24109-06-6

Usage

Uses

Used in Pharmaceutical Research:
N-(4-bromophenyl)-2,2-dimethylpropanamide serves as a building block in the synthesis of various pharmaceutical drugs. Its unique structure allows it to be a valuable component in the development of new medications.
Used in Organic Synthesis:
In the realm of organic synthesis, N-(4-bromophenyl)-2,2-dimethylpropanamide is used as a reagent to introduce bromine-containing groups into organic molecules. This capability is crucial for the creation of a wide range of chemical compounds.
Used in Medicinal Applications:
N-(4-bromophenyl)-2,2-dimethylpropanamide has been studied for its anti-inflammatory and analgesic effects, making it a potential candidate for the treatment of conditions that involve inflammation and pain.
Safety Note:
Due to its potential health and environmental hazards, N-(4-bromophenyl)-2,2-dimethylpropanamide should be handled with care and in accordance with established safety measures.

InChI:InChI=1/C11H14BrNO/c1-11(2,3)10(14)13-9-6-4-8(12)5-7-9/h4-7H,1-3H3,(H,13,14)

Upstream product

• 6625-74-7 N-pivaloylaniline 
• 75-98-9 Trimethylacetic acid 
• 3282-30-2 pivaloyl chloride 
• 106-40-1 4-bromo-aniline 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 2493-02-9 4-bromophenyl isocyanate 
• 193533-92-5 4-methyl-1,2,3-trifluorobenzene 
• 615-57-6 2,4-dibromo-aniline 
• 624-92-0 Dimethyldisulphide 
• 171881-32-6 N-(2,4-dibromophenyl)-2,2-dimethylpropanamide 
• 62-53-3 aniline 

Downstream Products

• 1433186-68-5 N-(4-bromo-2-(trifluoromethyl)phenyl)pivalamide 
• 10075-50-0 5-bromo-1H-indole 
• 171881-32-6 N-(2,4-dibromophenyl)-2,2-dimethylpropanamide 
• 165180-44-9 N-(4-bromo-2-fluorophenyl)pivalamide 
• 1609932-63-9 N-(4-(hydroxy(3-methoxyquinoxalin-6-yl)methyl)phenyl)pivalamide 
• 1609932-60-6 N-(4-(hydroxy(3-morpholinoquinoxalin-6-yl)methyl)phenyl)pivalamide 
• 1351696-94-0 C₁₈H₁₇BrClNO₂ 
• 1233967-38-8 C₁₃H₁₃BrF₃NO₂ 
• 240139-83-7 N-(4-(2-pyrimidinyl)phenyl)-2,2-dimethylpropanamide 

Relevant academic research and scientific papers

Equivalent Loading of Directed Arenes in Pd(II)-Catalyzed Oxidative Cross-Coupling of Aryl C-H Bonds at Room Temperature

The unsymmetrical biaryls (Ar1-Ar2) produced by the catalytic cross-couplings of aryl halides (Ar1-halo) with aryl metallics (Ar2-M) in the loading ratio of 1:1 are popular in chemical synthesis. In contrast, there has been less precedence on the same biaryls produced effectively from two normal aryl C-H bonds with equivalent loading. Here, we report that, in a palladium/oxidant/acid catalytic system at room temperature, one arene (Ar1-H, 1 equiv) can highly selectively couple with the other one (Ar2-H, 1 equiv) to afford the target Ar1-Ar2 just by controlling the directing groups and the substituted groups on their phenyl rings. The utility of this one-one cross-coupling is also demonstrated by synthesis of a few bioactive molecules.

Room temperature clickable coupling electron deficient amines with sterically hindered carboxylic acids for the construction of amides

A method for the synthesis of difficult-to-access amides was developed through the coupling of sterically hindered carboxylic acids and electron deficient amines via SO2F2-mediated dehydration. The method feathers with broad substrate scope, mild conditions, excellent functional group compatibility and high yields.

Exogenous Photosensitizer-, Metal-, and Base-Free Visible-Light-Promoted C-H Thiolation via Reverse Hydrogen Atom Transfer

Visible-light-driven, intramolecular C(sp2)-H thiolation has been achieved without addition of a photosensitizer, metal catalyst, or base. This reaction induces the cyclization of thiobenzanilides to benzothiazoles. The substrate absorbs visible light, and its excited state undergoes a reverse hydrogen-atom transfer (RHAT) with 2,2,6,6-tetramethylpiperidine N-oxyl to form a sulfur radical. The addition of the sulfur radical to the benzene ring gives an aryl radical, which then rearomatizes to benzothiazole via RHAT.

Photocatalytic Oxidative C-H Thiolation: Synthesis of Benzothiazoles and Sulfenylated Indoles

We report studies on the photocatalytic formation of C-S bonds to form benzothiazoles via an intramolecular cyclization and sulfenylated indoles via an intermolecular reaction. Cyclic voltammetry (CV) and density functional theory studies suggest that benzothiazole formation proceeds via a mechanism that involves an electrophilic sulfur radical, while the indole sulfenylation likely proceeds via a nucleophilic sulfur radical adding into a radical cationic indole. These conditions were successfully extended to several thiobenzamides and indole substrates.

A para-C–H Functionalization of Aniline Derivatives via In situ Generated Bulky Hypervalent Iodinium Reagents

A practical para-C-H functionalization of aniline derivatives has been developed using an in situ generated bulky hypervalent iodinium reagent. Para-iodo, bromo, chloro, nitro, trifluormethyl aniline derivatives can be obtained efficiently, in many cases in 10 min in a transition metal-free manner. Medicinal chemicals or intermediates can be purified without column chromatography or recrystallization, which significantly reduces the waste and simplifies the work-up process.

Palladium(II)-Catalyzed Oxidative Homo- and Cross-Coupling of Aryl ortho -sp2 C-H Bonds of Anilides at Room Temperature

The preparation of secondary 2,2'-bisanilides has been successfully achieved through an oxidative coupling of aryl ortho-sp2 C-H bonds of anilides in the presence of catalytic Pd(OAc)2 and K2S2O8 as an oxidant in MsOH/CF3CO2H (TFA) at room temperature (25 °C). The aromatic rings of anilides substituted by various electron-donating or electron-withdrawing groups are tolerant in these coupling reactions.

Oxidative C?H/C?H Cross-Coupling Reactions between N-Acylanilines and Benzamides Enabled by a Cp*-Free RhCl3/TFA Catalytic System

By making use of a dual-chelation-assisted strategy, a completely regiocontrolled oxidative C?H/C?H cross-coupling reaction between an N-acylaniline and a benzamide has been accomplished for the first time. This process constitutes a step-economic and highly efficient pathway to 2-amino-2′-carboxybiaryl scaffolds from readily available substrates. A Cp*-free RhCl3/TFA catalytic system was developed to replace the [Cp*RhCl2]2/AgSbF6 system generally used in oxidative C?H/C?H cross-coupling reactions between two (hetero)arenes (Cp=pentamethylcyclopentadienyl, TFA=trifluoroacetic acid). The RhCl3/TFA system avoids the use of the expensive Cp* ligand and AgSbF6. As an illustrative example, the procedure developed herein greatly streamlines the total synthesis of the naturally occurring benzo[c]phenanthridine alkaloid oxynitidine, which was accomplished in excellent overall yield.

Zwitterionic-Salt-Catalyzed Site-Selective Monobromination of Arenes

A zwitterionic-salt-catalyzed electrophilic monobromination of arenes with high regioselectivity has been developed. Under mild reaction conditions, a wide range of monobrominated aromatic compounds can be obtained in excellent yields. The reaction can be operated using an extremely low catalyst loading (0.05 mol %) with the inexpensive brominating agent N-bromosuccinimide. The versatility of this catalytic protocol has been demonstrated by the scale-up reaction with a 0.01 mol % catalyst loading to provide the selectively halogenated compound in quantitative yield.

Combining Eosin y with Selectfluor: A Regioselective Brominating System for Para-Bromination of Aniline Derivatives

A mild, metal-free, and absolutely para-selective bromination of aniline derivatives has been developed in excellent yields, wherein the organic dye Eosin Y is employed as the bromine source in company with Selectfluor. Neither air nor moisture sensitive, this facile reaction proceeds smoothly at room temperature and completes within a short time. Mechanistic studies indicate a radical pathway; therefore, the existence of an in situ generated brominating reagent, "Selectbrom", is postulated, which may reasonably account for the unique regioselectivity for the para-bromination of N-acyl- as well as N-sulfonylanilines.

Rhodium(III)-catalysed, redox-neutral C(sp2)-H alkenylation using pivalimide as a directing group with internal alkynes

In the presence of [RhCp?Cl2]2, N-pivaloyl anilines react with internal alkynes to give the corresponding 2-alkenylpivalimides under redox neutral conditions through C-H activation. This redox neutral hydroarylation, which does not require an external organic acid, unlocks a regioselective synthetic route to 2-alkenyl anilines and is generally applicable to diversely substituted electron rich and electron poor pivalimides.