106896-49-5

Usage

Chemical Properties

brown crystalline powder

InChI:InChI=1/C8H8BrNO2/c1-12-8(11)5-2-3-7(10)6(9)4-5/h2-4H,10H2,1H3

Upstream product

• 124-41-4 sodium methylate 
• 67-56-1 methanol 
• 6311-37-1 4-amino-3-bromo-benzoic acid 
• 150-13-0 4-amino-benzoic acid 
• 619-45-4 4-methoxycarbonyl aniline 

Downstream Products

• 1006863-61-1 C₁₆H₁₃BrN₂O₃S 
• 1006863-62-2 C₁₆H₁₂BrN₃O₅S 
• 619-45-4 4-methoxycarbonyl aniline 
• 6311-37-1 4-amino-3-bromo-benzoic acid 
• 1086063-75-3 C₁₈H₁₄BrN₃O₃S₂ 
• 1115276-62-4 tert-butyl 4-(methoxycarbonyl)-2-bromophenylcarbamate 
• 1032373-57-1 4-amino-3-naphthalen-2-ylbenzoic acid methyl ester 
• 1188322-48-6 methyl 3-bromo-4-(2-phenylacetamido)benzoate 
• 524916-42-5 methyl 4-amino-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 
• 162959-43-5 6-methoxycarbonyl-2-mercaptobenzothiazole 
• 1329167-04-5 4-amino-3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-benzoic acid methyl ester 
• 1150112-11-0 methyl 3-bromo-4-[(trimethylsilyl)ethynyl]benzoate 
• 1378284-27-5 methyl 3-[(4-methoxyphenyl)ethynyl]-4-[(trimethylsilyl)-ethynyl]benzoate 
• 1378284-29-7 methyl 4-ethynyl-3-[(4-methoxyphenyl)ethynyl]benzoate 

Relevant academic research and scientific papers

Synthesis of phenazine-2,8-dicarboxylates

Phenazine is a tricyclic heteroarene that forms the core of diverse functional molecules including DNA intercalators. However, 2,8-disubstituted phenazines are rare, and this potentially limits the medicinal development of this class of heterocycles. Here we describe the synthesis of two new members of this compound class (i.e. dimethyl phenazine-2,8-dicarboxylate and the corresponding diacid), following a synthetic route that involved inter- and intramolecular Buchwald-Hartwig N-arylations. We also detail a simple NMR-based method for proving the 2,8-disubstitution pattern, in order to counterbalance suspected structural misassignments elsewhere in the peer-reviewed and patent literature.

Synthesis and biological evaluation of an antibacterial azaborine retinoid isostere

Our continued synthetic interest in this class of retinoids, CD437 and its analogs, against methicillin-resistant Staphylococcus aureus (MRSA) has brought us to explore further isosteric substitutions within the scaffold. Although our previous findings ha

A Practical Procedure for Regioselective Bromination of Anilines

A highly practical procedure for the preparation of bromoanilines by using copper-catalyzed oxidative bromination has been developed. Treatment of free anilines with readily available NaBr and Na 2S 2O 8in the presence of a catalytic amount of CuSO 4·5H 2O enabled regioselective bromination.

METHOD FOR PRODUCING AROMATIC HALOGEN DERIVATIVE

PROBLEM TO BE SOLVED: To provide a highly efficient and economically advantageous method for producing a halogen compound. SOLUTION: The method produces a halogen compound represented by formula (2) (X is a halogen atom, and b is an integer of 1-5) by reacting an aniline derivative represented by formula (1) (R1 is an ester group, a carbonyl group, a nitrile group, a nitro group, an optionally substituted alkyl group or an optionally substituted aralkyl group, and a is an integer of 0-4) with a halogenating agent in the presence of a copper catalyst and a persulfate. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

NEW CLASS OF DNA GYRASE AND/OR TOPOISOMERASE IV INHIBITORS WITH ACTIVITY AGAINST GRAM-POSITIVE AND GRAM-NEGATIVE BACTERIA

The present invention relates to compounds having a structure of general formula (I), processes for their preparation, pharmaceutical compositions containing them as the active ingredient, to their use as medicaments and to their use in the manufacture of medicaments for use in the treatment of bacterial infections in humans and warm-blooded animals.

Cu-mediated selective bromination of aniline derivatives and preliminary mechanism study

A simple and efficient bromination of aniline, aniline derivatives, and analogs have been developed. Forty three examples were given and the highest yield reached was 98%. Different substrates including substituted aniline, pyridin-amine, N-substituted aniline, N,N-disubstituted aniline, N-phenyl-amide, N-phenyl-sulfonamide, and nitrogen-containing heterocycles were all reactive and selectively generated desired bromo-products. The method can be applied to synthesize drug intermediate and quinoxaline derivatives.

Direct Synthesis of Structurally Divergent Indole Alkaloids from Simple Chemicals

A direct and structurally divergent synthesis of indole alkaloids from very simple 2-vinylanilines, alkynes and TBN via a novel substrate fragmentation/cycloaddition strategy has been developed, which provides an efficient noble-metal-free approach to access a library of highly valuable indole derivatives of tryptamines and tryptamine-related oximes, lactams, and lactones, as well as β-carbolines, spiroindolines, and hexa-hydropyrrolo[2,3-b]indoles.

Direct Tryptophols Synthesis from 2-Vinylanilines and Alkynes via C - C Triple Bond Cleavage and Dioxygen Activation

An unexpected metal-free C - C triple bond cleavage, dioxygen activation, and reassembly into tryptophol derivatives has been developed. This chemistry provides a novel, simple, and efficient approach to highly valuable tryptophol derivatives from simple substrates under mild conditions. The mechanistic studies may promote the discovery of new methodologies through C-C bond cleavage and dioxygen activation.

Efficient and Practical Oxidative Bromination and Iodination of Arenes and Heteroarenes with DMSO and Hydrogen Halide: A Mild Protocol for Late-Stage Functionalization

An efficient and practical system for inexpensive bromination and iodination of arenes as well as heteroarenes by using readily available dimethyl sulfoxide (DMSO) and HX (X = Br, I) reagents is reported. This mild oxidative system demonstrates a versatile protocol for the synthesis of aryl halides. HX (X = Br, I) are employed as halogenating reagents when combined with DMSO which participates in the present chemistry as a mild and inexpensive oxidant. This oxidative system is amenable to late-stage bromination of natural products. The kilogram-scale experiment (>95% yield) shows great potential for industrial application.

Palladium-catalyzed carbonylative synthesis of benzoxazinones from N -(o -bromoaryl)amides using paraformaldehyde as the carbonyl source

Carbonylation reactions have been widely used in organic synthesis. However, the manipulation of toxic and pressurized carbon monoxide limited their applications in organic laboratories. The search for alternative carbonyl sources as an important method for carbonylative organic synthesis is spreading. Herein, a series of substituted benzoxazinones were synthesized from N-(o-bromoaryl)amides by palladium-catalyzed carbonylation with paraformaldehyde as the carbonyl source, which is inexpensive, stable, and easy to use. Notably, this is the first example of using paraformaldehyde as the CO source in palladium-catalyzed carbonylative synthesis of heterocycles.