589-21-9

Basic information

• Product Name: P-BROMOPHENYL HYDRAZINE
• Synonyms: P-BROMOPHENYL HYDRAZINE;1-(4-Bromophenyl)hydrazine;Hydrazine, (p-bromophenyl)-;4-BROMO-PHENYL-HYDRAZINE;AKOS B028819;BUTTPARK 145\18-30;4-Bromophenyl hydrazide;1-Bromo-4-hydrazinobenzene
• CAS NO: 589-21-9
• Molecular Formula: C₆H₇BrN₂
• Molecular Weight: 187.04
• EINECS: 209-640-7
• Mol File: 589-21-9.mol

Chemical Properties

• Melting Point: 102-104
• Boiling Point: 285.6 °C at 760 mmHg
• Flash Point: 126.5 °C
• Appearance: /
• Density: 1.5672 (rough estimate)
• Vapor Pressure: 0.00278mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 4.93±0.20(Predicted)
• CAS DataBase Reference: P-BROMOPHENYL HYDRAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: P-BROMOPHENYL HYDRAZINE(589-21-9)
• EPA Substance Registry System: P-BROMOPHENYL HYDRAZINE(589-21-9)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 589-21-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
P-BROMOPHENYL HYDRAZINE is used as a key intermediate in the synthesis of indoleacetic acid derivatives, which are important compounds in the pharmaceutical industry. These derivatives have potential applications as anti-inflammatory, analgesic, and antipyretic agents.
Used in Chemical Research:
P-BROMOPHENYL HYDRAZINE is also used in the study of transosazonation of sugar phenylosazones. This process involves the formation of osazones, which are derivatives of sugars that can be used for the identification and characterization of different types of sugars. The transosazonation process helps researchers understand the structure and properties of these sugar derivatives, contributing to the advancement of chemical research in the field.

Purification Methods

Crystallise the hydrazine from H2O. The hydrochloride crystallises from EtOH/H2O with m 213-214o, and the tosylate has m 212o (from EtOH). [Beilstein 15 H 434, 15 I 117, 15 II 160, 15 III 289, 15 IV 282.]

InChI:InChI=1/C6H7BrN2/c7-5-1-3-6(9-8)4-2-5/h1-4,9H,8H2

Upstream product

• 103-02-6 acetone phenylhydrazone 
• 108-86-1 bromobenzene 
• 1972-28-7 diethylazodicarboxylate 
• 412328-47-3 N-(4-bromophenyl)-nitramine 
• 7646-78-8 tin(IV) chloride 
• 106-40-1 4-bromo-aniline 
• 622-88-8 4-bromophenylhydrazine hydrochloride 
• 3623-23-2 4-bromonitrosobenzene 
• 7647-01-0 hydrogenchloride 
• 861323-94-6 N-acetyl-N-(4-bromo-phenyl)-N'-(3-nitro-benzoyl)-hydrazine 
• 7664-93-9 sulfuric acid 
• 123-91-1 1,4-dioxane 
• 100125-77-7 4-(4-bromo-phenylhydrazono)-valeric acid 
• 2028-85-5 (4-bromophenyl)diazonium chloride 

Downstream Products

• 91182-63-7 5-nitro-thiophene-2-carbaldehyde-(4-bromo-phenylhydrazone) 
• 92576-84-6 1-(4-nitro-[2]thienyl)-ethanone-(4-bromo-phenylhydrazone) 
• 20034-83-7 phenyl-glyoxal-bis-(4-bromo-phenylhydrazone) 
• 24834-98-8 1-(4-bromophenyl)pyrazolidin-3-one 
• 896736-82-6 N-(4-bromo-phenyl)-N^'-(2,4-dinitro-phenyl)-hydrazine 
• 1075-34-9 5-bromo-2-methyl-1H-indole 
• 1077-20-9 acetone p-bromophenylhydrazone 
• 87084-25-1 di(4-bromophenyl)carbazide 
• 106696-52-0 Quinoxaline-2-carboxaldehyde p-bromophenylhydrazone 
• 130947-83-0 3-<1-(p-Bromophenylhydrazono)-2-hydroxy-2-phenylethyl>quinoxalin-2(1H)-one 
• 130947-85-2 3-(Hydroxy-phenyl-methyl)-quinoxaline-2-carboxylic acid N'-(4-bromo-phenyl)-hydrazide 
• 712299-29-1 N’-(p-bromophenyl) p-toluenesulfonyl hydrazide 

Relevant articles and documents

NOVEL COMPOUNDS AS NADPH OXIDASE INHIBITORS

The present invention is related to new compounds, pharmaceutical composition thereof and to their use for the treatment and/or prophylaxis of disorders or conditions related to Nicotinamide adenine dinucleotide phosphate oxidase (NADPH Oxidase).

5-Bromo-1-(4-chlorobenzyl)-1h-indole-2-carboxamides as new potent antibacterial agents

Ten 5-bromoindole-2-carboxamides were synthesized, characterized and evaluated for antibacterial activity against pathogenic Gram-negative bacteria Klebsiella pneumoniae, Escherichia coli, Pseudomonas aeruginosa and Salmonella Typhi using gentamicin and ciprofloxacin as internal standards. Compounds 7a-c, 7g and 7h exhibit high antibacterial activity with a minimum inhibitory concentration (MIC) of 0.35-1.25 μg/mL. Compounds 7a-c exhibit antibacterial activities that are higher than those of the standards against E. coli and P. aeruginosa.

Lewis Acid Catalyzed Annulation of Cyclopropane Carbaldehydes and Aryl Hydrazines: Construction of Tetrahydropyridazines and Application Toward a One-Pot Synthesis of Hexahydropyrrolo[1,2- b]pyridazines

In this report, a facile synthesis of tetrahydropyridazines via a Lewis acid catalyzed annulation reaction of cyclopropane carbaldehydes and aryl hydrazines has been demonstrated. Moreover, the generated tetrahydropyridazine further participated in a cycloaddition reaction with donor-acceptor cyclopropanes to furnish hexahydropyrrolo[1,2-b]pyridazines. We also performed these two steps in one pot in a consecutive manner. In addition, a monodecarboxylation reaction of hexahydropyrrolo[1,2-b]pyridazine was achieved with a good yield.

Design, synthesis, and antimicrobial activity of novel 5-substituted indole-2-carboxamide derivatives

Abstract: A series of novel, bioactive 5-substituted indole-2-carboxamide derivatives (10a–t and 14a–k) are synthesized by the coupling of 5-substituted indole-2-carboxylic acids with various amines in the presence of EDC HCl/HOBt in DMF/CH2Cl2 as a solvent. In vitro, antibacterial activity of titled compounds against pathogenic bacteria Klebsiella pneumoniae, Escherichia coli, Pseudomonas aeruginosa, Salmonella typhi and antifungal activity against pathogenic fungi Candida albicans, Cryptococcus neoformans, Aspergillus fumigatus, and Candida parapsilosis are evaluated using gentamicin/ciprofloxacin and fluconazole/oxiconazole as standard drugs, respectively. The majority of the synthesized compounds exhibited good antibacterial activity, but surprisingly none showed antifungal activity. Compounds 10c, 10d, 10i, 10j, 10l–n, 14g, 14h, 14i, 14j, and 14k exhibited high inhibitory antibacterial activity with MIC values in the range of 0.12–6.25?μg/mL. Interestingly, compounds 14i, 14j, and 14k exhibited excellent antibacterial activity against K. pneumoniae and E. coli compare to synthesized compound. All the experimental results promote us to consider this series as a starting point for the development of novel and more potent antibacterial agents in the future. Graphical Abstract: [Figure not available: see fulltext.]

Synthesis and biological evaluation of benzimidazole phenylhydrazone derivatives as antifungal agents against phytopathogenic fungi

A series of benzimidazole phenylhydrazone derivatives (6a-6ai) were synthesized and characterized by 1H-NMR, ESI-MS, and elemental analysis. The structure of 6b was further confirmed by single crystal X-ray diffraction as (E)-configuration. All the compounds were screened for antifungal activity against Rhizoctonia solani and Magnaporthe oryzae employing a mycelium growth rate method. Compound 6f exhibited significant inhibitory activity against R. solani and M. oryzae with the EC50 values of 1.20 and 1.85 μg/mL, respectively. In vivo testing demonstrated that 6f could effectively control the development of rice sheath blight (RSB) and rice blast (RB) caused by the above two phytopathogens. This work indicated that the compound 6f with a benzimidazole phenylhydrazone scaffold could be considered as a leading structure for the development of novel fungicides.

Synthesis of benzofuro[3,2-b] indoline amines via deamination-interrupted Fischer indolization and their unexpected reactivity towards nucleophiles

We report the access to the benzofuro[3,2-b]indoline framework of phalarine from benzofuran-2-ones via the Fischer indolization reaction which was interrupted at the deamination step. Unexpectedly, allyl nucleophiles did not add to the aminal position of these benzofuro[3,2-b]indoline amines but to the adjacent ring junction center in the presence of trifluoroborane to deliver 3,3-disubstituted indolines containing a difluoroboron-containing six-membered ring with fluorescence properties.

MULTICYCLIC COMPOUND INCLUDING NITROGEN AND ORGANIC LIGHT EMITTING DEVICE USING THE SAME

The present invention relates to a nitrogen-containing polycyclic compound and an organic light emitting device including the same. According to an embodiment of the present invention, the nitrogen-containing polycyclic compound can be used to form an organic layer in the organic light emitting device.COPYRIGHT KIPO 2015

Probing the molecular and structural elements of ligands binding to the active site versus an allosteric pocket of the human farnesyl pyrophosphate synthase

In order to explore the interactions of bisphosphonate ligands with the active site and an allosteric pocket of the human farnesyl pyrophosphate synthase (hFPPS), substituted indole and azabenzimidazole bisphosphonates were designed as chameleon ligands. NMR and crystallographic studies revealed that these compounds can occupy both sub-pockets of the active site cavity, as well as the allosteric pocket of hFPPS in the presence of the enzyme's Mg2+ ion cofactor. These results are consistent with the previously proposed hypothesis that the allosteric pocket of hFPPS, located near the active site, plays a feed-back regulatory role for this enzyme.

Remazol-Catalyzed Hydroperoxyarylation of Styrenes

A mild photocatalytic hydroperoxyarylation of styrenes has been developed, in which a novel photocatalyst, remazol brilliant blue R (RBBR), is employed at low catalytic loading (1 mol%). The operationally easy procedure uses air as the dioxygen source. Simple mono-substituted styrenes react with aryl hydrazines in moderate-to-good yields. RBBR is proposed to act as a photosensitizer for the generation of singlet oxygen.

Design, synthesis and photophysical properties of A-D-A-D-A small molecules for photovoltaic application

A series of linear-conjugated small molecule compounds featured with the acceptor-donor-acceptor-donor-acceptor (A-D-A-D-A) structure were designed, synthesized and characterized. The films of the compounds showed a broad UV-Vis absorption range of 300-800 nm with high molar absorption coefficient of more than 1.0 × 104 cm-1. Their hole-mobility can be as high as 1.0 × 10-3 cm2 V-1 s-1. The compounds have a compatible HOMO energy level of -5.0 eV to PC71BM and a high solubility up to 20 mg mL-1 in chloroform. Therefore, compounds can blend with PC71BM in the chloroform and form an active layer for a photovoltaic cell device by spin-coating of the blend solution. A maximum power conversion efficiency of 3.2% was achieved with the DERH3TT solar cell device. These results indicate that the A-D-A-D-A small molecules with electron-withdrawing dyes as terminals are promising candidates for the high efficiency solution processed organic photovoltaic cells.