79606-46-5

Usage

Uses

Used in Research and Development:
4-Bromo-N,N-diisopropylbenzamide is used as a building block for the synthesis of other organic compounds, facilitating the creation of new chemical entities with diverse applications.
Used in Pharmaceutical Development:
4-Bromo-N,N-diisopropylbenzamide is used as a potential bioactive compound for the development of new drugs, particularly due to its demonstrated analgesic and anti-inflammatory properties.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 4-Bromo-N,N-diisopropylbenzamide is utilized for its potential to contribute to the discovery and design of novel therapeutic agents, enhancing the pharmacological landscape.
Used in Drug Discovery:
4-Bromo-N,N-diisopropylbenzamide is employed as a starting material in drug discovery processes, where its unique structural features and bioactivity may lead to the identification of new lead compounds for various therapeutic areas.

InChI:InChI=1/C13H18BrNO/c1-9(2)15(10(3)4)13(16)11-5-7-12(14)8-6-11/h5-10H,1-4H3

Upstream product

• 108-18-9 diisopropylamine 
• 586-75-4 4-chlorobenzoyl chloride 
• 7087-68-5 N-ethyl-N,N-diisopropylamine 
• 201230-82-2 carbon monoxide 
• 5467-74-3 4-Bromophenylboronic acid 
• 586-76-5 4-Bromobenzoic acid 
• 5419-55-6 Triisopropyl borate 
• 623-00-7 4-bromobenzenecarbonitrile 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 4111-54-0 lithium diisopropyl amide 

Downstream Products

• 586-76-5 4-Bromobenzoic acid 
• 336182-29-7 4-bromo-N-isopropyl-benzamide 
• 288093-12-9 N,N-bis(1-methylethyl)-4-(3-pyridyl)benzamide 
• 1058129-82-0 {5-bromo-2-[(diisopropylamino)carbonyl]phenyl}boronic acid 
• 67289-11-6 4-cyano-N,N-diisopropylbenzamide 
• 1360898-76-5 N,N-diisopropyl-4-(1-hydroxy-2,3-dimethoxy-4-oxocyclobut-2-en-1-yl)-benzamide 
• 1429609-72-2 C₁₆H₂₂N₂O₂ 
• 1609554-27-9 N,N-diisopropyl 4-[1-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl]benzamide 
• 1058129-84-2 9-bromo-1-butoxybenzo[c]-1,6-naphthyridin-6-ol 
• 1058129-83-1 2-(4-amino-2-butoxypyridin-3-yl)-4-bromo-N,N-diisopropylbenzamide 
• 1058129-60-4 2-(4-amino-2-butoxy-6-methylpyridin-3-yl)-4-bromo-N,N-diisopropylbenzamide 
• 850568-33-1 (4-(diisopropylcarbamoyl)phenyl)boronic acid 

Relevant academic research and scientific papers

Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates

Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.

Butylphthalide derivative and application thereof in preparation of drugs for protecting nerve cells

The invention relates to biological medicine. The invention provides a butylphthalide derivative and an application thereof in preparation of drugs for protecting nerve cells, and more specifically, the invention provides application of a butylphthalide d

Amide Effects in C?H Activation: Noncovalent Interactions with L-Shaped Ligand for meta Borylation of Aromatic Amides

A new concept for the meta-selective borylation of aromatic amides is described. It has been demonstrated that while esters gave para borylations, amides lead to meta borylations. For achieving high meta selectivity, an L-shaped bifunctional ligand has been employed and engages in an O???K noncovalent interaction with the oxygen atom of the moderately distorted amide carbonyl group. This interaction provides exceptional control for meta C?H activation/borylation.

A process for the preparation of boric acid P-carboxyl

The invention discloses a preparation method of p-carboxyphenylboronic acid. The preparation method comprises the steps of carrying out an amidation reaction on bromobenzoic acid and diisopropylamine to obtain a reaction intermediate 4-bromo-N,N-diisopropylbenzamide; carrying out the substitution reaction on the 4-bromo-N,N-diisopropylbenzamide at a reaction temperature ranging from -75 to -80 DEG C in a solvent which is dry tetrahydrofuran, thereby obtaining (4-(diisopropylcarbamyl)phenyl) boric acid; hydrolyzing (4-(diisopropylcarbamyl)phenyl) boric acid in the presence of lithium hydroxide monohydrate to obtain p-carboxyphenylboronic acid. The preparation method provided by the invention is high in product yield, simple and convenient to operate, low in reaction cost and applicable to industrial production.

Direct Hydroxylation and Amination of Arenes via Deprotonative Cupration

Deprotonative directed ortho cupration of aromatic/heteroaromatic C-H bond and subsequent oxidation with t-BuOOH furnished functionalized phenols in high yields with high regio- and chemoselectivity. DFT calculations revealed that this hydroxylation reaction proceeds via a copper (I → III → I) redox mechanism. Application of this reaction to aromatic C-H amination using BnONH2 efficiently afforded the corresponding primary anilines. These reactions show broad scope and good functional group compatibility. Catalytic versions of these transformations are also demonstrated.

An efficient method for the preparation of styrene derivatives via Rh(III)-catalyzed direct C-H vinylation

The development of a method for the Rh(III)-catalyzed direct vinylation of an aromatic C-H bond to give functionalized styrenes in good yield, using vinyl acetate as a convenient and inexpensive vinyl source, is reported. High functional group tolerance is demonstrated for electronically distinct arenes as well as different directing groups. Mechanistic investigation resulted in the characterization of a novel rhodium-metallacycle, which represents the first X-ray structure of a [1,2]-Rh(III)-alkenyl addition adduct.

Organoaluminum-Mediated Direct Cross-Coupling Reactions

We present a direct cross-coupling reaction between arylaluminum compounds (ArAlMe2·LiCl) and organic halides RX (R=aryl, alkenyl, alkynyl; X=I, Br, and Cl) without any external catalyst. The reaction takes place smoothly, simply upon heating, thereby enabling the efficient and chemo-/stereoselective formation of biaryl, alkene, and alkyne coupling products with broad functional group compatibility.

Rhodium-catalyzed direct coupling of benzothioamides with alkenes and alkynes through directed C-H bond cleavage

Rhodium-catalyzed direct coupling of benzothioamides with alkenes proceeds smoothly involving ortho-CH bond cleavage. The thioamides also couple with alkynes under similar conditions accompanied by desulfurization and CN bond cleavage to produce indenone derivatives.

Palladium-catalyzed aminocarbonylation of N-chloroamines with boronic acids

Abstract Aryl (pseudo)halide-based (C-X) carbonylation reactions have been extensively studied during the past few decades. From both academic and synthetic points of view, the carbonylative transformation of N-X bonds represents an interesting and attractive area of investigation. In light of this, the first carbonylative cross-coupling between N-chloroamines and organoboronic acids has been developed. This new type of aminocarbonylation proceeds at mild temperatures (45-55 °C) with 2 mol % Pd/C (10 wt %) as the ligand-free catalyst. Not only arylboronic acids, but also alkenyl- and alkylboronic acids can be applied as the substrates and bromide and iodide substituents in the substrates are well tolerated. Initial mechanistic investigations have also been performed. Umpolung aminocarbonylation: The first palladium-catalyzed carbonylative cross-coupling between N-chloroamines and organoboronic acids has been realized. Various amides were isolated in moderate to excellent yields from reactions under mild temperatures with ligand-free Pd/C as the catalyst. Not only arylboronic acids, but also alkenyl- and alkylboronic acids are applied as the substrates and bromide and iodide substituents in the substrates are well tolerated.

Efficient modulation of γ-aminobutyric acid type a receptors by piperine derivatives

Piperine activates TRPV1 (transient receptor potential vanilloid type 1 receptor) receptors and modulates γ-aminobutyric acid type A receptors (GABAAR). We have synthesized a library of 76 piperine analogues and analyzed their effects on GABAAR by means of a two-microelectrode voltage-clamp technique. GABAAR were expressed in Xenopus laevis oocytes. Structure-activity relationships (SARs) were established to identify structural elements essential for efficiency and potency. Efficiency of piperine derivatives was significantly increased by exchanging the piperidine moiety with either N,N-dipropyl, N,N-diisopropyl, N,N-dibutyl, p-methylpiperidine, or N,N-bis(trifluoroethyl) groups. Potency was enhanced by replacing the piperidine moiety by N,N-dibutyl, N,N-diisobutyl, or N,N-bistrifluoroethyl groups. Linker modifications did not substantially enhance the effect on GABAAR. Compound 23 [(2E,4E)-5-(1,3-benzodioxol-5-yl)-N,N-dipropyl-2,4-pentadienamide] induced the strongest modulation of GABAA (maximal GABA-induced chloride current modulation (IGABA-max = 1673% ± 146%, EC 50 = 51.7 ± 9.5 μM), while 25 [(2E,4E)-5-(1,3-benzodioxol- 5-yl)-N,N-dibutyl-2,4-pentadienamide] displayed the highest potency (EC 50 = 13.8 ± 1.8 μM, IGABA-max = 760% ± 47%). Compound 23 induced significantly stronger anxiolysis in mice than piperine and thus may serve as a starting point for developing novel GABA AR modulators.