126443-21-8

Basic information

• Product Name: (E)-4,4'-Dibromochalcone
• Synonyms: (E)-4,4'-Dibromochalcone
• CAS NO: 126443-21-8
• Molecular Formula: C₁₅H₁₀Br₂O
• Molecular Weight: 366.05
• Mol File: 126443-21-8.mol

Chemical Properties

• Melting Point: 184-185 °C
• Boiling Point: 450.6±45.0 °C(Predicted)
• Appearance: /
• Density: 1.647±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (E)-4,4'-Dibromochalcone(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4,4'-Dibromochalcone(126443-21-8)
• EPA Substance Registry System: (E)-4,4'-Dibromochalcone(126443-21-8)

Safety Data

• Hazardous Substances Data: 126443-21-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(E)-4,4'-Dibromochalcone is used as a pharmaceutical compound for its potential antibacterial, antifungal, and anti-inflammatory properties. These properties make it a promising candidate for the development of new drugs to treat various infections and inflammatory conditions.
Used in Drug Discovery and Development:
(E)-4,4'-Dibromochalcone is used as a lead compound in drug discovery and development due to its potential biological and pharmacological activities. Its unique structure and properties make it an interesting target for further research and exploration, with the aim of developing new drugs based on its chemical structure.
Used in Research and Exploration:
(E)-4,4'-Dibromochalcone is used as a subject of study in research and exploration, particularly in the fields of biology and pharmacology. Its potential applications and unique properties make it an important compound for understanding the structure-activity relationships in chalcones and flavonoids, which could lead to the development of new drugs and therapies.

Upstream product

• 99-90-1 para-bromoacetophenone 
• 1122-91-4 4-bromo-benzaldehyde 
• 1777-57-7 p-bromobenzoylmethylenetriphenylphosphorane 
• 99-73-0 para-bromophenacyl bromide 
• 5471-96-5 (E)-1,3-bis(4-bromophenyl)prop-2-en-1-one 

Downstream Products

• 5471-96-5 4,4'-dibromo-cis-chalcone 
• 100965-18-2 (2RS,3SR)-2,3-dibromo-1,3-bis-(4-bromo-phenyl)-propan-1-one 
• 399507-79-0 2,4,6-tris(4-bromophenyl)pyrimidine 
• 23274-53-5 (E)-1,3-di([1,1'-biphenyl]-4-yl)prop-2-en-1-one 
• 898761-28-9 1,3-bis(4-bromophenyl)propan-1-one 
• 61595-99-1 3-(4-bromophenyl)-5-(4-bromophenyl)-1-phenyl-2-pyrazoline 
• 101422-91-7 4,4'-dibromo-β-methoxy-trans-chalcone 
• 101422-91-7 4,4'-dibromo-β-methoxy-cis-chalcone 
• 33170-68-2 1,3-bis-(4-bromo-phenyl)-propane-1,3-dione 
• 100965-18-2 (2RS,3RS)-2,3-dibromo-1,3-bis-(4-bromo-phenyl)-propan-1-one 
• 494764-44-2 3,5-Bis-(4-bromo-phenyl)-4,5-dihydro-1H-pyrazole 
• 121392-37-8 1,3-bis(4-bromophenyl)propane 

Relevant articles and documents

Synthesis and antimicrobial evaluation of arylated 1,3,5-triphenyl pyrazoline derivatives using suzuki-miyaura reactions

The first palladium –catalyzed coupling reactions of 1,3,5-triphenyl pyrazoline are reported. The Suzuki-Miyaura reaction of 3-(4-bromophenyl)-1,5-diphenyl pyrazoline with one equivalent of arylboronic acids afforded 3-(biphenyl)-1,5-diphenyl pyrazoline in 53-78 % yield. While the Suzuki-Miyaura reactions of 3,5-bis(4-bromophenyl)-1-phenyl pyrazoline with two equivalent of arylboronic acids gave 3,5-bis(biphenyl)-1-phenyl pyrazoline in 55-80% yield. The characterization of the synthesized derivatives (5a-h) and (6a-h) were accomplished on the basis of NMR, FT-IR, and mass techniques. The newly pyrazoline derivatives have been investigated for their in vitro antibacterial activity against gram- negative and gram-positive bacteria. The di-coupling compounds (6a-h) exhibited promising antibacterial against all four bacterial strains compared to the mono-coupling compounds (5a-h) which displayed a slight activity. The compound 6d showed a potent activity significantly more active than Trimethoprim (100μg/ml).

Three-Component Synthesis of a Library of m-Terphenyl Derivatives with Embedded β-Aminoester Moieties

The three-component reaction between alkyl- or arylamines, β-ketoesters and chalcones in refluxing ethanol containing a catalytic amount of Ce(IV) ammonium nitrate allowed the construction of a large library of highly substituted dihydro-m-terphenyl derivatives containing β-alkylamino- or β-arylamino ester moieties. This process generates three new bonds and one ring and proceeds in high atom economy, having two molecules of water as the only side product. Another domino process, in which the original MCR was telescoped with a subsequent aza Michael/retro-aza Michael sequence, allowed the one-pot preparation of a library of compounds with a N-unsubstituted β-aminoester fragment. Finally, to extend the structural diversity of these libraries, we also examined the aromatization of the central ring of our compounds in the presence of dichlorodicyanoquinone. This reaction sequence did not affect the integrity of a stereogenic center belonging to the amino component.

Synthesis of symmetrical and unsymmetrical triarylpyrylium ions: Via an inverse electron demand Diels-Alder reaction

BF3·OEt2 mediated inverse electron demand Diels-Alder (IEDDA) reaction of chalcones with aryl acetylenes is reported for the synthesis of symmetrical and unsymmetrical 2,4,6-triarylpyrylium ions. The protocol provides an effective one-pot method for the utilization of readily available simple substrates under mild reaction conditions leading to a diverse array of pyrylium ions in moderately good yield.

Transition-Metal-Free Synthesis of Homo- and Hetero-1,2,4-Triaryl Benzenes by an Unexpected Base-Promoted Dearylative Pathway

An unprecedented approach for the synthesis of homo- and hetero-1,2,4-triaryl benzenes has been developed using a simple base-mediated reaction of either α-aryl cinnamyl alcohols or α,γ-di-aryl propanones. The salient feature of this strategy involves the sequential hydride transfer, regiospecific condensation, regiospecific dearylation, and aromatization under metal-free reaction conditions. The synthesis of unsymmetrically substituted triphenylenes by oxidative coupling of the synthesized 1,2,4-triaryl benzenes has also been demonstrated.

Mild and efficient reductive deoxygenation of epoxides to olefins with tin(II) chloride/sodium iodide as a novel reagent

A highly efficient and green protocol is reported for the reductive deoxygenation of organic epoxides to olefins using tin(II) chloride/sodium iodide as a novel reagent. The reaction gives an excellent yield (85-96%) in ethanol under reflux within 2-10 minutes, without affecting other functional groups. The advantages of our method are the use of inexpensive reagents, the eco-friendly and green reaction conditions, and the short reaction times and high yields.

Polyethyleneimine-Supported Triphenylphosphine and Its Use as a Highly Loaded Bifunctional Polymeric Reagent in Chromatography-Free One-Pot Wittig Reactions

A polyethyleneimine-supported triphenylphosphine reagent has been synthesized and used as a highly loaded bifunctional homogeneous reagent in a range of one-pot Wittig reactions that afforded high yields of the desired products after simple purification procedures. The approach also served efficiently in tandem reaction sequences involving a one-pot Wittig reaction followed by conjugate reduction of the newly formed alkene product in situ. In these transformations, the phosphine oxide groups generated in the Wittig reaction served as the catalyst for activating trichlorosilane in the subsequent reduction reaction.

Covalent Dimers of 1,3-Diphenylisobenzofuran for Singlet Fission: Synthesis and Electrochemistry

Abstract The synthesis of covalent dimers in which two 1,3-diphenylisobenzofuran units are connected through one phenyl substituent on each is reported. In three of the dimers, the subunits are linked directly, and in three others, they are linked via an

A general, mild and efficient palladium-catalyzed 2,2,2-trifluoroethoxylation of activated aryl bromides and bromo-chalcones: Bromo-chalcones a new coupling partner in cross-coupling reaction

An efficient protocol for Pd-catalyzed 2,2,2-trifluoroethoxylation of activated aryl bromides and bromo-chalcones has been developed. We unveil a fascinating insight into the Pd-catalyzed C-O cross-coupling reaction. Pd/tBuXPhos (L1) ligand system facilitates the C-O cross-coupling reaction between 2,2,2-trifluoroethanol and activated aryl bromides at both higher (115 °C) and lower temperatures (40 °C). Unprecedentedly, this catalyst system facilitates the C-O cross-coupling reaction in short span of reaction times, generally 5-25 min (at 115 °C). The structurally simple analogue of tBuXPhos ligand so called JohnPhos (L2) ligand is also facilitated the C-O bond formation with activated aryl bromides and bromo-chalcones. Interestingly, under the optimal conditions (L1), methanol is also coupled rapidly with activated aryl bromides. These catalyst systems (L1 and L2) fail to couple electron rich aryl bromides with 2,2,2-trifluoroethanol, thus these catalyst systems allow the reductive elimination through an electronic pathway of reductive elimination. The unusual reactivity of 2,2,2-trifluoroethanol in Pd-catalyzed C-O cross-coupling reaction makes that the chemistry of fluorinated molecules is unique than that of non-fluorinated analogues. The bromo-chalcones can be used as a new coupling partner in the cross-coupling reaction.

Montmorillonite clay-promoted, solvent-free cross-aldol condensations under focused microwave irradiation

An environmentally benign, clean and general protocol was developed for the synthesis of aryl and heteroaryl trans-chalcones. This method involved solvent-free reaction conditions under microwave irradiation in the presence of a clay-based catalyst, and afforded the target compounds in good yields and short reaction times. Furthermore, the same conditions allowed the synthesis of symmetrical, diarylmethylene-a,a-unsaturated ketones from aromatic aldehydes and ketones.

Copper-catalyzed oxidative transformation of secondary alcohols to 1,5-disubstituted tetrazoles

A mild and convenient oxidative transformation of secondary alcohols to 1,5-disubstituted tetrazoles is uncovered by employing trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of a catalytic amount of copper(II) perchlorate hexahydrate [Cu(ClO4)2 .6 H2O] (5 mol%) and 2,3-dichloro-5,6-dicyano-para- benzoquinone (DDQ) (1.2 equiv.) as an oxidant. This reaction is performed under ambient conditions and proceeds through C-C bond cleavage.