3756-40-9

Basic information

• Product Name: (-)-[(S)-1-Bromoethyl]benzene
• Synonyms: (-)-[(S)-1-Bromoethyl]benzene;[(S)-1-Bromoethyl]benzene;[(S)-1-Bromoethyl]benzene,99%e.e.
• CAS NO: 3756-40-9
• Molecular Formula: C₈H₉Br
• Molecular Weight: 185.06106
• Mol File: 3756-40-9.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (-)-[(S)-1-Bromoethyl]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-[(S)-1-Bromoethyl]benzene(3756-40-9)
• EPA Substance Registry System: (-)-[(S)-1-Bromoethyl]benzene(3756-40-9)

Safety Data

• Hazardous Substances Data: 3756-40-9(Hazardous Substances Data)

Usage

Description

(-)-[(S)-1-Bromoethyl]benzene is a chiral compound that features a benzene ring with a bromoethyl group attached to it. This clear, colorless liquid is not very soluble in water and is valued for its applications in various industries due to its unique properties.

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

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

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 articles and documents

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.

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.