7353-91-5

Basic information

• Product Name: 4-(N,N-DIMETHYL)ANILINEMAGNESIUM BROMIDE
• Synonyms: 4-DIMETHYLAMINOPHENYLMAGNESIUM BROMIDE;4-(N,N-DIMETHYL)ANILINEMAGNESIUM BROMIDE;4-(N,N-DIMETHYL)ANILINEMAGNESIUM BROMIDE, 0.5M SOLUTION IN TETRAHYDROFURAN;4-Dimethylaminophenylmagnesium Bromide, 0.75 M In Tetrahydrofuran;4-(n,n-dimethyl)aniline magnesium bromide solution;4-(N,N-Dimethyl)aniline magnesium bromide solution 0.5 in THF;4-(N,N-Dimethyl)aniline magnesium bromide 0.5M in THF;4-(N,N-Dimethyl)anilinemagnesium bromide 0.5M solution in THF
• CAS NO: 7353-91-5
• Molecular Formula: C₈H₁₀BrMgN
• Molecular Weight: 224.38
• Product Categories: Aryl;Grignard Reagents;Organometallic Reagents;Chemical Synthesis;Grignard Reagents;Organometallic Reagents
• Mol File: 7353-91-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 53-54℃
• Boiling Point: 65 °C
• Flash Point: <1 °F
• Appearance: /
• Density: 0.951 g/mL at 25 °C
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-(N,N-DIMETHYL)ANILINEMAGNESIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(N,N-DIMETHYL)ANILINEMAGNESIUM BROMIDE(7353-91-5)
• EPA Substance Registry System: 4-(N,N-DIMETHYL)ANILINEMAGNESIUM BROMIDE(7353-91-5)

Safety Data

• Hazard Codes: F,C
• Statements: 11-14-19-22-34-40-37
• Safety Statements: 16-23-26-36/37/39-45
• RIDADR: UN 2924 3/PG 2
• WGK Germany: 1
• Hazardous Substances Data: 7353-91-5(Hazardous Substances Data)

Usage

Description

4-(N,N-Dimethyl)anilinemagnesium bromide, also known as Bromo(4-(dimethylamino)phenyl)magnesium, is an organomagnesium compound that features a bromo substituent and a dimethylamino group attached to a phenyl ring. 4-(N,N-Dimethyl)anilinemagnesium bromide is a versatile reagent in organic synthesis, particularly for the preparation of various organic compounds and ligands.

Uses

Used in the Preparation of Penta-deuterium-substituted Malachite Green Salt:
4-(N,N-Dimethyl)anilinemagnesium bromide is used as a reagent for the synthesis of Penta-deuterium-substituted Malachite green salt. The incorporation of deuterium isotopes in the compound can provide valuable insights into the compound's properties and behavior, which can be useful in various research applications.
Used in the Preparation of Triaryl Phosphine Ligands:
In the field of catalysis, 4-(N,N-Dimethyl)anilinemagnesium bromide serves as a precursor for the preparation of triaryl phosphine ligands. These ligands are essential components in homogeneous catalysis, where they can modulate the activity and selectivity of catalysts in various chemical reactions.
Used in Catalyzing Coupling Reactions:
4-(N,N-Dimethyl)anilinemagnesium bromide is utilized as a coupling agent in organic synthesis, particularly in cross-coupling reactions. Its ability to form a magnesium-carbon bond allows it to participate in the formation of new carbon-carbon or carbon-heteroatom bonds, which are crucial in the synthesis of complex organic molecules and pharmaceutical compounds.

InChI:InChI=1/C8H10N.BrH.Mg/c1-9(2)8-6-4-3-5-7-8;;/h4-7H,1-2H3;1H;/q;;+1/p-1/rC8H10BrMgN/c1-11(2)8-5-3-7(10-9)4-6-8/h3-6H,1-2H3

Upstream product

• 586-77-6 4-bromo-N,N-dimethylaniline 
• 7439-95-4 magnesium 

Downstream Products

• 30008-07-2 1-methyl-1-p-dimethylaminophenyl-1-silacyclobutane 
• 7781-86-4 2-(4-Dimethylamino-phenyl)-pentafluorpropen 
• 56099-08-2 (4-dimethylamino-phenyl)-(octahydro-pyrido[2,1-c][1,4]oxazepin-4-yl)-phenyl-methanol 
• 14206-16-7 4-(dimethoxy-methyl-silanyl)-N,N-dimethyl-aniline 
• 5339-80-0 3,3-bis-p-dimethylaminophenylphthalide  
• 141423-20-3 α,α,α',α'-tetra<4-(dimethylamino)phenyl>-1,3-dioxolane-4,5-dimethanol 
• 39768-80-4 (4-Dimethylamino-phenyl)-(4-fluoro-phenyl)-methanol 
• 32507-38-3 (E)-4-(buta-1,3-dien-1-yl)-N,N-dimethylaniline 
• 344408-47-5 4-(but-3-enyl)-N,N-dimethylaniline 
• 2372-34-1 chlorodimethyl(4-dimethylaminophenyl)silane 
• 366-29-0 N,N,N',N'-tetramethylbenzidine 
• 51601-26-4 N,N-dimethyl-4-(2-propen-1-yl)benzenamine 
• 63620-87-1 di-isopropyl-p-(NN-dimethylamino)phenylphosphonite 
• 61103-53-5 [4-((1Z,3Z)-4-Chloro-1,2,3,4-tetrafluoro-buta-1,3-dienyl)-phenyl]-dimethyl-amine 

Relevant articles and documents

Preparation method for bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]dichloropalladium

The invention discloses a preparation method for bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]dichloropalladium. The preparation method comprises the following steps that 1, a Grignard reagent isprepared from the raw materials of N, N-dimethyl p-haloaniline and magnesium chips; 2, the Grignard reagent is taken and cooled, then a catalyst is added for reaction, then di-tert-butylchlorophosphane is dropwise added, and heating is carried out for reaction so as to obtain di-tert-butyl-4-dimethylaminophenylphosphine; 3, the di-tert-butyl-4-dimethylaminophenylphosphine is purified; and 4, complexing bis(acetonitrile)dichloropalladium and the purified di-tert-butyl-4-dimethylaminophenylphosphine so as to obtain a target product. The preparation method has the advantages that the di-tert-butyl-4-dimethylaminophenylphosphine is purified, the high-purity di-tert-butyl-4-dimethylaminophenylphosphine is used for reacting with the bis(acetonitrile)dichloropalladium, and therefore the yield loss of the noble metal palladium is greatly reduced, the preparation cost is greatly lowered, and the method has a good practical value.

Selective introducing of aryl and amino groups: Reaction of benzanthrone and organometallic reagents

The reaction of benzanthrone and aryl magnesium bromides produced 6-aryl-substituted benzanthrones in moderate to good yields. Similarly, 6-alkylaminobenzanthrones were selectively prepared by the reaction of benzanthrone and lithium alkylamides. In contrast, for the lithium arylamides, the arylamino groups were selectively introduced at the 4-position of the benzanthrone.

CATALYTIC RADIOFLUORINATION

One aspect of the present invention relates to a method of preparing radio fluorinated substituted alkyl, cycloalkyl, aryl, and alkenyl compounds. In a preferred embodiment, potassium fluoride-18 is used. Another aspect of the invention relates to arylammonium compounds containing fluorine-18 that are useful as imaging agents. In certain embodiments, the ammonium compound is a tetraaryl ammonium salt. Another aspect of the invention relates to arylsulfonium compounds containing fluorine-18 that are useful as imaging agents. In certain embodiments, the sulfonium compound is a triaryl sulfonium salt. Another aspect of the present invention relates to a method of obtaining a positron emission image of a mammal, comprising the steps of administering to a mammal a compound of the invention, and acquiring a positron emission spectrum of the mammal.