 C₂₉H₂₂O₂ 
• 1446340-57-3 C₂₇H₁₆Cl₂O₂ 
• 1446340-58-4 C₂₇H₁₆F₂O₂ 
• 1446340-59-5 C₂₇H₁₆F₂O₂ 
• 1446340-60-8 6-bromo-3-(4-methoxyphenyl)-2-phenyl-4H-chromen-4-one 
• 1446340-61-9 C₂₃H₁₇BrO₃ 
• 1446340-62-0 C₂₂H₁₅BrO₃ 
• 1446340-63-1 C₂₁H₁₂BrClO₂ 

Relevant articles and documents

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.

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.

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.