40530-18-5

Usage

Chemical Properties

Off-white crystalline

InChI:InChI=1/C7H4BrNO/c8-6-1-2-7(10)5(3-6)4-9/h1-3,10H

Upstream product

• 1761-61-1 5-bromosalicyclaldehyde 
• 611-20-1 salicylonitrile 
• 13589-72-5 5-chloro-2-hydroxybenzonitrile 
• 50-00-0 formaldehyd 
• 106-41-2 4-bromo-phenol 
• 82486-43-9 2-hydroxy-5-bromobenzaldehyde oxime 
• 144649-99-0 5-bromo-2-methoxybenzonitrile 
• 14804-31-0 2-methyl-4-bromoanisole 
• 184970-28-3 4-bromo-2-(bromomethyl)-1-methoxybenzene 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 98550-54-0 5-bromo-2-hydroxy-benzamide oxime 
• 636992-52-4 5-bromo-2-cyanomethoxy-benzonitrile 
• 328009-03-6 (4-bromo-2-cyanophenoxy)acetic acid ethyl ester 
• 295346-39-3 5-bromo-2-(2-oxopropoxy)benzonitrile 
• 688757-63-3 (3-Amino-5-bromobenzofuran-2-yl)(4-chlorophenyl)methanone 
• 609804-46-8 t-butyl (4-bromo-2-cyanophenoxy)acetate 
• 949019-88-9 5-bromo-2-(tert-butyldimethylsilanyloxy)benzonitrile 
• 851382-94-0 5-bromo-2-hydroxybenzimidamide 
• 876918-26-2 5-bromo-2-isobutoxy-benzonitrile 
• 52899-63-5 5-butyl-2-hydroxybenzonitrile 
• 1169559-70-9 4-bromo-2-cyanophenyl tert-butyl carbonate 
• 318259-87-9 2-(4-bromo-2-cyanophenoxy)acetamide 
• 1033602-66-2 5-bromo-2-(methoxymethoxy)benzonitrile 
• 1033602-79-7 5-bromo-2-(3,3-dimethyl-butoxy)benzonitrile 

Relevant academic research and scientific papers

Preparation method for 4-substituted piperidine derivative

The invention discloses a preparation method for a 4-substituted piperidine derivative, i.e., 4-((2-(aminomethyl)-4-bromophenoxyl)methyl)piperidine-1-t-butyl formate. According to the invention, 5-bromo-2-hydroxybenzaldehyde is used as a starting material and subjected to oximation, elimination, etherification and catalytic hydrogenation so as to prepare the target derivative. The prepared derivative is an important medical intermediate.

Method for preparing piperazine derivatives

The invention discloses a method for preparing piperazine derivatives 4-((2-(cyanobenzylamine hydrochloride)-4-bromobenzene oxygroup) methyl) piperazine-1-tert-butyl formate. The piperazine derivatives are made of 5-bromine-2-hydroxybenzaldehyde which is used as a starting material. The method includes carrying out oximation, elimination, etherification and catalytic hydrogenation reaction to obtain target products. The method has the advantage that the piperazine derivatives which are chemical compounds are important pharmaceutical intermediates.

Utility of Nitrogen Extrusion of Azido Complexes for the Synthesis of Nitriles, Benzoxazoles, and Benzisoxazoles

The utility of the nitrogen extrusion reaction of azido complexes, generated in situ from the corresponding aldehydes or ketones with TMSN3 in the presence of ZrCl4 or TfOH, has been described. These azido complexes could undergo three different pathways, depending on the substrates. First, azido methanolate complexes or imine diazonium ions could lead to benzisoxazole products via an intramolecular nucleophilic substitution. Second, imine diazonium ions could also undergo either the elimination of proton to provide nitrile products in good to excellent yields or an aryl migration, followed by an intramolecular nucleophilic addition, to give benzoxazole products in good yields.

Facile one-pot transformation of phenols into o-cyanophenols

The treatment of phenols with paraformaldehyde in the presence of MgCl2 and Et3N in THF at 80 C, followed by reaction with molecular iodine and aq. ammonia at room temperature provided the corresponding o-cyanophenols in moderate to good yields. The present reaction is a one-pot transformation of phenols into o-cyanophenols using much less expensive reagents than are typically used; the reaction is free of both transition-metals and cyanide. The utility of this reaction was highlighted during our preparation of Febuxostat from p-bromophenol.

Synthesis and biological evaluation of some novel benzofuranpyridine derivatives

5-Bromo-3-amino-2-acetyl benzofuran 3 was prepared by the reaction of 5- bromosalicylonitrile 2 with chloroacetone in dry acetone in presence of anhydrous potassium carbonate to maintain basic condition. The Claisen-Schmidt condensation of compound 3 with various substituted aromatic aldehydes in presence of strong base in absolute ethanol gave 5-bromo-3-amino-2-arylidine acetyl benzofuran 4a-f in good yields. The compounds 4a-f upon treatment with orthophosphoric acid in acetic acid underwent cyclisation and resulted in the formation of above titled compounds 5a-f. All synthesized compounds were characterized on the basis of its physical constant, analytical and spectral studies. Further these compounds were evaluated for their antibacterial and antifungal activities.

Direct oxidative conversion of methylarenes into aromatic nitriles

A variety of methylarenes were successfully converted into the corresponding aromatic nitriles in good to moderate yields by the treatment with NBS or DBDMH in the presence of a catalytic amount of AIBN or BPO, followed by the reaction with molecular iodine in aq NH3 in a one-pot procedure. The present reaction is a useful and practical transition-metal-free method for the preparation of aromatic nitriles from methylarenes.

Heterogeneous catalytic method for the conversion of aldoximes into nitriles using molecular sieve modified with Copper(II)

A simple heterogeneous metal-catalyzed method was developed for the transformation of aldoximes into nitriles. Molecular sieve (4 A) modified with copper(II) proved to be an efficient catalyst for the conversion. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

Synthesis and antiinflammatory activity of 1H-pyrazolines bearing 5-bromo-3-amino benzofuran

5-Bromo-3-amino-2-acetyl banzofuran 3 was prepared by the interaction of 5-bromosalicylonitrile and chloroacetone in presence of anhyd potassium carbonate in dry acetone. The compound 3 was treated with different substituted aromatic aldehydes in ethanol in presence of strong alkali to give 5-bromo-3-amino-2-arylidene acetylbenzofurans (4a-e). 5-(3-Amino-5- bromobenzofuran)-3-aryl-2-pyrazolines (5ae) were synthesized by the reaction of 5-bromo-3-amino-2-arylidene acetylbenzofurans (4a-e) with hydrazine hydrate. The reaction of compounds (5a-e) with chloroacetyl chloride in presence of triethylamine in dry toluene furnished 5-aryl-3-[5'-bromo-3'-(chloroacetyl)- aminobenzofuran-2-yl]-1H-pyrazolines (6a-e). All synthesized compounds were screened for their antimicrobial activities and some selected benzofuran pyrazoline derivatives were screened for antiinflammatory activities.

P-Hydroxyphenacyl photoremovable protecting groups Robust photochemistry despite substituent diversity

A broadly based investigation of the effects of a diverse array of substituents on the photochemical rearrangement of p-hydroxyphenacyl esters has demonstrated that common substituents such as F, MeO, CN, CO2R, CONH2, and CH3 have little effect on the rate and quantum efficiencies for the photo-Favorskii rearrangement and the release of the acid leaving group or on the lifetimes of the reactive triplet state. A decrease in the quantum yields across all substituents was observed for the release and rearrangement when the photolyses were carried out in buffered aqueous media at pHs that exceeded the ground-state pKa of the chromophore where the conjugate base is the predominant form. Otherwise, substituents have only a very modest effect on the photoreaction of these robust chromophores.

Synthesis of some pyrazole incorporated benzofurans and their antiinflammatory activity

The reaction of 5-bromosalicylaldehyde 1 with hydroxylamine hydrochloride gave 5-bromosalicylonitrile 2 which upon condensation with ethyl chloroacetate followed by cyclization gave ethyl 3-amino-5-bromo-1-benzofuran-2-carboxylate 4. The compound 4 on treatment with hydrazine hydrate in ethanol gave 3-amino-5-bromo-1-benzofuran-2-carbohydrazide 5 which further on reaction with various substituted acetophenones in abs ethanol in presence of catalytic quantity of hydrochloric acid furnished corresponding hydrazones 6a-e. The title compounds 7a-e were synthesized by the reaction of 6a-e with Vilsmerier-Haack reagent. The structures of all synthesized compounds were established using analytical and spectral data. 6a-e and 7a-e have been evaluated for antiinflammatory activities.