52311-59-8

Basic information

• Product Name: 4-Chloro-2-nitrobenzyl bromide
• Synonyms: 4-Chloro-2-nitrobenzyl bromide;2-Nitro-4-chlorobenzyl bromide
• CAS NO: 52311-59-8
• Molecular Formula: C₇H₅BrClNO₂
• Molecular Weight: 250.4771
• Mol File: 52311-59-8.mol

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4-Chloro-2-nitrobenzyl bromide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-2-nitrobenzyl bromide(52311-59-8)
• EPA Substance Registry System: 4-Chloro-2-nitrobenzyl bromide(52311-59-8)

Safety Data

• Hazardous Substances Data: 52311-59-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-2-nitrobenzyl bromide is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its ability to participate in nucleophilic substitution and reduction reactions allows for the creation of a diverse range of medicinal agents, contributing to the advancement of drug discovery and therapeutic options.
Used in Agrochemical Industry:
In the agrochemical sector, 4-Chloro-2-nitrobenzyl bromide serves as a key intermediate in the synthesis of agrochemicals. Its reactivity and capacity to form a variety of compounds make it instrumental in the production of pesticides, herbicides, and other agricultural chemicals that are essential for crop protection and yield enhancement.
Used in Dye Industry:
4-Chloro-2-nitrobenzyl bromide is utilized as a chemical intermediate in the dye industry. Its involvement in the synthesis of dyes facilitates the creation of a wide array of colorants used in various applications, including textiles, plastics, and printing inks, enriching the color palette and improving the performance of these products.
Used in Organic Synthesis:
As a reagent in organic synthesis, 4-Chloro-2-nitrobenzyl bromide is employed for its ability to undergo nucleophilic substitution and reduction, enabling the formation of a multitude of organic compounds. Its versatility in reactions makes it a valuable component in the synthesis of complex organic molecules for research and industrial applications.

Upstream product

• 89-59-8 4-chloro-2-nitrotoluene 
• 22996-18-5 (4-chloro-2-nitrophenyl)methanol 
• 6280-88-2 4-chloro-2-nitro-benzoic acid 
• 5551-11-1 4-Chloro-2-nitrobenzaldehyde 

Downstream Products

• 56465-80-6 2-(4-Chlor-2-nitro-benzyl)-2-acetamino-malonsaeure-diethylester 
• 114688-64-1 2-(2-nitro-4-chlorobenzyl)-1,2,3,4-tetrahydroisoquinoline 
• 114688-66-3 2-(4-chloro-2-nitrobenzyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline 
• 152436-72-1 2-(4-Chloro-2-nitro-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline 
• 85062-27-7 (4-Chloro-2-nitro-benzyl)-(4-methoxy-benzyl)-amine; hydrochloride 
• 122488-79-3 6-Chloro-9-(4-chloro-2-nitro-benzyl)-2-trifluoromethyl-9H-purine 
• 144619-17-0 N-Boc-L-alanine (4-chloro-2-nitro)benzyl ester 
• 121-73-3 3-Nitrochlorobenzene 
• 185826-39-5 (2S,5S)-1-(tert-Butyloxycarbonyl)-2-(tert-butyl)-3-methyl-5-(4'-chloro-2'-nitrobenzyl)-1,3-imidazolidine-4-one 
• 185826-41-9 (2S,5S)-1-(tert-Butyloxycarbonyl)-2-(tert-butyl)-3,5-dimethyl-5-(4'-chloro-2'-nitrobenzyl)-1,3-imidazolidine-4-one 
• 5551-11-1 4-Chloro-2-nitrobenzaldehyde 
• 52311-60-1 4-chloro-2-nitrobenzylphosphonic acid diethyl ester 
• 122488-36-2 [9-(2-Amino-4-chloro-benzyl)-2-trifluoromethyl-9H-purin-6-yl]-dimethyl-amine 
• 122488-35-1 [9-(4-Chloro-2-nitro-benzyl)-2-trifluoromethyl-9H-purin-6-yl]-dimethyl-amine 

Relevant articles and documents

3-OXAZOLINONE COMPOUND, PREPARATION METHOD THEREFOR AND PHARMACEUTICAL APPLICATION THEREOF

The present invention relates to a novel 3-indazolinone compound that regulates or inhibits the activity of indoleamine 2,3-dioxygenase (IDO), the method for the preparation thereof and the use thereof in medicine. In particular, the present invention relates to a compound represented by the general formula (I) and a pharmaceutically acceptable salt thereof, a pharmaceutical composition comprising the compound or a pharmaceutically acceptable salt thereof, a method for treating or preventing IDO-mediated diseases, especially tumors, by use of the compound or a pharmaceutically acceptable salt thereof, and a method for preparing the compound or a pharmaceutically acceptable salt thereof. The present invention further relates to use of the compound or a pharmaceutically acceptable salt thereof or a composition comprising the compound or a pharmaceutically acceptable salt thereof in the manufacture of a medicament for treating or preventing IDO-mediated diseases, especially tumors.Wherein the substituents of the general formula (I) are defined the same as that in the specification.

Intramolecular Pd-catalyzed reductive amination of enolizable sp3-C-H bonds

A palladium-catalyzed reductive cyclization of nitroarenes has been designed to construct sp3-C-NHAr bonds from sp3-C-H bonds by using an enolizable nucleophile to intercept a nitrosoarene intermediate. Exposure of ortho-substituted nitroarenes to 5 mol ?% of Pd(OAc)2 and 10 mol ?% of phenanthroline under 2 atm of CO constructs partially saturated 5-, 6-, or 7-membered N-heterocycles using α-pyridyl carboxylates, malonates, 1,3-dimethylbarbituric acid, 1,3-diones, or difurans as the nucleophile.

Access to Chiral Seven-Member Cyclic Amines via Rh-Catalyzed Asymmetric Hydrogenation

A highly efficient asymmetric hydrogenation of azepine/oxazepine-type seven-member cyclic imine hydrochlorides was successfully developed using Rh/bisphosphine-thiourea ligand ZhaoPhos, affording various chiral seven-member cyclic amines with full conversions, high yields, and excellent enantioselectivities (up to 96% yield, >99% ee). Additionally, this asymmetric hydrogenation can proceed well on gram scale with excellent ee value. Moreover, control experimental results displayed that the anion-bonding interaction between the chloride ion of the substrate and thiourea motif of the ZhaoPhos played an important role to obtain excellent enantioselectivity.

Rh2(II)-catalyzed selective aminomethylene migration from styryl azides

Rh2(II)-Carboxylate complexes were discovered to promote the selective migration of aminomethylenes in β,β-disubstituted styryl azides to form 2,3-disubstituted indoles. Mechanistic data are also presented that suggest that the migration occurs stepwise before diffusion of the iminium ion.

Discovery of a clinical stage multi-kinase inhibitor sodium (E)-2-{2-methoxy-5-[(2′,4′,6′-trimethoxystyrylsulfonyl)methyl] phenylamino}acetate (ON 01910.Na): Synthesis, structure-activity relationship, and biological activity

Cyclin D proteins are elevated in many cancer cells, and targeted deletion of cyclin D1 gene in the mammary tissues protects mice from breast cancer. Accordingly, there is an increasing awareness of this novel nonenzymatic target for cancer therapeutics. We have developed novel, nonalkylating styrylbenzylsulfones that induce cell death in wide variety of cancer cells without affecting the proliferation and survival of normal cells. The development of derivatized styrylbenzylsulfones followed logically from a tumor cell cytotoxicity screen performed in our laboratory that did not have an a priori target profile. Modifications of some of the precursor molecules led to lead optimization with regard to tumor cell cytotoxicity. In this report we describe the synthesis and structure-activity relationships of novel, nonalkylating (E)-styrylbenzylsulfones and the development of the novel anticancer agent sodium (E)-2-{2-methoxy-5-[(2′,4′,6′- trimethoxystyrylsulfonyl)methyl]phenylamino}acetate (ON 01910.Na), which is in phase III trials for myelodysplastic syndromes (MDS) associated with aberrant expression of cyclin D proteins.

AMINO SUBSTITUTED DIARYL [A, D] CYCLOHEPTENE ANALOGS AS MUSCARINIC AGONISTS AND METHODS OF TREATMENT OF NEUROPSYCHIATRIC DISORDERS

Disclosed herein are analogs of clozapine and pharmaceutically acceptable salts, esters, amides, or prodrugs thereof; methods of synthesizing the analogs; and methods of using the analogs for treating neuorpsychiatric disorders. In some embodiments, the analogs are amino substituted diaryl[a,d]cycloheptenes.

A general strategy for the synthesis of cyclic N-aryl hydroxamic acids via partial nitro group reduction

We describe a generalized approach to stereocontrolled synthesis of substituted cyclic hydroxamic acids (3-amino-1-hydroxy-3,4-dihydroquinolinones) by selective reduction of substituted 2-nitrophenylalanine substrates. Compounds in this series have antibacterial properties and have also recently been reported as KAT II inhibitors. The key nitrophenyl alanine intermediates are prepared enantioselectively in excellent yield by phase transfer catalyzed alkylation of the corresponding nitrobenzyl bromides. The scope and limitations of the reductive cyclization transformation have been explored with attention to the effects of substitution pattern and electronics on reaction efficiency and byproduct formation. In addition, a novel activated trifluoroethyl ester cyclization strategy has been developed as an alternate approach to the most sterically demanding systems in this series.

Selenium-catalyzed reductive cyclization and carbocyclization of 2,2′-dinitrostilbenes with carbon monoxide: One-shot synthesis of indolo[1,2-c]quinazolinones

When 2,2′-dinitrostilbene derivatives were allowed to react with carbon monoxide in the presence of a catalytic amount of selenium, reductive cyclization and carbocyclization proceeded to give indolo[1,2-c]quinazolin-6(5H) -ones, containing both indole an

Synthesis and structure-activity relationships of N-aryl(indol-3-yl)glyoxamides as antitumor agents

The synthesis and study of the structure-activity relationships of cytotoxic compounds based on N-pyridinyl or N-aryl-2-(1-benzylindol-3-yl)glyoxamide skeleton, represented by the lead structures D-24241 and D-24851, are described. The presence of N-(pyridin-4-yl) moiety was crucial for activity and 2-[1-(4-chloro-3-nitrobenzyl)-1H-indol-3-yl]-2-oxo-N-(pyridin-4-yl)aceta mide (55), the most potent derivative, showed IC50 = 39 nM, 51 nM and 11 nM against HeLa/KB (human cervix carcinoma), L1210 (murine leukemia) and SKOV3 (human ovarian carcinoma) cell lines proliferation assay, respectively, as active as the lead compounds.

Synthesis of substituted 10,11-dihydro-5H-dibenz[b,f]azepines; key synthons in syntheses of pharmaceutically active compounds

Substituted 10,11-dihydro-5H-dibenz[b,f]azepines are key synthons in the syntheses of a number of pharmaceutically active compounds such as imipramine, chlorimipramine, and desimipramine analogues. A facile synthesis of substituted 10,11-dihydro-5H-dibenz[b,f]azepines is described, starting out from commercially available 2-bromotoluenes or 2-nitrotoluenes. Initial α-bromination with N-bromosuccinimide and subsequent reaction with triethylphosphite afforded the corresponding benzyl phosphonic ester derivatives. After reaction with benzaldehyde derivatives, the expected Horner-Emmons reaction products were obtained. Hydrogenation gave the amino derivatives which were transformed into the corresponding formamides. Under Goldberg conditions [1], the final ring closing step was performed to give the substituted 10,11-dihydro-5H-dibenz[b,f]azepines in 46-75% yield.