16897-97-5

Usage

Appearance

White solid

Melting point

75-77°C

Usage

Organic synthesis, pharmaceutical research

Common applications

Intermediate in the production of pharmaceutical drugs, reagent in the synthesis of complex organic compounds

Importance

Versatile chemical, key building block for development of new drug candidates and biologically active molecules in pharmaceutical and chemical industries.

InChI:InChI=1/C14H11BrO/c15-13-9-5-4-8-12(13)10-14(16)11-6-2-1-3-7-11/h1-9H,10H2

Upstream product

• 98-88-4 benzoyl chloride 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 18698-97-0 ortho-bromophenylacetic acid 
• 71-43-2 benzene 
• 583-55-1 1-Bromo-2-iodobenzene 
• 98-86-2 acetophenone 
• 21375-88-2 1-bromo-2-(phenylethenyl)benzene 
• 1127955-48-9 2-(2-bromobenzyl)-2-phenyl-1,3-dithiane 
• 16717-64-9 1-azidostyrene 
• 16732-66-4 2-bromophenylhydrazine 
• 177756-64-8 2-(2-bromophenyl)-N-methoxy-N-methylacetamide 
• 100-58-3 phenylmagnesium bromide 
• 93-58-3 benzoic acid methyl ester 
• 95-46-5 2-methylphenyl bromide 

Downstream Products

• 948-65-2 2-phenyl-indole 
• 772339-91-0 α-(o-bromophenylmethyl)-β,β-difluorostyrene 
• 55962-04-4 2-phenyl-2,3-dihydrobenzofuran 

Relevant academic research and scientific papers

Tailoring the Molecular Properties with Isomerism Effect of AIEgens

It is challenging to achieve precise control on the properties of organic π-functional materials to widen their practical applications. On the other hand, the study of aggregation-induced emission luminogens (AIEgens) helps achieve such goals because of i

H2O2-mediated room temperature synthesis of 2-arylacetophenones from arylhydrazines and vinyl azides in water

An environmentally benign, cost-efficient and practical methodology for the room temperature synthesis of 2-arylacetophenones in water has been discovered. The facile and efficient transformation involves the oxidative radical addition of arylhydrazines with α-aryl vinyl azides in the presence of H2O2 (as a radical initiator) and PEG-800 (as a phase-transfer catalyst). From the viewpoint of green chemistry and organic synthesis, the present protocol is of great significance because of using cheap, non-toxic and readily available starting materials and reagents as well as amenability to gram-scale synthesis, which provides an attractive strategy to access 2-arylacetophenones.

Intramolecular Anti-Carbolithiation of Alkynes: Stereo-Directing Effect of Lithium-Coordinating Substituents

This paper presents the results of our investigations on the stereochemical course of intramolecular carbolithiation of alkynes. It is shown that the presence of a lithium-chelating propargylic substituent completely reverses the otherwise favored syn-pro

Benzylic Aroylation of Toluenes Mediated by a LiN(SiMe3)2/Cs+System

Chemoselective deprotonative functionalization of benzylic C-H bonds is challenging, because the arene ring contains multiple aromatic C(sp2)-H bonds, which can be competitively deprotonated and lead to selectivity issues. Recently it was found that bimetallic [MN(SiMe3)2 M = Li, Na]/Cs+ combinations exhibit excellent benzylic selectivity. Herein, is reported the first deprotonative addition of toluenes to Weinreb amides mediated by LiN(SiMe3)2/CsF for the synthesis of a diverse array of 2-arylacetophenones. Surprisingly, simple methyl benzoates also react with toluenes under similar conditions to form 2-arylacetophenones without double addition to give tertiary alcohol products. This finding greatly increases the practicality and impact of this chemistry. Some challenging substrates with respect to benzylic deprotonations, such as fluoro and methoxy substituted toluenes, are selectively transformed to 2-aryl acetophenones. The value of benzylic deprotonation of 3-fluorotoluene is demonstrated by the synthesis of a key intermediate in the preparation of Polmacoxib.

Palladium-catalyzed synthesis of α-aryl acetophenones from styryl ethers and aryl diazonium saltsviaregioselective Heck arylation at room temperature

Preparation of α-aryl acetophenones from styryl ethers and aryldiazonium salts is described. The reaction is catalyzed by palladium acetate at room temperature in the absence of ligand and base. The developed method is highly attractive in terms of reaction conditions, substrate scope, functional group tolerance and yields. Synthetic applications of the present method are demonstrated by preparing α-aryl indoles and 3-aryl isocoumarin from styryl ethers.

Ruthenium(II)-Catalyzed Cross-Coupling of Benzoyl Formic Acids with Toluenes: Synthesis of 2-Phenylacetophenones

Herein, we report a direct method to synthesize 2-phenylacetophenone through a ruthenium(II)-catalyzed cross-coupling reaction between acyl and benzyl radical. The various derivatives of 2-phenylacetophenone were prepared easily in moderate to good yields. These reactions provide a straightforward pathway to synthesize a variety of ketones bearing various functional groups.

Sequential Suzuki-Miyaura Coupling/Lewis Acid-Catalyzed Cyclization: An Entry to Functionalized Cycloalkane-Fused Naphthalenes

Functionalized angular cycloalkane-fused naphthalenes were prepared using a two-step process involving a Pd-catalyzed Suzuki-Miyaura coupling of aryl pinacol boronates and vinyl triflates followed by a boron trifluoride etherate-catalyzed cycloaromatization.

Parecoxib sodium substituted impurity and preparation method thereof

The invention relates to a parecoxib sodium substituted impurity and a preparation method thereof. The preparation method comprises the following steps: carrying out a reaction on a compound with a structure represented by a formula I with hydroxylamine h

Construction of 1,3-Dithio-Substituted Tetralins by [1,5]-Alkylthio Group Transfer Mediated Skeletal Rearrangement

A novel skeletal rearrangement involving a [1,5]-alkylthio group transfer/cyclization sequence is described. Treatment of benzylidene malonates having a thioketal moiety at the homobenzyl position with a catalytic amount of Sc(OTf)3 afforded alkylthio group rearranged adducts in good chemical yields. Detailed investigation of the reaction mechanism revealed that an intramolecular conjugate addition/ring opening sequence (not through-space transfer) is the key to achieving this reaction.

Strategy for Overcoming Full Reversibility of Intermolecular Radical Addition to Aldehydes: Tandem C-H and C-O Bonds Cleaving Cyclization of (Phenoxymethyl)arenes with Carbonyls to Benzofurans

An intermolecular addition of carbon radicals enabled by a cascade radical coupling strategy is developed. It includes an intermolecular alkyl radical addition to a carbonyl group followed by an intramolecular alkoxy radical addition to haloarenes and produces substituted benzofurans in high yields. The radical nature of this reaction is explored by radical trapping experiments and EPR analysis. The mechanism is investigated by KIE experiments and control experiments. This method could provide rapid and practical access to the key intermediate of TAM-16, a safe and potent antibacterial agent for treating tuberculosis, and, therefore, is of great importance for organic synthesis and the pharmaceutical industry.