39229-12-4

Basic information

• Product Name: 4-BroMobenzil
• Synonyms: 4-BroMobenzil;1-(4-bromophenyl)-2-phenylethane-1,2-dione;1-(4-bromophenyl)-2-phenyl-1,2-ethanedione
• CAS NO: 39229-12-4
• Molecular Formula: C₁₄H₉BrO₂
• Molecular Weight: 289.12406
• Mol File: 39229-12-4.mol

Chemical Properties

• Melting Point: 86.5 °C
• Boiling Point: 403.9°Cat760mmHg
• Flash Point: 127.5°C
• Appearance: /
• Density: 1.47g/cm³
• Vapor Pressure: 9.85E-07mmHg at 25°C
• Refractive Index: 1.618
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-BroMobenzil(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BroMobenzil(39229-12-4)
• EPA Substance Registry System: 4-BroMobenzil(39229-12-4)

Safety Data

• Hazardous Substances Data: 39229-12-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Bromobenzyl is used as a building block for the preparation of various pharmaceuticals, agrochemicals, and specialty chemicals. Its ability to participate in a range of chemical reactions makes it a key component in the creation of diverse organic compounds.
Used in Pharmaceutical Industry:
4-Bromobenzyl is used as a reagent in the production of pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its chemical properties allow for the synthesis of molecules with potential medicinal applications.
Used in Agrochemical Industry:
In the agrochemical sector, 4-Bromobenzyl is utilized as a precursor for the synthesis of compounds that have applications in crop protection and pest control, enhancing agricultural productivity and crop safety.
Used in Polymer Production:
4-Bromobenzyl is used as a reagent in the production of polymers, where its chemical properties can influence the polymer's characteristics, such as stability, reactivity, and functionality.
Used in Specialty Chemicals:
4-Bromobenzyl is employed in the synthesis of specialty chemicals that have specific applications in various industries, including but not limited to coatings, dyes, and fragrances, due to its unique chemical structure and reactivity.
Used in Chemical Research:
As a versatile compound, 4-Bromobenzyl is also used in chemical research for studying reaction mechanisms, exploring new synthetic routes, and developing innovative chemical processes.

InChI:InChI=1/C14H9BrO2/c15-12-8-6-11(7-9-12)14(17)13(16)10-4-2-1-3-5-10/h1-9H

Upstream product

• 74-96-4 ethyl bromide 
• 2001-29-8 1-(4-bromophenyl)-2-phenyl-ethan-1-one 
• 13041-70-8 (E)-4-bromostilbene 
• 53458-14-3 2-(4-bromophenyl)-2-hydroxy-1-phenylethan-1-one 
• 13667-12-4 1-bromo-4-phenylethynylbenzene 
• 33449-74-0 1-(4-bromophenyl)-2-hydroxy-2-phenylethanone 
• 103-80-0 phenylacetyl chloride 
• 108-86-1 bromobenzene 
• 589-87-7 1,4-bromoiodobenzene 
• 536-74-3 phenylacetylene 
• 1100-88-5 benzyltriphenylphosphonium chloride 
• 3462-94-0 4-bromobenzyltriphenylphosphonium chloride 
• 122-01-0 4-chloro-benzoyl chloride 
• 586-75-4 4-chlorobenzoyl chloride 

Downstream Products

• 56079-85-7 5-(4-bromo-phenyl)-5-phenyl-imidazolidine-2,4-dione 
• 40396-59-6 1-phenyl-2-p-bromophenyltetrafluoroethane 
• 88406-95-5 1,4-diphenyl-2-(4-bromophenyl)but-2-ene-1,4-dione 
• 97861-56-8 2,4-diphenyl-1-(4-bromophenyl)but-2-ene-1,4-dione 
• 97861-57-9 2,4-diphenyl-1-(4-cyanophenyl)but-2-ene-1,4-dione 
• 88406-97-7 1,4-diphenyl-2-(4-cyanophenyl)but-2-ene-1,4-dione 
• 95785-29-8 1-[4-(3-Hydroxy-3-methyl-but-1-ynyl)-phenyl]-2-phenyl-ethane-1,2-dione 
• 499982-64-8 3-(4-isopropylsilylethynylphenyl)-2,4,5-triphenylcyclopentadienone 
• 97861-37-5 3-(4-cyanophenyl)-3,5-diphenyl-2(3H)-furanone 
• 40396-61-0 4-(α,α,β,β-tetrafluorophenethyl)-benzylamine 
• 38375-72-3 4-(α,α,β,β-tetrafluorophenethyl)-α,α,N-trimethylbenzylamine 
• 40417-83-2 N-{1-Methyl-1-[4-(1,1,2,2-tetrafluoro-2-phenyl-ethyl)-phenyl]-ethyl}-formamide 
• 40396-60-9 4-(1,1,2,2-tetrafluoro-2-phenylethyl)benzonitrile 
• 40396-68-7 1-Isopropenyl-4-(1,1,2,2-tetrafluoro-2-phenyl-ethyl)-benzene 

Relevant articles and documents

Triphenylamine-functionalized tetraphenylpyrazine: Facile preparation and multifaceted functionalities

Aggregation-induced emission (AIE) is a unique photo-physical phenomenon and has become an emerging and hot research area. With the enthusiastic efforts paid by researchers, hundreds of AIE-active luminogens (AIEgens) have been generated but heterocyclic AIEgens are rarely reported. Recently, we enriched the family of AIEgens and reported a pyrazine-based AIEgen of tetraphenylpyrazine (TPP), which could be facilely functionalized by a post-synthetic strategy. In this work, we further expanded the TPP-based AIE system by covalently attaching one, two or four electron-donating triphenylamine moieties to the TPP core via Suzuki coupling, and TPP-TPA, TPP-2TPA and TPP-4TPA were produced, respectively. Thanks to their donor-π-acceptor structures, these luminogens exhibit multi-functional properties, such as excellent thermal stability (up to 504°C), large molar absorptivity, bright emission in the solid state (quantum yields up to 35.2%), solvatochromism, and high two-photon absorption cross-sections (up to 480 GM). Furthermore, using TPP-TPA as the emitting layer, a triple-layer device was fabricated and a turn-on voltage, maximum luminance, current efficiency, power efficiency, and external quantum efficiency of 3.7 V, 17 459 cd m-2, 5.49 cd A-1, 3.18 lm W-1 and 2.88% were realized, respectively. These results indicate a huge potential to develop high-tech applications based on these TPP-based AIEgens.

Catalyst-Free and Transition-Metal-Free Approach to 1,2-Diketones via Aerobic Alkyne Oxidation

A catalyst-free and transition-metal-free method for the synthesis of 1,2-diketones from aerobic alkyne oxidation was reported. The oxidation of various internal alkynes, especially more challenging aryl-alkyl acetylenes, proceeded smoothly with inexpensive, easily handled, and commercially available potassium persulfate and an ambient air balloon, achieving the corresponding 1,2-diketones with up to 85% yields. Meanwhile, mechanistic studies indicated a radical process, and the two oxygen atoms in the 1,2-diketons were most likely from persulfate salts and molecular oxygen, respectively, rather than water.

Visible-Light-Induced Photocatalytic Oxidative Decarboxylation of Cinnamic Acids to 1,2-Diketones

A concerted metallophotoredox catalysis has been realized for the efficient decarboxylative functionalization of α,β-unsaturated carboxylic acids with aryl iodides in the presence of perylene bisimide dye to afford 1,2-diketones.

One-pot cascade synthesis of α-diketones from aldehydes and ketones in water by using a bifunctional iron nanocomposite catalyst

A new methodology for the synthesis of α-diketones was reportedviaa one-pot cascade process from aldehydes and ketones catalyzed by a bifunctional iron nanocomposite using H2O2as a green oxidant in water. The one-pot strategy showed excellent catalytic stability, comprehensive suitability of substrates and important practical utility for directly synthesizing biologically active and medicinally valuable N-heterocyclesviaan intermittent process.

Nature of the Nucleophilic Oxygenation Reagent Is Key to Acid-Free Gold-Catalyzed Conversion of Terminal and Internal Alkynes to 1,2-Dicarbonyls

2,3-Dichloropyridine N-oxide, a novel oxygen transfer reagent, allows the conductance of the gold(I)-catalyzed oxidation of alkynes to 1,2-dicarbonyls in the absence of any acid additives and under mild conditions to furnish the target species, including those derivatized by highly acid-sensitive groups. The developed strategy is effective for a wide range of alkyne substrates such as terminal- and internal alkynes, ynamides, alkynyl ethers/thioethers, and even unsubstituted acetylene (40 examples; yields up to 99%). The oxidation was successfully integrated into the trapping of reactive dicarbonyls by one-pot heterocyclization and into the synthesis of six-membered azaheterocycles. This synthetic acid-free route was also successfully applied for the total synthesis of a natural 1,2-diketone.

Visible light-induced aerobic oxidation of diarylalkynes to α-diketones catalyzed by copper-superoxo at room temperature

We have developed the visible light induced simple copper(ii) chloride catalyzed oxidation of diarylacetylenes to α-diketones by molecular oxygen at room temperature. The in situ generated copper(ii)-superoxo complex is a light-absorbing species that oxidizes inert diarylacetylenes to α-diketones. In contrast to reported photochemical processes, the current oxidation protocol does not require any exogenous photocatalyst or radical initiator. The green chemistry metrics evaluation signifies that the E-factor for the current oxidation process is ～2.3 times better than that of reported photochemical processes. The current reaction scores 63 on the EcoScale of 0-100, indicating an adequate synthesis process. Thus, the overall oxidation process is simple, environmentally benign, and economically feasible. This journal is

A Bifunctional Iron Nanocomposite Catalyst for Efficient Oxidation of Alkenes to Ketones and 1,2-Diketones

We herein report the fabrication of a bifunctional iron nanocomposite catalyst, in which two catalytically active sites of Fe-Nx and Fe phosphate, as oxidation and Lewis acid sites, were simultaneously integrated into a hierarchical N,P-dual doped porous carbon. As a bifunctional catalyst, it exhibited high efficiency for direct oxidative cleavage of alkenes into ketones or their oxidation into 1,2-diketones with a broad substrate scope and high functional group tolerance using TBHP as the oxidant in water under mild reaction conditions. Furthermore, it could be easily recovered for successive recycling without appreciable loss of activity. Mechanistic studies disclose that the direct oxidation of alkenes proceeds via the formation of an epoxide as intermediate followed by either acid-catalyzed Meinwald rearrangement to give ketones with one carbon shorter or nucleophilic ring-opening to generate 1,2-diketones in a cascade manner. This study not only opens up a fancy pathway in the rational design of Fe-N-C catalysts but also offers a simple and efficient method for accessing industrially important ketones and 1,2-diketones from alkenes in a cost-effective and environmentally benign fashion.

Sequentially Pd/Cu-Catalyzed Alkynylation-Oxidation Synthesis of 1,2-Diketones and Consecutive One-Pot Generation of Quinoxalines

We report a simple and efficient one-pot synthesis of 1,2-diketones by concatenation of two Pd/Cu-catalyzed processes: Pd0/CuI-catalyzed Sonogashira coupling of terminal alkynes with aryl (pseudo)halides furnishes internal alkynes, which are directly transformed by PdII/CuII-catalyzed Wacker-type oxidation with DMSO and oxygen as dual oxidants to furnish 1,2-diketones. With this efficient, catalyst economical process, various aryl iodides and triflates are efficiently transformed in high yields into symmetrically and unsymmetrically substituted 1,2-diketones with various functional groups. This process can be readily extended to a consecutive one-pot synthesis of quinoxalines in a diversity-oriented fashion.

Rate Enhancement in CAN-Promoted Pd(PPh3)2Cl2-Catalyzed Oxidative Cyclization: Synthesis of 2-Ketofuran-4-carboxylate Esters

Stoichiometric ceric ammonium nitrate (CAN) and a catalytic amount of Pd(PPh3)2Cl2 (5 mol %) can rapidly produce multisubstituted 2-ketofuran-4-carboxylate esters from 2-propargylic 1,3-ketoesters via oxidative O-cyclization reaction. Pd(PPh3)2Cl2 was found to be the crucial catalyst as its inclusion greatly enhanced the rate of the reaction and cleanly afforded the products within minutes. Over 30 substrates were successfully converted to the desired compounds in mostly moderate to good yields.

Gold-Catalyzed Oxidation of Internal Alkynes into Benzils and its Application for One-Pot Synthesis of Five-, Six-, and Seven-Membered Azaheterocycles

Internal alkynes have been shown to undergo oxidation to substituted benzils (1,2-diarylethane-1,2-diones) by α-picoline N-oxide in the presence of Ph3PAuNТf2 (5 mol-%). In addition to the unsubstituted benzil, the method allows preparing, under markedly mild conditions (50 °C in chlorobenzene), various non-symmetrical products, including heteroaromatic versions thereof which are much more difficult to obtain otherwise. This gold(I)-catalyzed transformation was integrated into one-pot reaction sequence delivering a range of 5- to 7-membered ring systems (imidazoles, quinoxalines, 1,2,4-triazines, pyrazines, and 1,4-diazepines), thus linking these important heterocyclic motifs to the internal alkyne reagent space.