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| CAS No.: | 100-58-3 |
|---|---|
| Name: | PHENYLMAGNESIUM BROMIDE |
| Article Data: | 57 |
| Molecular Structure: | |
|
|
|
| Formula: | C6H5BrMg |
| Molecular Weight: | 181.315 |
| Synonyms: | Phenylmagnesiumbromide (6CI);Bromomagnesiobenzene;Bromophenylmagnesium; |
| EINECS: | 202-867-2 |
| Density: | 1.134 g/mL at 25 °C |
| Melting Point: | 153-154 °C |
| Boiling Point: | 78.8oC at 760 mmHg |
| Flash Point: | -11 °C |
| Solubility: | Reacts with water |
| Appearance: | powder |
| Hazard Symbols: |
 F+,  C,  F
|
| Risk Codes: | 12-14-22-34-19-11 |
| Safety: | 16-26-36/37/39-45-33-29-7/8-6A-43B |
| Transport Information: | UN 3399 4.3/PG 1 |
| PSA: | 0.00000 |
| LogP: | 2.33240 |
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| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| A 92% B n/a |
| Conditions | Yield |
|---|---|
| With magnesium In tetrahydrofuran | A 24% B n/a |
| Conditions | Yield |
|---|---|
| In tetrahydrofuran; toluene |
| Conditions | Yield |
|---|---|
| With hydrogenchloride In diethyl ether |
| Conditions | Yield |
|---|---|
| In tetrahydrofuran |
| Conditions | Yield |
|---|---|
| With ammonium chloride |
| Conditions | Yield |
|---|---|
| With biphenyl; ethylmagnesium bromide; phenylmagnesium bromide In o-xylene |
| Conditions | Yield |
|---|---|
| With hydrogenchloride; iodine In magnesium |
| Conditions | Yield |
|---|---|
| With magnesium |
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Chemistry
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):
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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.
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 .gif){kind=small}
F+: Extremely Flammable C: Corrosive.gif){kind=small}
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