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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

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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 3: Spontaneously combustible substances and water- reactive materials
Materials containing Organometallic compounds
Hazardous rank II
2nd spontaneously combustible materials and water reactive materials

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

171565-800ML:4548173109008
171565-50ML:4548173295978
171565-BULK:
171565-8L:4548173109015
171565-20L:
171565-VAR:
171565-PZ:
171565-100ML:4548173108988
171565-18L:4548173108995
171565-4X25ML:4548173371610
171565-18L-C:

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Certificates of Analysis (COA)

Lot/Batch Number
0000323948
0000323948
SHBP1908
SHBP5998
SHBN7422

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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)
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)
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)
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