6738-06-3

Basic information

• Product Name: PHENYLETHYNYLMAGNESIUM BROMIDE
• Synonyms: PHENYLETHYNYLMAGNESIUM BROMIDE;Phenylethynylmagnesium bromide solution;PHENYLETHYNYLMAGNESIUM BROMIDE, 1.0M SOL UTION IN TETRAHYDROFURAN;Phenylethynylmagnesium bromide solution 1.0 in THF;PhenylethynylMagnesiuM broMide solution 1.0 M in THF
• CAS NO: 6738-06-3
• Molecular Formula: C₈H₅BrMg
• Molecular Weight: 205.33
• Product Categories: Alkynyl;Grignard Reagents;Organometallic Reagents;Grignard Reagent
• Mol File: 6738-06-3.mol

Chemical Properties

• Boiling Point: 142.4°C at 760 mmHg
• Flash Point: −6 °F
• Appearance: /
• Density: 1.018 g/mL at 25 °C
• Vapor Pressure: 7.02mmHg at 25°C
• Storage Temp.: 2-8°C
• CAS DataBase Reference: PHENYLETHYNYLMAGNESIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYLETHYNYLMAGNESIUM BROMIDE(6738-06-3)
• EPA Substance Registry System: PHENYLETHYNYLMAGNESIUM BROMIDE(6738-06-3)

Safety Data

• Hazard Codes: F,C
• Statements: 11-14-19-20/21/22-34-40-37-17
• Safety Statements: 16-26-27-36/37/39-45
• RIDADR: UN 2924 3/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 6738-06-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Phenylethynylmagnesium bromide is used as a reagent for nucleophilic addition reactions, facilitating the formation of carbon-carbon bonds in organic synthesis processes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, phenylethynylmagnesium bromide is used as a key intermediate in the synthesis of complex organic molecules, contributing to the development of new drugs and medicinal compounds.
Used in Agricultural Industry:
Phenylethynylmagnesium bromide serves as a reagent in the synthesis of agrochemicals, aiding in the production of pesticides and other agricultural chemicals to enhance crop protection and yield.
Used in Material Science:
In material science, phenylethynylmagnesium bromide is utilized in the synthesis of advanced materials with specific properties, such as organic semiconductors and conductive polymers, which are essential for various technological applications.

InChI:InChI=1/C8H5.BrH.Mg/c1-2-8-6-4-3-5-7-8;;/h3-7H;1H;/q-1;;+2/p-1

Upstream product

• 536-74-3 phenylacetylene 
• 925-90-6 ethylmagnesium bromide 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 74-96-4 ethyl bromide 
• 103-64-0 bromostyrene 

Downstream Products

• 10229-11-5 4-phenyl-but-3-yn-1-ol 
• 857223-20-2 3-chloro-2-phenylethynyl-tetrahydro-pyran 
• 4437-24-5 1-phenyl-3-(2-furyl)prop-1-yne 
• 89458-21-9 3,4-dimethyl-1-phenyl-1-pentyn-4-ol 
• 50428-40-5 Tris(phenylethynyl)methyl alcohol 
• 15814-32-1 1,5-diphenylpenta-1,4-diyn-3-ol 
• 100518-52-3 2-methyl-5-phenylpent-1-en-4-yn-3-ol 
• 622-76-4 1-phenyl-1-butyne 
• 1522-13-0 1,1,3-triphenylprop-2-yn-1-ol 
• 849-01-4 1,3,3-triphenylprop-2-en-1-one 
• 18402-75-0 1-triethoxysilyl-2-phenylacetylene 
• 13124-91-9 1-[1]naphthyl-1,3-diphenyl-prop-2-yn-1-ol 
• 52801-49-7 1-methoxy-2-methyl-4-phenyl-but-3-yn-2-ol 
• 95466-12-9 (+/-)-1-phenylnon-1-yn-3-ol 

Relevant articles and documents

Synthesis and transformations of 4-phenylethynyl- and 4-styrylpyrazolo[5,1-c][1,2,4]triazines

[Figure not available: see fulltext.] Rearrangements of 3-tert-butyl-8-methyl-4-phenylethynyl-1,4-dihydropyrazolo[5,1-c][1,2,4]triazine derivatives by the action of bases led to the formation of aromatic (E)- or (Z)-4-styryl-functionalized compounds. At t

Tandem Suzuki-Miyaura coupling/acid-catalyzed cyclization between vinyl ether boronates and vinyl halides: A concise approach to polysubstituted furans

Polysubstituted 2-(ω-hydroxyalkyl)furans were prepared by tandem Suzuki-Miyaura coupling/acid-catalyzed cyclization starting from appropriately substituted 3-haloallylic alcohols and dihydrofuran-, dihydropyran- or glycal-derived pinacol boronates.

Cu(II)-catalyzed aerobic hydroperoxidation of Meldrum's acid derivatives and application in intramolecular oxidation: A conceptual blueprint for O 2/H2 dihydroxylation

Aerobic hydroperoxidation of Meldrum's acid derivatives via a Cu(II)-catalyzed process is presented. The mild reaction conditions are tolerant to pendant unsaturation allowing the formation of endoperoxides via electrophilic activation. Cleavage of the O-

Palladium-catalyzed coupling of propargylic carbonates with N-tosylhydrazones: Highly selective synthesis of substituted propargylic N-sulfonylhydrazones and vinylallenes

An efficient palladium-catalyzed coupling of propargylic carbonates (1) with N-tosylhydrazones (2, 2′) has been carried out. A wide range of propargylic N-sulfonylhydrazones (3) and multisubstituted vinylallenes (4) can be obtained selectively by using either [PdCl2(CH3CN) 2] or [Pd2(dba)3] as catalysts. (dba=trans,trans-dibenzylideneacetone, dppp=propane-l,3- diylbis(diphenylphosphane), Ts=4-toluenesulfonyl.) Copyright

Iron-catalyzed quick homocoupling reaction of aryl or alkynyl Grignard reagents using a phosphonium ionic liquid solvent system

The iron-catalyzed homocoupling reaction of aryl Grignard reagent was completed very quickly when the reaction was carried out in a phosphonium salt ionic liquid solvent system at 0°C for 5 min. Using a similar reaction system, the first example of the iron-catalyzed homocoupling reaction of alkynyl Grignard reagents has also been accomplished using the ionic liquid technology.

Tandem Zn-Brook rearrangement/ene-allene carbocyclization

The addition of metalated alkynes to acylsilanes leads to the corresponding α-propargylsilanol derivatives. On addition of ZnBr2, Zn-promoted Brook rearrangements take place to produce the propargyl/allenylzinc bromides, which undergo cyclization to give functionalized carbocycles as single diastereoisomers. Wiley-VCH Verlag GmbH & Co. KGaA.

CLICKPHOSPHINES FOR TRANSITION METAL-CATALYZED REACTIONS

Phosphine triazole ligand compounds, prepared through click chemistry, complex with transition metals to form transition metal-phosphine triazole ligand complexes. These complexes are useful catalysts in coupling reactions such as Suzuki-Miyaura coupling, Stille coupling, Negishi coupling, Sonagashira coupling, carbon-heteroatom bond-forming reactions (C-O and C-N), alpha alkylation of carbonyls, Heck coupling reactions, and hydrogenation reactions.

Cascade reactions: Sequential homobimetallic catalysis leading to benzofurans and β,γ-unsaturated esters

The concatenation between a Pd(0)-promoted deallylation catalytic cycle and a Pd(II)-promoted heterocyclization catalytic cycle (an example of what we have named "sequential homobimetallic catalysis") has been shown to occur starting from 1-(2-allyloxyphenyl)-2-yn-1-ols 1 to afford 2-benzofuran-2- ylacetic esters 2 and β,γ-unsaturated esters in high yields under carbonylative conditions. In view of the conceptual as well as the synthetic importance of the process, the mechanistic aspects and the synthetic scope of the reaction have been investigated in detail. All the experimental evidence is in agreement with the sequential homobimetallic mechanism, and the reaction has proven to be of general synthetic applicability.

Reaction of an electrogenerated 'iminium cation pool' with organometallic reagents. Direct oxidative α-alkylation and -arylation of amine derivatives

We have developed an efficient direct oxidative α-alkylation and -arylation of carbamates based on the 'cation pool' method. Grignard reagents, organozinc compounds, and organoaluminum compounds are effective as carbon nucleophiles toward iminium cation pools generated by low temperature electrolysis of carbamates.

Vinyl Cations in Organic Synthesis. Part 2. A Novel Synthesis of Methylene-1H-indenes (Benzofulvenes) by Cyclisation of Phenyl-substituted But-1-en-3-ynes

A series of phenyl-substituted but-1-en-3-ynes has been prepared and their reactivity toward acid-catalysed cycloisomerisation investigated.In boiling dichloromethane of 1,2-dibromoethane in the presence of a catalytic amount of methanesulfonic acid, 1,1,