171565

Phenylmagnesium bromide solution

3.0 M in diethyl ether

• Synonym(s): Bromomagnesiobenzene, Bromophenylmagnesium
• 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

Properties

• 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

Description

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

Safety Information

• Pictograms: GHS02,GHS05,GHS07
• Signal Word: Danger
• Hazard Statements: H225,H314,H336
• Precautionary Statements: P210 - P233 - P240 - P280 - P303 + P361 + P353 - P305 + P351 + P338
• 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