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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.

7353-91-5

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7353-91-5 Usage

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.

Check Digit Verification of cas no

The CAS Registry Mumber 7353-91-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,3,5 and 3 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 7353-91:
(6*7)+(5*3)+(4*5)+(3*3)+(2*9)+(1*1)=105
105 % 10 = 5
So 7353-91-5 is a valid CAS Registry Number.
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

7353-91-5 Well-known Company Product Price

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  • Aldrich

  • (561061)  4-(N,N-Dimethyl)anilinemagnesiumbromidesolution  0.5 M in THF

  • 7353-91-5

  • 561061-50ML

  • 2,438.28CNY

  • Detail

7353-91-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name magnesium,N,N-dimethylaniline,bromide

1.2 Other means of identification

Product number -
Other names 4-N,N-dimethylanilinemagnesium bromide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:7353-91-5 SDS

7353-91-5Relevant academic research and scientific papers

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

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Paragraph 0062; 0063, (2018/11/03)

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.

Nickel-Catalyzed Cross-Coupling of Functionalized Organo manganese Reagents with Aryl and Heteroaryl Halides Promoted by 4-Fluorostyrene

Benischke, Andreas D.,Desaintjean, Alexandre,Juli, Thomas,Cahiez, Gérard,Knochel, Paul

supporting information, p. 5396 - 5412 (2017/12/14)

A catalytic system consisting of Ni(acac) 2 (5 mol%) and 4-fluorostyrene (20 mol%) allows a convenient cross-coupling of functionalized organomanganese reagents with a variety of aryl and heteroaryl halides leading to polyfunctionalized diaryl- and arylheteroarylmethane derivatives.

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

Umeda, Rui,Namba, Teruaki,Yoshimura, Tomohiro,Nakatsukasa, Masamichi,Nishiyama, Yutaka

, p. 1526 - 1531 (2013/02/23)

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.

Cross-coupling of aryl/alkenyl silyl ethers with grignard reagents through nickel-catalyzed CO bond activation

Zhao, Fei,Yu, Da-Gang,Zhu, Ru-Yi,Xi, Zhenfeng,Shi, Zhang-Jie

supporting information; experimental part, p. 1001 - 1003 (2011/12/05)

CO activation and its application have drawn much attention since oxygen-based electrophiles are easily available, less toxic, and more environmentally benign. This letter presents systematically results on the Ni-catalyzed KumadaTamaoCorriu coupling based on siloxy arenes/alkenes, which provides a new strategy of silyl protection/CC bond formation sequence in organic synthesis.

CATALYTIC RADIOFLUORINATION

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Page/Page column 94-95, (2010/11/30)

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.

Arylzinc species by microwave assisted Grignard formation-transmetallation sequence: Application in the Negishi coupling

Mutule, Ilga,Suna, Edgars

, p. 11168 - 11176 (2007/10/03)

Arylmagnesium species can be efficiently generated from magnesium turnings and aryl chlorides or aryl bromides under dielectric heating conditions. Subsequent microwave assisted transmetallation using ZnCl2-TMEDA afforded the corresponding arylzinc reagents. A sequential microwave assisted arylmagnesium formation-transmetallation-Negishi coupling protocol suitable for automated multiple parallel synthesis has been developed.

Activation of Mg metal for safe formation of Grignard reagents on plant scale

Tilstam, Ulf,Weinmann, Hilmar

, p. 906 - 910 (2013/09/06)

A general and reliable method for the activation of magnesium metal for the formation of various kinds of Grignard reagents has been developed. Utilizing diisobutylaluminum hydride (DIBAH) for the activation of the surface and drying of the reaction mixtu

Effect of a 17α-(3-hydroxypropyl)-17β-acetyl substituent pattern on the glucocorticoid and progestin receptor binding of 11β-arylestra-4,9-dien-3-ones

Cook, C. Edgar,Raje, Prasad,Lee, David Y.-W.,Kepler, John A.

, p. 1013 - 1016 (2007/10/03)

(matrix presented) Replacing the 17α-acetoxy substituent in an antiprogestational 17β-acetyl-11β-arylestra-4,9-dien-3-one by 3-hydroxypropyl significantly diminished glucocorticoid receptor binding with little effect on progestin receptor binding.

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