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171565

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
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
24850350
MDL number:
MFCD00000038
Beilstein/REAXYS Number:
3588849
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Quality Segment

reaction suitability

reaction type: Grignard Reaction

packaging

Kilo-Lab™ of , Sure/Seal™ of

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

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

Legal Information

Kilo-Lab is a trademark of Merck KGaA, Darmstadt, Germany
Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

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Signal Word

Danger

Hazard Codes

H225,H314,H336

Hazard Classifications

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

Target Organs

Respiratory system

supp_hazards

EUH014,EUH019

Storage Class

3 - Flammable liquids

WGK

WGK 3

Flash Point (°F)

-40.0 °F - closed cup

Flash Point (°C)

-40 °C - closed cup

PPE (personal protective equipment)

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

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