1589-82-8

Basic information

• Product Name: BENZYLMAGNESIUM BROMIDE
• Synonyms: BENZYLMAGNESIUM BROMIDE;benzylbromomagnesium;Benzylmagnesium Bromide (19% in Tetrahydrofuran, ca. 1mol/L);Bromo(phenylmethyl)magnesium;Bromobenzylmagnesium;magnesium methanidylbenzene bromide;Benzylmagnesium Bromide (ca. 12% in Tetrahydrofuran, ca. 0.6mol/L);BenzylMagnesiuM BroMide 1M in Tetrahydrofuran
• CAS NO: 1589-82-8
• Molecular Formula: C₇H₇BrMg
• Molecular Weight: 195.34
• EINECS: 216-459-7
• Product Categories: Classes of Metal Compounds;Grignard Reagents;Grignard Reagents & Alkyl Metals;Mg (Magnesium) Compounds;Synthetic Organic Chemistry;Typical Metal Compounds;Grignard Reagent
• Mol File: 1589-82-8.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 110.6°C at 760 mmHg
• Flash Point: 10°C
• Appearance: powder
• Vapor Pressure: 27.7mmHg at 25°C
• CAS DataBase Reference: BENZYLMAGNESIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYLMAGNESIUM BROMIDE(1589-82-8)
• EPA Substance Registry System: BENZYLMAGNESIUM BROMIDE(1589-82-8)

Safety Data

• RIDADR: 2924
• HazardClass: 3/8
• PackingGroup: II
• Hazardous Substances Data: 1589-82-8(Hazardous Substances Data)

Usage

Description

Benzylmagnesium bromide is an organometallic compound that consists of a benzyl group attached to a magnesium atom with a bromine atom as a counterion. It is a strong nucleophile used in organic synthesis, particularly in Grignard reactions, to form carbon-carbon bonds with various electrophiles. This versatile reagent is valuable for the formation of compounds such as alcohols, ketones, and esters, and its selective reactivity with specific functional groups makes it an essential tool in molecular and material development. However, its high reactivity requires careful handling due to sensitivity to air and moisture.

Uses

Used in Organic Synthesis:
Benzylmagnesium bromide is used as a nucleophilic reagent for the formation of carbon-carbon bonds with a wide variety of electrophiles in Grignard reactions. Its strong nucleophilic nature allows for the creation of diverse organic compounds, making it a fundamental component in the synthesis of complex molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, benzylmagnesium bromide is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its ability to form carbon-carbon bonds selectively with specific functional groups enables the development of new drugs with targeted therapeutic effects.
Used in Material Science:
Benzylmagnesium bromide is utilized as a reagent in the synthesis of advanced materials, such as polymers and organometallic complexes. Its selective reactivity allows for the precise construction of molecular structures with desired properties, contributing to the development of innovative materials for various applications.
Used in Academic Research:
In academic research, benzylmagnesium bromide serves as a valuable tool for exploring new reaction mechanisms and developing novel synthetic methodologies. Its unique properties and reactivity provide opportunities for chemists to investigate and expand the boundaries of organic chemistry.

InChI:InChI=1/C7H7.BrH.Mg/c1-7-5-3-2-4-6-7;;/h2-6H,1H2;1H;/q-1;;+2/p-1

Upstream product

• 100-39-0 benzyl bromide 
• 7439-95-4 magnesium 
• 162271-10-5 2-Bromo-3-(methoxymethoxy)pyridine 
• 100-44-7 benzyl chloride 

Downstream Products

• 1745-77-3 2-benzylquinoline 
• 66487-97-6 1-(furan-2-yl)-2-phenylethanol 
• 3783-65-1 (E)-2-(2-phenylethenyl)thiophene 
• 27049-45-2 benzyl 2-pyridyl ketone 
• 50845-68-6 1-phenyl-2-(3-pyridyl)propan-2-ol 
• 17275-73-9 1-phenyl-2-furylpropan-2-ol 
• 93015-37-3 2-methyl-1,3-diphenyl-propane-1,2-diol 
• 108884-71-5 (+/-)-3ξ-benzyl-3ξ-hydroxy-2-methyl(3ac,7ac)-2,3,3a,4,7,7a-hexahydro-4r,7c-methano-isoindol-1-one 
• 4428-13-1 1,1,2-Triphenylethanol 
• 531522-38-0 1,2-diphenyl-4-piperidino-butan-2-ol 
• 110462-09-4 3,3-diethyl-6-benzyl-piperidine-2,4-dione 
• 300-57-2 allylbenzene 
• 538-68-1 pentylbenzene 
• 101868-39-7 1-(4-chloro-phenyl)-2-phenyl-1-[4]pyridyl-ethanol 

Relevant articles and documents

Discovery of 2,4-diaminopyrimidine derivatives targeting p21-activated kinase 4: Biological evaluation and docking studies

In this study, novel 2,4-diaminopyrimidine derivatives targeting p21-activated kinase 4 (PAK4) were discovered and evaluated for their biological activity against PAK4. Among the derivatives studied, promising compounds A2, B6, and B8 displayed the highest inhibitory activities against PAK4 (IC50 = 18.4, 5.9, and 20.4 nM, respectively). From the cellular assay, compound B6 exhibited the highest potency with an IC50 value of 2.533 μM against A549 cells. Some compounds were selected for computational ADME (absorption, distribution, metabolism, and elimination) properties and molecular docking studies against PAK4. The detailed structure–activity relationship based on the biochemical activities and molecular docking studies were explored. According to the docking studies, compound B6 had the lowest docking score (docking energy: ?7.593 kcal/mol). The molecular docking simulation indicated the binding mode between compound B6 and PAK4. All these results suggest compound B6 as a useful candidate for the development of a PAK4 inhibitor.

Iron-Catalyzed Cross-Coupling of Alkynyl and Styrenyl Chlorides with Alkyl Grignard Reagents in Batch and Flow

Transition-metal-catalyzed cross-coupling chemistry can be regarded as one of the most powerful protocols to construct carbon–carbon bonds. While the field is still dominated by palladium catalysis, there is an increasing interest to develop protocols that utilize cheaper and more sustainable metal sources. Herein, we report a selective, practical, and fast iron-based cross-coupling reaction that enables the formation of Csp?Csp3 and Csp2?Csp3 bonds. In a telescoped flow process, the reaction can be combined with the Grignard reagent synthesis. Moreover, flow allows the use of a supporting ligand to be avoided without eroding the reaction selectivity.

Syntheses of arabinose-derived pyrrolidine catalysts and their applications in intramolecular Diels-Alder reactions

Six chiral hydroxylated pyrrolidine catalysts were synthesized from commercially available D-arabinose in seven steps. Various aromatic substituents α to the amine can be introduced readily by a Grignard reaction, which enables facile optimization of the catalyst performance. The stereoselectivities of these catalysts have been assessed by comparing with those of MacMillan's imidazolidinone in a known intramolecular Diels-Alder (IMDA) reaction of a triene. Two additional IMDA reactions of symmetrical dienals with concomitant desymmetrisation further established the potential use of these novel amine catalysts. These pyrrolidines are valuable catalysts for other synthetic transformations.