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PHENYLMAGNESIUM BROMIDE

Base Information Edit
  • Chemical Name:PHENYLMAGNESIUM BROMIDE
  • CAS No.:100-58-3
  • Molecular Formula:C6H5BrMg
  • Molecular Weight:181.315
  • Hs Code.:29319090
  • Mol file:100-58-3.mol
PHENYLMAGNESIUM BROMIDE

Synonyms:Phenylmagnesiumbromide (6CI);Bromomagnesiobenzene;Bromophenylmagnesium;

Suppliers and Price of PHENYLMAGNESIUM BROMIDE
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • Usbiological
  • Phenylmagnesium Bromide
  • 25ml
  • $ 319.00
  • TRC
  • PhenylmagnesiumBromide(1.0MsolutioninTHF)
  • 500ml
  • $ 250.00
  • TRC
  • PhenylmagnesiumBromide(1.0MsolutioninTHF)
  • 50ml
  • $ 80.00
  • TCI Chemical
  • Phenylmagnesium Bromide (16% in Tetrahydrofuran, ca. 1mol/L)
  • 250g
  • $ 124.00
  • Strem Chemicals
  • Phenylmagnesium bromide, 2.9M (45wt% ±1wt%) in 2-methyltetrahydrofuran
  • 1mole
  • $ 178.00
  • Strem Chemicals
  • Phenylmagnesium bromide, 3M in ether
  • 1mole
  • $ 155.00
  • Strem Chemicals
  • Phenylmagnesium bromide, 2.9M (45wt% ±1wt%) in 2-methyltetrahydrofuran
  • 0.25mole
  • $ 78.00
  • Strem Chemicals
  • Phenylmagnesium bromide, 3M in ether
  • 0.25mole
  • $ 52.00
  • Sigma-Aldrich
  • Phenylmagnesium bromide solution 3.0M in diethyl ether
  • 800ml
  • $ 217.00
  • Sigma-Aldrich
  • Phenylmagnesium bromide solution 3.0M in diethyl ether
  • 200ml
  • $ 204.00
Total 15 raw suppliers
Chemical Property of PHENYLMAGNESIUM BROMIDE Edit
Chemical Property:
  • Appearance/Colour:powder 
  • Melting Point:153-154 °C 
  • Boiling Point:78.8oC at 760 mmHg 
  • Flash Point:-11 °C 
  • PSA:0.00000 
  • Density:1.134 g/mL at 25 °C 
  • LogP:2.33240 
  • Storage Temp.:water-free area 
  • Sensitive.:Air & Moisture Sensitive 
  • Solubility.:Miscible with tetrahydrofuran. 
  • Water Solubility.:reacts 
Purity/Quality:

99.9% *data from raw suppliers

Phenylmagnesium Bromide *data from reagent suppliers

Safty Information:
  • Pictogram(s): HighlyF+, CorrosiveC, Flammable
  • Hazard Codes:F+,C,F 
  • Statements: 12-14-22-34-19-11-67-40-37 
  • Safety Statements: 16-26-36/37/39-45-33-29-7/8-6A-43B 
MSDS Files:

SDS file from LookChem

Useful:
  • Uses Phenylmagnesium Bromide is a reagent used in the preparation of arylcarbonimidic dichlorides via dichloroiodobenzene-mediated gem-dichlorination of aryl isonitriles. Grignard reagent in greener solvent, 2-methyltetrahydrofuran (2-MeTHF)2-Methyltetrahydrofuran (2-MeTHF): A Biomass-Derived Solvent with Broad Application in Organic Chemistry
Technology Process of PHENYLMAGNESIUM BROMIDE

There total 17 articles about PHENYLMAGNESIUM BROMIDE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
With magnesium; In tetrahydrofuran; at 40 ℃; for 0.25h; Inert atmosphere; Flow reactor;
DOI:10.1021/acs.oprd.9b00493

Reference yield: 98.0%

Guidance literature:
Refernces Edit

Design, synthesis, and structure-activity relationships of pyrazolo[3,4-d]pyrimidines: A novel class of potent enterovirus inhibitors

10.1016/j.bmcl.2004.02.092

The study focuses on the design, synthesis, and evaluation of a novel class of pyrazolo[3,4-d]pyrimidines as potent inhibitors of enteroviruses, specifically coxsackieviruses. The researchers synthesized a series of these compounds and tested their antiviral activity using a plaque reduction assay. They discovered that these compounds showed remarkable specificity for human enteroviruses, with some derivatives highly effective at nanomolar concentrations. Structure-activity relationship (SAR) studies indicated that the phenyl group at the N-1 position and the hydrophobic diarylmethyl group at the piperazine significantly influenced the in vitro antienteroviral activity. Notably, compounds with a thiophene substituent, such as 20–24, exhibited high activity against coxsackievirus B3 and moderate activity against enterovirus 71, without apparent cytotoxic effects on RD cell lines. The findings highlight the potential of these compounds as new antiviral agents against enteroviral infections, for which effective treatments are currently lacking.

New fused heterocyclic systems derived from pyridine-2,3-dicarboximides

10.1039/C39880000623

The research aimed to synthesize new pyrido[2',3':3,4]pyrrolo fused heterocyclic systems derived from pyridine-2,3-dicarboximides. The authors utilized a widely known procedure of cyclodehydration of α-hydroxylactams, which were formed by regioselective reduction or Grignard addition to the starting pyridine-2,3-dicarboximides. Sodium borohydride and phenylmagnesium bromide were used as reducing agents to selectively reduce the imides, yielding mixtures of regioisomeric hydroxylactams. These hydroxylactams were then subjected to acid-catalyzed cyclodehydration in refluxing trifluoroacetic acid to produce the desired fused heterocyclic products.

Domino Grignard Addition and Oxidation for the One-Pot Synthesis of C2-Quaternary 2-Hydroxyindoxyls

10.1021/acs.orglett.9b03022

The research explores a novel synthetic method to produce a broad range of unnatural C2-quaternary 2-hydroxyindoxyls using a one-pot domino Grignard addition and oxidation process. The purpose of this study is to address the challenge of synthesizing 2-hydroxyindoxyls, which are less explored but significant due to their presence in various natural products and biologically active compounds. The key chemicals involved include 3-hydroxyoxindoles as starting materials and various Grignard reagents such as phenylmagnesium bromide. The reaction proceeds via a 1,2-hydride shift followed by autoxidation, yielding 2-hydroxyindoxyls in high yields. The study concludes that this method offers a simple, scalable, and operationally easy approach to synthesizing a wide range of 2-hydroxyindoxyls with different functional groups. Additionally, the synthesized 2-hydroxyindoxyls can serve as precursors for further transformations, such as the synthesis of bis-indoxyl spirofurans and differentially substituted 3-oxindoles, demonstrating the versatility and potential of this synthetic protocol in organic chemistry.

HOMOALLYLIC ALCOHOLS FROM (Z)-1,4-DI(2-TETRAHYDROPYRANYLOXY)-BUT-2-ENE AND GRIGNARD REAGENTS: A PROMISING FOUR-CARBON HOMOLOGATION.

10.1016/0040-4039(88)85165-7

The research focuses on the development of a promising four-carbon homologation method using (Z)-1,4-di(2-tetrahydro-pyranyloxy)-but-2-ene and Grignard reagents in the presence of a nickel catalyst (Nidppe). The purpose of this study was to achieve a regio-controlled allylic alkylation, resulting in the formation of 2-alkylbut-3-enols with an unaffected functional group. The researchers found that using this method, they could prepare protected 2-alkylbut-3-enols with high yields and regioselectivity, particularly with primary and secondary Grignard reagents. However, the use of t.BuMgBr led to a different product due to its reducing character, and PhMgBr resulted in an unexpected α,α' disubstitution. The study concluded with the identification of 1 as a useful C4-building block for the synthesis of the target compounds. Further studies were ongoing to clarify the observed regioselectivity and reaction mechanism. The chemicals used in the process include (Z)-1,4-di(2-tetrahydro-pyranyloxy)-but-2-ene, various Grignard reagents (RMgX), and the nickel catalyst Nidppe.

Sequential nucleophilic addition/1,2-rearrangement of N-iminolactam: A ring-contractive strategy for the synthesis of 2-acyl pyrrolidines

10.1016/j.tetlet.2021.153098

The research presents a novel method for synthesizing 2-acyl pyrrolidines through a sequential nucleophilic addition/ring contraction of α-bromo N-iminolactam using various organometallic reagents such as Grignard and organolithium reagents. The study focuses on developing an efficient strategy to synthesize 2-acyl pyrrolidines, which are significant due to their presence in many biologically active natural products and pharmaceuticals. The key chemicals involved in this research include α-bromo N-iminolactam as the substrate, phenylmagnesium bromide (PhMgBr) and phenyllithium (PhLi) as organometallic reagents, and other Grignard and organolithium reagents with different aryl, heteroaryl, alkenyl, alkynyl, and alkyl groups. The reaction conditions, such as the use of THF as a solvent and quenching with 1 M HCl, are crucial for achieving high yields of the desired 2-acyl pyrrolidines. The study also explores the scalability and synthetic utility of the method by converting the 2-acyl pyrrolidine products into other derivatives like pyrrolidinyl alcohol, epoxide, β-lactam, and pyrazole.

Mechanistic Aspects of the Silver(I)-Promoted Rearrangement of Cyclopropene Derivatives

10.1021/jo00140a025

The research investigates the silver(1)-promoted rearrangement of cyclopropene derivatives, comparing these reactions to thermolysis and photolysis. Key chemicals involved include various cyclopropene compounds such as 1,3-diphenyl-2-methyl-3-benzylcyclopropene and 3-benzyl-1,2,3-triphenylcyclopropene, which undergo rearrangement to form indene derivatives under the influence of silver perchlorate. Other chemicals like benzylmagnesium chloride and phenylmagnesium bromide are used in the synthesis of intermediate compounds. The study also explores the effects of substituents on the cyclopropene ring, such as allyl and methyl groups, and how these influence the reaction outcomes. Silver perchlorate plays a crucial role as the catalyst for the rearrangement reactions, leading to the formation of products like bicyclo[3.1.0]hex-2-ene derivatives and indenes. The research provides insights into the regioselectivity and stereochemistry of these reactions, proposing mechanisms involving the formation of argentio- carbonium ions and subsequent cyclization or bond cleavage.

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