フェニルヒドラジン
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Phenylhydrazine[1][2]
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Names |
IUPAC name
Phenylhydrazine
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Other names
Hydrazinobenzene
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Identifiers |
CAS Registry Number
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100-63-0 Y |
ChEBI |
CHEBI:27924 Y |
ChEMBL |
ChEMBL456807 Y |
ChemSpider |
7235 Y |
InChI
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InChI=1S/C6H8N2/c7-8-6-4-2-1-3-5-6/h1-5,8H,7H2 Y
Key: HKOOXMFOFWEVGF-UHFFFAOYSA-N Y
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InChI=1/C6H8N2/c7-8-6-4-2-1-3-5-6/h1-5,8H,7H2
Key: HKOOXMFOFWEVGF-UHFFFAOYAN
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Jmol-3D images |
Image |
KEGG |
C02304 Y |
PubChem |
7516 |
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Properties |
Chemical formula
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C6H8N2 |
Molar mass |
108.14 g/mol |
Appearance |
Colorless to pale-yellow liquid or solid[3] |
Odor |
faint, aromatic[3] |
Density |
1.0978 g/cm3 |
Melting point |
19.5 °C (67.1 °F; 292.6 K) (24 °C for hemihydrate) |
Boiling point |
243.5 °C (470.3 °F; 516.6 K) (decomposition) |
Vapor pressure |
0.04 mmHg (25°C)[3] |
Hazards |
NFPA 704 |
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Flash point |
88 °C; 190 °F; 361 K [3] |
Lethal dose or concentration (LD, LC): |
LD50 (Median dose)
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188 mg/kg (rat, oral)
175 mg/kg (mouse, oral)
80 mg/kg (rabbit, oral)
80 mg/kg (guinea pig, oral)
200-250 mg/kg (dog, oral)[4] |
US health exposure limits (NIOSH): |
PEL (Permissible)
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TWA 5 ppm (22 mg/m3) [skin][3] |
REL (Recommended)
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Ca C 0.14 ppm (0.6 mg/m3) [2-hr] [skin][3] |
IDLH (Immediate danger
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Ca [15 ppm][3] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Y verify (what is: Y/N?) |
Infobox references |
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Phenylhydrazine is the chemical compound with the formula C6H5NHNH2. Organic chemists abbreviate the compound as PhNHNH2.
Contents
- 1 Chemical properties
- 2 Preparation
- 3 History
- 4 Uses
- 5 Safety
- 6 See also
- 7 References
- 8 External links
Chemical properties
Phenylhydrazine forms monoclinic prisms that melt to an oil around room temperature which may turn yellow to dark red upon exposure to air.[1] Phenylhydrazine is miscible with ethanol, diethyl ether, chloroform, and benzene. It is sparingly soluble in water.
Preparation
Phenylhydrazine is prepared by oxidizing aniline with sodium nitrite in the presence of hydrogen chloride to form the diazonium salt, which is subsequently reduced using sodium sulfite in the presence of sodium hydroxide to form the final product.[5]
History
Phenylhydrazine was the first hydrazine derivative characterized, reported by Emil Fischer in 1875.[6][7] He prepared it by reduction of a phenyl diazonium salt using sulfite salts. Fischer used phenylhydrazine to characterize sugars via formation of hydrazones with the sugar aldehyde. He also demonstrated in this first paper many of the key properties recognized for hydrazines.
Uses
Phenylhydrazine is used to prepare indoles via the Fischer Indole Synthesis, which are intermediates in the synthesis of various dyes and pharmaceuticals.
Phenylhydrazine is used to form phenylhydrazones of natural mixtures of simple sugars in order to render the differing sugars easily separable from each other.[8]
The compound is also used to induce acute hemolytic anemia in studies examining the hematopoietic system.
Safety
Exposure to phenylhydrazine may cause contact dermatitis, hemolytic anemia, and liver and kidney injury.[1]
See also
References
- ^ a b c Merck Index, 11th Edition, 7264.
- ^ Pure component properties
- ^ a b c d e f g "NIOSH Pocket Guide to Chemical Hazards #0499". National Institute for Occupational Safety and Health (NIOSH).
- ^ "Phenylhydrazine". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
- ^ Merck Index of Chemicals and Drugs, 9th ed. monograph 7098
- ^ Nobel Committee Emil Fischer - Biographical
- ^ Fischer, E. (1875) "Ueber aromatische Hydrazinverbindungen," Berichte der deutschen chemischen Gesellschaft, 8: 589-594.
- ^ Streitweiser, Andrew Jr.; Heathcock, Clayton H. (1976). Introduction to Organic Chemistry. Macmillan. ISBN 0-02-418010-6.
External links
- Phenylhydrazines at the US National Library of Medicine Medical Subject Headings (MeSH)
- PubChem
- Additional chemical properties of phenylhydrazine
- CDC - NIOSH Pocket Guide to Chemical Hazards
Hydrazines
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- 4-PTSC
- Acylhydrazine
- ADH
- Adjudin
- Agaritine
- Benmoxin
- Cadralazine
- Carbazide
- Carbidopa
- Carbohydrazide
- Daminozide
- Dihydralazine
- DNPH
- Endralazine
- Gyromitrin
- HBT
- Hydralazine
- Hydrazide
- Hydrazine
- Hydrazone
- Iproclozide
- Iproniazid
- Isocarboxazid
- Isoniazid
- Mebanazine
- Metfendrazine
- MMH
- Nialamide
- Octamoxin
- PEH
- Phenelzine
- Pheniprazine
- Phenoxypropazine
- Phenylhydrazine
- Pildralazine
- Pimagedine
- Pivalylbenzhydrazine
- Procarbazine
- Safrazine
- Semicarbazide
- Semicarbazone
- SDMH
- Tetrafluorohydrazine
- UDMH
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UpToDate Contents
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English Journal
- Convenient one-pot synthesis, anti-mycobacterial and anticancer activities of novel benzoxepinoisoxazolones and pyrazolones.
- Saidachary G1, Veera Prasad K1, Divya D2, Singh A2, Ramesh U2, Sridhar B3, China Raju B4.Author information 1Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.2Center for Chemical Biology, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.3Laboratory of X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.4Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India. Electronic address: chinaraju@iict.res.in.AbstractSeries of new benzoxepinoisoxazolones 4a-d and pyrazolones 6a-t were prepared by the cyclocondensation of substituted (E)-ethyl 3-oxo-2,3-dihydrobenzo[b]oxepine-4-carboxylates 3a-d with hydroxylamine hydrochloride and phenylhydrazine hydrochlorides 5a-k. Synthesized compounds were screened for their in vitro anti-mycobacterial activity and anticancer activity. Ten compounds displayed good anti-mycobacterial activity, among these; compound 4d and 6b found to be potent when compared to standard drug isoniazid. Eleven compounds displayed good anticancer activity and compounds 4b-d displayed equipotent activity on HeLa cell lines when compared to standard drug doxorubicin. Activation of caspase-3 and caspase-9 has been measured for compounds 4b-d on HeLa cell lines (apoptosis). This is the first report assigning in vitro anti-mycobacterial, anticancer and structure-activity relationship for this new class of benzoxepinoisoxazolones and pyrazolones.
- European journal of medicinal chemistry.Eur J Med Chem.2014 Apr 9;76:460-9. doi: 10.1016/j.ejmech.2014.02.042. Epub 2014 Feb 15.
- Series of new benzoxepinoisoxazolones 4a-d and pyrazolones 6a-t were prepared by the cyclocondensation of substituted (E)-ethyl 3-oxo-2,3-dihydrobenzo[b]oxepine-4-carboxylates 3a-d with hydroxylamine hydrochloride and phenylhydrazine hydrochlorides 5a-k. Synthesized compounds were screened for their
- PMID 24607876
- Synthesis and Anticancer Activity of Some New Pyrazolo[3,4-d]pyrimidin-4-one Derivatives.
- Abdellatif KR1, Abdelall EK2, Abdelgawad MA3, Ahmed RR4, Bakr RB5.Author information 1Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62514, Egypt. khaled.ahmed@bsu.edu.eg.2Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62514, Egypt. Emansherif94@yahoo.com.3Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62514, Egypt. mhmdgwd@yahoo.com.4Cell Biology and Histology Division, Zoology Department, Faculty of Science, Beni-Suef University, Beni-Suef 62514, Egypt. shorouk2002os@yahoo.com.5Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62514, Egypt. raniabakr@ymail.com.Abstract3,6-Dimethyl-1-phenyl-1H-pyrazolo[3,4-d][1,3]oxazin-4-one (3) was prepared by hydrolysis of ethyl 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carboxylate (1) to afford the corresponding carboxylic acid 2, which was reacted with acetic anhydride to give 3. The pyrazolo[3,4-d][1,3]oxazin-4-one 3 was reacted with hydroxylamine hydrochloride, urea, thiourea, thiosemicarbazide, phenylhydrazine and aromatic amines to afford the corresponding pyrazolo[3,4-d]pyrimidin-4-ones 4, 5a,b, 6, 7, 8a-e, respectively. Condensation of pyrazoloxazine derivative 3 with 99% hydrazine hydrate afforded the 5-aminopyrazolo[3,4-d] pyrimidine derivative 9. Coupling of 9 with aromatic aldehydes yielded a series of 3,6-dimethyl-5-(4-substitutedbenzylideneamino)-1-phenyl-1,5-dihydropyrazolo[3,4-d]pyrimidin- 4-ones 10a-e. The new compounds were tested for their antitumor activity on the MCF-7 human breast adenocarcinoma cell line. Almost all the tested compounds revealed antitumor activity, especially 3,6-dimethyl-5-(4-nitrobenzylideneamino)-1-phenyl-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one (10e) which displayed the most potent inhibitory activity with a half maximal inhibitory concentration (IC50) of 11 µM.
- Molecules (Basel, Switzerland).Molecules.2014 Mar 18;19(3):3297-309. doi: 10.3390/molecules19033297.
- 3,6-Dimethyl-1-phenyl-1H-pyrazolo[3,4-d][1,3]oxazin-4-one (3) was prepared by hydrolysis of ethyl 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carboxylate (1) to afford the corresponding carboxylic acid 2, which was reacted with acetic anhydride to give 3. The pyrazolo[3,4-d][1,3]oxazin-4-one 3 was react
- PMID 24647032
- (E)-1-[(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)methylidene]-2-phenylhydrazine: sheets built from π-stacked hydrogen-bonded chains.
- Trilleras J1, Utria M1, Cobo J2, Glidewell C3.Author information 1Grupo de Investigación en Compuestos Heterocíclicos, Programa de Química, Facultad de Ciencias Básicas, Universidad del Atlántico, Km 7 Antigua vía Puerto Colombia, Barranquilla, Colombia.2Departamento de Química Inorgánica y Orgánica, Universidad de Jaén, 23071 Jaén, Spain.3School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland.AbstractThe reaction between 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde and phenylhydrazine proceeds via condensation to provide the title compound, C17H15ClN4, (I), rather than via the alternative routes of simple nucleophilic substitution or cyclocondensation. With the exception of the phenyl group bonded directly to the pyrazole ring, the non-H atoms of (I) are nearly coplanar, with an r.m.s. deviation of 0.058 Å. The molecules are linked into C(7) chains by a single N-H···N hydrogen bond, and the chains are linked by π-π stacking interactions to form sheets.
- Acta crystallographica. Section C, Structural chemistry.Acta Crystallogr C Struct Chem.2014 Feb;70(Pt 2):216-9. doi: 10.1107/S2053229614000680. Epub 2014 Jan 17.
- The reaction between 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde and phenylhydrazine proceeds via condensation to provide the title compound, C17H15ClN4, (I), rather than via the alternative routes of simple nucleophilic substitution or cyclocondensation. With the exception of the phenyl g
- PMID 24508973
Japanese Journal
- Regioselective Synthesis of Trifluoromethyl Group Substituted Pyrazole Derivatives from 1-Aryl-3,4,4,4-tetrafluoro-2-buten-1-ones
- Sano Keisuke,Hara Shoji
- Heterocycles 80(1), 349-357, 2010-01-01
- … The reaction proceeded regioselectively and 5-aryl-3-trifluoromethyl-1-phenyl-1H-pyrazole was obtained from phenylhydrazine. …
- NAID 120002834747
- Analysis of Saccharides Possessing Post-translational Protein Modifications by Phenylhydrazine Labeling Using High-Performance Liquid Chromatography
- SUZUKI Hiroshi,KATO Eri,MATSUZAKI Ayako,ISHIKAWA Masako,HARADA Yushi,TANIKAWA Kenichi,NAKAGAWA Hiroaki
- Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 25(8), 1039-1042, 2009-08-10
- NAID 10025214242
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