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Phenylmagnesium bromide information


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
CAS Number
  • 100-58-3 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:51238
ChemSpider
  • 10254417 checkY
ECHA InfoCard 100.002.607 Edit this at Wikidata
EC Number
  • 202-867-2
PubChem CID
  • 66852
CompTox Dashboard (EPA)
  • DTXSID3059214 Edit this at Wikidata
InChI
  • 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
SMILES
  • Br[Mg]c1ccccc1
Properties
Chemical formula
C6H5MgBr
Molar mass 181.31 g mol−1
Appearance Colorless crystals
Density 1.14 g cm−3
Solubility in water
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:
Pictograms
GHS02: FlammableGHS05: Corrosive
Signal word
Danger
Hazard statements
H225, H314
Precautionary statements
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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Infobox references

Phenylmagnesium bromide, with the simplified formula C
6
H
5
MgBr
, 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.

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Phenylmagnesium bromide

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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...

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Bromobenzene

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compounds. One method involves its conversion to the Grignard reagent, phenylmagnesium bromide. This reagent can be used, e.g. in the reaction with carbon dioxide...

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Grignard reagent

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Two typical examples are methylmagnesium chloride Cl−Mg−CH3 and phenylmagnesium bromide (C6H5)−Mg−Br. They are a subclass of the organomagnesium compounds...

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Benzyl alcohol

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toluene to benzoic acid. For laboratory use, Grignard reaction of phenylmagnesium bromide (C6H5MgBr) with formaldehyde and the Cannizzaro reaction of benzaldehyde...

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Diphenylzinc

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phenyllithium with zinc bromide: 2 PhLi + ZnBr2 → Ph2Zn + 2 LiBr It may also be prepared by the reaction of phenylmagnesium bromide with zinc chloride or...

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Phenyl group

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cation. Representative reagents include phenyllithium (C6H5Li) and phenylmagnesium bromide (C6H5MgBr). Electrophiles are attacked by benzene to give phenyl...

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Syringe

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include the transfer of air-sensitive or pyrophoric reagents such as phenylmagnesium bromide and n-butyllithium respectively. Glass syringes are also used to...

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Imine

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example, benzophenone imine can also be synthesized by addition of phenylmagnesium bromide to benzonitrile followed by careful hydrolysis (lest the imine...

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Benzoic acid

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converted to benzoic acid by "carboxylation" of the intermediate phenylmagnesium bromide. This synthesis offers a convenient exercise for students to carry...

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Magnesium

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with haloalkanes. Examples of Grignard reagents are phenylmagnesium bromide and ethylmagnesium bromide. The Grignard reagents function as a common nucleophile...

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Triphenylbismuthine

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solvents. It is prepared by treatment of bismuth trichloride with phenylmagnesium bromide. BiCl3 + 3 C6H5MgBr3 → Bi(C6H5)3 + 3 MgBrCl Structurally it resembles...

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Phenylboronic acid

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synthesize phenylboronic acid. One of the most common synthesis uses phenylmagnesium bromide and trimethyl borate to form the ester PhB(OMe)2, which is then...

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Triphenylstibine

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C6H5Cl + SbCl3 → (C6H5)3Sb + 6 NaCl An alternative method treats phenylmagnesium bromide with SbCl3. "Triphenylantimony". pubchem.ncbi.nlm.nih.gov. Retrieved...

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Biphenyl

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In the laboratory, biphenyl can also be synthesized by treating phenylmagnesium bromide with copper(II) salts. It can also be prepared using diazonium...

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Diphenylmethanol

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Diphenylmethanol may be prepared by a Grignard reaction between phenylmagnesium bromide and benzaldehyde[citation needed]. An alternative method involves...

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Phenylsilane

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Phenylsilane is produced in two steps from Si(OEt)4. In the first step, phenylmagnesium bromide is added to form Ph−Si(OEt)3 via a Grignard reaction. Reduction...

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Organoselenium chemistry

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known in organic chemistry is diphenyldiselenide, prepared from phenylmagnesium bromide and selenium followed by oxidation of the product PhSeMgBr. Selanyl...

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Triphenylphosphine

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in the laboratory by treatment of phosphorus trichloride with phenylmagnesium bromide or phenyllithium. The industrial synthesis involves the reaction...

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MPTP

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a potential analgesic in 1947 by Ziering et al. by reaction of phenylmagnesium bromide with 1-methyl-4-piperidinone. It was tested as a treatment for...

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Boronic acid

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borate esters. For example, phenylboronic acid is produced from phenylmagnesium bromide and trimethyl borate followed by hydrolysis PhMgBr + B(OMe)3 →...

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Group 2 organometallic chemistry

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Rieke magnesium. Examples of Grignard reagents are phenylmagnesium bromide and ethylmagnesium bromide. These simplified formulas are deceptive: Grignard...

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Sodium tetraphenylborate

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synthesized by the reaction between sodium tetrafluoroborate and phenylmagnesium bromide: NaBF4 + 4 PhMgBr → 2 MgBr2 + 2 MgF2 + NaBPh4 (where Ph = phenyl)...

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Benzeneselenol

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organic synthesis. Benzeneselenol is prepared by the reaction of phenylmagnesium bromide and selenium: PhMgBr + Se → PhSeMgBr PhSeMgBr + HCl → PhSeH + MgBrCl...

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DEA list of chemicals

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reagents) (e.g. ethylmagnesium bromide and phenylmagnesium bromide) phencyclidine ortho-Toluidine methaqualone 2-Phenylethyl bromide fentanyl Phenylethanolamine...

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Methylmagnesium chloride

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tetrahydrofuran. Relative to the more commonly encountered methylmagnesium bromide and methylmagnesium iodide, methylmagnesium chloride offers the advantages...

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Organomercury chemistry

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point 121–123 °C) can be prepared by reaction of mercury chloride and phenylmagnesium bromide. A related preparation entails formation of phenylsodium in the...

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