Basic information Reduction agent for preparation of metal carbonyl compound Related chemical reaction Safety Supplier Related
ChemicalBook >  Product Catalog >  Organic Chemistry >  Organometallic compounds >  Organomagnesium >  PHENYLMAGNESIUM BROMIDE

PHENYLMAGNESIUM BROMIDE

Basic information Reduction agent for preparation of metal carbonyl compound Related chemical reaction Safety Supplier Related

PHENYLMAGNESIUM BROMIDE Basic information

Product Name:
PHENYLMAGNESIUM BROMIDE
Synonyms:
  • bromophenylmagnesium
  • Phenylmagnesium bromide, 2.8M solution in Diethyl ether
  • PHENYLMAGNESIUM BROMIDE, 1.0-1.2M in TETRAHYDROFURAN
  • Phenylmagnesiumbromide,3Minether
  • Magnesium, bromophenyl-
  • phenylmagnesium bromide, 3m in ether, packaged under argon in resealable chemseal
  • Phenylmagnesium bromide, 3M in ether, packaged under Argon in resealable ChemSealTM bottles
  • Phenylmagnesium Bromide (32% in Tetrahydrofuran, ca. 2mol/L)
CAS:
100-58-3
MF:
C6H5BrMg
MW:
181.31
EINECS:
202-867-2
Product Categories:
  • Chemical Synthesis
  • Organometallic Reagents
  • Organometallics
  • grignard reagent
  • WB
  • Imidazoles ,Benzimidazoles
  • GRIGNARD REAGENTS
  • Classes of Metal Compounds
  • Grignard Reagents & Alkyl Metals
  • Mg (Magnesium) Compounds
  • Synthetic Organic Chemistry
  • Typical Metal Compounds
  • Aryl
  • Grignard Reagents
  • Organometallic Reagents
Mol File:
100-58-3.mol
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PHENYLMAGNESIUM BROMIDE Chemical Properties

Melting point:
153-154 °C
Density 
1.134 g/mL at 25 °C
Flash point:
−40 °F
storage temp. 
water-free area
solubility 
Miscible with tetrahydrofuran.
form 
Liquid
Specific Gravity
1.14
color 
Yellow to brown
Water Solubility 
reacts
Sensitive 
Air & Moisture Sensitive
BRN 
3588849
InChIKey
ANRQGKOBLBYXFM-UHFFFAOYSA-M
CAS DataBase Reference
100-58-3(CAS DataBase Reference)
EPA Substance Registry System
Magnesium, bromophenyl- (100-58-3)
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Safety Information

Hazard Codes 
F+,C,F
Risk Statements 
12-14-22-34-19-11-67-40-37
Safety Statements 
16-26-36/37/39-45-33-29-7/8-6A-43B
RIDADR 
UN 3399 4.3/PG 1
WGK Germany 
1
1-3-10
TSCA 
Yes
HazardClass 
4.3
PackingGroup 
II
HS Code 
29319090
Hazardous Substances Data
100-58-3(Hazardous Substances Data)

MSDS

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PHENYLMAGNESIUM BROMIDE Usage And Synthesis

Reduction agent for preparation of metal carbonyl compound

In 1890, L.Mond found that when carbon monoxide was burned after being put through the active metal nickel powder, it emitted green light flame. After the resulting gas was cooled, he could obtain colorless liquid (melting point 298K, the boiling point of 316K); if this gas is flowed through a heated glass tube, then it can be seen that the metallic nickel was deposited on the wall. This gas is tetracarbonyl nickel Ni(CO)4. Since the 1960s, people have synthesized a hundreds kinds of such carbonyl compounds and their derivatives. Almost all of the transition metal can form such compounds. This kind of special complex formed through transition metal with carbon monoxide ligands is called metal carbonyls, otherwise known as carbonyl complexes. Metal carbonyl occupies an important position in both theoretical research and practical application in modern inorganic chemistry.
Preparation of metal carbonyl compound can usually via the following methods:
1. Direct synthesis. Most metal carbonyl complexes are prepared by direct combination between metal and carbon monoxide. However, the metal must be new reduction products, and is in a very activated state.
2. Reduction carbonylation effect at high pressure. Apply reducing agent under high pressure to enable the carbonylation reaction between the metal and carbonyl group with the major reducing agents mainly including hydrogen, active metals, phenylmagnesium bromide (C6H5MgBr) and so on.
3. With thermal decomposition or UV irradiation decomposition, we can obtain certain polynuclear carbonyl compounds.
4. Two different kinds of metal carbonyl compounds can interact with each other to give hetero-nuclear carbonyl compound.

Related chemical reaction

1. Phenylmagnesium bromide can react with ferric chloride to give the coupling product. Cyclopentadienyl magnesium bromide can react with ferric chloride to give ferrocene.
2. It can react with chromium trichloride in diethyl ether solution to generate dibenzenechromium.
3. Hexaphenyldilead can be used as the antioxidant of polyphenylene ether lubricant that can be produced from the reaction of lead chloride with phenyl lithium or phenyl magnesium bromide.
4. Take tetrahydrofuran as the solvent, have phenylmagnesium bromide reacted with germanium tetrachloride to obtain tetraphenyl germane.
5. It can be obtained through the low-temperature reaction between lead chloride and phenylmagnesium bromide (Or phenyllithium) in the presence of iodobenzene to derive tetraphenyl lead.
6. Sodium tetraphenylborate is mainly used for the determination of potassium ion, ammonium ion, rubidium ion and cesium ion. It can be obtained with the following process: phenylmagnesium bromide is interacted with boron trifluoride/diethyl ether to generate Tetraphenylboron magnesium bromide first. Evaporate the diethyl ether; add water and then used the calculated amount of sodium carbonate for treatment to obtain it.
The above information is edited by the chemicalbook of Dai Xiongfeng.

Chemical Properties

Clear light brown to brown solution when properly

Uses

Phenylmagnesium Bromide is a reagent used in the preparation of arylcarbonimidic dichlorides via dichloroiodobenzene-mediated gem-dichlorination of aryl isonitriles.

Uses

Grignard reagent in greener solvent, 2-methyltetrahydrofuran (2-MeTHF)

2-Methyltetrahydrofuran (2-MeTHF): A Biomass-Derived Solvent with Broad Application in Organic Chemistry

Definition

ChEBI: Phenylmagnesium bromide is an arylmagnesium halide. It has a role as a Grignard reagent.

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