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:
Molecular Weight:
181.31
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3588849
Quality Level
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:
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
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 registered trademark of Merck KGaA, Darmstadt, Germany
Sure/Seal is a trademark of Sigma-Aldrich Co. LLC
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Danger
hcodes
Hazard Classifications
Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3
target_organs
Respiratory system
supp_hazards
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
-40.0 °F - closed cup
flash_point_c
-40 °C - closed cup
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Regulatory Information
监管及禁止进口产品
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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)
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)
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 171565-18L | 04061838751065 |
| 171565-800ML | 04061838751089 |
| 171565-50ML | 04061838751072 |
| 171565-18L-C | 04061838234902 |
| 171565-4X25ML | 04065268444450 |
| 171565-100ML | 04061838751058 |