N-Phenylhydroxylamine

Base Information

• Chemical Name: N-Phenylhydroxylamine
• CAS No.: 100-65-2
• Molecular Formula: C6H7 N O
• Molecular Weight: 109.128
• Hs Code.: 2928000090
• European Community (EC) Number: 202-875-6
• NSC Number: 223099
• UN Number: 2811
• UNII: 282MU82Z9A
• DSSTox Substance ID: DTXSID3025889
• Nikkaji Number: J29.543D
• Wikipedia: Phenylhydroxylamine
• Wikidata: Q3048694
• Metabolomics Workbench ID: 51885
• ChEMBL ID: CHEMBL320474
• Mol file: 100-65-2.mol

Synonyms:hydroxylaminobenzene;phenylhydroxylamine;phenylhydroxylamine hydrochloride

Chemical Property of N-Phenylhydroxylamine

Chemical Property:

• Appearance/Colour: tan powder or crystals
• Vapor Pressure: 0.085mmHg at 25°C
• Melting Point: 83 - 84 C
• Refractive Index: 1.649
• Boiling Point: 215.8°Cat760mmHg
• PKA: 9.00±0.70(Predicted)
• Flash Point: 120.2°C
• PSA: 32.26000
• Density: 1.214g/cm³
• LogP: 1.56070
• Storage Temp.: ?20°C
• Water Solubility.: 20g/L(5 oC)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 109.052763847
• Heavy Atom Count: 8
• Complexity: 59.5
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

N-Phenylhydroxylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Hydroxylamines
• Canonical SMILES: C1=CC=C(C=C1)NO
• Uses: Manufacture of cupferron. N-Phenylhydroxylamine can be used as a starting material for the synthesis of: 2-alkylindoles by treating with aliphatic terminal alkynes using gold catalyst via sequential 3,3-rearrangements and cyclodehydrations.Isoxazolidines by reacting with aldehydes and α, β-unsaturated aldehydes via a three-component one-pot catalytic reaction.Tetrahydro-1,2-oxazines by treating with an aldehyde and cyclopropane via homo 3+2 dipolar cycloaddition reaction.

Technology Process of N-Phenylhydroxylamine

There total 148 articles about N-Phenylhydroxylamine 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: 84.0%

nitrobenzene (98-95-3,26969-40-4) → N-Phenylhydroxylamine (100-65-2) + azoxybenzene (495-48-7,55599-32-1)

Guidance literature:

With ammonium chloride; zinc; In water; at 80 ℃; for 3.33333h; Concentration; Temperature; Time; Catalytic behavior; Inert atmosphere;

Reference yield: 63.0%

N-acetoacetylphenylhydroxyloamine (27991-08-8) → hydrazodicarboxamide (110-21-4) + N-Phenylhydroxylamine (100-65-2) + 1-carbamido-3-methyl-2-pyrazolin-5-one (57303-41-0) + azoxybenzene (495-48-7,55599-32-1)

Guidance literature:

With semicarbazide hydrochloride; sodium carbonate; In ethanol; for 24h; Further byproducts given; Ambient temperature;

DOI:10.1248/cpb.29.244

Reference yield: 39.5%

N-acetoacetylphenylhydroxyloamine (27991-08-8) + isoniazid (54-85-3,7640-37-1) → N,N'-bis(isonicotinoyl)hydrazine (4329-75-3) + N-Phenylhydroxylamine (100-65-2) + N-hydroxy-N-phenylisonicotinamide (143997-57-3) + 3-methyl-2-pyrazoline-5-one (108-26-9)

Guidance literature:

triethylamine; In chloroform; for 24h; Further byproducts given; Heating;

DOI:10.1248/cpb.29.244

upstream raw materials:

diazomethane

diethyl ether

Nitrosobenzene

glyoxime-N_.N'-diphenyl ether

Downstream raw materials:

N,N'-dihydroxy-N,N'-diphenyl-methanediyldiamine

aniline

3-(phenylamino)pyrrolidine-2,5-dione

1,4-diphenyl-2-(phenylamino) but-2-ene-1,4-dione

Refernces

• 1、 Awano, Hiroshi,Hirabayashi, Tetsuya,Tagaki, Waichiro. "ACID CATALYZED REDUCTION OF NITROSOBENZENE BY 3,5-DIPYRROLIDINOCARBAMOYL-N-BENZYL-1,4-DIHYDROPYRIDINE AS A NADH ANALOG". . p. 2005 - 2008. Retrieved 1984.
• 2、 Karuppiah, Chelladurai,Muthupandi,Chen, Shen-Ming,Ali, M. Ajmal,Palanisamy, Selvakumar,Rajan,Prakash,Al-Hemaid, Fahad M. A.,Lou, Bih-Show. "Green synthesized silver nanoparticles decorated on reduced graphene oxide for enhanced electrochemical sensing of nitrobenzene in waste water samples". . p. 31139 - 31146. Retrieved 2015.
• 3、 Meenakshisundaram, Subbiah,Selvaraju,Made Gowda,Rangappa, Kanchugarakoppal S.. "Effect of substituents on the rate of oxidation of anilines with peroxomonosulfate monoanion (HOOSO3-) in aqueous acetonitrile: A mechanistic study". . p. 649 - 657. Retrieved 2005.
• 4、 Zhang, Ting-Ting,Jiang, Jing-Yang,Wang, Yan-Hua. "Supported bimetallic catalyst Pt-Pb/SiO2for selective conversion of nitrobenzene to p-aminophenol in pressurized CO2/H2O system". . p. 307 - 311. Retrieved 2017.
• 5、 Liu, Shijuan,Wang, Yanhua,Jiang, Jingyang,Jin, Zilin. "The selective reduction of nitroarenes to N-arylhydroxylamines using Zn in a CO2/H2O system". . p. 1397 - 1400. Retrieved 2009.
• 6、 Hashimotu,Kano. "-". . p. 3509. Retrieved 1970.
• 7、 Makaryan, I. A.,Savchenko, V. I.,Brikenshtein, Kh. A.. "INFLUENCE OF PROCESS CONDITIONS ON THE KINETICS OF THE LIQUID-PHASE CATALYTIC HYDROGENATION OF AROMATIC NITRO COMPOUNDS". . p. 692 - 695. Retrieved 1983.
• 8、 Vishu Kumar,Dhananjaya,Rangappa. "Synthesis, characterization, and biological studies of novel isoxazolidines: 1,3-Dipolar cycloaddition reactions". . p. 1887 - 1890. Retrieved 2002.
• 9、 Novak, Michael,Bonham, Gayl A.,Mohler, Linda K.,Peet, Kristine M.. "Acid-Catalyzed Hydrolysis of N-Hydroxyacetanilides: Amide Hydrolysis vs N-O Bond Heterolysis". . p. 3903 - 3908. Retrieved 1988.
• 10、 Torres, Cecilia,Campos, Cristian,Fierro, Jose Luis Garcia,Oportus, Marcelo,Reyes, Patricio. "Nitrobenzene hydrogenation on Au/TiO2 and Au/SiO2 catalyst: Synthesis, characterization and catalytic activity". . p. 763 - 771. Retrieved 2013.