100-16-3

Basic information

• Product Name: 4-Nitrophenylhydrazine
• Synonyms: (4-nitrophenyl)-hydrazin;(p-nitrophenyl)-hydrazin;Hydrazine, (4-nitrophenyl)-;Hydrazine, (p-nitrophenyl)-;Hydrazine,(4-nitrophenyl)-;p-Hydrazinonitrobenzene;p-Nitrophenylhydrazide;1-(4-NITROPHENYL)HYDRAZINE
• CAS NO: 100-16-3
• Molecular Formula: C₆H₇N₃O₂
• Molecular Weight: 153.14
• EINECS: 202-824-8
• Product Categories: Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes;Phenylhydrazine;HydrazinesDerivatization Reagents;Derivatization Reagents HPLC;Nitrogen Compounds;Organic Building Blocks;UV-VIS
• Mol File: 100-16-3.mol

Chemical Properties

• Melting Point: 156 °C (dec.)(lit.)
• Boiling Point: 276.04°C (rough estimate)
• Flash Point: 161.8 °C
• Appearance: White to light yellow crystal powder
• Density: 1.00
• Vapor Pressure: 6.79E-05mmHg at 25°C
• Refractive Index: 1.6910 (estimate)
• Storage Temp.: Explosives area
• PKA: 3.81±0.20(Predicted)
• Water Solubility: soluble in hot water
• Merck: 14,6624
• BRN: 608107
• CAS DataBase Reference: 4-Nitrophenylhydrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitrophenylhydrazine(100-16-3)
• EPA Substance Registry System: 4-Nitrophenylhydrazine(100-16-3)

Safety Data

• Hazard Codes: F,Xn
• Statements: 5-11-22-36/37/38-43-21/22
• Safety Statements: 16-26-36/37/39-37/39-36
• RIDADR: UN 3376 4.1/PG 1
• WGK Germany: 3
• RTECS: MV8225000
• F: 4.6
• HazardClass: 4.1
• PackingGroup: I
• Hazardous Substances Data: 100-16-3(Hazardous Substances Data)

Usage

Uses

1. Analytical Chemistry:
4-Nitrophenylhydrazine is used as an analytical reagent for the detection and identification of aldehydes and ketones. Its chemical properties allow it to react with these compounds, providing a means to analyze their presence in a sample.
2. Potential Anticancer Activity:
4-Nitrophenylhydrazine has shown potential anticancer activity, making it a compound of interest for further research and development in the field of oncology. Its irritant properties may also be explored for their potential applications in cancer treatment.
3. Chemical Research:
As a member of the phenylhydrazine class, 4-Nitrophenylhydrazine can be used in various chemical research applications, including the synthesis of other compounds and the study of reaction mechanisms involving aryl hydrazines.

Reactivity Profile

4-NITROPHENYLHYDRAZINE is a powerful explosive. 4-Nitrophenylhydrazine can SELF-IGNITE in the presence of contaminants. Auto-ignition temperature may vary for 4-nitrophenylhydrazine similar to that of hydrazine which has an autoignition of as low as 74oC in contact with iron rust. Dangerous fire hazard or severe explosion can occur when exposed to heat, flame or oxidizing agents. Severe explosion may also occur by chemical reaction with alkali metals; BaO; CaO; K; Na; NH3; Cl2; chromates; CuO; Cu++ salts; F2; H2O2; iron rust; metallic oxides; PbO2;Ni; Ni(ClO4)2; HNO3; N2O; O2; liquid O2; K2Cr2O7; Na2Cr2O7; tetryl; zinc diamide; Zn(C2H5)2. Dangerous; when heated to decomposition 4-Nitrophenylhydrazine emits highly toxic nitrogen compounds; may explode by heat or chemical reaction. (Sax and Lewis, 1987) under Hydrazine p. 538-539.

Health Hazard

Some are toxic and may be fatal if inhaled, swallowed or absorbed through skin. Contact may cause burns to skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may cause pollution.

Safety Profile

Poison by intraperitoneal route.Mutation data reported. When heated to decomposition itemits toxic fumes of NOx. See also NITROCOMPOUNDS OF AROMATIC HYDROCARBONS

Purification Methods

Crystallise the hydrazine from EtOH. The hydrochloride has m 212o(dec) (from EtOH, also m 202-203o dec). [Beilstein 15 III 331, 15 IV 317.]

InChI:InChI=1/C6H7N3O2/c7-8-5-1-3-6(4-2-5)9(10)11/h1-4,8H,7H2

Upstream product

• 100-01-6 4-nitro-aniline 
• 100-05-0 4-nitrobenzenediazonium chloride 
• 603-35-0 triphenylphosphine 
• 91363-26-7 p-nitrophenylazobenzenethiosulfonate 
• 123434-37-7 4-nitrophenylhydrazone of (diisopropoxyphosphoryl)formyl bromide 
• 95-54-5 1,2-diamino-benzene 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 7783-06-4 hydrogen sulfide 
• 7732-18-5 water 
• 64-19-7 acetic acid 
• 40078-29-3 4-nitro-benzenediazo hydroxide 
• 64-17-5 ethanol 
• 2091-61-4 1-chloro-2-(4-nitrophenoxy)benzene 
• 7803-57-8 hydrazine hydrate 

Downstream Products

• 59156-21-7 2-(4-nitrophenyl)thiophene 
• 100128-06-1 tetrahydro-furan-2-carbaldehyde-(4-nitro-phenylhydrazone) 
• 63014-24-4 Ameisensaeure-(4-nitrophenyl)-hydrazid-(4-nitrophenyl)-hydrazon 
• 125663-16-3 syn-(pyridine-4-aldehyde-4-nitrophenylhydrazone) 
• 6294-58-2 3-pyridinealdehyde 4-nitrophenylhydrazone 
• 76160-66-2 hexane-2,5-dione bis-p-nitrophenylhydrazone 
• 91332-46-6 tetrahydro-pyran-4-one-(4-nitro-phenylhydrazone) 
• 20302-89-0 5-methyl-furfurol-(4-nitro-phenylhydrazone) 
• 99989-36-3 1-[3]furyl-ethanone-(4-nitro-phenylhydrazone) 
• 349476-10-4 1-thiophen-2-yl-ethanone (4-nitro-phenyl)-hydrazone 
• 2406-14-6 2,5-dimethyl-pyrrole-3-carbaldehyde-(4-nitro-phenylhydrazone) 
• 108539-94-2 1-[3]furyl-propan-1-one-(4-nitro-phenylhydrazone) 
• 103647-60-5 5-methylsulfanyl-thiophene-2-carbaldehyde-(4-nitro-phenylhydrazone) 
• 29418-58-4 (p-nitrophenylazo)toluene 

Relevant articles and documents

Novel chemoselective reduction of aryldiazonium fluoroborates with Zn- NiCl2·6H2O-THF

Substituted aryldiazonium fluoroborates are selectively reduced to the corresponding phenylhydrazines by using Zn-NiCl2·6H2O in THF as a reducing agent.

Tuned structure and DNA binding properties of metal complexes based on a new 4-acylpyrazolone derivative

It is common knowledge that the spatial structure of substrates is the major influencing factor in DNA binding. To tune the binding affinity of DNA, a new 4-acylpyrazolone derivative ligand, (2-hydroxy-N′-((5-hydroxy-3-methyl-1-(4-nitrophenyl)-4,5-dihydro-1H-pyrazol-4-yl)(phenyl)methylene)benzohydrazide) (H2L) and its three complexes have been prepared and well characterized. Reaction of H2L with CuCl2 resulted in a mononuclear compound with tetra-coordinated quadrilateral plane, [Cu(HL)Cl] (1). When H2L was coordinated to Cu(OAc)2, a dinuclear Cu(ii) compound with chemical formula of [Cu2L2(CH3OH)2]·CH3OH (2) was obtained, and the coordination geometry of Cu(ii) is a square pyramid. Upon assembly of H2L with Mn(OAc)2, a quite different dinuclear compound with chemical composition of [Mn2L2(O CH3)2(H2O)2]·CH3OH (3) was afforded, where Mn(iii) displayed distorted octahedral configurations. DNA binding studies were performed on H2L and its three complexes by means of electron absorption titration and EB-DNA competition experiments, and the results indicate they all bind DNA in an intercalation mode, and their binding affinity follows the order of 1 > 2 > 3 > H2L. In addition, time-dependent density functional theory (TD-DFT) calculations were performed for H2L and its three complexes to better clarify the electronic transitions in the UV-vis spectra.

Visible-light-mediated phosphonylation reaction: formation of phosphonates from alkyl/arylhydrazines and trialkylphosphites using zinc phthalocyanine

In this work, we developed a ligand- and base-free visible-light-mediated protocol for the photoredox syntheses of arylphosphonates and, for the first time, alkyl phosphonates. Zinc phthalocyanine-photocatalyzed Csp2-P and Csp3-P bond formations were efficiently achieved by reacting aryl/alkylhydrazines with trialkylphosphites in the presence of air serving as an abundant oxidant. The reaction conditions tolerated a wide variety of functional groups.

SUBSTITUTED SULFONYL HYDRAZIDES AS INHIBITORS OF LYSINE BIOSYNTHESIS VIA THE DIAMINOPIMELATE PATHWAY

The present invention relates to substituted sulfonyl hydrazides that have the ability to inhibit lysine biosynthesis via the diaminopimelate pathway in certain organisms. As a result of this activity these compounds can be used in applications where inhibition of lysine biosynthesis is useful applications of this type include the use of the compound as herbicides and/or anti- bacterial agents.

Amination of Aromatic Halides and Exploration of the Reactivity Sequence of Aromatic Halides

A base-promoted amination of aromatic halides has been developed using a limited amount of dimethylformamide (DMF) or amine as an amino source. Various aryl halides, including F, Cl, Br, and I, have been successfully aminated in good to excellent yields. Although the amination of aromatic halides with amines or DMF is usually considered as an aromatic nucleophilic substitution (SNAr) process, and the reactivity of an aromatic halide is F > Cl > Br > I, the reactivity of aromatic halides in this system was found to be I > Br a‰ F > Cl. This protocol also showed a good regioselectivity for multihalogenated aromatics. This protocol is valuable for industrial application due to the simplicity of operation, the unrestricted availability of amino sources and aromatic halides, transition metal-free conditions, no requirement for solvent, and scalability.

Oxazolidinones compound and application thereof

The invention provides an oxazolidinones compound shown as the formula VI, or salt, an aquo-complex, or a crystal form of the oxazolidinones compound, which are pharmaceutically acceptable. The invention also provides a preparation method of the compound. In the current field of a chemical drug, activity of most compounds with changed structures becomes better, while toxicity is obviously enhanced, so that the compounds cannot be used as drugs. Compared with a compound in the prior art, the oxazolidinones compound provided in the invention has excellent anti-drug-resistance and antimicrobial activity. What is unexpected is that the oxazolidinones compound has better safety and benefits safe drug use and therapy of a patient.

Synthesis and antifungal activity of substituted 2,4,6-pyrimidinetrione carbaldehyde hydrazones

Opportunistic fungal infections caused by the Candida spp. are the most common human fungal infections, often resulting in severe systemic infections - a significant cause of morbidity and mortality in at-risk populations. Azole antifungals remain the mainstay of antifungal treatment for candidiasis, however development of clinical resistance to azoles by Candida spp. limits the drugs' efficacy and highlights the need for discovery of novel therapeutics. Recently, it has been reported that simple hydrazone derivatives have the capability to potentiate antifungal activities in vitro. Similarly, pyrimidinetrione analogs have long been explored by medicinal chemists as potential therapeutics, with more recent focus being on the potential for pyrimidinetrione antimicrobial activity. In this work, we present the synthesis of a class of novel hydrazone-pyrimidinetrione analogs using novel synthetic procedures. In addition, structure-activity relationship studies focusing on fungal growth inhibition were also performed against two clinically significant fungal pathogens. A number of derivatives, including phenylhydrazones of 5-acylpyrimidinetrione exhibited potent growth inhibition at or below 10 μM with minimal mammalian cell toxicity. In addition, in vitro studies aimed at defining the mechanism of action of the most active analogs provide preliminary evidence that these compound decrease energy production and fungal cell respiration, making this class of analogs promising novel therapies, as they target pathways not targeted by currently available antifungals.

Efficient synthesis of aryl hydrazines using copper-catalyzed cross-coupling of aryl halides with hydrazine in PEG-400

An efficient and convenient method for the synthesis of aryl hydrazines is described via copper-catalyzed cross-coupling of aryl halides with aqueous hydrazine in PEG-400. This protocol is applicable to both electron-deficient and electron-rich aryl iodides and bromides, and even to sterically hindered substrates, giving aryl hydrazines in good to excellent yields.

One-pot synthesis of pyrrolo[3,2-f]-and pyrrolo[2,3-h]quinoline derivatives: Observation of an unexpected mechanistic pathway

One-pot synthesis of pyrrolo[3,2-f]- and pyrrolo[2,3-h]quinolines were obtained starting from substituted 5-aminoindoles, benzaldehydes, and phenylacetylenes in the presence of La(OTf)3 as a catalyst in good yields. The indole moiety in 5-aminoindole is believed to be mainly responsible for the observation of unexpected mechanistic pathway to the formation of pyrrolo[2,3-h]quinoline. Georg Thieme Verlag Stuttgart · New York.

Synthesis and biological activity of pyrazolidine-3,5-dione substituted benzimidazole derivatives

Condensation of o-phenylene diamine with chloro acetic acid gave 2-chloromethyl benzimdazole, which undergoes halide replacement with phenylhydrazines to give the corresponding N,N'-disubstituted hydrazines. Later these compounds were treated with diethyl malonate in presence of acetic acid to get the pyrazolidine-3,5-dione substituted benzimidazole derivatives. The synthesized compounds were subjected to microbiological screening and in vitro antiinflammatory activity.