100-63-0 Usage
Chemical Description
Phenylhydrazine and benzoylhydrazine are both hydrazine derivatives that contain a phenyl and benzoyl group, respectively.
Uses
1. Used in Pesticide Production:
Phenylhydrazine is used as an intermediate for synthesizing various organophosphorus pesticides, such as triazophos, pyridaphenthione, famoxadone, and fenamidone.
2. Used in Dye and Pharmaceutical Industries:
Phenylhydrazine serves as an intermediate for the production of Naphthol AS-G and drugs like antipyrine. It is also used in the preparation of various dyes and pharmaceutical compounds.
3. Used in Chemical Analysis:
Phenylhydrazine is used as a reagent for aldehydes, ketones, and sugars in chemical analysis. It can be used for the photometric determination of aluminum, chromium, copper, molybdenum, titanium, and zirconium, as well as for the verification of gold, iridium, molybdenum, palladium, platinum, and silver.
4. Used in Organic Synthesis:
Phenylhydrazine is used as an intermediate in organic synthesis, including the production of phenylhydrazone, which can be used for further synthesis.
5. Used in the Investigation of Oligosaccharides and Photosystem II Structure:
Phenylhydrazine is used in the preparation of osazones or diphenylhydrazones, which are yellow solids with definite melting points and are utilized in the identification of sugars and the investigation of oligosaccharides and the structure of photosystem II.
6. Used as a Stabilizer for Explosives:
Phenylhydrazine is used as a stabilizer in the manufacture of explosives.
7. Used as a Reducing Agent:
Phenylhydrazine can be used as a reducing agent for colorimetric assay of phosphorus acid.
8. Used in Precipitation of Metals:
As a weak base, phenylhydrazine can be used to precipitate lead, chromium, and other trivalent and tetravalent elements in the form of hydroxides.
Hydrazine derivative
Phenylhydrazine is also known as the hydrazinobenzene. It was first successfully synthesized by the German organic chemist Hermann-Emil-Fischer in 1875 and is the first synthesized hydrazine derivatives. At room temperature, it is a pale yellow crystalline or oily liquid while at low temperature it appears as monoclinic prismatic crystals. It can be easily subject to oxidization in the air and exhibit dark brown or dark red.
Phenylhydrazine is one of the hydrazine derivatives and is often abbreviated as PhNHNH2. It is slightly soluble in water and alkali solution and can be dissolved in dilute acid. It is miscible with ethanol, ethyl ether, chloroform and benzene. Common method of its preparation is through the reaction between aniline and sodium nitrite under the action of hydrochloric acid for generation of diazonium salt which is then reduced by sulfite/sodium reduction for obtaining it. Acid precipitation can generate phenylhydrazine hydrochloride with neutralization generating phenylhydrazine.
Phenylhydrazine can be applied to making dyes, drugs, and being used as developer. It is also an important reagent for identification of carbonyl group and can be used for identifying aldehydes, ketones and carbohydrates. It can react with benzaldehyde to generate phenylhydrazine. We can use the hydrazone generated through phenylhydrazine or 2, 4-dinitrophenylhydrazine to identify aldehydes and ketones, It can trigger Fischer indole synthesis upon reaction with aldehydes and ketones (first found by the Emil Hermann Fischer in 1883, the reaction is using phenylhydrazine and aldehyde, ketone for heating and rearrangement under acid-catalysis for the elimination of one molecule of ammonia to give 2-or 3-substituted indole.) to give indole ring-class compound.
Hermann Emil Fischer
Phenylhydrazine (Hydrazinobenzene) is the chemical compound characterized by Hermann Emil Fischer in 1895. Fischer is a German organic chemist. He used phenylhydrazine to react with carbohydrate and generate hydrazone and osazone and form a crystalline compound which is easy for purification. Then it is decomposed into pure sugar. This is a powerful means for studying carbohydrate structures and synthesis of a variety of sugars and enables the theoretic clarification of the structure of glucose and summarizing of the general stereoisomerism phenomenon of saccharides and further using of Fischer projection for describing it. He has also demonstrated that the caffeine, theophylline, uric acid all belongs to purine derivatives and also had successfully synthesized purine. He also had opened up the study of proteins and had demonstrated that amino acids forms polypeptide via peptide bond and successfully synthesized polypeptides. In 1902, Fischer, because of the synthesis of purine and carbohydrate, was awarded for the Nobel Prize in Chemistry.
The above information is edited by the lookchem of Dai Xiongfeng.
Phenylhydrazine: preparation and application
Phenylhydrazine is the first synthetic hydrazine derivatives which can often be used as intermediates of organic dyes, pharmaceuticals and pesticide. It can also be used as organic intermediates for synthesis of pyrazoline, triazole, and indole; It can also be used as dye intermediates like disazo dye intermediates such as 1-phenyl-3-methyl-5-pyrazolone and so on; It can also be used as pharmaceutical intermediates for preparation of antipyretic, analgesic, anti-inflammatory drugs such as antipyrine and aminopyrine, etc; it can also be used as photography drugs (photosensitive dye); phenylhydrazine is also the raw material for the production of pesticides "imputed phosphorus"; phenylhydrazine is also an important kind of carbonyl group identification reagents used for identifying aldehydes, ketones and carbohydrates.
Phenylhydrazine is toxic. After inhalation, due to hemolysis, it can cause anemia and headache and can even cause jaundice in severe cases. It can also have stimulating effect on the eyes such as causing corneal disorders. Rat-oral LD50:188 mg/kg. Workplace: maximum allowable concentration: 0.44mg/m3.
Lab often uses aniline as raw materials for reaction with sodium nitrite in hydrochloric acid for generating diazonium salt and then reacted with sulfur dioxide and sulfurous acid for reduction to produce phenylhydrazine sodium sulfonate and further salting via hydrochloric acid to form phenylhydrazine hydrochloride. After neutralization and deacidification, we can obtain phenylhydrazine.
Production method
It can be produced from aniline which undergoes diazotization, reduction, acid precipitation to obtain phenylhydrazine hydrochloride and then further neutralization to obtain phenylhydrazine.
The preparation method is based on aniline which successively undergoes diazotization, reduction, acid precipitation, and neutralization to derive it.
Diazotization: add a certain amount of water, 30% hydrochloric acid and aniline to the reaction pot, cooled to 2 ℃, control the temperature at around 0~5 ℃ and add drop wise of solution of sodium nitrite to until the starch iodide test solution turns blue, stir for 30 mins for completion of the reaction and obtain the diazonium solution.
Reduction: add water, sodium bisulfite and 30% alkaline solution to the reduction kettle, heated to 80 ℃, maintain the temperature in 80~85 ℃ and pH = 6.2~6.7, within 20min trickle add the above diazo solution, stirring was continued for 1.5 h, then add zinc powder, diatomaceous earth, stirred filtrate with the filtrate suck into the acid precipitation tank.
Acid precipitation: to the above filtrate add 30% hydrochloric for acid precipitation at 70 ℃, the temperature is maintained in 85~90 ℃, stir for 10min and cool to below 20 ℃, suck, filtration to yield phenylhydrazine hydrochloride.
Neutralization: add the alkaline solution to the reaction pot, stir and simultaneously add the above phenylhydrazine hydrochloride and an appropriate amount of water, heated to 50 ℃, stirred at 50~60 ℃ for 1 h, allowed to stand for more than 8h, separate out the lower aqueous solution, It was the top oil that was phenylhydrazine with the content of about 80% and the total yield of 83.5%.
Mutagenicity and Toxicity of Carcinogenic
Phenylhydrazine is toxic by single exposure via the oral route (LD50 80–188 mg/kg body weight) and is expected to be toxic by the inhalation and dermal routes (data from these routes of exposure are less clear). Phenylhydrazine has potential for skin and eye irritation,and there is evidence that it has skin-sensitizing properties in humans. Exposure to phenylhydrazine may cause damage to red blood cells, potentially resulting in anaemia and consequential secondary involvement of other tissues, such as the spleen and liver. Phenylhydrazine is mutagenic in vitro, and there is some evidence to indicate that it may express genotoxic activity in vivo. The substance is clearly carcinogenic in mice following oral dosing, inducing tumours of the vascular system. The mechanism for tumour formation is unclear, but a genotoxic component cannot be excluded. Hence, it is not considered possible to reliably identify a level of exposure at which there will be no risk of carcinogenic or genotoxic effects.
environmental effects
Phenylhydrazine is degraded photochemically and autoxidizes in water. It is readily biodegradable, and this is expected to be the major route of breakdown in the environment. There is minimal sorption to particulates.
Phenylhydrazine is toxic to aquatic organisms, with the lowest reported no-observed-effect concentration (NOEC) in standard acute fish tests at 0.01 mg/litre; fish are generally more sensitive than either daphnids or bacteria. A NOEC of 0.49 :g/litre has been reported for embryo-larval stages of the zebra fish (Brachydanio rerio).
Flammable and hazard characteristics
it is combustible upon fire with heating emitting toxic nitrogen compound gas
Storage characteristics
Treasury: ventilation, low-temperature and dry; store it separately from oxidants, acids and food additives
Extinguishing agent
water, spray, foam, CO2, sand
Professional Standards
TLV-TWA 0.1 PPM; TWA 5 PPM (22 mg/cubic meter); STEL 2 mg/m3
Synthesis Reference(s)
Synthesis, p. 738, 1975 DOI: 10.1055/s-1975-23917
Air & Water Reactions
When exposed to air becomes red-brown. Slightly denser than water and slightly soluble in water.
Reactivity Profile
Phenylhydrazine may ignite spontaneously when in contact with oxidants such as hydrogen peroxide or nitric acid, oxides of iron or copper, or manganese, lead, copper or their alloys. Will not polymerize [USCG, 1999].
Health Hazard
Phenylhydrazine is a moderate to highlytoxic compound and a carcinogen. Acutetoxic symptoms include hematuria, changesin liver and kidney, vomiting, convulsions,and respiratory arrest. Additional symptomsare lowering of body temperature and fallin blood pressure. Chronic exposure to thiscompound caused hemolytic anemia andsignificant body weight loss in rats. Anoral administration of 175 mg/kg was lethalto mice. An oral LD50 value in rat is188 mg/kgPhenylhydrazine caused adverse repro ductive effect when dosed intraperitoneallyin pregnant mice. It caused jaundice, anemia,and behavioral deficit in offspring Oral or subcutaneous administration ofphenylhydrazine or its hydrochloride produced lung and liver tumors in experimental animals. ACGIH lists this compoundas a suspected human carcinogen. The evidence of carcinogenicity of this compoundin human is inadequate.
Fire Hazard
Combustible liquid; flash point (closed cup)
89°C (192°F). It reacts with lead dioxide
and strong oxidizing compounds vigorous to
violently.
Safety Profile
Confirmed carcinogen with experimental carcinogenic data. Poison by ingestion, subcutaneous, and intravenous routes experimental reproductive effects Mutation data reported. Ingestion or subcutaneous injection can cause hemolysis of red blood cells. Other effects are damage to the spleen, liver, kidneys, and bone marrow. The most common effect of occupational exposure is the development of dermatitis, which, in sensitized persons, may be quite severe. Systemic effects include anemia and general weakness, gastrointestinal dsturbances, and injury to the kidneys. Flammable when exposed to heat, flame, or oxidizers. To fight fire, use alcohol foam. Violent reaction with 2phenylamino-3-phenyloxazirane. Reacts with perchloryl fluoride to form an explosive product. Vigorous reaction with lead(Ⅳ) oxide. Used as a chemical reagent, in organic synthesis, and in the manufacture of dyes and drugs. Dangerous; when heated to decomposition it emits highly toxic fumes of NOx; can react with oxidizing materials
Potential Exposure
Phenylhydrazine is a widely used reagent in conjunction with sugars, aldehydes, and ketones. In addition, to its use in the synthesis of dyes; pharmaceuticals, such as antipyrin; cryogenin, and pyramidone; and other organic chemicals. The hydrochloride salt is used in the treatment of polycythemia vera.
Carcinogenicity
Mice given 1mg phenylhydrazine
orally each day, 7 days/week for 42 weeks had an
increased incidence of total lung tumors. The incidence of
malignant tumors also increased. In another study,
mice administered 0.01% of the hydrochloride salt in drinking
water (average of 0.63–0.81 mg/day) over their lifetimes
had an increased incidence of blood vessel tumors. In
contrast, mice given phenylhydrazine orally 5 days/week for
40 weeks at doses of 0.5 mg during the first 5 weeks and
0.25 mg thereafter failed to develop tumors.Higher
doses could not be tested because of the marked anemia
encountered. No leukemias occurred in mice treated with
phenylhydrazine, and pulmonary tumors were infrequent
. Oral administration or intraperitoneal injection
(eight doses, each of 2.9 mg) of phenylhydrazine hydrochloride
in mice failed to increase either pulmonary tumors or
leukemia. The carcinogenic activity of hydrazine
itself has been closely linked to its toxicity, that is, its irritant
effect. The mechanism of action, it is postulated, is
indirect alkylation of DNA, which is also closely connected
to the toxic end point.
Shipping
UN2572 Phenylhydrazine, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
Purification Methods
Purify phenylhydrazine by chromatography, then crystallise it from pet ether (b 60-80o)/*benzene. Store it in the dark under N2 as it turns yellow, then red, on exposure to air. It is best stored as the hydrochloride salt; see below. [Coleman Org Synth Coll Vol I 442 1941, Shaw & Stratton J Chem Soc 5004 1962, Beilstein 15 IV 50.]
Incompatibilities
Phenylhydrazine is very reactive with carbonyl compounds, strong oxidizers; strong bases; alkali metals; ammonia, lead dioxide (violent). Attacks copper salts, nickel, and chromates.
Waste Disposal
Controlled incineration whereby oxides of nitrogen are removed from the effluent gas by scrubber, catalytic or thermal device.
Check Digit Verification of cas no
The CAS Registry Mumber 100-63-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 0 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 100-63:
(5*1)+(4*0)+(3*0)+(2*6)+(1*3)=20
20 % 10 = 0
So 100-63-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H5.H3N2/c1-2-4-6-5-3-1;1-2/h1-6H;1-2H2
100-63-0Relevant articles and documents
Synthesis of 1H-indazole: A combination of experimental and theoretical studies
Chen, Xinzhi,Zhou, Shaodong,Qian, Chao,He, Chaohong
, p. 1619 - 1628 (2012)
A new practical synthesis of 1H-indazole is presented. A previous mechanism for the cyclization step is proved to be nonfeasible and a hydrogen bond propelled mechanism is proposed. The new mechanism is suitable for similar cyclization, and a new reaction is predicted. Springer Science+Business Media B.V. 2012.
A novel potent metal-binding NDM-1 inhibitor was identified by fragment virtual, SPR and NMR screening
Bai, Weiqi,Cheng, Kai,Gao, Yan,Guo, Huifang,He, Wei,Li, Conggang,Li, Zhuorong,Wu, Cai
, (2020)
NDM-1 can hydrolyze nearly all available β-lactam antibiotics, including carbapenems. NDM-1 producing bacterial strains are worldwide threats. It is still very challenging to find a potent NDM-1 inhibitor for clinical use. In our study, we used a metal-binding pharmacophore (MBP) enriched virtual fragment library to screen NDM-1 hits. SPR screening helped to verify the MBP virtual hits and identified a new NDM-1 binder and weak inhibitor A1. A solution NMR study of 15N-labeled NDM-1 showed that A1 disturbed all three residues coordinating the second zinc ion (Zn2) in the active pocket of NDM-1. The perturbation only happened in the presence of zinc ion, indicating that A1 bound to Zn2. Based on the scaffold of A1, we designed and synthesized a series of NDM-1 inhibitors. Several compounds showed synergistic antibacterial activity with meropenem against NDM-1 producing K. pneumoniae.
Indole-3-carbinol and 1,3,4-oxadiazole hybrids: Synthesis and study of anti-proliferative and anti-microbial activity
Gokhale, Nikhila,Panathur, Naveen,Dalimba, Udayakumar,Kumsi, Manjunatha
, p. 1603 - 1613 (2015)
In the present study, molecular hybrids of indole-3-carbinol and 1,3,4-oxadiazole-2-thiols have been designed and synthesized. The thiol analogues consisted of diversely substituted benzyl and alkyl groups with different electronic properties. The structures of all the newly synthesized scaffolds and target compounds were ascertained using 1H NMR, 13C NMR, mass spectrometry, and elemental analyses. All the final compounds were screened in vitro for their anti-proliferative and anti-microbial activity. Three compounds showed excellent anti-proliferative activity with more than 70% cell growth inhibition against three cancer cell lines, HepG2 (human liver hepatocellular carcinoma), HeLa (human cervix carcinoma), and MCF-7 (human breast carcinoma). In the anti-microbial studies, compounds with electron-withdrawing fluoro or nitro substituent displayed appreciable activity similar to that of standard drugs. Also, the final compounds are non-toxic to non-cancerous Vero cell line.
Hydrolysis mechanisms for the acetylpyridinephenylhydrazone ligand in sulfuric acid
Garcia, Begona,Munoz, Maria S.,Ibeas, Saturnino,Leal, Jose M.
, p. 3781 - 3786 (2000)
The excess acidity method was applied to rate data obtained for 2-acetylpyridinephenylhydrazone hydrolysis in strong acid media using various aqueous/organic solvents, and it was observed that the reaction rate decreases with increasing permittivity of the medium. Two hydrolysis mechanisms are indicated. Below 0.6 M H2SO4, no hydrolysis was observed; between 0.6 and 6.0 M H2SO4, the substrate hydrolyzes by an A-SE2 mechanism and switches to an A-2 mechanism at higher acidity. This change of mechanism was justified on the basis of the syn and anti rotational conformers of the diene -N(1)D=C-C=N(2)- group; the greater stability of the former can be explained by the formation of hydrogen bonds between the proton and the N(1) and N(2) nitrogen atoms, giving rise to a very stable five-membered ring. If the syn conformer is predominant, then no hydrolysis is observed; above 0.6 M, the attack of a second proton gives rise to a balance between the syn and anti forms, the latter being responsible for the hydrolysis of the hydrazone group.
Synthesis and Characterization of Telmisartan-Derived Cell Death Modulators to Circumvent Imatinib Resistance in Chronic Myeloid Leukemia
Schoepf, Anna M.,Salcher, Stefan,Hohn, Verena,Veider, Florina,Obexer, Petra,Gust, Ronald
, p. 1067 - 1077 (2020)
New strategies to eradicate cancer stem cells in chronic myeloid leukemia (CML) include a combination of imatinib with peroxisome proliferator-activated receptor gamma (PPARγ) ligands. Recently, we identified the partial PPARγ agonist telmisartan as effective sensitizer of resistant K562 CML cells to imatinib treatment. Here, the importance of the heterocyclic core on the cell death-modulating effects of the telmisartan-derived lead 4′-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1′-biphenyl]-2-carboxylic acid (3 b) was investigated. Inspired by the pharmacodynamics of HYL-6d and the selective PPARγ ligand VSP-51, the benzimidazole was replaced by a carbazole or an indole core. The results indicate no correlation between PPARγ activation and sensitization of resistant CML cells to imatinib. The 2-COOH derivatives of the carbazoles or indoles achieved low activity at PPARγ, while the benzimidazoles showed 60-100 % activation. Among the 2-CO2CH3 derivatives, only the ester of the lead (2 b) slightly activated PPARγ. Sensitizing effects were further observed for this non-cytotoxic 2 b (80 % cell death), and to a lesser extent for the lead 3 b or the 5-Br-substituted ester of the benzimidazoles (5 b).
Cross-Coupling between Hydrazine and Aryl Halides with Hydroxide Base at Low Loadings of Palladium by Rate-Determining Deprotonation of Bound Hydrazine
Borate, Kailaskumar,Choi, Kyoungmin,Goetz, Roland,Hartwig, John F.,Shinde, Harish,Wang, Justin Y.,Zuend, Stephan J.
supporting information, p. 399 - 408 (2020/10/29)
Reported here is the Pd-catalyzed C–N coupling of hydrazine with (hetero)aryl chlorides and bromides to form aryl hydrazines with catalyst loadings as low as 100 ppm of Pd and KOH as base. Mechanistic studies revealed two catalyst resting states: an arylpalladium(II) hydroxide and arylpalladium(II) chloride. These compounds are present in two interconnected catalytic cycles and react with hydrazine and base or hydrazine alone to give the product. The selectivity of the hydroxide complex with hydrazine to form aryl over diaryl hydrazine was lower than that of the chloride complex, as well as the catalytic reaction. In contrast, the selectivity of the chloride complex closely matched that of the catalytic reaction, indicating that the aryl hydrazine is derived from this complex. Kinetic studies showed that the coupling process occurs by rate-limiting deprotonation of a hydrazine-bound arylpalladium(II) chloride complex to give an arylpalladium(II) hydrazido complex.
Visible-light-mediated phosphonylation reaction: formation of phosphonates from alkyl/arylhydrazines and trialkylphosphites using zinc phthalocyanine
Hosseini-Sarvari, Mona,Koohgard, Mehdi
supporting information, p. 5905 - 5911 (2021/07/12)
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.
Discovery of novel inhibitors of human phosphoglycerate dehydrogenase by activity-directed combinatorial chemical synthesis strategy
Gou, Kun,Luo, Youfu,Luo, Yuan,Sun, Qingxiang,Tan, Yuping,Tao, Lei,Zhao, Yinglan,Zhou, Xia,Zhou, Yue,Zuo, Zeping
, (2021/07/26)
Serine, the source of the one-carbon units essential for de novo purine and deoxythymidine synthesis plays a crucial role in the growth of cancer cells. Phosphoglycerate dehydrogenase (PHGDH) which catalyzes the first, rate-limiting step in de novo serine biosynthesis has become a promising target for the cancer treatment. Here we identified H-G6 as a potential PHGDH inhibitor from the screening of an in-house small molecule library based on the enzymatic assay. We adopted activity-directed combinatorial chemical synthesis strategy to optimize this hit compound. Compound b36 was found to be the noncompetitive and the most promising one with IC50 values of 5.96 ± 0.61 μM against PHGDH. Compound b36 inhibited the proliferation of human breast cancer and ovarian cancer cells, reduced intracellular serine synthesis, damaged DNA synthesis, and induced cell cycle arrest. Collectively, our results suggest that b36 is a novel PHGDH inhibitor, which could be a promising modulator to reprogram the serine synthesis pathway and might be a potential anticancer lead worth further exploration.
Synthesis and biological activity of conformationally restricted indole-based inhibitors of neurotropic alphavirus replication: Generation of a three-dimensional pharmacophore
Barraza, Scott J.,Sindac, Janice A.,Dobry, Craig J.,Delekta, Philip C.,Lee, Pil H.,Miller, David J.,Larsen, Scott D.
supporting information, (2021/06/18)
We have previously reported the development of indole-based CNS-active antivirals for the treatment of neurotropic alphavirus infection, but further optimization is impeded by a lack of knowledge of the molecular target and binding site. Herein we describe the design, synthesis and evaluation of a series of conformationally restricted analogues with the dual objectives of improving potency/selectivity and identifying the most bioactive conformation. Although this campaign was only modestly successful at improving potency, the sharply defined SAR of the rigid analogs enabled the definition of a three-dimensional pharmacophore, which we believe will be of value in further analog design and virtual screening for alternative antiviral leads.
N-Amino-1,8-Naphthalimide is a Regenerated Protecting Group for Selective Synthesis of Mono-N-Substituted Hydrazines and Hydrazides
Manoj Kumar, Mesram,Venkataramana, Parikibanda,Yadagiri Swamy, Parikibanda,Chityala, Yadaiah
supporting information, p. 17713 - 17721 (2021/11/10)
A new route to synthesis of various mono-N-substituted hydrazines and hydrazides by involving in a new C?N bond formation by using N-amino-1,8-naphthalimide as a regenerated precursor was invented. Aniline and phenylhydrazines are reproduced upon reacting these individually with 1,8-naphthalic anhydride followed by hydrazinolysis. The practicality and simplicity of this C?N dihalo alkanes; developed a synthon for bond formation protocol was exemplified to various hydrazines and hydrazides. N-amino-1,8-naphthalimide is suitable synthon for transformation for selective formation of mono-substituted hydrazine and hydrazide derivatives. Those are selective mono-amidation of hydrazine with acid halides; mono-N-substituted hydrazones from aldehydes; synthesis of N-aminoazacycloalkanes from acetohydrazide scaffold and inserted to hydroxy derivatives; distinct synthesis of N,N-dibenzylhydrazines and N-benzylhydrazines from benzyl halides; synthesis of N-amino-amino acids from α-halo esters. Ecofriendly reagent N-amino-1,8-naphthalimide was regenerated with good yields by the hydrazinolysis in all procedures.
