Conditions | Yield |
---|---|
With palladium on activated charcoal; hydrogen at 30℃; under 3000.3 Torr; for 2h; Temperature; Pressure; Reagent/catalyst; Autoclave; | 94% |
With hydrogenchloride; potassium chloride Electrolysis; | |
With hydrogenchloride; tin(ll) chloride |
Conditions | Yield |
---|---|
With ammonium hydrogen sulfite; ammonium nitrite; ammonium bisulfite; sulfuric acid at 40 - 70℃; for 4h; pH=3; | 87.5% |
Stage #1: aniline With hydrogenchloride; sodium nitrite In water at 65℃; pH=2.5; Stage #2: With ammonium hydrogen sulfite In water at 8 - 70℃; for 1.75h; Temperature; pH-value; Further stages; | 84% |
Stage #1: aniline With hydrogenchloride; sodium nitrite In water for 2h; Stage #2: With hydrogenchloride; sodium sulfite In water at 0 - 100℃; for 4h; | 78.74% |
Conditions | Yield |
---|---|
With potassium phosphate; copper(l) iodide; Oxalsaeure-bis-<β-benzoylhydrazid>; hydrazine hydrate In dimethyl sulfoxide at 20℃; for 12h; | 83% |
With hydrazine hydrate for 3h; Reflux; | |
With potassium phosphate; copper(l) iodide; hydrazine hydrate at 120℃; for 6h; Sealed tube; Inert atmosphere; | |
Stage #1: iodobenzene With oxalic acid hydrazide; potassium phosphate; cetyltrimethylammonim bromide; 2,5-hexanedione; copper(I) bromide In water at 110℃; for 0.166667h; Sealed tube; Stage #2: With hydrazine hydrate In water at 110℃; for 1h; Sealed tube; | 68 %Chromat. |
Conditions | Yield |
---|---|
With nickel dichloride; zinc In tetrahydrofuran Reduction; | 80% |
Multi-step reaction with 2 steps 1: water; tetrahydrofuran / 0 - 20 °C 2: sulfuric acid / water; isopropyl alcohol / 6 h / Reflux View Scheme |
phenylhydrazine
Conditions | Yield |
---|---|
With sulfuric acid In water; isopropyl alcohol for 6h; Reflux; | 79% |
phenylhydrazine
Conditions | Yield |
---|---|
With sulfuric acid In water; isopropyl alcohol for 6h; Reflux; | 75% |
phenylhydrazine
Conditions | Yield |
---|---|
With sulfuric acid In water; isopropyl alcohol for 6h; Reflux; | 70% |
4-tert-butyl-1,3-diphenyl-5-(E)-styryl-1,2,4-triazoline
A
N-t-butylbenzamide
B
3-phenyl-propenal
C
phenylhydrazine
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 4h; Ambient temperature; | A n/a B n/a C n/a D 37% |
aniline
A
1,2-diamino-benzene
B
phenylhydrazine
C
1,4-phenylenediamine
Conditions | Yield |
---|---|
With chloroamine; cationic exchanger KU-23 In diethyl ether at 20℃; for 1.5h; Product distribution; var. time; | A 11% B 12% C 5% |
Conditions | Yield |
---|---|
With alkali sulfite anschl. mit H2SO3; | |
With alkali sulfite anschl. mit Zink-Staub und Essigsaeure; | |
With hydrogenchloride; sodium sulfite | |
With sodium carbonate; sodium sulfite anschliessend Behandeln mit Schwefeldioxid und Erwaermen mit wss. Salzsaeure; | |
With alkali disulfite und anschl. Erhitzen mit HCl; |
6-methyl-3-(1-phenylhydrazono-ethyl)-pyran-2,4-dione
phenylhydrazine
benzenediazonium; hydroxide
phenylhydrazine
Conditions | Yield |
---|---|
With zinc at 0℃; | |
With sulphurous acid |
phenylhydrazine
Conditions | Yield |
---|---|
With hydrogenchloride at 0℃; durch elektrolytische Reduktion an einer Quecksilber-Kathode; |
Conditions | Yield |
---|---|
anschliessende Hydrolyse; |
3-phenyl-carbazic acid ; phenylhydrazine salt
A
methylammonium carbonate
B
phenylhydrazine
Conditions | Yield |
---|---|
im geschlossenen Rohr; |
Menthone
phenylhydrazine
Conditions | Yield |
---|---|
Kinetics; l-menthone; |
1-anilinomalonyl-3-methyl-4-(4'-nitrobenzeneazo)-5-pyrazolone
A
4-amino-N-hydroxybenzenamine
B
1-anilinomalonyl-3-methyl-4-aminopyrazolone
D
phenylhydrazine
Conditions | Yield |
---|---|
In water; N,N-dimethyl-formamide Mechanism; electrochemical reduction, buffer; pH range of 2-10; |
3-(N-Nitro-N-phenylhydrazono)pentane-2,4-dione
A
3-Aminopentan-2,4-dion
B
phenylhydrazine
Conditions | Yield |
---|---|
In water; N,N-dimethyl-formamide at 25℃; Product distribution; Mechanism; coulometry: E = -1.8V, pH 2.5; variation of condition; |
A
bromobenzene
B
biphenyl
C
chlorobenzene
D
phenylhydrazine
E
benzene
F
phenol
Conditions | Yield |
---|---|
for 0.5h; Product distribution; Ambient temperature; in the absence and presence of reductant, stimulants ( SnCl2, Fe salts, ascorbic acid) and halide ions; |
aniline
A
4-Aminobiphenyl
B
2-phenylaniline
C
diphenylamine
D
phenylhydrazine
Conditions | Yield |
---|---|
With alkaline chloramine at 50℃; Product distribution; var. time; |
Conditions | Yield |
---|---|
With hydrogenchloride; water In ethanol at 25℃; Rate constant; Thermodynamic data; Equilibrium constant; other cond.: further reagents; other obj. of st.: E(excit.), ΔH(excit.), -(DS(excit.)); |
5-methyl-3-phenyl-1,3,4-oxadiazol-2(3H)-one
phenylhydrazine
Conditions | Yield |
---|---|
at 100℃; |
phenylhydrazine
pyridine-2-carbaldehyde
phenylhydrazine
(E)-1-(2-pyridinyl)methylene-2-phenylhydrazine
Conditions | Yield |
---|---|
In ethanol for 6h; Reflux; | 100% |
With acetic acid In ethanol for 3h; Reflux; | 91% |
With 1-deoxy-1-(methylamino)-D-glucitol In ethanol; water at 20℃; for 0.666667h; Green chemistry; | 85% |
succinic acid anhydride
phenylhydrazine
4-oxo-4-(2-phenylhydrazinyl)butanoic acid
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 24h; | 100% |
With ethanol |
Conditions | Yield |
---|---|
In diethyl ether at 0℃; for 10h; | 100% |
Stage #1: phenylhydrazine With triethylamine In dichloromethane at 0℃; Inert atmosphere; Stage #2: acetic anhydride In dichloromethane at 0 - 20℃; Inert atmosphere; | 97% |
With pyridine; aluminum oxide at 90 - 92℃; for 1h; microwave irradiation; | 65% |
4-methyl-benzaldehyde
phenylhydrazine
4-methylbenzaldehyde phenylhydrazone
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane | 100% |
In neat (no solvent) at 20℃; for 0.00277778h; | 97% |
With oxidized single-walled carbon nanotubes(SWCNs-COOH) In ethanol at 80℃; for 1.25h; | 96% |
Conditions | Yield |
---|---|
In acetic acid Heating; | 100% |
for 0.166667h; Irradiation; | 100% |
at 0 - 90℃; for 1.5h; | 100% |
2-chloro-benzaldehyde
phenylhydrazine
2-chlorobenzaldehyde phenylhydrazone
Conditions | Yield |
---|---|
In 1-methyl-pyrrolidin-2-one at 160℃; for 0.166667h; microwave irradiation; | 100% |
With pyridinium p-toluenesulfonate In dichloromethane | 100% |
4-chloro-benzoyl chloride
phenylhydrazine
2-(4-Chlorbenzoyl)-1-phenylhydrazid
Conditions | Yield |
---|---|
With pyridine In tetrahydrofuran at 5 - 20℃; for 2h; | 100% |
With pyridine for 20h; | 70% |
With pyridine |
cyclotridecanone
phenylhydrazine
5,6,7,8,9,10,11,12,13,14,15,16-dodecahydrocyclotridecan[b]indole
Conditions | Yield |
---|---|
With trichloroacetic acid at 100℃; for 0.0833333h; Fischer indole synthesis; | 100% |
With hydrogenchloride; acetic acid |
Conditions | Yield |
---|---|
In ethanol for 6h; Reflux; | 100% |
In water for 0.0833333h; Sonication; | 95% |
With 1-deoxy-1-(methylamino)-D-glucitol In ethanol; water at 20℃; for 0.666667h; Reagent/catalyst; Solvent; Concentration; Green chemistry; | 91% |
Conditions | Yield |
---|---|
piperidine In ethanol for 5h; Heating; | 100% |
With oxidized single-walled carbon nanotubes(SWCNs-COOH) In ethanol at 80℃; for 0.75h; | 98% |
With Dowex resin acid form In ethanol for 0.75h; | 88% |
2-Adamantanone
phenylhydrazine
1-(adamantan-2-ylidene)-2-phenylhydrazine
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 2h; Inert atmosphere; | 100% |
In ethanol; acetic acid | 98% |
With 1-deoxy-1-(methylamino)-D-glucitol In ethanol; water at 20℃; for 0.583333h; Green chemistry; | 82% |
With acetic acid for 0.25h; Ambient temperature; |
2-carbethoxy-<11>-α-cyclothien-1-one
phenylhydrazine
Conditions | Yield |
---|---|
In toluene at 110℃; for 1h; | 100% |
2-bromophenyl methyl ketone
phenylhydrazine
N-[1-(2-Bromo-phenyl)-eth-(Z)-ylidene]-N'-phenyl-hydrazine
Conditions | Yield |
---|---|
In 1-methyl-pyrrolidin-2-one at 160℃; for 0.166667h; microwave irradiation; | 100% |
In diethyl ether Heating; | |
With acetic acid In ethanol for 0.166667h; Heating; Yield given; |
2,2,2-trichloro-1-(4-chlorophenyl)ethanone
phenylhydrazine
2-(4-Chlorbenzoyl)-1-phenylhydrazid
Conditions | Yield |
---|---|
With triethylamine In hexane at 25℃; for 3h; | 100% |
N,N-Dimethyl-2,4-bis(trifluoroacetyl)-1-naphthylamine
phenylhydrazine
2,2,2-trifluoro-1-(2-phenyl-3-(trifluoromethyl)-2H-benzo[g]indazol-5-yl)ethanone
Conditions | Yield |
---|---|
In acetonitrile for 24h; Heating; | 100% |
2-ethyl-4-oxo-1,3-benzoxazinium perchlorate
phenylhydrazine
2-(5-Ethyl-2-phenyl-2H-[1,2,4]triazol-3-yl)-phenol
Conditions | Yield |
---|---|
In acetic acid Heating; | 100% |
4-Dimethylaminomethylene-2,6-dimethyl-heptane-3,5-dione
phenylhydrazine
1-(5-Isopropyl-1-phenyl-1H-pyrazol-4-yl)-2-methyl-propan-1-one
Conditions | Yield |
---|---|
In acetic acid; butan-1-ol for 1h; Heating; | 100% |
2-((dimethylamino)methylene)-1,3-diphenylpropane-1,3-dione
phenylhydrazine
4-Benzoyl-1,5-diphenyl-pyrazol
Conditions | Yield |
---|---|
In acetic acid; butan-1-ol for 3h; Heating; | 100% |
In ethanol at 20℃; for 12h; Solvent; Inert atmosphere; regioselective reaction; | 89% |
2-(4-chloro-phenyl)-benzo[e][1,3]oxazin-4-one; perchlorate
phenylhydrazine
2-[5-(4-Chloro-phenyl)-2-phenyl-2H-[1,2,4]triazol-3-yl]-phenol
Conditions | Yield |
---|---|
In acetic acid Heating; | 100% |
Conditions | Yield |
---|---|
With hydrogenchloride In water | 100% |
In water at 20℃; for 1h; | 95% |
With hydrogenchloride In water at 0 - 20℃; for 1h; | 94% |
Conditions | Yield |
---|---|
With trichloroacetic acid at 100℃; for 0.0833333h; Fischer indole synthesis; | 100% |
With 1,3-bis(3-sulfopropyl)-1H-imidazol-3-ium hydrogensulfate In water at 80℃; for 1h; Fischer indole synthesis; | 88% |
With acetic acid for 0.5h; Heating; | 74% |
Conditions | Yield |
---|---|
With trichloroacetic acid at 100℃; for 0.0833333h; Fischer indole synthesis; | 100% |
With phosphorus trichloride In benzene | 80% |
With Amberlite IR 120 In ethanol at 80℃; for 12h; Fischer Indole Synthesis; | 80% |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 110℃; for 0.25h; Fischer indole synthesis; Microwave irradiation; Sealed vessel; | 77% |
1-(2-chloro-phenyl)-3-phenyl-2-propen-1-one
phenylhydrazine
Conditions | Yield |
---|---|
With acetic acid In ethanol for 0.5h; Heating; | 100% |
phenylhydrazine
ortho-bromobenzaldehyde
2-Brombenzaldehyd-Phenylhydrazon
Conditions | Yield |
---|---|
100% |
phenylhydrazine
Conditions | Yield |
---|---|
With water | 100% |
phenylhydrazine
methyl 5-(2-methylphenyl)-1-phenylpyrazole-3-carboxylate
Conditions | Yield |
---|---|
With acetic acid for 2h; Heating; | 100% |
phenylhydrazine
ethyl 3-(diethoxyphosphoryl)-3,3-difluoro-2-oxopropionate
Conditions | Yield |
---|---|
In benzene for 2h; Substitution; | 100% |
phenylhydrazine
(E)-benzalacetone
(E)-1-phenyl-2-((E)-4-phenylbut-3-en-2-ylidene)hydrazine
Conditions | Yield |
---|---|
at 20℃; for 0.0833333h; | 100% |
With acetic acid In methanol at 20℃; Inert atmosphere; | 85% |
With acetic acid In methanol for 0.75h; Heating; | |
With acetic acid In methanol at 20℃; |
phenylhydrazine
S-tert-butyl cyclohexylcarbamoylthioacetate
N-Cyclohexyl-2-(N'-phenyl-hydrazinocarbonyl)-acetamide
Conditions | Yield |
---|---|
With silver trifluoroacetate In 1,2-dimethoxyethane at 20℃; | 100% |
phenylhydrazine
4,4,4-trifluoro-1-(2-fluorophenyl)butane-1,3-dione
Conditions | Yield |
---|---|
With sulfuric acid In ethanol | 100% |
IUPAC Name: Phenylhydrazine
Synonyms of Phenylhydrazine (CAS NO.100-63-0): 4-15-00-00050 (Beilstein Handbook Reference) ; AI3-15399 ; BRN 0606080 ; CCRIS 511 ; EINECS 202-873-5 ; Fenilidrazina ; Fenilidrazina [Italian] ; Fenylhydrazine ; Fenylhydrazine [Dutch] ; HSDB 1117 ; Hydrazine, phenyl- ; Hydrazine-benzene ; Hydrazinobenzene ; Hydrazobenzene ; Monophenylhydrazine ; Phenylhydrazin ; Phenylhydrazin [German] ; Phenylhydrazine [UN2572] [Poison] ; Phenylhydrazine and its salts ; UN2572
CAS NO: 100-63-0
Classification Code: Mutation data ; Noxae ; Oxidants ; Reproductive Effect ; Tumor data
Molecular Formula: C6H8N2
Molecular Weight: 108.1411
Molecular Structure:
Melting Point: 19 °C
Polar Surface Area: 6.48 Å2
Index of Refraction: 1.643
Molar Refractivity: 34.76 cm3
Molar Volume: 96 cm3
Surface Tension: 49.9 dyne/cm
Density: 1.125 g/cm3
Flash Point: 115.4 °C
Enthalpy of Vaporization: 48 kJ/mol
Boiling Point: 243 °C at 760 mmHg
Vapour Pressure: 0.0329 mmHg at 25°C
Phenylhydrazine (CAS NO.100-63-0) is mainly used to produce dyes, pharmaceuticals, reagents,etc.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LDLo | intravenous | 120mg/kg (120mg/kg) | U.S. Public Health Service, Public Health Bulletin. Vol. 271, Pg. 159, 1941. | |
dog | LDLo | oral | 200mg/kg (200mg/kg) | U.S. Public Health Service, Public Health Bulletin. Vol. 271, Pg. 159, 1941. | |
frog | LDLo | unreported | 300mg/kg (300mg/kg) | U.S. Public Health Service, Public Health Bulletin. Vol. 271, Pg. 159, 1941. | |
guinea pig | LD50 | oral | 80mg/kg (80mg/kg) | BEHAVIORAL: EXCITEMENT BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) | Hygiene and Sanitation Vol. 30(7-9), Pg. 191, 1965. |
mouse | LC50 | inhalation | 2120mg/m3 (2120mg/m3) | Trudy Leningradskogo Sanitarno-Gigienicheskogo Meditsinskogo Instituta. Vol. 115, Pg. 59, 1977. | |
mouse | LD50 | intraperitoneal | 170mg/kg (170mg/kg) | Cancer Research. Vol. 41, Pg. 1469, 1981. | |
mouse | LD50 | oral | 175mg/kg (175mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 30(8), Pg. 21, 1965. |
mouse | LDLo | subcutaneous | 170mg/kg (170mg/kg) | LUNGS, THORAX, OR RESPIRATION: DYSPNEA LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES LUNGS, THORAX, OR RESPIRATION: CYANOSIS | Journal of Industrial Hygiene and Toxicology. Vol. 18, Pg. 1, 1936. |
rabbit | LD50 | oral | 80mg/kg (80mg/kg) | BEHAVIORAL: EXCITEMENT BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) | Hygiene and Sanitation Vol. 30(7-9), Pg. 191, 1965. |
rabbit | LDLo | skin | 90mg/kg (90mg/kg) | LUNGS, THORAX, OR RESPIRATION: CYANOSIS LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION KIDNEY, URETER, AND BLADDER: HEMATURIA | National Technical Information Service. Vol. OTS0546542, |
rat | LC50 | inhalation | 2610mg/m3 (2610mg/m3) | Trudy Leningradskogo Sanitarno-Gigienicheskogo Meditsinskogo Instituta. Vol. 115, Pg. 59, 1977. | |
rat | LD50 | oral | 188mg/kg (188mg/kg) | BEHAVIORAL: EXCITEMENT BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) | Hygiene and Sanitation Vol. 30(7-9), Pg. 191, 1965. |
Reported in EPA TSCA Inventory.
Hazard Codes of Phenylhydrazine (CAS NO.100-63-0): T,N
Risk Statements: 45-23/24/25-36/38-43-48-50-68
R45: May cause cancer.
R23/24/25: Toxic by inhalation, in contact with skin and if swallowed.
R36/38: Irritating to eyes and skin.
R43: May cause sensitization by skin contact.
R48: Danger of serious damage to health by prolonged exposure.
R50: Very toxic to aquatic organisms.
R68: Possible risk of irreversible effects.
Safety Statements: 53-45-61
S53: Avoid exposure - obtain special instructions before use.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S61: Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 2572 6.1/PG 2
WGK Germany: 3
RTECS: MV8925000
F: 8-10-23
HazardClass: 6.1
PackingGroup: II
Confirmed carcinogen with experimental carcinogenic data. Poison by ingestion, subcutaneous, and intravenous routes. Experimental reproductive effects. Mutation data reported. Ingestion or subcutaneous injection can cause hemolysis of red blood cells. Other effects are damage to the spleen, liver, kidneys, and bone marrow. The most common effect of occupational exposure is the development of dermatitis, which, in sensitized persons, may be quite severe. Systemic effects include anemia and general weakness, gastrointestinal disturbances, and injury to the kidneys. Flammable when exposed to heat, flame, or oxidizers. To fight fire, use alcohol foam. Violent reaction with 2-phenylamino-3-phenyloxazirane. Reacts with perchloryl fluoride to form an explosive product. Vigorous reaction with lead(IV) oxide. Used as a chemical reagent, in organic synthesis, and in the manufacture of dyes and drugs. Dangerous; when heated to decomposition it emits highly toxic fumes of NOx; can react with oxidizing materials.
OSHA PEL: TWA 5 ppm (skin); STEL 10 ppm
ACGIH TLV: TWA 0.1 ppm (skin); Animal Carcinogen
DFG MAK: Confirmed Animal Carcinogen with Unknown Relevance to Humans
NIOSH REL: CL 0.6 mg/m3/2H
DOT Classification: 6.1; Label: Poison
For occupational chemical analysis use NIOSH: Phenyl Hydrazine, S160.
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