Phenylmagnesium bromide
CAS No.:
100-58-3
M. Wt:
181.313
M. Fa:
C6H5BrMg
InChI Key:
NIXOIRLDFIPNLJ-UHFFFAOYSA-M
Appearance:
Clear
Names and Identifiers of Phenylmagnesium bromide
CAS Number |
100-58-3 |
|---|---|
EC Number |
202-867-2 |
MDL Number |
MFCD00000038 |
IUPAC Name |
magnesium;benzene;bromide |
InChI |
InChI=1S/C6H5.BrH.Mg/c1-2-4-6-5-3-1;;/h1-5H;1H;/q-1;;+2/p-1 |
InChIKey |
NIXOIRLDFIPNLJ-UHFFFAOYSA-M |
Canonical SMILES |
C1=CC=[C-]C=C1.[Mg+2].[Br-] |
UNSPSC Code |
12352100 |
Physical and chemical properties of Phenylmagnesium bromide
Boiling Point |
78.8ºC at 760 mmHg |
|---|---|
BRN |
3588849 |
Density |
Relative density: 1.134 mg/L at 25 °C |
Exact Mass |
179.942490 |
Flash Point |
−40 °F |
LogP |
2.33240 |
Melting Point |
153-154 °C |
Molecular Formula |
C6H5BrMg |
Molecular Weight |
181.313 |
Sensitivity |
Air & Moisture Sensitive |
Solubility |
Miscible with tetrahydrofuran. |
Storage condition |
water-free area |
Water Solubility |
reacts |
Safety Information of Phenylmagnesium bromide
Applications of Phenylmagnesium bromide
Phenylmagnesium bromide has various applications in organic synthesis:
- Synthesis of Alcohols: It serves as a key reagent for producing secondary and tertiary alcohols from carbonyl compounds.
- Formation of Carboxylic Acids: Its reaction with carbon dioxide facilitates the synthesis of carboxylic acids.
- Preparation of Complex Organic Molecules: It is used in multi-step syntheses involving complex organic molecules, including pharmaceuticals and agrochemicals.
Interaction Studies of Phenylmagnesium bromide
Studies on phenylmagnesium bromide primarily focus on its interactions in synthetic pathways rather than direct biological interactions. Its reactivity profile indicates that it can form various intermediates when reacting with different electrophiles, making it valuable for studying reaction mechanisms in organic chemistry.
Similar CompoundsPhenylmagnesium bromide shares similarities with other Grignard reagents and organometallic compounds. Below is a comparison highlighting its uniqueness:
| Compound | Formula | Key Characteristics |
|---|---|---|
| Phenylmagnesium bromide | C₆H₅MgBr | Strong nucleophile; used for phenyl group addition |
| Methylmagnesium bromide | C₂H₃MgBr | Used for methylation reactions |
| Ethylmagnesium bromide | C₄H₇MgBr | Similar applications but larger alkyl group |
| Benzylmagnesium chloride | C₇H₇MgCl | Reactivity similar to phenylmagnesium bromide |
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