3756-40-9

Usage

Uses

Used in Pharmaceutical Industry:
(-)-[(S)-1-Bromoethyl]benzene is used as an intermediate in the synthesis of pharmaceuticals for its ability to contribute to the creation of chiral compounds, which are essential in the development of many drugs that interact with biological targets in a stereospecific manner.
Used in Agrochemical Industry:
In the agrochemical sector, (-)-[(S)-1-Bromoethyl]benzene is utilized as an intermediate in the synthesis of agrochemicals, playing a crucial role in the development of chiral pesticides and other compounds that target specific pests while minimizing environmental impact.
Used in Organic Compounds Synthesis:
(-)-[(S)-1-Bromoethyl]benzene is used as a building block in the synthesis of other organic compounds, leveraging its chiral nature to construct complex molecules with specific properties for various applications.
Used in Chemical Research and Development:
(-)-[(S)-1-Bromoethyl]benzene is employed in research and development within the chemical industry to explore and create new materials and compounds, taking advantage of its chiral properties to advance scientific understanding and innovation.
It is crucial to handle (-)-[(S)-1-Bromoethyl]benzene with care due to its toxic nature and potential to cause irritation to the skin, eyes, and respiratory system if not properly managed.

Upstream product

• 1517-69-7 (R)-1-phenylethanol 
• 1445-91-6 (S)-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 1-Phenylethanol 
• 98-85-1 (-)-α-phenethyl alcohol 
• 33533-53-8 (+/-)-α-methylbenzyl hydrogen phthalate 
• 1459-14-9 (R)-(1-bromoethyl)benzene 
• 19052-01-8 (S)-4-methyl-N-(1-phenylethyl)benzamide 

Downstream Products

• 46051-05-2 S-((R)-1-phenyl-ethyl)-isothiourea 
• 219590-66-6 tert-butyl (S)-3-phenyl-2-<(S)-phenylethyl>butanoate 
• 219590-67-7 (S)-3-phenyl-2-<(S)-phenylethyl>butanoic acid 
• 100-42-5 styrene 
• 100-41-4 ethylbenzene 
• 4613-11-0 2,3-diphenylbutane 
• 2726-21-8 2,3-diphenylbutane 
• 71698-86-7 (R)-(-)-1-deuterioethylbenzene 
• 68566-80-3 (S)-(+)-1-phenylethane-1-d₁ 
• 1064708-33-3 (S)-N-(1-phenylethyl)-4-benzoylmethyl-4-piperidinol hydrochloride 
• 1064709-06-3 (S)-N-(1-phenylethyl)-4-benzoylmethyl-4-piperidinol 
• 36617-91-1 (R)-pent-4-en-2-ylbenzene 
• 78330-53-7 (S)-pent-4-en-2-ylbenzene 
• 1861-02-5 (-)deuteriophenylethane 

Relevant academic research and scientific papers

One-Pot Deoxygenation and Substitution of Alcohols Mediated by Sulfuryl Fluoride

Sulfuryl fluoride is a valuable reagent for the one-pot activation and derivatization of aliphatic alcohols, but the highly reactive alkyl fluorosulfate intermediates limit both the types of reactions that can be accessed as well as the scope. Herein, we report the SO2F2-mediated alcohol substitution and deoxygenation method that relies on the conversion of fluorosulfates to alkyl halide intermediates. This strategy allows the expansion of SO2F2-mediated one-pot processes to include radical reactions, where the alkyl halides can also be exploited in the one-pot deoxygenation of primary alcohols under mild conditions (52-95% yield). This strategy can also enhance the scope of substitutions to nucleophiles that are previously incompatible with one-pot SO2F2-mediated alcohol activation and enables substitution of primary and secondary alcohols in 54-95% yield. Chiral secondary alcohols undergo a highly stereospecific (90-98% ee) double nucleophilic displacement with an overall retention of configuration.

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.

Promotion of Appel-type reactions by N-heterocyclic carbenes

N-Heterocyclic carbenes (NHCs) have been extensively used as a versatile class of catalysts and ligands in organocatalytic and organometallic chemistry. However, there are only a small number of synthetic applications where they act as reagents. Here we demonstrate that NHCs can be used as stoichiometric redox reagents for Appel-type halogenation reactions of alcohols. This new reactivity reveals a fresh and interesting aspect and enriches the chemistry of NHCs in an underexplored area. The potential of performing this chemical transformation at the catalytic level using an NHC-oxide derivative is also investigated.

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.

POLYCYCLIC COMPOUNDS AS LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS

Described herein are compounds that are antagonists of lysophosphatidic receptor(s). Also described are pharmaceutical compositions and medicaments that include the compounds described herein, as well as methods of using such antagonists, alone and in combination with other compounds, for treating LPA-dependent or LPA-mediated conditions or diseases.

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.

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.

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.

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.