1,2-diphenylhydrazine appears as orange powder or a bright orange crystalline solid. (NTP, 1992)
颜色/状态：
Tablets from alcohol and ether
蒸汽压力：
4.4X10-4 mm Hg at 25 °C
稳定性/保质期：
Hydrazobenzene (10 ug/L) in dilute aqueous solution was found to be unstable with less than 10% remaining for longer than one day of preservation (in the dark) under any of the conditions tested (ie, room temperature or 4 °C at pH 2,7, or 10 and with or without chlorine).
Thin layer chromatographic analysis of the urine of rats given an oral dose of 200 or 400 mg/kg revealed the presence of hydrazobenzene, benzidine, and two other unidentified metabolites. At an ip dose of 100 or 200 mg/kg, hydrazobenzene, aniline, benzidine, p-aminophenol, and o-aminophenol were identified in the urine. After iv or intratracheal administration of hydrazobenzene, only one urinary metabolite, which appeared to be phenolic, was found.
来源:Hazardous Substances Data Bank (HSDB)
代谢
在胃中，1,2-二苯基肼可以转化为苯肼，这是一种已知的人类致癌物。
In the stomach, 1,2-diphenylhydrazine can be converted into benzidine, a known human carcinogen.
The enzyme systems in rat liver and lung responsible for the oxidative metabolism of hydrazine derivatives were studied to determine whether these enzymes, cytochrome P450 and monoamine oxidase, were responsible for metabolically activating hydrazines to carcinogenic/toxic metabolites. Cytochrome P450 preferentially oxidized the nitrogen to nitrogen bond of 1,2-disubstituted hydrazines and hydrazides, while monoamine oxidase oxidized the nitrogen to nitrogen bond of all the classes of hydrazine derivatives that were tested. Oxidation of the nitrogen to nitrogen bond led to the formation of stable azo intemediates in the case of 1,2-disubstituted hydrazines and to unstable monoazo (diazene) metabolites in the case of monosubstituted hydrazines and hydrazides. /Substituted hydrazines/
Unchanged 1,2-diphenylhydrazine was detected following treatment by all routes, and aniline and benzidine were identified following oral and intraperitoneal treatments. Other metabolites included two unspecified hydroxy derivatives of benzidine (oral route), 2- and 4- aminophenol (intraperitoneal route), and unidentified compounds (oral, intravenous, and intratracheal routes). Aniline is oxidized by hydroxylation of a ring carbon to form 2-or 4-aminophenol or of the nitrogen to form phenylhydroxylamine, and then is conjugated to glucuronic or sulfuric acid. Benzidine is formed readily from 1,2-diphenylhydrazine by acid rearrangement. It has been suggested that benzidine may be produced from 1,2-diphenylhydrazine by acidity in the stomach. (L463)
Two of the known metabolites, aniline and benzidine, may contribute to the toxicity and/or carcinogenicity of 1,2-diphenylhydrazine. Nonneoplastic liver lesions, hepatocellular carcinomas and/or neoplastic liver nodules indicate that the liver is a target of 1,2-diphenylhydrazine toxicity. As aniline and other aromatic amino metabolites of 1,2-diphenylhydrazine (e.g., aminophenols) are methemoglobinforming compounds by either oral or inhalation routes of exposure, it is possible that 1,2-diphenylhydrazine may cause methemoglobinemia in humans. (L463)
CLASSIFICATION: B2; probable human carcinogen. BASIS FOR CLASSIFICATION: Positive results of studies in both rats and mice form the basis for this classification. Two apparently negative studies lack information on compound purity, experimental design, and statistical treatment. HUMAN CARCINOGENICITY DATA: None.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
致癌性证据
偶氮苯：合理预期为人类致癌物。
Hydrazobenzene: reasonably anticipated to be a human carcinogen.
Not listed by IARC. Benzidine, a metabolite of 1,2-diphenylhydrazine, is carcinogenic to humans (Group 1). Aniline, another metabolite, is not classifiable as to its carcinogenicity to humans (Group 3). (L135)
Chiral Pincer Carbodicarbene Ligands for Enantioselective Rhodium-Catalyzed Hydroarylation of Terminal and Internal 1,3-Dienes with Indoles
作者：Justin S. Marcum、Courtney C. Roberts、Rajith S. Manan、Tia N. Cervarich、Simon J. Meek
DOI：10.1021/jacs.7b08575
日期：2017.11.8
Catalytic enantioselective addition of N-heteroarenes to terminal and internal 1,3-dienes is reported. Reactions are promoted by 5 mol % of Rh catalyst supported by a new chiral pincer carbodicarbene ligand that delivers allylic substituted arenes in up to 95% yield and up to 98:2 er. Mechanistic and X-ray evidence is presented that supports that the reaction proceeds via a Rh(III)-η3-allyl.
A highly efficient palladium-catalyzed cascade annulation of pyrazolones and aryl iodides to access various benzo[c]cinnoline derivatives has been achieved at 80 °C. A pyridine-type ligand could improve the reaction efficiency under current reaction conditions, giving a higher product yield up to 94%. This novel approach provided a one-pot dual C–H activation strategy with good functional group tolerance
在80°C时，已经实现了高效的钯催化吡唑啉酮和芳基碘的级联环化反应，以得到各种苯并[ c ]肉桂酸衍生物。吡啶类配体可提高当前反应条件下的反应效率，最高收率可达94％。这种新颖的方法提供了具有良好官能团耐受性的一锅双C–H活化策略，例如卤素，甲氧基，硝基，酯，苯酚等。该产物可以很容易地转化为cinnoline衍生物。
Microwave‐assisted reduction of aromatic nitro compounds with novel oxo‐rhenium complexes
作者：Gabriele Grieco、Olivier Blacque
DOI：10.1002/aoc.6452
日期：2022.1
The reduction of several aromatic nitro compounds to amines by means of the two novel catalytic systems ([IMes]2ReOBr3)/PhSiH3 and ([Py]3ReNOBr2)/PhSiH3 under microwave irradiation is here reported. These two systems were able to perform the reduction of nitro groups with higher TON and TOF when compared with previously reported systems based on oxo-rhenium core under standard heating, although they
Recently, inexpensive and readily available tBuOK has seen widespread use in transition-metal-free reactions. Herein, we report the use of tBuOK for S–S, S–Se, NN and CN bond formations, which significantly extends the scope of tBuOK in chemical synthesis. Compared with traditional methods, we have realized mild and general methods for disulfide, azobenzenes imine etc. synthesis.
