• 1. Nickel catalyzed alkylation of N-aromatic heterocycles with Grignard reagents through direct C–H bond functionalization
  Peng-Yang Xin,Hong-Ying Niu,Gui-Rong Qu,Rui-Fang Ding,Hai-Ming Guo Chem. Commun. 2012 48 6717
• 2. Synthesis, absolute configuration and in vitro cytotoxicity of deschloroketamine enantiomers: rediscovered and abused dissociative anaesthetic
  Bronislav Jurásek,Franti?ek Králík,Silvie Rimpelová,Jan ?ejka,Vladimír Setni?ka,Tomá? Ruml,Martin Kucha?,Michal Kohout New J. Chem. 2018 42 19360
• 3. Enantiopure methoxetamine stereoisomers: chiral resolution, conformational analysis, UV-circular dichroism spectroscopy and electronic circular dichroism
  Kun Won Lee,Ahmed H. E. Hassan,Youngdo Jeong,Seolmin Yoon,Seung-Hwan Kim,Cheol Jung Lee,Hye Rim Jeon,Suk Woo Chang,Ji-Young Kim,Dae Sik Jang,Hee Jin Kim,Jae Hoon Cheong,Yong Sup Lee New J. Chem. 2021 45 4354
• 4. 664. Chemical constitution and sex-hormonal activity: the synthesis of of some 1-cyclopentyl- and 1-cyclohexyl-1 : 2-diarylethylenes
  D. H. Hey,O. C. Musgrave J. Chem. Soc. 1949 3156
• 5. Preparation and rearrangement of some α-hydroxy-aldehydes
  T. D. Inch,P. Watts,N. Williams J. Chem. Soc. D 1971 174

• Solvents and Organic Chemicals Organic Compounds Organometallic compounds Organoalkaline-earth metal compounds Organomagnesium compounds Organomagnesium halides
• Other Chemical Reagents Organic Metal Reagents

Bromocyclopentylmagnesium: A Comprehensive Overview of CAS No. 33240-34-5

Bromocyclopentylmagnesium, identified by the CAS number 33240-34-5, is a highly reactive organomagnesium compound commonly used in organic synthesis. This compound, typically supplied as a 2.0 M solution in diethyl ether, is a key reagent in Grignard reactions, enabling the formation of complex carbon frameworks with high precision. Its structure consists of a cyclopentyl group attached to a magnesium bromide moiety, making it an essential tool for constructing cyclic and acyclic hydrocarbons.

The synthesis of Bromocyclopentylmagnesium involves the reaction of cyclopentyl bromide with magnesium metal in an ether solvent, often diethyl ether, under strictly anhydrous conditions. The choice of solvent is critical, as diethyl ether stabilizes the Grignard reagent through solvation, preventing premature reaction with atmospheric moisture or oxygen. Recent studies have explored alternative solvents to enhance stability and reactivity, with tetrahydrofuran (THF) showing promise due to its higher dielectric constant and ability to stabilize the magnesium complex more effectively.

In terms of applications, Bromocyclopentylmagnesium has been widely utilized in the construction of bicyclic and polycyclic compounds, which are integral to natural product synthesis and drug discovery. For instance, researchers have employed this reagent in the synthesis of terpenoids, where its ability to form six-membered transition states facilitates the construction of complex ring systems. Additionally, its use in cross-coupling reactions has been optimized through ligand-assisted strategies, enhancing both reaction efficiency and selectivity.

Recent advancements in green chemistry have led to investigations into the sustainability of Grignard reagents like Bromocyclopentylmagnesium. Efforts are being made to develop recyclable systems where the magnesium byproduct can be recovered and reused, significantly reducing waste and environmental impact. Furthermore, computational studies using density functional theory (DFT) have provided deeper insights into the reaction mechanisms involving this compound, elucidating how steric and electronic factors influence its reactivity.

The stability and shelf life of Bromocyclopentylmagnesium solutions are critical considerations for their practical application. Studies have shown that storage temperature and exposure to light significantly affect stability, with optimal conditions being below -10°C in dark containers. Moreover, the presence of trace impurities can catalyze side reactions; thus, rigorous purification protocols are essential to ensure consistent performance.

In conclusion, Bromocyclopentylmagnesium (CAS No. 33240-34-5) remains a cornerstone in organic synthesis due to its versatility and reactivity. Ongoing research continues to uncover new applications and improve its utilization efficiency, underscoring its importance in both academic and industrial settings.

• 51243-73-3(MAGNESIUM, BICYCLO[2.2.1]HEPT-2-YLBROMO-)
• 922-66-7(sec-Butylmagnesiumbromide)
• 931-50-0(Cyclohexylmagnesium Bromide (~1.0 M in THF))
• 13058-86-1(Magnesium, bicyclo[2.2.1]hept-2-ylbromo-, exo- (9CI))
• 671795-46-3(sec-BuMgBr)
• 102992-58-5(Magnesium, bicyclo[2.2.1]hept-7-ylbromo-)
• 883984-15-4(MAGNESIUM, BROMO(1,1-DIMETHYLPENTYL)-)
• 78378-13-9(MAGNESIUM, BROMOCYCLOOCTYL-)
• 13384-48-0(Magnesium, bromocyclobutyl-)
• 126979-68-8(bromo-(1-ethylpentyl)magnesium)