Phenylhydrazine

Base Information

• Chemical Name: Phenylhydrazine
• CAS No.: 100-63-0
• Deprecated CAS: 1057722-40-3
• Molecular Formula: C6H8N2
• Molecular Weight: 108.143
• Hs Code.: 2928.00
• European Community (EC) Number: 202-873-5
• ICSC Number: 0938
• UN Number: 2572
• UNII: 064F424C9K
• DSSTox Substance ID: DTXSID8021147
• Nikkaji Number: J38.250G
• Wikipedia: Phenylhydrazine
• Wikidata: Q290862
• Pharos Ligand ID: P5SWBUCPDRMU
• Metabolomics Workbench ID: 49837
• ChEMBL ID: CHEMBL456807
• Mol file: 100-63-0.mol

Synonyms:Hydrazinobenzene;Monophenylhydrazine;AI3-15399;BRN 0606080;CCRIS 511;Fenilidrazina;Fenilidrazina [Italian];Fenylhydrazine;Fenylhydrazine [Dutch];HSDB 1117;Hydrazine, phenyl-;Hydrazine-benzene;Hydrazobenzene;Phenylhydrazin [German];Phenylhydrazine [UN2572] [Poison];Phenylhydrazine and its salts;UN2572;

Chemical Property of Phenylhydrazine

Chemical Property:

• Appearance/Colour: colourless to pale yellow liquid
• Vapor Pressure: <0.1 mm Hg ( 20 °C)
• Melting Point: 19 °C
• Refractive Index: 1.6080
• Boiling Point: 243 °C at 760 mmHg
• PKA: 8.79(at 15℃)
• Flash Point: 115.4 °C
• PSA: 38.05000
• Density: 1.125 g/cm³
• LogP: 1.74550
• Storage Temp.: Store at RT.
• Sensitive.: Air & Light Sensitive
• Solubility.: Soluble in dilute acids.
• Water Solubility.: 145 g/L (20 ºC)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 108.068748264
• Heavy Atom Count: 8
• Complexity: 57.5
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Phenylhydrazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 45-23/24/25-36/38-43-48/23/24/25-50-68
• Safety Statements: 53-45-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Hydrazines
• Canonical SMILES: C1=CC=C(C=C1)NN
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the blood. This may result in haemolysis. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the blood. This may result in anaemia. This substance is possibly carcinogenic to humans.
• Uses: In the field of pesticide production, phenylhydrazine can be used for synthesizing the intermediate 1-phenyl-semicarbazide of the organophosphorus pesticides, triazophos as well as the intermediate 1-phenyl-3, 6-hydroxy pyridazine of pyridaphenthione. It is also the intermediates of the novel bactericidal varieties, famoxadone and fenamidone. In addition, hydrazine benzene, as a raw material for organic synthesis, can also be used as the intermediates of dye and pharmaceutical industry as well as being used as an analytical reagent. The product is the intermediate of dye, pharmaceuticals and pesticides. It can be used for the production of Naphthol AS-G, drugs such as antipyrine and so on. Dissolving the phenylhydrazine in 95% ethanol and following by addition of benzaldehyde and reflux for 1 h can obtain the phenylhydrazone. Phenylhydrazone can also be used as the intermediate of organic synthesis. Phenylhydrazine is also used as an analytical reagent. As a weak base, it can be used to precipitate lead, chromium and other trivalent, tetravalent element in the form of hydroxide. It can also be used for photometric determination of aluminum, chromium, copper, molybdenum, titanium, and zirconium. It can also be used for verification of gold, iridium, molybdenum, palladium, platinum, and silver. It can be used as the reducing agent for colorimetric assay of phosphorus acid. It can also react with aldehydes, ketones and sugars to get phenylhydrazone with different melting points according which we will be able to identify these substances. Phenylhydrazine, as hydrochloride solution plus sodium acetate, reacts with polyhydroxy aldehydes or ketones yielding osazones or diphenylhydrazones, yellow solids, of definite melting point and utilized in identification of sugars, e.g., phenyl-d-glucosazone, CH2OH (CHOH)3C: (NNHC6H5)CH:(NNHC6H5) plus aniline C6H5NH2 plus NH3. Phenylhydrazine is used in the manufactureof dyes and pharmaceuticals; as a stabilizerfor explosive; as a reagent for aldehydes,ketones, and sugars in chemical analysis; andin organic synthesis. An aryl hydrazine used in the preparation of various dyes and pharmaceutical compounds. It is used in the investigation of oligosaccharides as well as the structure of photosystem II.
• 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%.
• Physical properties: Yellow monoclinic crystals with a faint, aromatic odor. Turns red-brown on exposure to air.

Technology Process of Phenylhydrazine

There total 230 articles about Phenylhydrazine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

phenyl-phenylphosphinylidene-hydrazine (40040-57-1) → phenylphosphinic acid (1779-48-2) + phenylhydrazine (100-63-0)

Guidance literature:

Reference yield:

phenyl-phenylphosphinylidene-hydrazine (40040-57-1) → phenylphosphinic acid (1779-48-2) + phenylhydrazine (100-63-0)

Guidance literature:

Reference yield:

benzaldehyde phenylhydrazone (588-64-7) → benzaldehyde (100-52-7) + phenylhydrazine (100-63-0)

Guidance literature:

With hydrogenchloride; water; In ethanol; at 25 ℃; Rate constant; Thermodynamic data; Equilibrium constant; other cond.: further reagents; other obj. of st.: E(excit.), ΔH(excit.), -(DS(excit.));

upstream raw materials:

methanol

benzenediazonium

6-methyl-3-(1-phenylhydrazono-ethyl)-pyran-2,4-dione

benzene diazonium chloride

Downstream raw materials:

N-(2-amino-ethyl)-N'-phenyl-hydrazine

glyoxal bis(phenylhydrazone)

(E)-1-(2-pyridinyl)methylene-2-phenylhydrazine

pyridine-4-carbaldehyde phenylhydrazone

Refernces

• 1、 Chen, Xinzhi,Zhou, Shaodong,Qian, Chao,He, Chaohong. "Synthesis of 1H-indazole: A combination of experimental and theoretical studies". . p. 1619 - 1628. Retrieved 2012.
• 2、 Forster,Withers. "". . p. 266. Retrieved 1913.
• 3、 Gokhale, Nikhila,Panathur, Naveen,Dalimba, Udayakumar,Kumsi, Manjunatha. "Indole-3-carbinol and 1,3,4-oxadiazole hybrids: Synthesis and study of anti-proliferative and anti-microbial activity". . p. 1603 - 1613. Retrieved 2015.
• 4、 Garcia, Begona,Munoz, Maria S.,Ibeas, Saturnino,Leal, Jose M.. "Hydrolysis mechanisms for the acetylpyridinephenylhydrazone ligand in sulfuric acid". . p. 3781 - 3786. Retrieved 2000.
• 5、 Reisenegger. "-". . p. 662. Retrieved 1883.
• 6、 AL-Khazraji, Shaima Ibraheem Chyad. "Synthesis of and characterization of some Heterocyclic Compounds derived from Thiophenol". . p. 5655 - 5662. Retrieved 2021/09/11.
• 7、 Hosseini-Sarvari, Mona,Koohgard, Mehdi. "Visible-light-mediated phosphonylation reaction: formation of phosphonates from alkyl/arylhydrazines and trialkylphosphites using zinc phthalocyanine". supporting information. p. 5905 - 5911. Retrieved 2021/07/12.