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171565

Sigma-Aldrich

Phenylmagnesium bromide solution

3.0 M in diethyl ether

Synonym(s):

Bromomagnesiobenzene, Bromophenylmagnesium

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About This Item

Linear Formula:
C6H5MgBr
CAS Number:
100-58-3
Molecular Weight:
181.31
Beilstein:
3588849
MDL number:
MFCD00000038
UNSPSC Code:
12352103
PubChem Substance ID:
24850350
NACRES:
NA.22

Quality Level

200

reaction suitability

reaction type: Grignard Reaction

concentration

3.0 M in diethyl ether

density

1.134 g/mL at 25 °C

SMILES string

Br[Mg]c1ccccc1

InChI

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

InChI key

ANRQGKOBLBYXFM-UHFFFAOYSA-M

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General description

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

Packaging

View returnable container options.

Other Notes

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

Signal Word

Danger

Hazard Statements

H225 - H314 - H336

Hazard Classifications

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

Target Organs

Respiratory system

Supplementary Hazards

EUH014 - EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-40.0 °F - closed cup

Flash Point(C)

-40 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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