Description

Bromo[4-(dimethylamino)phenyl]magnesium (CAS No. 7353-91-5) is a highly reactive Grignard reagent with the molecular formula C₈H₁₀BrMgN. This organomagnesium compound is widely used in synthetic organic chemistry for nucleophilic addition reactions, enabling the formation of carbon-carbon bonds. It is typically supplied as a solution in diethyl ether or tetrahydrofuran (THF) at concentrations ranging from 0.5M to 1.0M. The reagent features a dimethylamino substituent on the phenyl ring, enhancing its electron-donating properties and reactivity. Proper handling under inert atmosphere (argon or nitrogen) is essential due to its sensitivity to moisture and air. Ideal for researchers in pharmaceuticals, agrochemicals, and materials science seeking to introduce functionalized aryl groups into target molecules.

Properties

• CAS Number: 7353-91-5
• Complexity: 166
• IUPAC Name: magnesium;N,N-dimethylaniline;bromide
• InChI: InChI=1S/C8H10N.BrH.Mg/c1-9(2)8-6-4-3-5-7-8;;/h4-7H,1-2H3;1H;/q-1;;+2/p-1
• InChI Key: OFDIPUNYMRLSER-UHFFFAOYSA-M
• Exact Mass: 222.98470
• Molecular Formula: C8H10BrMgN
• Molecular Weight: 224.38
• SMILES: CN(C)C1=CC=[C-]C=C1.[Mg+2].[Br-]
• Topological: 3.2
• Monoisotopic Mass: 222.98470
• Synonyms: 4-(dimethylamino)phenylmagnesium bromide, bromo[4-(dimethylamino)phenyl]magnesium, Bromo(4-(dimethylamino)phenyl)magnesium, 615-983-7, 7353-91-5, 4-(n,n-dimethyl)anilinemagnesium bromide, magnesium;N,N-dimethylaniline;bromide, EC 615-983-7, MFCD00672006, SCHEMBL544887, OWWWKAXERYRWAU-UHFFFAOYSA-M, p-dimethylaminophenylmagnesium bromide, AKOS015894789, p-dimethylaminophenyl magnesium bromide, (4-(dimethylamino)phenyl)magnesium bromide, N,N-dimethyl-4-aminophenylmagnesium bromide, 4-(Dimethylamino)phenylmagnesium bromide, 0.5M in THF, 4-(N,N-Dimethyl)anilinemagnesium bromide, 0.5M 2-MeTHF, 4-N,N-Dimethylanilinemagnesium bromide 0.5 M in Tetrahydrofuran, 4-N,N-Dimethylanilinemagnesium bromide, 0.5M in tetrahydrofuran

Application

Bromo[4-(dimethylamino)phenyl]magnesium is primarily employed in the synthesis of complex organic molecules through Grignard reactions. It serves as a key intermediate for constructing pharmaceuticals, ligands, and advanced materials. The dimethylamino group enhances electron density, making it valuable in catalytic systems and optoelectronic applications. Researchers utilize this reagent to introduce aryl moieties in cross-coupling reactions and nucleophilic additions.

Safety and Hazards

GHS Hazard Statements

• H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

Precautionary Statements

• P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501

Hazard Classes and Categories

• Skin Corr. 1C (100%)

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