Conditions | Yield |
---|---|
With ammonia In isopropyl alcohol | 96.4% |
With ammonia In 2-methyl-propan-1-ol | 95.8% |
With potassium hydroxide In ethanol for 4h; Heating; | 83% |
Conditions | Yield |
---|---|
With potassium carbonate at 130 - 135℃; Temperature; Inert atmosphere; | 95.4% |
Conditions | Yield |
---|---|
With potassium carbonate at 150 - 160℃; Temperature; Inert atmosphere; | 94.3% |
2-nitro-5-phenylthioaniline
Conditions | Yield |
---|---|
With ammonia In methanol at 180 - 200℃; under 13501.4 - 26252.6 Torr; for 10h; Pressure; Solvent; Temperature; Autoclave; | 93.1% |
Conditions | Yield |
---|---|
With ammonia In isopropyl alcohol | 89.5% |
4-methylsulfanyl-thiophenol
A
2-Bromo-4-(4-methylsulphanylphenylsulphanyl)nitrobenzene
B
2-nitro-5-phenylthioaniline
5-chloro-2-nitroaniline
1,2-diamino-4-phenylthiobenzene
1-(methyl)-thiourea
thiophenol
methyl chloroformate
B
2-nitro-5-phenylthioaniline
Conditions | Yield |
---|---|
With sodium hydroxide In N-methyl-acetamide; water; potassium carbonate; acetic acid |
1,3-Dichlorobenzene
2-nitro-5-phenylthioaniline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: nitric acid; sulfuric acid / 3 h / 10 - 15 °C 2: potassium hydroxide / 5,5-dimethyl-1,3-cyclohexadiene / 4 h / Reflux 3: ammonia / methanol / 10 h / 180 - 200 °C / 13501.4 - 26252.6 Torr / Autoclave View Scheme |
2,4-dichloronitrobenzene
2-nitro-5-phenylthioaniline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide / 5,5-dimethyl-1,3-cyclohexadiene / 4 h / Reflux 2: ammonia / methanol / 10 h / 180 - 200 °C / 13501.4 - 26252.6 Torr / Autoclave View Scheme |
3-chloro-aniline
2-nitro-5-phenylthioaniline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: nitric acid / acetic acid; sulfuric acid / 10.5 h / 20 - 25 °C 2: sodium hydroxide / methanol / 10.25 h / 90 - 95 °C View Scheme |
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 90 - 95℃; for 10.25h; Temperature; |
methyl methoxyacetate
2-nitro-5-phenylthioaniline
2-methoxy-N-(2-nitro-5-(phenylsulfanyl)phenyl)acetamide
Conditions | Yield |
---|---|
at 120 - 130℃; Temperature; | 95.5% |
2-nitro-5-phenylthioaniline
2-methoxyacetic acid
2-methoxy-N-(2-nitro-5-(phenylsulfanyl)phenyl)acetamide
Conditions | Yield |
---|---|
With pyridine; thionyl chloride In toluene at 75 - 110℃; for 10.5h; Reagent/catalyst; Solvent; Temperature; | 94.8% |
Methoxyacetyl chloride
2-nitro-5-phenylthioaniline
N-(2-Amino-5-benzenesulfinyl-phenyl)-2-methoxy-acetamide
Conditions | Yield |
---|---|
(i) Py, benzene, (ii) H2O2, Ac2O, (iii) H2, Raney-Ni, THF; Multistep reaction; |
ethoxyacetyl chloride
2-nitro-5-phenylthioaniline
N-(2-Amino-5-phenylsulfanyl-phenyl)-2-ethoxy-acetamide
Conditions | Yield |
---|---|
(i) Py, benzene, (ii) H2, Raney-Ni, THF; Multistep reaction; |
ethoxyacetyl chloride
2-nitro-5-phenylthioaniline
N-(2-Amino-5-benzenesulfinyl-phenyl)-2-ethoxy-acetamide
Conditions | Yield |
---|---|
(i) Py, benzene, (ii) H2O2, Ac2O, (iii) H2, Raney-Ni, THF; Multistep reaction; |
2-nitro-5-phenylthioaniline
propionyl chloride
2-propionamido-4-phenylthioaniline
Conditions | Yield |
---|---|
(i) Py, benzene, (ii) H2, Raney-Ni, THF; Multistep reaction; |
2-nitro-5-phenylthioaniline
propionyl chloride
2-propionamido-4-phenylsulfinylaniline
Conditions | Yield |
---|---|
(i) Py, benzene, (ii) H2O2, Ac2O, (iii) H2, Raney-Ni, THF; Multistep reaction; |
2-nitro-5-phenylthioaniline
chloroformic acid ethyl ester
(2-Amino-5-phenylsulfanyl-phenyl)-carbamic acid ethyl ester
Conditions | Yield |
---|---|
(i) Py, benzene, (ii) H2, Raney-Ni, THF; Multistep reaction; |
2-nitro-5-phenylthioaniline
chloroformic acid ethyl ester
(2-Amino-5-benzenesulfinyl-phenyl)-carbamic acid ethyl ester
Conditions | Yield |
---|---|
(i) Py, benzene, (ii) H2O2, Ac2O, (iii) H2, Raney-Ni, THF; Multistep reaction; |
2-nitro-5-phenylthioaniline
n-valeryl chloride
2-Amino-5-phenylthio-valeranilid
Conditions | Yield |
---|---|
(i) Py, benzene, (ii) H2, Raney-Ni, THF; Multistep reaction; |
2-nitro-5-phenylthioaniline
n-valeryl chloride
Pentanoic acid (2-amino-5-benzenesulfinyl-phenyl)-amide
Conditions | Yield |
---|---|
(i) Py, benzene, (ii) H2O2, Ac2O, (iii) H2, Raney-Ni, THF; Multistep reaction; |
2-nitro-5-phenylthioaniline
Hexanoyl chloride
Hexanoic acid (2-amino-5-phenylsulfanyl-phenyl)-amide
Conditions | Yield |
---|---|
(i) Py, benzene, (ii) H2, Raney-Ni, THF; Multistep reaction; |
2-nitro-5-phenylthioaniline
Hexanoyl chloride
Hexanoic acid (2-amino-5-benzenesulfinyl-phenyl)-amide
Conditions | Yield |
---|---|
(i) Py, benzene, (ii) H2O2, Ac2O, (iii) H2, Raney-Ni, THF; Multistep reaction; |
2-nitro-5-phenylthioaniline
acetyl chloride
2-Amino-5-phenylthioacetanilid
Conditions | Yield |
---|---|
(i) Py, benzene, (ii) H2, Raney-Ni, THF; Multistep reaction; |
2-nitro-5-phenylthioaniline
acetyl chloride
2-acetamido-1-amino-4-phenylsulfinylbenzene
Conditions | Yield |
---|---|
(i) Py, benzene, (ii) H2O2, Ac2O, (iii) H2, Raney-Ni, THF; Multistep reaction; |
2-nitro-5-phenylthioaniline
butyryl chloride
2-Amino-5-phenylthio-butyranilid
Conditions | Yield |
---|---|
(i) Py, benzene, (ii) H2, Raney-Ni, THF; Multistep reaction; |
2-nitro-5-phenylthioaniline
butyryl chloride
2-butyramido-4-phenylsulfinylaniline
Conditions | Yield |
---|---|
(i) Py, benzene, (ii) H2O2, Ac2O, (iii) H2, Raney-Ni, THF; Multistep reaction; |
2-nitro-5-phenylthioaniline
Phenoxyacetyl chloride
N-(2-Amino-5-phenylsulfanyl-phenyl)-2-phenoxy-acetamide
Conditions | Yield |
---|---|
(i) Py, benzene, (ii) H2, Raney-Ni, THF; Multistep reaction; |
2-nitro-5-phenylthioaniline
Phenoxyacetyl chloride
N-(2-Amino-5-benzenesulfinyl-phenyl)-2-phenoxy-acetamide
Conditions | Yield |
---|---|
(i) Py, benzene, (ii) H2O2, Ac2O, (iii) H2, Raney-Ni, THF; Multistep reaction; |
methoxycarbonylisothiocyanate
2-nitro-5-phenylthioaniline
methyl iodide
C16H17N3O2S2
Conditions | Yield |
---|---|
Multistep reaction; |
methoxycarbonylisothiocyanate
2-nitro-5-phenylthioaniline
2-nitro-5-phenylthiophenylallophanic acid methyl ester
Conditions | Yield |
---|---|
In acetonitrile for 15h; Heating; | 3.5 g |
In acetonitrile | |
In acetonitrile |
2-nitro-5-phenylthioaniline
1,2-diamino-4-phenylthiobenzene
Conditions | Yield |
---|---|
With hydrogen; nickel In ethanol under 2660 Torr; for 12h; | |
With hydrogen; palladium on activated charcoal In ethanol at 20℃; under 3102.89 Torr; | |
With platinum on activated charcoal; hydrogen In ethanol at 70 - 90℃; under 7500.75 - 15001.5 Torr; for 8h; Solvent; Reagent/catalyst; | 21.2 g |
With iron(III) chloride; hydrazine hydrate; pyrographite In methanol at 45 - 50℃; under 3750.38 - 7500.75 Torr; for 0.75h; Temperature; Pressure; |
2-nitro-5-phenylthioaniline
Fenbendazole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: H2 / Pd/C / ethanol / 20 °C / 3102.89 Torr 2.1: NaOH / H2O / 0.67 h / 3 - 6 °C 2.2: 88 percent / AcOH / H2O; ethanol / 24 h / 95 °C View Scheme |
2-nitro-5-phenylthioaniline
5-Phenylthiobenzimidazole-2-thione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: H2 / Raney-nickel / ethanol / 12 h / 2660 Torr 2: KOH / ethanol / 4 h / Heating View Scheme |
Molecular Structure of 2-Nitro-5-(phenylthio)aniline (CAS NO.43156-47-4):
IUPAC Name: 2-Nitro-5-phenylsulfanylaniline
Canonical SMILES: C1=CC=C(C=C1)SC2=CC(=C(C=C2)[N+](=O)[O-])N
InChI: InChI=1S/C12H10N2O2S/c13-11-8-10(6-7-12(11)14(15)16)17-9-4-2-1-3-5-9/h1-8H,13H2
InChIKey: AJGJUXSVUPXOHL-UHFFFAOYSA-N
Molecular Weight: 246.285 [g/mol]
Molecular Formula: C12H10N2O2S
XLogP3: 3.3
H-Bond Donor: 1
H-Bond Acceptor: 3
EINECS: 256-121-6
Index of Refraction: 1.696
Molar Refractivity: 69.12 cm3
Molar Volume: 179.5 cm3
Surface Tension: 67.5 dyne/cm
Density: 1.37 g/cm3
Flash Point: 239.6 °C
Enthalpy of Vaporization: 73.55 kJ/mol
Boiling Point: 472.5 °C at 760 mmHg
Vapour Pressure: 4.26E-09 mmHg at 25 °C
Product Categories: API intermediates
2-Nitro-5-(phenylthio)aniline (CAS NO.43156-47-4), its Synonyms are 2-Nitro-5-(phenylthio)benzenamine ; 4-Phenylthio-2-aminonitrobenzene ; Benzenamine, 2-nitro-5-(phenylthio)- .
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