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PHENYLMAGNESIUM BROMIDE

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Name

PHENYLMAGNESIUM BROMIDE

EINECS 202-867-2
CAS No. 100-58-3 Density 1.134 g/mL at 25 °C
PSA 0.00000 LogP 2.33240
Solubility Reacts with water Melting Point 153-154 °C
Formula C6H5BrMg Boiling Point 78.8oC at 760 mmHg
Molecular Weight 181.315 Flash Point -11 °C
Transport Information UN 3399 4.3/PG 1 Appearance powder
Safety 16-26-36/37/39-45-33-29-7/8-6A-43B Risk Codes 12-14-22-34-19-11
Molecular Structure Molecular Structure of 100-58-3 (PHENYLMAGNESIUM BROMIDE) Hazard Symbols HighlyF+, CorrosiveC, FlammableF
Synonyms

Phenylmagnesiumbromide (6CI);Bromomagnesiobenzene;Bromophenylmagnesium;

Article Data 57

PHENYLMAGNESIUM BROMIDE Synthetic route

108-86-1

bromobenzene

100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
With magnesium In tetrahydrofuran at 40℃; for 0.25h; Inert atmosphere; Flow reactor;100%
With magnesium In tetrahydrofuran
With magnesium In diethyl ether at 19.9℃; Rate constant; various concentrations of aryl halide;
5922-60-1

2-amino-5-chlorobenzonitrile

A

5606-39-3

(2-amino-5-chlorophenyl)-phenyl-methane-imine

B

100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
A 92%
B n/a
108-86-1

bromobenzene

A

1-phenyltetrafluoro-2-propenylacetate

B

100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
With magnesium In tetrahydrofuranA 24%
B n/a
626-39-1

1,3,5-trisbromobenzene

dichlorobis(triphenylphosphine)palladium[II]

Diisobutylaluminium hydride(1 M solution in tetrahydrofuran, 4.9 mL, 4.9 mmol)

100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
In tetrahydrofuran; toluene
108-86-1

bromobenzene

N-Z-(S)-serine methyl ester

N-Z-(S)-serine methyl ester

100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether
108-86-1

bromobenzene

(S)-Carbomethoxy oxazolidinone

(S)-Carbomethoxy oxazolidinone

100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
In tetrahydrofuran
105-56-6

ethyl 2-cyanoacetate

100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
With ammonium chloride
[NitriphosCl]PF6

[NitriphosCl]PF6

95-50-1

1,2-dichloro-benzene

100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
With biphenyl; ethylmagnesium bromide; phenylmagnesium bromide In o-xylene
103-63-9

1-phenyl-2-bromoethane

105-56-6

ethyl 2-cyanoacetate

100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
With hydrogenchloride; iodine In magnesium
108-86-1

bromobenzene

105-56-6

ethyl 2-cyanoacetate

100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
With magnesium

PHENYLMAGNESIUM BROMIDE Chemical Properties

Molecular Formula: C6H5BrMg
Molecular Weight: 181.31
EINECS: 202-867-2
Flash point: -11 ºC
Water solubility: reacts
Density: 1.134 g/mL at 25 °C
Storage temp: water-free area
Sensitive: Air & Moisture Sensitive 
IUPAC Name
: magnesium benzene bromide
Appearance: Clear light brown to brown solution when properly
Synonyms: Phenylmagnesium bromide ; Phenyl magnesium bromide(in ethyl ether) ; Bromophenyl-magnesiu ; Phenylmagnesiumbromidesolution ; Bromophenylmagnesium ; Phenylmagnesium bromide, 3.0m solution i n diethyl ether ; Phenylmagnesium bromide solution, ~1 m i n thf ; Phenylmagnesium bromide sol., ~3 m in di ethyl ether
Following is the molecular structure of Phenyl magnesium bromide (100-58-3):

PHENYLMAGNESIUM BROMIDE Production

Preparation of Phenyl magnesium bromide (100-58-3):
Phenylmagnesium bromide is commercially available as solutions of diethyl ether or THF. It may be prepared in the laboratory by treating bromobenzene with magnesium metal, usually in the form of ribbon. A small amount of iodine may be used to activate the magnesium to initiate the reaction.
Polar solvents, such as ether or THF, are required to solvate (complex) the magnesium(II) center. The solvent must be aprotic since alcohols and water react with phenylmagnesium bromide to give benzene. Carbonyl-containing solvents such as acetone and ethyl acetate are incompatible with the reagent.
 

PHENYLMAGNESIUM BROMIDE Safety Profile

Reacts with chlorine to form an explosive product. When heated to decomposition it emits toxic fumes of Br.
Safety Information of Phenyl magnesium bromide (100-58-3):
Hazard Codes: F+,C,F
F: Highly Flammable   F+: Extremely Flammable  C: Corrosive
Risk Statements: 12-14-22-34-19-11
12: Extremely Flammable 
14: Reacts violently with water 
22: Harmful if swallowed 
34: Causes burns 
19: May form explosive peroxides 
11: Highly Flammable 
Safety Statements: 16-26-36/37/39-45-33-29-7/8-6A-43B
16: Keep away from sources of ignition - No smoking 
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 36/37/39: Wear suitable protective clothing, gloves and eye/face protection 
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
33: Take precautionary measures against static discharges 
29: Do not empty into drains 
7/8: Keep container tightly closed and dry 
6: Keep under ... (inert gas to be specified by the manufacturer) 
43: In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add - Never use water) 
RIDADR: UN 3399 4.3/PG 1
WGK Germany: 1

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