Phenylmagnesium bromide

Phenylmagnesium bromide
Phenylmagnesium bromide, OR2 = ether or THF
Complex with ethers
Ball-and-stick model of the PhMgBr-diethyl ether adduct
Complex with diethyl ether
Space-filling model of the PhMgBr-diethyl ether adduct
Names
IUPAC name
Bromido(phenyl)magnesium
Other names
PMB, (bromomagnesio)benzene [citation needed]
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.607 Edit this at Wikidata
EC Number
  • 202-867-2
  • InChI=1S/C6H5.BrH.Mg/c1-2-4-6-5-3-1;;/h1-5H;1H;/q;;+1/p-1 ☒N
    Key: ANRQGKOBLBYXFM-UHFFFAOYSA-M ☒N
  • InChI=1/C6H5.BrH.Mg/c1-2-4-6-5-3-1;;/h1-5H;1H;/q;;+1/p-1/rC6H5BrMg/c7-8-6-4-2-1-3-5-6/h1-5H
    Key: ANRQGKOBLBYXFM-ZAQPMBKGAV
  • Br[Mg]c1ccccc1
Properties
C6H5MgBr
Molar mass 181.31 g mol−1
Appearance Colorless crystals
Density 1.14 g cm−3
Reacts with water
Solubility 3.0M in diethyl ether, 1.0M in THF, 2.9M in 2Me-THF
Acidity (pKa) 45 (conjugate acid)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 flammable, volatile
GHS labelling:
GHS02: FlammableGHS05: Corrosive
Danger
H225, H314
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P403+P235, P405, P501
Flash point −45 °C (−49 °F; 228 K)
Safety data sheet (SDS) External MSDS
Related compounds
Related compounds
 Phenyllithium
Magnesium bromide
Methylmagnesium chloride
Dibutylmagnesium
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Phenylmagnesium bromide, with the simplified formula C
6H
5MgBr, is a magnesium-containing organometallic compound. It is commercially available as a solution in diethyl ether or tetrahydrofuran (THF). Phenylmagnesium bromide is a Grignard reagent. It is often used as a synthetic equivalent for the phenyl "Ph−" synthon.