1459-14-9

Usage

Uses

Used in Pharmaceutical Industry:
(+)-[(R)-1-Bromoethyl]benzene is used as a key intermediate in the synthesis of various pharmaceuticals due to its ability to be transformed into a range of biologically active molecules. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, (+)-[(R)-1-Bromoethyl]benzene is utilized as a precursor for the production of agrochemicals, contributing to the development of pesticides and other compounds that protect crops and enhance agricultural productivity.
Used in Chiral Ligand and Catalyst Preparation:
(+)-[(R)-1-Bromoethyl]benzene is employed as a starting material for the preparation of chiral ligands and catalysts, which are essential for asymmetric synthesis. These chiral catalysts and ligands play a crucial role in the production of enantiomerically pure compounds, important in various chemical and pharmaceutical processes.
Used in Polymer and Specialty Chemicals Production:
(+)-[(R)-1-Bromoethyl]benzene also serves as a starting material in the synthesis of polymers and other specialty chemicals, where its unique structural features can be leveraged to create materials with specific properties for various applications.
Used as a Chemical Reagent:
(+)-[(R)-1-Bromoethyl]benzene functions as a versatile chemical reagent that can undergo nucleophilic substitution and other types of reactions. This allows for the creation of a variety of derivatives and products, expanding the compound's utility across different chemical processes and industries.

Upstream product

• 1445-91-6 (S)-1-phenylethanol 
• 1517-69-7 (R)-1-phenylethanol 
• 585-71-7 (1-bromoethyl)benzne 
• 205517-34-6 (3S)-N,N'-bis-(p-methoxybenzyl)-3-isopropyl-piperazine-2,5-dione 
• 98-85-1 (-)-α-phenethyl alcohol 
• 98-85-1 1-Phenylethanol 
• 33533-53-8 (+/-)-α-methylbenzyl hydrogen phthalate 
• 19052-01-8 (S)-4-methyl-N-(1-phenylethyl)benzamide 
• 76375-45-6 C₈H₉F₅Si^(2-)*2K⁽¹⁺⁾ 

Downstream Products

• 4613-11-0 2,3-diphenylbutane 
• 2726-21-8 2,3-diphenylbutane 
• 40390-78-1 [(1-phenylethyl)thio]benzene 
• 1066-37-1 trimethylbromogermane 
• 100-42-5 styrene 
• 585-71-7 (1-bromoethyl)benzne 
• 3756-40-9 (S)-(-)-α-phenethyl bromide 
• 100-41-4 ethylbenzene 
• 1445-91-6 (S)-1-phenylethanol 
• 1517-69-7 (R)-1-phenylethanol 
• 5789-35-5 (RR)/(SS)-2,3-diphenylbutane 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 492-37-5 hydratropic acid 
• 1064709-05-2 (R)-N-(1-phenylethyl)-4-benzoylmethyl-4-piperidinol 

Relevant academic research and scientific papers

1,2-Dibromotetrachloroethane: An efficient reagent for many transformations by modified Appel reaction

An efficient and facile method has been developed for the synthesis of alkyl bromides from various alcohols under mild conditions using a triphenylphosphine (PPh 3) /1,2-dibromotetrachloroethane (DBTCE) complex in excellent yields and very short time (5 min). This method can also be applied for the transformation of chiral alcohols to their corresponding bromides in very high enantiomeric excess. The PPh 3 /DBTCE complex is also successfully applied to ring-opening reactions of cyclic ethers in mild conditions. Esterification, amidation, and formation of acid anhydrides under very mild experimental conditions are also successfully accomplished by following a modification of the Appel reaction protocol in this work.

In Situ Generated Gold Nanoparticles on Active Carbon as Reusable Highly Efficient Catalysts for a Csp3 ?Csp3 Stille Coupling

Gold nanoparticle catalysts are important in many industrial production processes. Nevertheless, for traditional Csp2-Csp2 cross-coupling reactions they have been rarely used and Pd catalysts usually give a superior performance. Herein we report that in situ formed gold metal nanoparticles are highly active catalysts for the cross coupling of allylstannanes and activated alkylbromides to form Csp3-Csp3 bonds. Turnover numbers up to 29 000 could be achieved in the presence of active carbon as solid support, which allowed for convenient catalyst recovery and reuse. The present study is a rare case where a gold metal catalyst is superior to Pd catalysts in a cross-coupling reaction of an organic halide and an organometallic reagent.

Transition-Metal-Free Stereospecific Cross-Coupling with Alkenylboronic Acids as Nucleophiles

We herein report a transition-metal-free cross-coupling between secondary alkyl halides/mesylates and aryl/alkenylboronic acid, providing expedited access to a series of nonchiral/chiral coupling products in moderate to good yields. Stereospecific SN2-type coupling is developed for the first time with alkenylboronic acids as pure nucleophiles, offering an attractive alternative to the stereospecific transition-metal-catalyzed C(sp2)-C(sp3) cross-coupling.

Cosolvent-Promoted O-Benzylation with Silver(I) Oxide: Synthesis of 1′-Benzylated Sucrose Derivatives, Mechanistic Studies, and Scope Investigation

A cosolvent-promoted O-benzylation strategy with Ag2O was developed. The cosolvent consisting of CH2Cl2 and n-hexane can not only improve the reaction solubility for carbohydrates but also increase the benzylation efficiency. The formation of byproducts is greatly inhibited in the developed method. This method is simple, mild, and highly effective, and numerous 1′-benzylated sucrose derivatives were prepared including a photoreactive (trifluoromethyl)phenyldiazirine-based sucrose. The mechanisms of benzylation with primary and secondary benzyl bromides were also elaborated. Furthermore, the application scope with alcohols, glucose, and ribose derivatives was investigated.

Kinetics and mechanism of the reaction of benzyl bromide with copper in dimethylacetamide in the presence of oxygen

The reaction of copper metal with benzyl bromide in dimethylacetamide in the presence of oxygen has been studied. Oxidative dissolution of copper follows the single-electron transfer mechanism with formation of benzaldehyde, benzyl alcohols, and copper(II

High-throughput method for determining the enantioselectivity of enzyme-catalyzed hydroxylations based on mass spectrometry

(Chemical equation presented) Up to speed: An accurate, sensitive, high-throughput, and simple method for measuring the product ee value of enzyme-catalyzed hydroxylations (see scheme) is based on the use of enantiopure or enantioenriched deuterated substrates and mass spectrometric detection.

Kinetics and mechanism of nickel reaction with benzyl bromide in dimethylformamide

Abstarct: The reaction of nickel with benzyl bromide in DMF has been studied. The reaction intermediates were investigated by different methods and the kinetic and thermodynamic parameters were determined. The reaction of benzyl bromide with nickel was shown to occur on the metal surface by the Langmuir-Hinshelwood scheme, with the formation of benzyl radicals which are recombined and isomerized in solution to form 1,2-diphenylethane and trace amounts of 4.4'-dimethylbiphenyl.

Palladium-catalyzed cross-coupling reaction of secondary benzylic bromides with grignard reagents

"Chemical Equation Presented" A mild palladium-catalyzed Kumada-Corriu reaction of secondary benzylic bromides with aryl and alkenyl Grignard reagents has been developed. In the presence of the Xantphos ligand, the undesired β-elimination pathway Is minimized, affording the corresponding cross-coupling products In acceptable to good yields. The reaction proceeds with inversion of the configuration.

A mild synthesis of nitriles by von Braun degradation of amides using triphenyl phosphite-halogen-based reagents

A mild procedure for the synthesis of aromatic and aliphatic nitriles is disclosed. In the presence of bromotriphenoxyphosphonium bromide (TPPBr 2), N-alkyl and N,N-dialkyl amides undergo von Braun degradation to nitriles in good to excellent yields under the mildest conditions ever reported. The reaction proceeds via formation of an iminoyl bromide intermediate at -60°C, which subsequently dealkylate upon refluxing in chloroform or even at room temperature. In the case of N-tert-butyl, N-α-phenylethyl and N-benzhydryl amides, chlorotriphenoxyphosphonium chloride (TPPCl2) generated at -30°C was also effective. Georg Thieme Verlag Stuttgart.

Enantiodiscrimination of racemic electrophiles by diketopiperazine enolates: asymmetric synthesis of methyl 2-amino-3-aryl-butanoates and 3-methyl-aspartates

Enolates of (S)-N,N′-bis-(p-methoxybenzyl)-3-iso-propylpiperazine-2,5-dione exhibit high levels of enantiodiscrimination in alkylations with (RS)-1-aryl-1-bromoethanes and (RS)-2-bromoesters, affording substituted diketopiperazines containing two new stereogenic centres in high de. Deprotection and hydrolysis of the resultant substituted diketopiperazines provides a route to the asymmetric synthesis of homochiral methyl 2-amino-3-aryl-butanoates and 3-methyl-aspartates in high de and ee.