59-88-1 Usage
Chemical Properties
Phenylhydrazine is a colorless to pale yellow liquid or solid with a weak aromatic odor.
Uses
Different sources of media describe the Uses of 59-88-1 differently. You can refer to the following data:
1. manufacture of dyes, antipyrine, nitron (a stabilizer for explosives); reagent for sugars, aldehydes, ketones.
2. Phenylhydrazine hydrochloride is used as a selective mannosidase inhibitor. It is used in the study of tyrosine phosphorylation of janus protein tyrosine kinase in the EPO-responsive normal erythroblastoid cells of anemic mice. It is used in steroid assays and as an N-protecting reagent. Its free base, phenylhydrazine is used to prepare indoles, which find application as intermediates in the synthesis of various dyes and pharmaceuticals.
General Description
White to tan solid with a weak aromatic odor.
Air & Water Reactions
Forms corrosive acidic solutions.
Reactivity Profile
Phenylhydrazine hydrochloride may be corrosive to metals [USCG, 1999].
Health Hazard
Phenylhydrazine hydrochloride is poisonous if swallowed or if fumes are inhaled. Dust is irritating to eyes, nose, and throat. Phenylhydrazine is a chronic poison. Phenylhydrazine is an industrial substance suspect of carcinogenic potential for humans.
Fire Hazard
Toxic and irritating hydrogen chloride and oxides of nitrogen may be produced in fire. May be corrosive to metals. Hazardous polymerization may not occur.
Biochem/physiol Actions
Phenylhydrazine hydrochloride causes acute hemolysis when injected intraperitoneally in to wild-type and Hp and Hx single-null mice. It suppresses the horseradish peroxide (HRP) residual activity in tissue sections of animals.
Safety Profile
Poison by ingestion, intraperitoneal, and subcutaneous routes. Experimental reproductive effects. Questionable carcinogen with experimental neoplastigenic and tumorigenic data. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and HCl.
Purification Methods
Dissolve 100g of phenylhydrazine hydrochloride in 200mL of warm H2O (60-70o) during 1-3hours, then add 1L of boiling EtOH. The solution is filtered, while still hot, through Whatman No 2 filter paper and cooled in a refrigerator. The precipitate is collected on a medium sintered-glass filter and recrystallised twice this way, then washed with cold EtOH, dried thoroughly and stored in a stoppered brown bottle. [Peterson et al. Anal Chem 29 144 1957.] Hough, Powell and Woods [J Chem Soc 4799 1956] boiled the hydrochloride with three times its weight of water, filtered hot (charcoal), added one-third volume of concentrated HCl and cooled to 0o. The crystals were washed with acetone, and dried over P2O5 under vacuum. The salt has also been crystallised from 95% EtOH, and it can be sublimed. [Coleman Org Synth Coll Vol I 442 1941, Beilstein 15 III 71.]
Check Digit Verification of cas no
The CAS Registry Mumber 59-88-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 9 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 59-88:
(4*5)+(3*9)+(2*8)+(1*8)=71
71 % 10 = 1
So 59-88-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H8N2.ClH/c7-8-6-4-2-1-3-5-6;/h1-5,8H,7H2;1H
59-88-1Relevant articles and documents
Chilou, Valerie,Gouzerh, Pierre,Jeannin, Yves,Olivares, Giuseppe,Robert, Francis,et al.
, p. 29 - 38 (1989)
Design, Synthesis, and Antifungal Activity of 2,6-Dimethyl-4-aminopyrimidine Hydrazones as PDHc-E1 Inhibitors with a Novel Binding Mode
Zhou, Yuan,Zhang, Shasha,Cai, Meng,Wang, Kaixing,Feng, Jiangtao,Xie, Dan,Feng, Lingling,Peng, Hao,He, Hongwu
, p. 5804 - 5817 (2021/06/25)
A series of novel 2,6-dimethyl-4-aminopyrimidine hydrazones 5 were rationally designed and synthesized as pyruvate dehydrogenase complex E1 (PDHc-E1) inhibitors. Compounds 5 strongly inhibited Escherichia coli (E. coli) PDHc-E1 (IC50 values 0.94-15.80 μM). As revealed by molecular docking, site-directed mutagenesis, enzymatic, and inhibition kinetic analyses, compounds 5 competitively inhibited PDHc-E1 and bound in a "straight"pattern at the E. coli PDHc-E1 active site, which is a new binding mode. In in vitro antifungal assays, most compounds 5 at 50 μg/mL showed more than 80% inhibition against the mycelial growth of six tested phytopathogenic fungi, including Botrytis cinerea, Monilia fructigena, Colletotrichum gloeosporioides, andBotryosphaeria dothidea. Notably, 5f and 5i were 1.8-380 fold more potent against M. fructigena than the commercial fungicides captan and chlorothalonil. In vivo, 5f and 5i controlled the growth of M. fructigena comparably to the commercial fungicide tebuconazole. Thus, 5f and 5i have potential commercial value for the control of peach brown rot caused by M. fructigena.
Allylic and Allenylic Dearomatization of Indoles Promoted by Graphene Oxide by Covalent Grafting Activation Mode
Lombardi, Lorenzo,Bellini, Daniele,Bottoni, Andrea,Calvaresi, Matteo,Monari, Magda,Kovtun, Alessandro,Palermo, Vincenzo,Melucci, Manuela,Bandini, Marco
supporting information, p. 10427 - 10432 (2020/07/24)
The site-selective allylative and allenylative dearomatization of indoles with alcohols was performed under carbocatalytic regime in the presence of graphene oxide (GO, 10 wt percent loading) as the promoter. Metal-free conditions, absence of stoichiometric additive, environmentally friendly conditions (H2O/CH3CN, 55 °C, 6 h), broad substrate scope (33 examples, yield up to 92 percent) and excellent site- and stereoselectivity characterize the present methodology. Moreover, a covalent activation model exerted by GO functionalities was corroborated by spectroscopic, experimental and computational evidences. Recovering and regeneration of the GO catalyst through simple acidic treatment was also documented.