1,2-Diphenylhydrazine

Base Information

• Chemical Name: 1,2-Diphenylhydrazine
• CAS No.: 122-66-7
• Molecular Formula: C12H12N2
• Molecular Weight: 184.241
• Hs Code.: 29280000
• European Community (EC) Number: 204-563-5
• ICSC Number: 0263
• NSC Number: 3510
• UN Number: 2811,3077
• UNII: 1G3CS09TUK
• DSSTox Substance ID: DTXSID7020710
• Nikkaji Number: J5.359G
• Wikipedia: Hydrazobenzene
• Wikidata: Q424993
• NCI Thesaurus Code: C44392
• Pharos Ligand ID: AUR7F23GPWG8
• ChEMBL ID: CHEMBL558459
• Mol file: 122-66-7.mol

Synonyms:1,2-diphenylhydrazine;hydrazobenzene

Chemical Property of 1,2-Diphenylhydrazine

Chemical Property:

• Appearance/Colour: yellow crystalline powder
• Vapor Pressure: 0.07mmHg at 25°C
• Melting Point: 123-126 °C(lit.)
• Refractive Index: 1.7
• Boiling Point: 229.3 °C at 760 mmHg
• PKA: 3.02±0.70(Predicted)
• Flash Point: 87.7 °C
• PSA: 24.06000
• Density: 1.179 g/cm³
• LogP: 3.27160
• Storage Temp.: Refrigerator
• Solubility.: Soluble in ethanol (Weast, 1986).
• Water Solubility.: 221 mg/L at 25 °C (U.S. EPA, 1980a)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 184.100048391
• Heavy Atom Count: 14
• Complexity: 128
• Transport DOT Label: Poison

Purity/Quality:

98% ^*data from raw suppliers

1,2-DiphenylHydrazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, N
• Hazard Codes: T,N
• Statements: 45-22-50/53
• Safety Statements: 53-45-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Hydrazines
• Canonical SMILES: C1=CC=C(C=C1)NNC2=CC=CC=C2
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: May cause mechanical irritation.
• Effects of Long Term Exposure: This substance is probably carcinogenic to humans.
• Description: Diphenylhydrazine is a man-made chemical that occurs in two isomeric forms: 1,1-diphenylhydrazine and 1,2-diphenylhdrazine. Diphenylhydrazine is produced by the reduction of nitrobenzene. Little or no information is available for 1,1-diphenylhydrazine. Most toxicological and use data pertain to 1,2-diphenylhydrazine.
• Uses: Impurity in the production of Phenylbutazone (P319570). Hydrazobenzene is a metabolic intermediate of Azobenzene Carcinogenic Formerly used as a starting material in the production of benzidine for dyes; production of certain drugs. Previously, 1,2-diphenylhydrazine was used for producing benzidine that was used in the synthesis of benzidine-based dyes. However, these dyes are no longer produced in the United States. The primary use of 1,2-diphenylhydrazine is in the production of the anti-inflammatory agent phenylbutazone and sulfinpyrazone, a uricosuric agent.

Technology Process of 1,2-Diphenylhydrazine

There total 194 articles about 1,2-Diphenylhydrazine 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: 69.0%

nitrobenzene (98-95-3,26969-40-4) → aniline (62-53-3) + diphenyl hydrazine (122-66-7) + Azobenzene (1227476-15-4) + azoxybenzene (495-48-7,55599-32-1)

Guidance literature:

With indium; iodine; In methanol; at 50 ℃; for 12h; Further Variations:; reagents molar ratio; Product distribution;

DOI:10.1016/j.tetlet.2006.08.027

Reference yield: 21.2%

tetrachloromethane (56-23-5) + aniline (62-53-3) → N,N',N''-triphenylguanidine (101-01-9) + diphenyl hydrazine (122-66-7) + phenylcarbonimidic dichloride (622-44-6) + Azobenzene (1227476-15-4) + N-phenylphenylene-1,4-diamine (101-54-2) + N-phenyl-1,2-benzenediamine (534-85-0)

Guidance literature:

at 15 ℃; for 24h; Product distribution; Mechanism; Irradiation; also in methanol and 1,4-dioxane;

Reference yield: 9.0%

nitrobenzene (98-95-3,26969-40-4) → aniline (62-53-3) + diphenyl hydrazine (122-66-7) + azoxybenzene (495-48-7,55599-32-1)

Guidance literature:

With triethylsilane; indium(III) bromide; In chloroform; at 60 ℃; for 12h; Inert atmosphere;

DOI:10.1039/c000383b

upstream raw materials:

N,N'-diphenyl-isobutylidenediamine

bis-dibenzo[a,kl]xanthen-1-yl-peroxide

hydroquinone

diethyl ether

Downstream raw materials:

N,N'-diphenylbenzohydrazide

1,2-dibenzoyl-1,2-diphenylhydrazine

acetoacetic acid-(N,N'-diphenyl-hydrazide)

1,1'-biphenyl-4,4'-diyl-bis-pyrrolidine-2,5-dione

Refernces

• 1、 Gilman,Adams. "-". . p. 2004. Retrieved 1926.
• 2、 Sahoo, Manoj K.,Saravanakumar, Krishnasamy,Jaiswal, Garima,Balaraman, Ekambaram. "Photocatalysis Enabling Acceptorless Dehydrogenation of Diaryl Hydrazines at Room Temperature". . p. 7727 - 7733. Retrieved 2018.
• 3、 Henriksen,Jakobsen. "Dissociative cycloelimination, a new selenium based pericyclic reaction". . p. 2448 - 2449. Retrieved 2001.
• 4、 Wang, Miao,Tang, Bo-Cheng,Xiang, Jia-Chen,Chen, Xiang-Long,Ma, Jin-Tian,Wu, Yan-Dong,Wu, An-Xin. "Aryldiazonium Salts Serve as a Dual Synthon: Construction of Fully Substituted Pyrazoles via Rongalite-Mediated Three-Component Radical Annulation Reaction". . p. 8934 - 8937. Retrieved 2019.
• 5、 Olah. "-". . p. 3165. Retrieved 1959.
• 6、 Gao, Wen-Zheng,Xu, Yong,Chen, Yong,Fu, Wen-Fu. "Highly efficient and selective photocatalytic reduction of nitroarenes using the Ni2P/CdS catalyst under visible-light irradiation". . p. 13217 - 13220. Retrieved 2015.
• 7、 West,Stewart. "-". . p. 853,857. Retrieved 1970.
• 8、 Shultz, Lorianne R.,Hu, Lin,Feng, Xiaofeng,Jurca, Titel. "Using a Nitrophenol Cocktail Screen to Improve Catalyst Down-selection". . p. 1627 - 1631. Retrieved 2020.
• 9、 Subotkowski, Witold,Kupczyk-Subotkowska, Lidia,Shine, Henry J.. "The benzidine and diphenyline rearrangements revisited. 1-14C and 1,1′-13C2 kinetic isotope effects, transition state differences, and coupled motion in a 10-atom sigmatropic rearrangement". . p. 5073 - 5076. Retrieved 1993.
• 10、 Tsai et al.. "-". . p. 1186,1188. Retrieved 1960.