4001-73-4

Basic information

• Product Name: 2-BROMOBENZAMIDE
• Synonyms: Benzamide, 2-bromo-;Benzamide, o-bromo-;2-Bromobenzamide,98%;2-BROMOBENZAMIDE 98%;2-Bromobenzenecarboxamide;2-Bromobenzamide, 97+%;O-BROMOBENZAMIDE;2-BROMOBENZAMIDE
• CAS NO: 4001-73-4
• Molecular Formula: C₇H₆BrNO
• Molecular Weight: 200.03
• EINECS: 223-650-9
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Anilines, Amides & Amines;Bromine Compounds;Amides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 4001-73-4.mol

Chemical Properties

• Melting Point: 160-162 °C(lit.)
• Boiling Point: 298 °C at 760 mmHg
• Flash Point: 134 °C
• Appearance: Beige/Powder
• Density: 1.5488 (rough estimate)
• Vapor Pressure: 0.0013mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 15.36±0.50(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 2-BROMOBENZAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMOBENZAMIDE(4001-73-4)
• EPA Substance Registry System: 2-BROMOBENZAMIDE(4001-73-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 4001-73-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-BROMOBENZAMIDE is used as a synthetic intermediate for the production of various organic compounds. Its application in chemical synthesis is due to its reactivity and ability to be involved in multiple reaction pathways.
Used in Microwave-Assisted One-Pot Synthesis:
In the field of organic chemistry, 2-BROMOBENZAMIDE is used as a reactant in microwave-assisted one-pot synthesis of substituted 3-(phenylmethylene)isoindolin-1-ones. This method allows for the efficient and rapid synthesis of these compounds, which are of interest in various chemical and pharmaceutical applications.
Used in Palladium-Catalyzed Synthesis:
2-BROMOBENZAMIDE is also utilized in the palladium-catalyzed synthesis of phenanthridinones. These compounds are important in the field of medicinal chemistry, as they possess potential biological activities and can be used as building blocks for the development of new drugs.
Used in the Synthesis of Water-Soluble Iminophosphorane Ligands:
Furthermore, 2-BROMOBENZAMIDE is employed in the synthesis of new water-soluble iminophosphorane ligands. These ligands are essential in homogeneous catalysis, as they can improve the efficiency and selectivity of various chemical reactions, particularly in the field of pharmaceuticals and materials science.

InChI:InChI=1/C7H6BrNO/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H2,9,10)

Upstream product

• 7154-66-7 2-bromobenzoic acid chloride 
• 36081-66-0 2'-bromo-2-phenylacetophenone 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 6630-33-7 ortho-bromobenzaldehyde 
• 766-46-1 2-bromo-1-ethynylbenzene 
• 583-55-1 1-Bromo-2-iodobenzene 
• 201230-82-2 carbon monoxide 
• 55-21-0 benzamide 
• 3959-05-5 2-bromobenzylamine 
• 1973-22-4 1-bromo-2-ethylbenzene 
• 18982-54-2 o-bromobenzyl alcohol 
• 2039-88-5 2-bromostyrene 
• 108-86-1 bromobenzene 
• 127099-85-8 N-Cyanoguanidine 

Downstream Products

• 7114-80-9 3-methylisoquinolone 
• 871-22-7 dibutyl acetal 
• 77197-82-1 C₁₆H₁₄Br₂N₂O₂ 
• 122889-65-0 N-Acetyl-2-bromo-benzamide 
• 13670-91-2 3-(4-methoxyphenyl)-2H-isoquinolin-1-one 
• 54705-17-8 o-ethylmercapto-benzamine 
• 89549-37-1 N-pivaloyl benzamide 
• 137092-45-6 2-Brom-N-thiopivaloylbenzamid 
• 30216-44-5 2-bromobenzothioamide 
• 62632-15-9 2-Bromobenzoyl isocyanate 
• 1109247-35-9 2-bromo-N-butyryl-benzamide 
• 939989-89-6 2-(2'-bromophenyl)-5-methyloxazole 
• 28144-70-9 anthranilic acid amide 

Relevant articles and documents

From Quinoline to Quinazoline-Based S. aureus NorA Efflux Pump Inhibitors by Coupling a Focused Scaffold Hopping Approach and a Pharmacophore Search

Antibiotic resistance breakers, such as efflux pump inhibitors (EPIs), represent a powerful alternative to the development of new antimicrobials. Recently, by using previously described EPIs, we developed pharmacophore models able to identify inhibitors of NorA, the most studied efflux pump of Staphylococcus aureus. Herein we report the pharmacophore-based virtual screening of a library of new potential NorA EPIs generated by an in-silico scaffold hopping approach of the quinoline core. After chemical synthesis and biological evaluation of the best virtual hits, we found the quinazoline core as the best performing scaffold. Accordingly, we designed and synthesized a series of functionalized 2-arylquinazolines, which were further evaluated as NorA EPIs. Four of them exhibited a strong synergism with ciprofloxacin and a good inhibition of ethidium bromide efflux on resistant S. aureus strains coupled with low cytotoxicity against human cell lines, thus highlighting a promising safety profile.

Efficient nitriding reagent and application thereof

The invention discloses an efficient nitriding reagent and application thereof, wherein the nitriding reagent comprises nitrogen oxide, an active agent, a reducing agent and an organic solvent. By applying the nitriding reagent, nitrogen-containing compounds such as amide, nitrile and the like can be produced, and the method is simple in condition, low in waste discharge amount and simple in reaction equipment.

Visible light-mediated synthesis of amides from carboxylic acids and amine-boranes

Here, a photocatalytic deoxygenative amidation protocol using readily available amine-boranes and carboxylic acids is described. This approach features mild conditions, moderate-to-good yields, easy scale-up, and up to 62 examples of functionalized amides with diverse substituents. The synthetic robustness of this method was also demonstrated by its application in the late-stage functionalization of several pharmaceutical molecules.

Design of an Electron-Withdrawing Benzonitrile Ligand for Ni-Catalyzed Cross-Coupling Involving Tertiary Nucleophiles

The design of new ligands for cross-coupling is essential for developing new catalytic reactions that access valuable products such as pharmaceuticals. In this report, we exploit the reactivity of nitrile-containing additives in Ni catalysis to design a benzonitrile-containing ligand for cross-coupling involving tertiary nucleophiles. Kinetic and Hammett studies are used to elucidate the role of the optimized ligand, which demonstrate that the benzonitrile moiety acts as an electron-acceptor to promote reductive elimination over β-hydride elimination and stabilize low-valent Ni. With these conditions, a protocol for decyanation-metalation and Ni-catalyzed arylation is conducted, enabling access to quaternary α-arylnitriles from disubstituted malononitriles.

Transamidation for the Synthesis of Primary Amides at Room Temperature

Various primary amides have been synthesized using the transamidation of various tertiary amides under metal-free and mild reaction conditions. When (NH4)2CO3 reacts with a tertiary amide bearing an N-electron-withdrawing substituent, such as sulfonyl and diacyl, in DMSO at 25 °C, the desired primary amide product is formed in good yield with good funcctional group tolerance. In addition, N-tosylated lactam derivatives afforded their corresponding N-tosylamido alkyl amide products via a ring opening reaction.

Nitromethane as a nitrogen donor in Schmidt-type formation of amides and nitriles

The Schmidt reaction has been an efficient and widely used synthetic approach to amides and nitriles since its discovery in 1923. However, its application often entails the use of volatile, potentially explosive, and highly toxic azide reagents. Here, we report a sequence whereby triflic anhydride and formic and acetic acids activate the bulk chemical nitromethane to serve as a nitrogen donor in place of azides in Schmidt-like reactions. This protocol further expands the substrate scope to alkynes and simple alkyl benzenes for the preparation of amides and nitriles.

Arene-ruthenium(II)-phosphine complexes: Green catalysts for hydration of nitriles under mild conditions

Three new arene-ruthenium(II) complexes were prepared by treating [{RuCl(μ-Cl)(η6-arene)}2] (η6-arene = p-cymene) dimer with tri(2-furyl)phosphine (PFu3) and 1,3,5-triaza-7-phosphaadamantane (PTA), respectively to obtain [RuCl2(η6-arene)PFu3] [Ru]-1, [RuCl(η6-arene)(PFu3)(PTA)]BF4 [Ru]-2 and [RuCl(η6-arene)(PFu3)2]BF4 [Ru]-3. All the complexes were structurally identified using analytical and spectroscopic methods including single-crystal X-ray studies. The effectiveness of resulting complexes as potential homogeneous catalysts for selective hydration of different nitriles into corresponding amides in aqueous medium and air atmosphere was explored. There was a remarkable difference in catalytic activity of the catalysts depending on the nature and number of phosphorus-donor ligands and sites available for catalysis. Experimental studies performed using structural analogues of efficient catalyst concluded a structural-activity relationship for the higher catalytic activity of [Ru]-1, being able to convert huge variety of aromatic, heteroaromatic and aliphatic nitriles. The use of eco-friendly water as a solvent, open atmosphere and avoidance of any organic solvent during the catalytic reactions prove the reported process to be truly green and sustainable.

Selectivity-tunable amine aerobic oxidation catalysed by metal-free N,O-doped carbons

Herein, we present a series of N,O-doped mesoporous carbons obtained at different pyrolysis temperatures as the first metal-free catalysts which successfully switch between imine and nitrile products for amine oxidation. Systematic characterization studies and control experiments revealed that the C-O group on the surface could function as a catalytically active site for nitrile synthesis and the N-doping environment was essential.

Method for preparing derivatives of benzamide under microwave condition in aqueous phase

The invention discloses a method for preparing derivatives of benzamide under a microwave condition in an aqueous phase. A coupling reaction is carried out between substituted benzoic acid and amine under the microwave condition in the aqueous phase. The method for preparing the derivatives of benzamide is environmentally friendly, easy and convenient to operate, safe, low in cost and efficient. Compared with the prior art, the method can be applicable to a large number of functional groups, is high in yield, produces fewer by-products, and further is easy to operate, safe, low in cost and environmentally friendly. A formula is shown in the description.

Nickel-catalyzed regioselective C-H halogenation of electron-deficient arenes

A straightforward Ni(ii)-catalyzed general strategy was developed for the ortho-halogenation of electron-deficient arenes with easily available halogenating reagents N-halosuccinimides (NXS; X = Br, Cl and I). The transformation was highly regioselective and a wide substrate scope and functional group tolerance were observed. This discovery could be of great significance for the selective halogenation of amides, benzoic esters and other substances with guiding groups. Mechanistic investigations were also described.