PHENYLMAGNESIUM BROMIDE Property

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)

Safety

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

F 

1-3-10

TSCA 

Yes

HazardClass 

4.3

PackingGroup 

II

HS Code 

29319090

Hazardous Substances Data

100-58-3(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

PHENYLMAGNESIUM BROMIDE Chemical Properties,Usage,Production

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.