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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

59-88-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • Alfa Aesar

  • (A14645)  Phenylhydrazine hydrochloride, 99%   

  • 59-88-1

  • 100g

  • 764.0CNY

  • Detail
  • Alfa Aesar

  • (A14645)  Phenylhydrazine hydrochloride, 99%   

  • 59-88-1

  • 500g

  • 1605.0CNY

  • Detail
  • Aldrich

  • (114715)  Phenylhydrazinehydrochloride  ≥99%

  • 59-88-1

  • 114715-5G

  • 223.47CNY

  • Detail
  • Aldrich

  • (114715)  Phenylhydrazinehydrochloride  ≥99%

  • 59-88-1

  • 114715-100G

  • 1,546.74CNY

  • Detail
  • Aldrich

  • (114715)  Phenylhydrazinehydrochloride  ≥99%

  • 59-88-1

  • 114715-500G

  • 6,458.40CNY

  • Detail

59-88-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Phenylhydrazine Hydrochloride

1.2 Other means of identification

Product number -
Other names Hydrazine, phenyl-, monohydrochloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:59-88-1 SDS

59-88-1Synthetic route

aniline
62-53-3

aniline

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

Conditions
ConditionsYield
Stage #1: aniline With hydrogenchloride; sodium nitrite In water at 0℃; for 1h;
Stage #2: With hydrogenchloride; tin(ll) chloride In water at 20℃; for 2h;
98%
Stage #1: aniline With hydrogenchloride In water for 0.166667h; Cooling with ice;
Stage #2: With sodium nitrite In water for 1h; Cooling with ice;
Stage #3: With hydrogenchloride; tin(ll) chloride In water for 3h; Cooling with ice;
94.1%
Stage #1: aniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1h;
Stage #2: With sodium sulfite In water at 80℃; for 2h;
Stage #3: With hydrogenchloride In water at 100℃; for 2h;
94%
di-tert-butyl 1-phenylhydrazine-1,2-dicarboxylate
65578-58-7

di-tert-butyl 1-phenylhydrazine-1,2-dicarboxylate

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane; isopropyl alcohol for 0.25h; Heating;88%
iodobenzene
591-50-4

iodobenzene

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

Conditions
ConditionsYield
Stage #1: iodobenzene With potassium phosphate; copper(l) iodide; N,N′-bis(2,6-dimethylphenyl)oxalamide; cetyltrimethylammonim bromide In water at 80℃; for 0.25h; Schlenk technique; Inert atmosphere; Sealed tube;
Stage #2: With hydrazine hydrate In water at 80℃; Inert atmosphere; Schlenk technique; Sealed tube;
Stage #3: With hydrogenchloride In water pH=3 - 4; Inert atmosphere; Schlenk technique; Sealed tube;
87%
buta-1,3-diene-1,4-diylbis(triphenylphosphonium chloride)

buta-1,3-diene-1,4-diylbis(triphenylphosphonium chloride)

phenylhydrazine
100-63-0

phenylhydrazine

A

(2-(phenylhydrazono)butane-1,4-diyl)bis(triphenylphosphonium chloride)

(2-(phenylhydrazono)butane-1,4-diyl)bis(triphenylphosphonium chloride)

B

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

Conditions
ConditionsYield
With chloroform at 60℃;A 85%
B 0.5 g
bromobenzene
108-86-1

bromobenzene

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

Conditions
ConditionsYield
Stage #1: bromobenzene With potassium phosphate; copper(l) iodide; N,N′-bis(2,6-dimethylphenyl)oxalamide; cetyltrimethylammonim bromide In water at 80℃; for 0.25h; Schlenk technique; Inert atmosphere; Sealed tube;
Stage #2: With hydrazine hydrate In water at 80℃; Inert atmosphere; Schlenk technique; Sealed tube;
Stage #3: With hydrogenchloride In water pH=3 - 4; Inert atmosphere; Schlenk technique; Sealed tube;
85%
Stage #1: bromobenzene With potassium phosphate; N,N'-bis(2,5-dimethylpyrrol-1-yl)oxalamide; cetyltrimethylammonim bromide; copper(I) bromide In water at 110℃; for 0.166667h; Sealed tube; Inert atmosphere;
Stage #2: With hydrazine hydrate In water at 110℃; for 1h; Sealed tube; Inert atmosphere;
Stage #3: With hydrogenchloride In dichloromethane; water
71%
Multi-step reaction with 2 steps
1: bis(triphenylphosphine)nickel(II) chloride; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride; sodium t-butanolate / 1,4-dioxane / 5 h / 50 °C / Inert atmosphere
2: hydrogenchloride / water / 20 °C
View Scheme
phenylazobenzenethiosulfonate
91363-25-6

phenylazobenzenethiosulfonate

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; sodium sulfite at 40 - 60℃; for 4h;79%
benzophenone N-phenylhydrazone
574-61-8

benzophenone N-phenylhydrazone

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water at 20℃;56%
but-2-ene-1,4-diylbis(triphenylphosphinium) dichloride
53643-43-9, 61893-91-2, 106423-29-4

but-2-ene-1,4-diylbis(triphenylphosphinium) dichloride

phenylhydrazine
100-63-0

phenylhydrazine

A

C24H21N2P*ClH
1092094-57-9

C24H21N2P*ClH

B

triphenyl(4-phenylhydrazonobut-2-enyl)phosphonium chloride
1299467-45-0

triphenyl(4-phenylhydrazonobut-2-enyl)phosphonium chloride

C

(2-(phenylhydrazono)butane-1,4-diyl)bis(triphenylphosphonium chloride)

(2-(phenylhydrazono)butane-1,4-diyl)bis(triphenylphosphonium chloride)

D

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

E

Triphenylphosphine oxide
791-28-6

Triphenylphosphine oxide

Conditions
ConditionsYield
In chloroform at 55 - 57℃; for 10h;A 19%
B 46%
C 7%
D 0.37 g
E 34%
{Et4N}{oxomolybdenum(Cl)4(H2O)}
125329-73-9, 57127-49-8

{Et4N}{oxomolybdenum(Cl)4(H2O)}

phenylhydrazine
100-63-0

phenylhydrazine

{molybdenum(cis-(bisdiazenido)Cl(μ-OC3H7)(phenylhydrazine)2}

{molybdenum(cis-(bisdiazenido)Cl(μ-OC3H7)(phenylhydrazine)2}

B

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

Conditions
ConditionsYield
In propan-1-ol addn. of org. compd. to suspn. of Mo-compd. in propanol, stirring (5 h, room temp.); filtn., standing (room temp., 48 h); elem. anal.;A 39%
B n/a
2,4,6-tris(trichloromethyl)-s-triazine
6542-67-2

2,4,6-tris(trichloromethyl)-s-triazine

phenylhydrazine
100-63-0

phenylhydrazine

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

tetrachloromethane
56-23-5

tetrachloromethane

phenylhydrazine
100-63-0

phenylhydrazine

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

Conditions
ConditionsYield
in der Waerme;
ethanol
64-17-5

ethanol

4-chloro-3-phenyl-1,2,3-λ5-oxadiazol-3-ium-5-olate
5226-93-7

4-chloro-3-phenyl-1,2,3-λ5-oxadiazol-3-ium-5-olate

A

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

B

ethyl 1-phenylhydrazinecarboxylate hydrochloride

ethyl 1-phenylhydrazinecarboxylate hydrochloride

Conditions
ConditionsYield
With hydrogenchloride
hydrogenchloride
7647-01-0

hydrogenchloride

1-phenylsemicarbazide
103-03-7

1-phenylsemicarbazide

A

1-phenylurazole
6942-46-7

1-phenylurazole

B

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

Conditions
ConditionsYield
at 120℃; schliesslich bei 140-150grad;
hydrogenchloride
7647-01-0

hydrogenchloride

N-phenyl-N,N'-dibenzylhydrazine
32293-59-7

N-phenyl-N,N'-dibenzylhydrazine

A

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

B

benzyl chloride
100-44-7

benzyl chloride

phenylhydrazine
100-63-0

phenylhydrazine

HCl

HCl

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

benzene diazonium chloride
100-34-5

benzene diazonium chloride

2 mol Na2S2O4

2 mol Na2S2O4

hydrochloric acid

hydrochloric acid

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

hydrogenchloride
7647-01-0

hydrogenchloride

1-benzylidene-3-formyl-2-phenyl-triazane
24720-71-6

1-benzylidene-3-formyl-2-phenyl-triazane

A

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

B

benzaldehyde
100-52-7

benzaldehyde

Chloro<(1S)-7,7-dimethyl-2-oxobicyclo<2.2.1>hept-1-yl>sulfine
100679-91-2, 173937-68-3

Chloro<(1S)-7,7-dimethyl-2-oxobicyclo<2.2.1>hept-1-yl>sulfine

phenylhydrazine
100-63-0

phenylhydrazine

A

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

B

norcamphoryl sulfoxide N-phenylpyrazolone

norcamphoryl sulfoxide N-phenylpyrazolone

tris-(N'-phenyl-hydrazino)-methane; trihydrochloride

tris-(N'-phenyl-hydrazino)-methane; trihydrochloride

water

water

A

formic acid
64-18-6

formic acid

B

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

aniline hydrochloride
142-04-1

aniline hydrochloride

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

Conditions
ConditionsYield
Stage #1: aniline hydrochloride With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1h;
Stage #2: With tin(ll) chloride for 2h;
aniline
62-53-3

aniline

α-chloro-propionic acid amide

α-chloro-propionic acid amide

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) NaNO2, aq. HCl, 2.) NaHCO3 / 2.) -5 - -3 deg C
2: 79 percent / 1.) sodium sulfite, 2.) conc. aq. HCl / 4 h / 40 - 60 °C
View Scheme
phenyllithium
591-51-5

phenyllithium

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60 percent / tetrahydrofuran / 0.17 h / -78 °C
2: 88 percent / HCl / propan-2-ol; dioxane / 0.25 h / Heating
View Scheme
With di-tert-butyl-diazodicarboxylate In tetrahydrofuran; cyclohexane
active charcoal

active charcoal

sodium salt of phenyldiazosulfonic acid
30983-82-5

sodium salt of phenyldiazosulfonic acid

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; platinum In water
Nitrosophenylamine
36966-84-4

Nitrosophenylamine

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; tin(ll) chloride In water at 0℃;
2-Hydroxy-cyclohexanon-2-carbonsaeureamid
61889-72-3

2-Hydroxy-cyclohexanon-2-carbonsaeureamid

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

3a-Hydroxy-2-phenyl-3,3a,4,5,6,7-hexahydro-2H-indazol-3-on
112178-55-9

3a-Hydroxy-2-phenyl-3,3a,4,5,6,7-hexahydro-2H-indazol-3-on

Conditions
ConditionsYield
In water for 0.0333333h; Heating;100%
phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

4-(2-tert-butoxycarbonyl-2-oxo-ethyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester
237421-80-6

4-(2-tert-butoxycarbonyl-2-oxo-ethyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester

4-[2-tert-butoxycarbonyl-2-(phenyl-hydrazono)-ethyl]-5-oxo-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester

4-[2-tert-butoxycarbonyl-2-(phenyl-hydrazono)-ethyl]-5-oxo-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester

Conditions
ConditionsYield
With sodium acetate In methanol for 1h; Ambient temperature;100%
4-oxocyclohexanecarboxylic acid
874-61-3

4-oxocyclohexanecarboxylic acid

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid
143121-58-8, 26088-66-4

2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid

Conditions
ConditionsYield
With zinc(II) chloride In acetic acid at 70℃; for 20h;100%
In ethanol for 3h; Heating / reflux;84%
In ethanol for 3h; Reflux;84%
molybdenum pentachloride

molybdenum pentachloride

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

MoCl3NNH(C6H5)

MoCl3NNH(C6H5)

Conditions
ConditionsYield
In dichloromethane (N2); stirring (-78°C, 0.08 h); warming to room temp., solvent removal (vac.), drying (vac., 0.5 h), pentane addn., stirring (0.2 h), filtn., washing (pentane), drying (vac.);100%
2'-chloro-5'-nitroacetophenone
23082-50-0

2'-chloro-5'-nitroacetophenone

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

2-(2-chloro-5-nitrophenyl)-1H-indole
1184871-71-3

2-(2-chloro-5-nitrophenyl)-1H-indole

Conditions
ConditionsYield
Stage #1: 2'-chloro-5'-nitroacetophenone; phenylhydrazine hydrochloride With acetic acid In ethanol at 80℃;
Stage #2: at 120℃;
Stage #3: With sodium hydroxide Cooling with ice;
100%
phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

ethyl phenylhydrazocarboxylate
6233-02-9

ethyl phenylhydrazocarboxylate

Conditions
ConditionsYield
With pyridine In acetonitrile at 0 - 20℃;100%
With pyridine In acetonitrile at 0℃; for 1.25h;90%
2-methyl-3-(1-methyl-1H-pyrazol-4-yl)-3-oxopropanenitrile
1414571-72-4

2-methyl-3-(1-methyl-1H-pyrazol-4-yl)-3-oxopropanenitrile

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

1′-4-dimethyl-1-phenyl-1H,1′H-[3,4′-bipyrazol]-5-amine
1414571-73-5

1′-4-dimethyl-1-phenyl-1H,1′H-[3,4′-bipyrazol]-5-amine

Conditions
ConditionsYield
In ethanol at 20℃; Reflux;100%
In ethanol for 17h; Time; Reflux;100%
In ethanol at 20℃; Reflux;100%
2-methyl-3-(1-methyl-1H-pyrazol-4-yl)-3-oxopropanenitrile
1414571-72-4

2-methyl-3-(1-methyl-1H-pyrazol-4-yl)-3-oxopropanenitrile

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

1',4-dimethyl-1-phenyl-1H,1'H-3,4'-bipyrazol-5-amine

1',4-dimethyl-1-phenyl-1H,1'H-3,4'-bipyrazol-5-amine

Conditions
ConditionsYield
In ethanol Reflux;100%
phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

2-trifluoromethyl-Δ1-pyrroline

2-trifluoromethyl-Δ1-pyrroline

5,5,5-trifluoro-4-(phenylhydrazono)pentan-1-amine hydrochloride

5,5,5-trifluoro-4-(phenylhydrazono)pentan-1-amine hydrochloride

Conditions
ConditionsYield
In methanol for 0.5h; Reflux;100%
2-(pentafluoroethyl)-3,4-dihydro-2H-pyrrole
1105579-06-3

2-(pentafluoroethyl)-3,4-dihydro-2H-pyrrole

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

5,5,6,6,6-pentafluoro-4-(phenylhydrazono)hexan-1-amine hydrochloride

5,5,6,6,6-pentafluoro-4-(phenylhydrazono)hexan-1-amine hydrochloride

Conditions
ConditionsYield
In methanol for 0.5h; Reflux;100%
7-(trifluoromethyl)-3,4,5,6-tetrahydro-2H-azepine
1146222-77-6

7-(trifluoromethyl)-3,4,5,6-tetrahydro-2H-azepine

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

7,7,7-trifluoro-6-(phenylhydrazono)heptan-1-amine hydrochloride

7,7,7-trifluoro-6-(phenylhydrazono)heptan-1-amine hydrochloride

Conditions
ConditionsYield
In methanol for 0.5h; Reflux;100%
6-(trifluoromethyl)-2,3,4,5-tetrahydropyridine
1146222-76-5

6-(trifluoromethyl)-2,3,4,5-tetrahydropyridine

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

6,6,6-trifluoro-5-(phenylhydrazono)hexan-1-amine hydrochloride

6,6,6-trifluoro-5-(phenylhydrazono)hexan-1-amine hydrochloride

Conditions
ConditionsYield
In methanol for 0.5h; Reflux;100%
acetamidine hydrochloride
124-42-5

acetamidine hydrochloride

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid
84358-13-4

N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid

tert-butyl 4-(3-methyl-1-phenyl-1H-1,2,4-triazol-5-yl)piperidine-1-carboxylate

tert-butyl 4-(3-methyl-1-phenyl-1H-1,2,4-triazol-5-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: acetamidine hydrochloride; N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h;
Stage #2: phenylhydrazine hydrochloride With acetic acid In N,N-dimethyl-formamide at 80℃; for 4h;
100%
1,1,1-trifluoro-4-(1-methoxynaphthalen-4-yl)but-3-yn-2-one

1,1,1-trifluoro-4-(1-methoxynaphthalen-4-yl)but-3-yn-2-one

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

5-(4-methoxynaphthalen-1-yl)-1-phenyl-3-(trifluoromethyl)-1H-pyrazole

5-(4-methoxynaphthalen-1-yl)-1-phenyl-3-(trifluoromethyl)-1H-pyrazole

Conditions
ConditionsYield
Stage #1: phenylhydrazine hydrochloride With 1,8-diazabicyclo[5.4.0]undec-7-ene
Stage #2: 1,1,1-trifluoro-4-(1-methoxynaphthalen-4-yl)but-3-yn-2-one for 24h; regioselective reaction;
100%
phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

pivaloyl chloride
3282-30-2

pivaloyl chloride

N’-phenyl-N-pivaloylhydrazine
42054-12-6

N’-phenyl-N-pivaloylhydrazine

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 0.0833333h;99.6%
phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

cyclohexanone
108-94-1

cyclohexanone

1,2,3,4-tetrahydrocarbazole
942-01-8

1,2,3,4-tetrahydrocarbazole

Conditions
ConditionsYield
With acetic acid at 90 - 120℃; for 1h; Temperature;99%
With L-(+)-tartaric acid-urea melt at 70℃; for 0.25h; Fischer Indole Synthesis;97%
With 1-(3-sulfopropyl)pyridinium p-toluenesulfonate In water at 100℃; for 0.166667h;96%
t-Boc-L-valine
13734-41-3

t-Boc-L-valine

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

Boc-Val-NHNHPh
95499-91-5

Boc-Val-NHNHPh

Conditions
ConditionsYield
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;99%
C13H17N3O3
1257542-03-2

C13H17N3O3

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

C17H16N4O2
1257542-09-8

C17H16N4O2

Conditions
ConditionsYield
With acetic acid at 20℃;99%
phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

2-Methylcyclohexanone
583-60-8

2-Methylcyclohexanone

4a-methyl-2,3,4,4a-tetrahydro-1H-carbazole
18781-72-1

4a-methyl-2,3,4,4a-tetrahydro-1H-carbazole

Conditions
ConditionsYield
With L-(+)-tartaric acid-urea melt at 70℃; for 0.5h; Fischer Indole Synthesis;99%
With acetic acid for 2h; Reflux;65%
With acetic acid at 120℃; for 14h; Inert atmosphere; Schlenk technique;
In acetic acid for 2h; Inert atmosphere; Reflux;12.5 g
1-(1-benzyl-5-methyl-1H-1,2,3-triazol-4-yl)-3-(4-methoxyphenyl)prop-2-en-1-one

1-(1-benzyl-5-methyl-1H-1,2,3-triazol-4-yl)-3-(4-methoxyphenyl)prop-2-en-1-one

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

1-benzyl-4-(5-(4-methoxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-5-methyl-1H-1,2,3-triazole
1605292-79-2

1-benzyl-4-(5-(4-methoxyphenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-5-methyl-1H-1,2,3-triazole

Conditions
ConditionsYield
In water for 1h; Solvent; Reflux; Green chemistry;99%
C19H16FN3O

C19H16FN3O

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

1-benzyl-4-(5-(4-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-5-methyl-1H-1,2,3-triazole
1605292-82-7

1-benzyl-4-(5-(4-fluorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-5-methyl-1H-1,2,3-triazole

Conditions
ConditionsYield
In water for 1.5h; Solvent; Reflux; Green chemistry;99%
β-D-mannose
7322-31-8

β-D-mannose

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

D-mannose phenylhydrazone
962-53-8

D-mannose phenylhydrazone

Conditions
ConditionsYield
With sodium acetate In water99%
phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

4-(4-chlorophenyl)-1,1,1-trifluorobut-3-yn-2-one
77063-21-9

4-(4-chlorophenyl)-1,1,1-trifluorobut-3-yn-2-one

5-(4-chlorophenyl)-1-phenyl-3-(trifluoromethyl)-1H-pyrazole
586333-28-0

5-(4-chlorophenyl)-1-phenyl-3-(trifluoromethyl)-1H-pyrazole

Conditions
ConditionsYield
Stage #1: phenylhydrazine hydrochloride With 1,8-diazabicyclo[5.4.0]undec-7-ene
Stage #2: 4-(4-chlorophenyl)-1,1,1-trifluorobut-3-yn-2-one for 24h; regioselective reaction;
99%
4-(4-bromophenyl)-1,1,1-trifluorobut-3-yn-2-one

4-(4-bromophenyl)-1,1,1-trifluorobut-3-yn-2-one

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

1-phenyl-3-(trifluoromethyl)-5-(4-bromophenyl)-1H-pyrazole
586333-33-7

1-phenyl-3-(trifluoromethyl)-5-(4-bromophenyl)-1H-pyrazole

Conditions
ConditionsYield
Stage #1: phenylhydrazine hydrochloride With 1,8-diazabicyclo[5.4.0]undec-7-ene
Stage #2: 4-(4-bromophenyl)-1,1,1-trifluorobut-3-yn-2-one for 24h; regioselective reaction;
99%
1,1,1-trifluoro-4-(2,3-dihydrobenzo[b][1,4]dioxin-7-yl)but-3-yn-2-one

1,1,1-trifluoro-4-(2,3-dihydrobenzo[b][1,4]dioxin-7-yl)but-3-yn-2-one

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

3-(trifluoromethyl)-5-(2,3-dihydrobenzo[b][1,4]dioxin-7-yl)-1-phenyl-1H-pyrazole

3-(trifluoromethyl)-5-(2,3-dihydrobenzo[b][1,4]dioxin-7-yl)-1-phenyl-1H-pyrazole

Conditions
ConditionsYield
Stage #1: phenylhydrazine hydrochloride With 1,8-diazabicyclo[5.4.0]undec-7-ene
Stage #2: 1,1,1-trifluoro-4-(2,3-dihydrobenzo[b][1,4]dioxin-7-yl)but-3-yn-2-one for 24h; regioselective reaction;
99%
naltrexone Hydrochloride
16676-29-2

naltrexone Hydrochloride

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

naltrindole
111555-53-4

naltrindole

Conditions
ConditionsYield
In water at 20℃; Fischer indole synthesis;98%
With acetic acid Heating; further reagent;
phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

Norhydromorphone hydrochloride
14140-35-3

Norhydromorphone hydrochloride

6,7-dehydro-4,5α-epoxy-3-hydroxy-6,7-2',3'-indolomorphinan hydrochloride

6,7-dehydro-4,5α-epoxy-3-hydroxy-6,7-2',3'-indolomorphinan hydrochloride

Conditions
ConditionsYield
In acetic acid at 90℃; for 16h;98%
phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

noroxymorphone
33522-95-1

noroxymorphone

6,7-dehydro-4,5α-epoxy-3,14-dihydroxy-6,7-2',3'-indolomorphinan hydrochloride

6,7-dehydro-4,5α-epoxy-3,14-dihydroxy-6,7-2',3'-indolomorphinan hydrochloride

Conditions
ConditionsYield
With hydrogenchloride for 16h; Heating;98%
With hydrogenchloride In methanol Reflux;
ethyl 2-(1H-indol-3-yl)-2-oxoacetate
51079-10-8

ethyl 2-(1H-indol-3-yl)-2-oxoacetate

phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

2-phenylpyrazolo[3,4-c]quinolin-4(5H)-one
109740-09-2

2-phenylpyrazolo[3,4-c]quinolin-4(5H)-one

Conditions
ConditionsYield
With acetic acid In ethanol at 140℃; for 0.05h; microwave irradiation;98%
With acetic acid In ethanol at 140℃; for 0.05h; Microwave irradiation;98%
With acetic acid In ethanol for 3h; Heating;72%
phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

cycloheptanone
502-42-1

cycloheptanone

5,6,7,8,9,10-hexahydrocyclohept[b]indole
2047-89-4

5,6,7,8,9,10-hexahydrocyclohept[b]indole

Conditions
ConditionsYield
With L-(+)-tartaric acid-urea melt at 70℃; for 1h; Fischer Indole Synthesis;98%
With 1-(3-sulfopropyl)pyridinium p-toluenesulfonate In water at 100℃; for 0.166667h;93%
With 1,3-bis(3-sulfopropyl)-1H-imidazol-3-ium trifluoromethanesulfonate In water at 100℃; for 0.25h; Fischer Indole Synthesis; Microwave irradiation; Green chemistry;91%

59-88-1Relevant articles and documents

Chilou, Valerie,Gouzerh, Pierre,Jeannin, Yves,Olivares, Giuseppe,Robert, Francis,et al.

, p. 29 - 38 (1989)

REACTION OF SOME X-PHENYLAZIDES DERIVATIVES WITH DIETHYL 1,3-ACETONEDICARBOXYLATE

Fatmi, Chames Eddine,Bouasla, Souad,Teguiche, Mabrouk

, p. 445 - 448 (2022/03/09)

A series of ethyl 5-(2-ethoxy-2-oxoethyl)-1-(X-phenyl)-1H-1,2,3-triazole-4-carboxylate was synthesized through a condensation reaction of some aryl azides and diethyl-1,3-acetondicarboxylate (DEAD) in the presence of sodium ethoxide as a base. An unexpected heterocycle was isolated in the case of 2-trifluoromethylphenylazide. All the compounds are elucidated using FT-IR, NMR and MS spectroscopic techniques.

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.

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