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171565

Sigma-Aldrich

Phenylmagnesium bromide solution

3.0 M in diethyl ether

Synonyme(s) :

Bromomagnesiobenzene, Bromophenylmagnesium

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About This Item

Formule linéaire :
C6H5MgBr
Numéro CAS:
100-58-3
Poids moléculaire :
181.31
Numéro Beilstein :
3588849
Numéro MDL:
MFCD00000038
Code UNSPSC :
12352103
ID de substance PubChem :
24850350
Nomenclature NACRES :
NA.22

Niveau de qualité

200

Capacité de réaction

reaction type: Grignard Reaction

Concentration

3.0 M in diethyl ether

Densité

1.134 g/mL at 25 °C

Chaîne SMILES 

Br[Mg]c1ccccc1

InChI

1S/C6H5.BrH.Mg/c1-2-4-6-5-3-1;;/h1-5H;1H;/q;;+1/p-1

Clé InChI

ANRQGKOBLBYXFM-UHFFFAOYSA-M

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Description générale

Phenylmagnesium bromide solution contains 3M phenylmagnesium bromide in diethyl ether. It can act as a strong acid and Lewis acid. It can undergo addition reaction with many unsaturated functional groups. The phenyl group can displace halide from other organic compounds. Phenylmagnesium bromide is a Grignard reagent. Reaction of β-cyclohexanedione (dihydroresorcinol) with phenylmagnesium bromide has been investigated.

Application

Phenylmagnesium bromide was used for the synthesis of end-functionalized regioregular poly(3-alkylthiophene)s. It was also used for the monoalkylation of aliphatic primary amine to generate secondary amines by the Grignard reaction of 1-[(alkylamino) methyl] benzotriazoles.
It may be used for synthesis of the following:
  • 1,3,3-trimethyl-6-phenyl-2-oxabicyclo[2.2.2]octan-6-ol
  • 6-benzyl-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-ol
  • (3-(2-Dithiobenzoatepropionyl)propyl)dimethylmethoxysilane, reversible addition-fragmentation chain transfer polymerization (RAFT)-silane agent
  • series of o-substituted benzophenones

Conditionnement

View returnable container options.

Autres remarques

Storage below 25°C may cause formation of crystalline magnesium salts. Moving container to a warm location and occasional gentle swirling should redissolve the solid

Pictogrammes

FlameCorrosionExclamation mark
GHS02,GHS05,GHS07

Mention d'avertissement

Danger

Mentions de danger

H225,H314,H336

Classification des risques

Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3

Organes cibles

Respiratory system

Risques supp

EUH014,EUH019

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

-40.0 °F - closed cup

Point d'éclair (°C)

-40 °C - closed cup

Équipement de protection individuelle

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Synthesis of O-substituted benzophenones by Grignard reaction of 3-substituted isocoumarins.
Manivel P, et al.
Journal of the Chilean Chemical Society, 53(3), 1609-1610 (2008)
The reaction of beta-cyclohexanedione (dihydroresorcinol) and its ethyl enol ether with phenylmagnesium bromide.
G F WOODS et al.
Journal of the American Chemical Society, 70(6), 2174-2177 (1948-06-01)
Synthesis of well-defined polymer brushes grafted onto silica nanoparticles via surface reversible addition-fragmentation chain transfer polymerization.
Li C and Benicewicz BC.
Macromolecules, 38(14), 5929-5936 (2005)
S Schenone et al.
Farmaco (Societa chimica italiana : 1989), 45(12), 1309-1325 (1990-12-01)
The synthesis of 1,3,3-trimethyl-6-phenyl-2-oxabicyclo[2.2.2]octan-6-ol 2 and 6-benzyl-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-ol 3 starting from (+)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-one and phenylmagnesium bromide or benzylmagnesium chloride, respectively, is described. Alcohols 2 and 3 gave a series of omega-dialkylaminoalkyl ethers 4 by reaction as sodium salts with omega-chloroalkyldialkylamines in toluene
Phenylmagnesium Bromide.
Richey HG, et al.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2009)
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