20191-75-7

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Amino-1-bromonaphthalene is used as a building block for the production of pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique structure allows for versatile chemical modifications, facilitating the creation of diverse medicinal compounds.
Used in Dye Production:
In the dye industry, 2-Amino-1-bromonaphthalene is utilized as a precursor for the synthesis of various dyes. Its chemical properties enable the production of dyes with specific color characteristics and stability, catering to the needs of different applications.
Used in Specialty Chemicals:
2-AMINO-1-BROMONAPHTHALENE also serves as a key intermediate in the synthesis of specialty chemicals, which are used in a wide range of industries, including plastics, coatings, and textiles. Its versatility in chemical reactions makes it a valuable component in the production of these high-value products.
Used in Research Laboratories:
2-Amino-1-bromonaphthalene is employed as a reagent in research laboratories for conducting various organic reactions. Its presence can influence the course of reactions, providing insights into chemical behavior and aiding in the discovery of new reaction pathways.
It is crucial to handle 2-amino-1-bromonaphthalene with care due to its potential environmental and health hazards, ensuring safe practices in its use and disposal.

InChI:InChI=1/C10H8BrN/c11-10-8-4-2-1-3-7(8)5-6-9(10)12/h1-6H,12H2

Upstream product

• 77-48-5 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione 
• 91-59-8 naphthalen-2-ylamine 
• 18271-18-6 N-(2-naphthyl)-p-toluenesulphonamide 
• 5043-27-6 3-amino-4-bromo-2-naphthoic acid 
• 7597-73-1 N-(1-bromonaphthalen-2-yl)acetamide 
• 708258-18-8 (1-bromo-[2]naphthyl)-oxalamic acid ethyl ester 
• 81-16-3 2-aminonaphthalenesulfonic acid 
• 36199-71-0 1-Brom-2-azido-naphthalin 
• 93-09-4 naphthalene-2-carboxylate 
• 454713-45-2 naphthalen-2-yl-carbamic acid tert-butyl ester 
• 612-52-2 2-naphthylamine hydrochloride 
• 5959-52-4 2-Amino-3-naphthoic acid 
• 856074-57-2 4-bromo-3-(toluene-4-sulfonylamino)-[2]naphthoic acid 
• 60178-65-6 3-((4-methylphenyl)sulfonamido)-2-naphthoic acid 

Downstream Products

• 666856-03-7 2-(1-bromo-[2]naphthylamino)-4-chloro-benzoic acid 
• 875844-31-8 N-(1-bromo-[2]naphthyl)-benzenesulfonamide 
• 73825-25-9 3-(1-Bromo-naphthalen-2-ylamino)-cyclohex-2-enone 
• 73825-26-0 3-(1-Bromo-naphthalen-2-ylamino)-5,5-dimethyl-cyclohex-2-enone 
• 137840-33-6 2-[(1-Bromo-naphthalen-2-ylcarbamoyl)-methyl]-benzoic acid 
• 40168-12-5 [2]naphthyl-triphenylphosphoranyliden-amine 
• 91-59-8 naphthalen-2-ylamine 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 118898-15-0 2-aminonaphtho[2,1-d]-1,3-selenazole 
• 38829-78-6 2-phenyl-3H-benzo(e)indole 
• 63077-00-9 12,13-dihydro-7H-dibenzo[a,g]carbazole 

Relevant academic research and scientific papers

Axially Chiral Dibenzazepinones by a Palladium(0)-Catalyzed Atropo-enantioselective C?H Arylation

Atropo-enantioselective C?H functionalization reactions are largely limited to the dynamic kinetic resolution of biaryl substrates through the introduction of steric bulk proximal to the axis of chirality. Reported herein is a highly atropo-enantioselective palladium(0)-catalyzed methodology that forges the axis of chirality during the C?H functionalization process, enabling the synthesis of axially chiral dibenzazepinones. Computational investigations support experimentally determined racemization barriers, while also indicating C?H functionalization proceeds by an enantio-determining CMD to yield configurationally stable eight-membered palladacycles.

A unique class of duocarmycin and CC-1065 analogues subject to reductive activation

N-Acyl O-amino phenol derivatives of CBI-TMI and CBI-indole2 are reported as prototypical members of a new class of reductively activated prodrugs of the duocarmycin and CC-1065 class of antitumor agents. The expectation being that hypoxic tumor environments, with their higher reducing capacity, carry an intrinsic higher concentration of "reducing" nucleophiles (e.g., thiols) capable of activating such derivatives (tunable N-O bond cleavage) and increasing their sensitivity to the prodrug treatment. Preliminary studies indicate the prodrugs effectively release the free drug in functional cellular assays for cytotoxic activity approaching or matching the activity of the free drug, yet remain essentially stable and unreactive to in vitro DNA alkylation conditions (1/2 = 3 h). Characterization of a representative O-(acylamino) prodrug in vivo indicates that they approach the potency and exceed the efficacy of the free drug itself (CBI-indole2), indicating that not only is the free drug effectively released from the inactive prodrug but also that they offer additional advantages related to a controlled or targeted release in vivo.

KRAS G12D INHIBITORS

The present invention relates to compounds that inhibit KRas G12D. In particular, the present invention relates to compounds that inhibit the activity of KRas G12D, pharmaceutical compositions comprising the compounds and methods of use therefor.

Compound for organic photoelectric device Composition for organic photoelectric device, organic photoelectric device, and display device

A compound for an organic optoelectronic device, a composition for an organic optoelectronic device including the same, an organic optoelectronic device, and a display device, the compound being represented by a combination of Chemical Formula 1 and Chemical Formula 2:

Atroposelective Synthesis of Conjugated Diene-Based Axially Chiral Styrenes via Pd(II)-Catalyzed Thioether-Directed Alkenyl C-H Olefination

The efficient stereoselective synthesis of conjugated dienes, especially those with axial chirality, remains a great challenge. Herein, we report the highly atroposelective synthesis of axially chiral styrenes with a conjugated 1,3-diene scaffold via a Pd(II)-catalyzed thioether-directed alkenyl C-H olefination strategy. This strategy features easy operation, mild reaction conditions, high functional group tolerance (69 examples), complete Z-selectivity, and excellent enantioselectivities (up to 99% ee). Notably, the highly enantioselective synthesis of atropisomers with two stereogenic axes were also achieved using this strategy (up to 99% ee and 97:3 dr). Moreover, the reaction could be scaled up, and the resulting axially chiral styrenes could be easily oxidized into chiral sulfoxide derivatives with high diastereoselectivities, which showed great promise as a new type of sulfur-olefin ligand.

Synthesis, kinetics, and mechanism of bromophenols by N-bromophthalimide in aqueous acetic acid

The kinetics and mechanism of bromination of phenol and its substituents, viz. 4-chlorophenol, 4-bromophenol, 4-methylphenol, and 4-methoxyphenol by N-bromophthalimide (NBP) in the presence of mercuric acetate in the temperature range of 303–318?K in aqueous acetic acid medium have been investigated. The reaction follows first-order dependence on [NBP] and fractional order dependence of rate on [Phenol]. The activation parameters have been evaluated, and based on the observed kinetic results the probable mechanism has been proposed. Observed kinetic features and Hammett's reaction constant (ρ) suggests that bromination occurs through electrophilic substitution of bromonium ion (Br+) into the aromatic ring in the transition state. Large negative entropy of activation values probably suggests the rigid nature of transition state.

Selenium-catalyzed oxidative c(sp2)-h amination of alkenes exemplified in the expedient synthesis of (Aza-)indoles

A new selenium-catalyzed protocol for the direct, intramolecular amination of C(sp2)-H bonds using N-fluorobenzenesulfonimide as the terminal oxidant is reported. This method enables the facile formation of a broad range of diversely functionalized indoles and azaindoles derived from easily accessible ortho-vinyl anilines and vinylated aminopyridines, respectively. The procedure exploits the pronounced carbophilicity of selenium electrophiles for the catalytic activation of alkenes and leads to the formation of C(sp2)-N bonds in high yields and with excellent functional group tolerance.

A Planar-Chiral Phosphino(alkenyl)ferrocene for Suzuki-Miyaura C-C Coupling Reactions

Planar-chiral phosphinoferrocene [Fe(η5-C5H3-1-PPh2-2-(E)-CH=CHPh)(η5-C5H5)] (4) was applied in the presence of palladium in Suzuki-Miyaura couplings for the synthesis of sterically congested biaryls. The catalytic activity arises from homogeneous palladium phosphine complexes, of which the potential pre-catalyst [Pd(4)2Cl2] was characterized structurally. The catalytic system is excellently suited for the synthesis of tri-ortho-substituted biaryls under mild conditions (0.1 mol-%, 50-100 C), whereas its application towards the synthesis of tetra-ortho-substituted biaryls is quite limited. Comparing the performance of the reaction with 4 as catalyst and a range of substrates with differing ortho substituents suggests that transmetalation is rate determining. Complex (Sp)-4 was used in atropselective couplings, wherein enantioenrichments of up to 36 % were achieved. The stereoselectivity depends to some extent on the steric properties of the boronic acids; however, slight changes at the aryl halides influence the enantioselectivity.

Asymmetric formation of bridged benzoxazocines through an organocatalytic multicomponent dienamine-mediated one-pot cascade

An organocatalytic one-pot cascade leading to the stereoselective formation of novel bridged benzoxazocines is presented. The developed methodology is based on the first example of a γ-selective-Mannich-initiated cascade reaction and allows for direct annulation of the bridged benzoxazocines by incorporation of various α,β-unsaturated aldehydes, electron-rich anilines, and electron-deficient salicylaldehydes. The synthetic applicability of the products is demonstrated by relevant transformations.

A High-Throughput Assay for Arylamine Halogenation Based on a Peroxidase-Mediated Quinone-Amine Coupling with Applications in the Screening of Enzymatic Halogenations

Arylhalides are important building blocks in many fine chemicals, pharmaceuticals and agrochemicals, and there has been increasing interest in the development of more "green" halogenation methods based on enzyme catalysis. However, the screening and development of new enzymes for biohalogenation has been hampered by a lack of high-throughput screening methods. Described herein is the development of a colorimetric assay for detecting both chemical and enzymatic arylamine halogenation reactions in an aqueous environment. The assay is based on the unique UV/Vis spectrum created by the formation of an ortho-benzoquinone-amine adduct, which is produced by the peroxidase-catalysed benzoquinone generation, followed by Michael addition of either a halogenated or non-halogenated arylamine. This assay is sensitive, rapid and amenable to high-throughput screening platforms. We have also shown this assay to be easily coupled to a flavin-dependent halogenase, which currently lacks any convenient colorimetric assay, in a "one-pot" workflow.