42498-38-4

Usage

Uses

Used in Dental Industry:
4-BROMO-N-(1,1-DIMETHYLETHYL)BENZAMIDE is used as a photoinitiator for the polymerization of dental restorative materials, such as composites and adhesive resins. It facilitates the curing process by initiating the polymerization reaction when exposed to light, ensuring the formation of a stable and durable dental restoration.
It is important to handle and store 4-BROMO-N-(1,1-DIMETHYLETHYL)BENZAMIDE with care, as it can be harmful if ingested or inhaled, and could cause skin and eye irritation upon contact. Proper safety measures should be taken during its use in dental applications to minimize potential health risks.

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

Upstream product

• 586-76-5 4-Bromobenzoic acid 
• 540-88-5 acetic acid tert-butyl ester 
• 623-00-7 4-bromobenzenecarbonitrile 
• 119072-55-8 tert-butylisonitrile 
• 1712-82-9 p-bromodibenzoyl peroxide 
• 62058-74-6 (2R,3R)-3-(4-Bromo-phenyl)-2-tert-butyl-oxaziridine 
• 1122-91-4 4-bromo-benzaldehyde 
• 586-61-8 4-iso-propylbromobenzene 
• 62058-74-6 3-(4-bromo-phenyl)-2-tert-butyl-oxaziridine 
• 873-75-6 4-bromobenzenemethanol 
• 75-64-9 tert-butylamine 
• 673-40-5 4-bromobenzenediazonium tetrafluoroborate 
• 56075-37-7 1-(methylsulfonyl)-2-(4-bromophenyl)diazene 
• 75-65-0 tert-butyl alcohol 

Downstream Products

• 288093-13-0 N-(1,1-dimethylethyl)-4-(3-pyridyl)benzamide 
• 147223-89-0 1-benzyl-5-[4-(4-fluorophenyl)-1-hydroxy-1-(4-tert-butylaminocarbonylphenyl)butyl]-1H-imidazole 
• 698-67-9 p-bromobenzamide 
• 288093-19-6 N-tert-butyl-4-(1-methyl-2-oxo-1,2-dihydro-pyridin-3-yl)-benzamide 
• 288093-16-3 N-tert-butyl-4-(1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-benzamide 
• 1425194-11-1 N-tert-butyl-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)benzamide 
• 1404220-37-6 4-bromo-N-tert-butyl-2-(4-nitrophenylamino)benzamide 
• 1452393-98-4 4-(benzofuran-3-yl)-N-(tert-butyl)benzamide 
• 1450753-68-0 4-bromo-N-tert-butyl-2-(4-nitrobenzamido)benzamide 

Relevant academic research and scientific papers

Electrochemical Benzylic C-H Functionalization with Isocyanides

We report the challenging direct carbamoylation or cyanation of benzylic C(sp3)-H bonds with an isocyanide via an electrochemical process giving rise to structures that are encountered in several biologically relevant compounds and drugs. This transformation proceeds under mild conditions without the need for any external oxidant and avoids the necessity to start from a prefunctionalized benzylic substrate or the deployment of the cation pool method. The anodic oxidation of the benzylic position and the subsequent addition of the isocyanide lead to the formation of a C-C bond and to a nitrilium cation that hydrolyzes to yield α-Aryl acetamide derivatives, whereas the elimination of a t-butyl cation delivers α-Aryl acetonitrile derivatives.

Weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis

The selective rearrangement of oxaziridines to amidesviaa single electron transfer (SET) pathway is unexplored. In this study, we present a weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis. The developed method shows excellent functional group tolerance with a broad substrate scope and good to excellent yields. Furthermore, control experiments and density functional theory (DFT) calculations are performed to gain insight into the reactivity and selectivity.

CoFe2O4?SiO2-NH-βCD-BF3 as a supramolecular nanocomposite: Synthesis, characterization and catalytic activity

This manuscript describes synthesis of BF3-functionlized β-cylcodextrine grafted magnetic CoFe2O4 nanaoparticles as a hybrid magnetic nano-composite (CoFe2O4?SiO2-NH-βCD-BF3). The CoFe2O4?SiO2-NH-βCD-BF3 was fabricated by grafting of 6-O-toluenesulfonyl cyclodextrin (6-Ts-βCD) to 3-aminopropyl triethoxysilane coated magnetic CoFe2O4?SiO2 nanoparticles followed by combination with BF3. The CoFe2O4?SiO2-NH-βCD-BF3was characterized by FT-IR, TGA, VSM and SEM techniques. The feasibility of using CoFe2O4?SiO2-NH-βCD-BF3 as a magnetically recoverable catalyst was confirmed in the modified-Ritter reaction. The result showed that this novel nano-composite could serve as an efficient nanoreactor bearing super-acidic sites formed by immobilized BF3 and reuse at least for 6 times without loss in activity.

Organophotoredox-Mediated Amide Synthesis by Coupling Alcohol and Amine through Aerobic Oxidation of Alcohol

The combination of an organic photocatalyst [4CzIPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6 dicyanobenzene) or 5MeOCzBN (2,3,4,5,6-pentakis(3,6-dimethoxy-9 H-carbazol-9-yl)benzonitrile)], quinuclidine, and tetra-n-butylammonium phosphate (hydrogen-bonding catalyst) was employed for amide bond formations. The hydrogen-bonded OH group activated the adjacent C?H bond of alcohols towards hydrogen atom transfer (HAT) by a radical species. The quinuclidinium radical cation, generated through single-electron oxidation of quinuclidine by the photocatalyst, employed to abstract a hydrogen atom from the α-C?H bond of alcohols selectively due to a polarity effect-produced α-hydroxyalkyl radical, which subsequently converted to the corresponding aldehyde under aerobic conditions. Then the coupling of the aldehyde and an amine formed a hemiaminal intermediate that upon photocatalytic oxidation produced the amide.

Ionic liquid catalyzed Ritter reaction/Pd-catalyzed directed Ortho-arylation; facile access to diverse libraries of biaryl-amides from Aryl-nitriles

Diverse libraries of biaryl-amides bearing N-t-butyl and N-adamantyl groups were synthesized in two steps by the Ritter reaction of aryl-nitriles, using tBuOH and AdaOH as carbocation precursors, and employing [BMIM(SO3H)][OTf] (neat or with [B

Structure-Guided Modification of Heterocyclic Antagonists of the P2Y14 Receptor

The P2Y14 receptor (P2Y14R) mediates inflammatory activity by activating neutrophil motility, but few classes of antagonists are known. We have explored the structure-activity relationship of a 3-(4-phenyl-1H-1,2,3-triazol-1-yl)-5-(aryl)benzoic acid antagonist scaffold, assisted by docking and molecular dynamics (MD) simulation at a P2Y14R homology model. A computational pipeline using the High Throughput MD Python environment guided the analogue design. Selection of candidates was based upon ligand-protein shape and complementarity and the persistence of ligand-protein interactions over time. Predictions of a favorable substitution of a 5-phenyl group with thiophene and an insertion of a three-methylene spacer between the 5-aromatic and alkyl amino moieties were largely consistent with empirical results. The substitution of a key carboxylate group on the core phenyl ring with tetrazole or truncation of the 5-aryl group reduced affinity. The most potent antagonists, using a fluorescent assay, were a primary 3-aminopropyl congener 20 (MRS4458) and phenyl p-carboxamide 30 (MRS4478).

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.

Atom economical synthesis of: N -alkylbenzamides via the iron(III) sulfate catalyzed rearrangement of 2-alkyl-3-aryloxaziridines in water and in the presence of a surfactant

A green and mild synthetic route to N-alkylbenzamides involves eco-friendly one pot synthesis of 2-alkyl-3-aryloxaziridines from N-alkylamines and benzaldehydes followed by iron(iii) sulfate catalyzed rearrangement to the corresponding amides in water as the solvent and in the presence of sodium dodecyl sulfate as the surfactant. This green approach affords N-alkylbenzamides in high overall yields under simple and minimum manipulation.

Cp?CoIII-Catalyzed syn-Selective C-H Hydroarylation of Alkynes Using Benzamides: An Approach Toward Highly Conjugated Organic Frameworks

Hydroarylation of internal alkynes by cost-effective CoIII-catalysis, directed by N-tert-butyl amides, is achieved to avail mono- or dihydroarylated amide products selectively in an atom and step economic way. Several important functional groups were tolerated under the reaction conditions, and syn-hydroarylation products were exclusively isolated. Notably, a 4-fold C-H hydroarylation provided a highly conjugated organic framework in one step. Kinetic study with extensive deuterium labeling experiments were performed to support the proposed mechanism.

A Visible-Light-Driven, Metal-free Route to Aromatic Amides via Radical Arylation of Isonitriles

The photochemical metal-free carboamidation of aryl radicals has been exploited for the preparation of aromatic amides, including hetero- and polyaromatic derivatives, under visible light irradiation of arylazo sulfones in the presence of isocyanides in aqueous acetonitrile. The process was useful for the smooth preparation of the antidepressant moclobemide. (Figure presented.).