59278-65-8

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-4-Bromobenzaldehyde is used as a key intermediate in the synthesis of various pharmaceutical drugs for its ability to form complex molecular structures.
Used in Organic Synthesis:
2-Amino-4-Bromobenzaldehyde is used as a building block in the synthesis of other organic compounds, contributing to the development of new chemical entities with potential applications in various industries.

Upstream product

• 5551-12-2 4-bromo-2-nitrobenzaldehyde 
• 60956-26-5 4-bromo-2-nitrotoluene 
• 20712-12-3 (2-amino-5-bromophenyl)methanol 
• 20776-50-5 2-amino-4-bromobenzoic acid 
• 946122-05-0 (2-amino-4-bromophenyl)methanol 
• 135484-83-2 2-amino-4-bromo-benzoic acid methyl ester 
• 22996-19-6 (4-bromo-2-nitrophenyl)methanol 
• 99277-71-1 4-bromo-2-nitrobenzoic acid 
• 99474-21-2 (E)-2-(4-bromo-2-nitrophenyl)-N,N-dimethylethyleneamine 

Downstream Products

• 22532-62-3 4-bromosalicylaldehyde 
• 883149-59-5 7-bromo-3-(2,5-dimethoxyphenyl)-1H-quinolin-2-one 
• 953039-65-1 7-bromo-quinazolin-2-ol 
• 1203578-65-7 7-bromo-2-phenylquinoline 
• 953039-66-2 7-bromo-2-chloroquinazoline 
• 892874-34-9 7-bromoquinoline-3-carboxylic acid 
• 1226762-74-8 7-bromoquinoline-3-carboxylic acid ethyl ester 
• 1375108-41-0 7-bromo-3-methylquinoline 
• 332135-42-9 2-benzyl-7-bromo-3-methoxyquinoline 
• 332135-43-0 2-benzyl-7-pyrazyl-3-methoxyquinoline 

Relevant academic research and scientific papers

Cationic Iridium-Catalyzed Asymmetric Decarbonylative Aryl Addition of Aromatic Aldehydes to Bicyclic Alkenes

We report an unprecedented catalytic protocol for the enantioselective decarbonylative transformation of aryl aldehydes. In this process, the decarbonylation of aldehydes catalyzed by chiral iridium complexes enabled the formation of asymmetric C?C bonds

Silver-Catalyzed Three-Component Coupling Reaction of Amines, 2-Isocyanobenzaldehydes, and 2,2,2-Trifluorodiazoethane and Synthesis of Trifluoromethyl-Substituted Indolo[1,2-c]quinazolines

A silver-catalyzed three-component coupling reaction of amines, 2-isocyanobenzaldehydes, and 2,2,2-trifluorodiazoethane has been developed. This reaction provides an efficient method for the construction of CF3-containing dihydroquinazolines. On the basis of this reaction, using trifluorodiazoethyl-substituted dihydroquinazolines as synthons, trifluoromethyl-substituted indolo[1,2-c]quinazolines were prepared in high yields via a TBHP/KI-mediated sequential intramolecular cyclization and aromatization process. (Figure presented.).

PPTS-Catalyzed Bicyclization Reaction of 2-Isocyanobenzaldehydes with Various Amines: Synthesis of Diverse Fused Quinazolines

A PPTS (pyridinium p-toluenesulfonate)-catalyzed bicyclization reaction of 2-isocyanobenzaldehydes as 1,5-dielectrophiles with various amines has been developed. The reaction not only provides a simple and efficient strategy for the assembly of structurally diverse fused quinazoline derivatives from readily available substrates under metal-free and mild conditions in a single step with only water and hydrogen as the by-products, but also opens the way to the application of o-formyl arylisocyanides in the synthesis of nitrogen-containing heterocycles. (Figure presented.).

Visible-Light-Induced Amination of Quinoline at the C8 Position via a Postcoordinated Interligand-Coupling Strategy under Mild Conditions

The postcoordinated interligand-coupling strategy provides a useful and complementary protocol for synthesizing polydentate ligands. Herein, diastereoselective photoreactions of Λ-[Ir(pq)2(d-AA)] (Λ-d) and Λ-[Ir(pq)2(l-AA)] (Λ-l, where pq is 2-phenylquino

AMINOQUINOLINE COMPOUNDS, IMMUNOCONJUGATES, AND USES THEREOF

The invention provides immunoconjugates of Formula (I) comprising an antibody linked by conjugation to one or more aminoquinoline derivatives. The invention also provides aminoquinoline derivative intermediate compositions of Formula (III) comprising a re

Repurposing an Aldolase for the Chemoenzymatic Synthesis of Substituted Quinolines

Quinoline derivatives are important natural products and pharmaceuticals, but their synthesis can be challenging due to poor yields, harsh reaction conditions, and instability of starting materials. Here we report the chemoenzymatic synthesis of quinaldic acids under mild conditions using an aldolase, trans-o-hydroxybenzylidenepyruvate hydratase-aldolase (NahE, or HBPA). A series of 2-aminobenzaldehydes derived from reduction of the corresponding nitro analogue were reacted with pyruvate in the presence of NahE to give substituted quinolines in up to 93% isolated yield. This reaction differs from the aldol condensation catalyzed by NahE in vivo, instead resembling the heterocycle formation catalyzed by its homologue, dihydrodipicolinate synthase.

3-(1H-PYRAZOL-4-YL)PYRIDINE ALLOSTERIC MODULATORS OF M4 MUSCARINIC ACETYLCHOLINE RECEPTOR

Provided are cinnolinyl and quinolinyl pyrazol-4-yl-pyridine compounds which are allosteric modulators of the M4 muscarinic acetylcholine receptor, compositions comprising said compounds, and uses of said compounds in the treatment or prevention of diseases in which M4 muscarinic acetylcholine receptors are involved, especially neurological and psychiatric disorders and diseases.

Effective and Sustainable Access to Quinolines and Acridines: A Heterogeneous Imidazolium Salt Mediates C–C and C–N Bond Formation

Quinoline and acridine derivatives have been prepared using a functionalized imidazolium salt as heterogeneous catalyst. Different ketones have been coupled with 2-aminobenzaldehydes and 2-aminoaryl ketones under solvent-free conditions, employing 1,3-bis(carboxymethyl)-imidazolium chloride as a catalyst. The protocol is simple and effective for the synthesis of a variety of nitrogen containing heterocycles (> 35 examples) with moderate to excellent yields (up to 96 %), being possible to perform the reaction in preparative scale. Additionally, 3-acetylquinolines have been transformed, under solvent-free conditions, into quinolyl chalcone derivatives by means of the same catalyst. Thus, the catalytic system mediates both reactions effectively in a tandem procedure. Furthermore, the catalyst is easily separated from the reaction mixture and can be reused without loss of activity (up to 8 cycles) which remarks its sturdiness. The E-factors are in the range of 14–23, both for the formation of quinolines and for the tandem reaction, which demonstrates the sustainability of the protocols described.

Chiral Phosphoric-Acid-Catalyzed Cascade Prins Cyclization

Asymmetric Prins cyclization of in situ generated quinone methides and o-aminobenzaldehyde has been developed with chiral phosphoric acid as an efficient catalyst. This unconventional method provides a facile access to diverse functionalized trans-fused pyrano-/furo-tetrahydroquinoline derivatives in excellent yield and with excellent diastereo- and enantioselectivities (up to 99% yield and 99% ee). Mechanistic studies suggested that the three adjacent tertiary stereocenters were constructed through the sequential formation of C-O, C-C, and C-N bonds.

Vasicine from Adhatoda vasica as an organocatalyst for metal-free Henry reaction and reductive heterocyclization of o-nitroacylbenzenes

Vasicine, a quinazoline alkaloid, from the leaves of Adhatoda vasica, has been utilized as an efficient catalyst for metal and base free Henry reaction of various aldehydes with nitro alkanes. The method can be used in the synthesis of various β-nitro alcohols under mild reaction conditions without use of hazardous organic solvents and expensive catalysts. Vasicine is also applied successfully for one pot synthesis of 2,1-benzisoxazoles from o-nitroacylbenzenes in good yields under mild conditions.