Conditions | Yield |
---|---|
With copper(ll) sulfate pentahydrate; ethane-1,2-dithiol; potassium hydroxide In water; dimethyl sulfoxide at 90℃; for 20h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; iodine In water; dimethyl sulfoxide at 60℃; | 98% |
With potassium hydroxide at 110℃; for 24h; Reagent/catalyst; | 87% |
With iodine; potassium hydroxide In water; dimethyl sulfoxide at 100℃; | 82% |
Conditions | Yield |
---|---|
With indium; ammonium chloride In ethanol for 2h; Reduction; Heating; | 96% |
With sodium tetrahydroborate; lithium chloride In tetrahydrofuran at 0 - 35℃; | 93% |
With magnesium In methanol for 2h; Ambient temperature; | 85% |
2-(2-aminophenylthio)-4-phenyl-2,3-dihydro-1,5-benzothiazepine
A
2-Phenylquinoline
B
2-amino-benzenethiol
C
2-Aminophenyl disulfide
Conditions | Yield |
---|---|
In toluene for 4h; Heating; | A 95% B n/a C n/a |
Conditions | Yield |
---|---|
With hydrogen bromide In water at 30℃; for 2h; Temperature; Inert atmosphere; | 92.7% |
2-Aminophenyl disulfide
ethyl 2-(4-fluorophenyl)acetate
A
2-(4-fluorophenyl)-3-oxo-3,4-dihydro-2H-1,4-benzothiazine
B
2-amino-benzenethiol
Conditions | Yield |
---|---|
With sodium hydride In dimethyl sulfoxide; N,N-dimethyl-formamide at 100℃; for 0.333333h; | A 92% B n/a |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; zirconium(IV) chloride In tetrahydrofuran at 35℃; for 0.5h; Reduction; | A 10% B 90% |
With sodium tetrahydroborate; zirconium(IV) chloride In tetrahydrofuran at 35℃; for 0.166667h; Reduction; | A 80% B 20% |
4-methoxy-phenyl acetic acid methyl ester
2-Aminophenyl disulfide
A
2-(4-methoxy-phenyl)-4H-benzo[1,4]thiazin-3-one
B
2-amino-benzenethiol
Conditions | Yield |
---|---|
With sodium hydride In dimethyl sulfoxide; N,N-dimethyl-formamide at 100℃; for 0.333333h; | A 88% B n/a |
benzeneacetic acid methyl ester
2-Aminophenyl disulfide
A
3,4-dihydro-2-phenyl-2H-1,4-benzothiazin-3-one
B
2-amino-benzenethiol
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h; | A 86% B n/a |
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h; other methyl or ethyl aryl- or pyridylacetates; |
2-amino-benzenethiol
Conditions | Yield |
---|---|
With sodium tetrahydroborate; zirconium(IV) chloride In tetrahydrofuran at 35℃; for 0.25h; Reduction; | 85% |
methyl 1-naphthylacetate
2-Aminophenyl disulfide
A
2-Naphthalen-1-yl-4H-benzo[1,4]thiazin-3-one
B
2-amino-benzenethiol
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h; | A 82% B n/a |
Conditions | Yield |
---|---|
With potassium hydroxide at 110℃; for 24h; Reagent/catalyst; | 82% |
(4-chloro-phenyl)-acetic acid methyl ester
2-Aminophenyl disulfide
A
2-amino-benzenethiol
B
2-(4-chlorophenyl)-1,4-benzothiazin-3-one
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h; | A n/a B 81% |
methyl 2-(3-bromo-4-methoxyphenyl)acetate
2-Aminophenyl disulfide
A
2-(3-Bromo-4-methoxy-phenyl)-4H-benzo[1,4]thiazin-3-one
B
2-amino-benzenethiol
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h; | A 80% B n/a |
methyl (2-chlorophenyl)acetate
2-Aminophenyl disulfide
A
2-amino-benzenethiol
B
2-(2-chloro-phenyl)-4H-benzo[1,4]thiazin-3-one
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h; | A n/a B 79% |
Conditions | Yield |
---|---|
With potassium hydroxide; water In ethylene glycol at 125℃; for 15h; | 78% |
With potassium hydroxide at 110℃; for 24h; Reagent/catalyst; | 75% |
With hydroxide |
p-tolylacetic acid ethyl ester
2-Aminophenyl disulfide
A
2-(4-methylphenyl)-1,4-benzothiazin-3-one
B
2-amino-benzenethiol
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h; | A 77% B n/a |
benzo[1,3]dioxol-5-yl-acetic acid methyl ester
2-Aminophenyl disulfide
A
2-Benzo[1,3]dioxol-5-yl-4H-benzo[1,4]thiazin-3-one
B
2-amino-benzenethiol
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h; | A 73% B n/a |
pyridin-3-yl-acetic acid ethyl ester
2-Aminophenyl disulfide
A
2-(3-pyridyl)-3-oxo-3,4-dihydro-2H-1,4-benzothiazine
B
2-amino-benzenethiol
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h; | A 72% B n/a |
ethyl 3,4-dimethoxyphenylacetate
2-Aminophenyl disulfide
A
2-(3,4-Dimethoxy-phenyl)-4H-benzo[1,4]thiazin-3-one
B
2-amino-benzenethiol
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h; | A 71% B n/a |
2,3-dihydro-3-methoxycarbonyl-2-benzothiazolecarbonitrile
2-amino-benzenethiol
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol for 2h; Heating; | 70% |
With potassium hydroxide In ethanol for 2h; Heating; | 70% |
2-Mercaptobenzothiazole
A
N,N',N''-triaminoguanidine
B
2-amino-benzenethiol
C
2-hydrazono-2,3-dihydro-1,3-benzothiazole
D
2-Aminophenyl disulfide
Conditions | Yield |
---|---|
With hydrazine hydrate at 105 - 110℃; for 76h; Product distribution; Mechanism; also reaction with ethylenediamine, propylenediamine; other temp. (150 deg C); | A n/a B 70% C 20% D n/a |
With hydrazine hydrate at 105 - 110℃; for 76h; | A n/a B 70% C 20% D n/a |
ethyl 2-(pyridinyl-2)acetate
2-Aminophenyl disulfide
A
2-(2-pyridyl)-3-oxo-3,4-dihydro-2H-1,4-benzothiazine
B
2-amino-benzenethiol
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h; | A 69% B n/a |
methyl 2-(4-isopropylphenyl)acetate
2-Aminophenyl disulfide
A
2-(4-Isopropyl-phenyl)-4H-benzo[1,4]thiazin-3-one
B
2-amino-benzenethiol
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h; | A 69% B n/a |
(3-trifluoromethyl-phenyl)-acetic acid methyl ester
2-Aminophenyl disulfide
A
2-(3-Trifluoromethyl-phenyl)-4H-benzo[1,4]thiazin-3-one
B
2-amino-benzenethiol
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h; | A 65% B n/a |
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate In water at 100℃; | A 63% B 33% |
Conditions | Yield |
---|---|
With titanium(III) chloride; lithium In tetrahydrofuran for 20h; Heating; | 55% |
2-(2-propen-1-ylsulfanyl)aniline
2-amino-benzenethiol
Conditions | Yield |
---|---|
With titanium(III) chloride; lithium In tetrahydrofuran at 25℃; for 2h; | 47% |
2,3-dihydro-3-(4-methylbenzoyl)-2-benzothiazolecarbonitrile
2-amino-benzenethiol
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol for 2h; Heating; | 46% |
cyclohexanone
2-amino-benzenethiol
3H-spiro{benzothiazole-2,1'-cyclohexane}
Conditions | Yield |
---|---|
With trifluoroacetic acid at 80℃; for 16h; Reagent/catalyst; | 100% |
In toluene Heating; | 93.8% |
With aluminum oxide In neat (no solvent) at 20℃; for 0.5h; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
With Yb/MCM-41 molecular sieve In ethanol at 80℃; for 4h; Concentration; Temperature; | 100% |
Stage #1: benzaldehyde; 2-amino-benzenethiol With oxygen; scandium tris(trifluoromethanesulfonate) In tetrahydrofuran; water for 3h; Cycloaddition; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone for 0.25h; Oxidation; | 99% |
With 1-pentyl-3-methylimidazolium bromide for 0.05h; microwave irradiation; | 99% |
Conditions | Yield |
---|---|
In toluene at 20℃; for 0.25h; | 100% |
In neat (no solvent) for 4h; Time; Temperature; Green chemistry; | 91% |
In toluene at 20℃; for 0.416667h; | 85% |
Conditions | Yield |
---|---|
at 0℃; for 2h; gas/solid reaction; | 100% |
Stage #1: 2-amino-benzenethiol; acetone In neat (no solvent) at 50℃; for 1h; Green chemistry; Stage #2: With o-benzenedisulfonimide In neat (no solvent) at 50℃; for 48h; Green chemistry; | 87% |
With aluminum oxide at 20℃; for 0.5h; | 84% |
Conditions | Yield |
---|---|
With trifluoroacetic acid In dimethyl sulfoxide at 80℃; for 16h; Reagent/catalyst; | 100% |
With imino urea In methanol for 0.0833333h; Ambient temperature; | 99% |
With nanophase manganese (VII) oxide coated clay (NM7O coated clay) In chloroform at 20℃; | 99% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 60℃; for 2h; Molecular sieve; | 100% |
With yttrium(III) chloride In ethanol for 0.5h; Time; Reflux; Inert atmosphere; | 98% |
In ethanol for 0.666667h; Ambient temperature; | 94% |
4-chlorobenzaldehyde
2-amino-benzenethiol
2-(4-chlorophenyl)-2,3-dihydrobenzo[d]thiazole
Conditions | Yield |
---|---|
In ethanol for 0.666667h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With sodium hydride In acetonitrile at 0℃; for 7h; | 100% |
With sodium methylate In methanol for 6h; Reflux; | 97% |
Stage #1: 2-amino-benzenethiol With potassium tert-butylate In ethanol at 0℃; for 0.75h; Stage #2: ethyl iodide In ethanol at 0 - 20℃; for 0.75h; Further stages.; | 85% |
1,3-diphenylpropanedione
2-amino-benzenethiol
1-(2-mercaptophenylimino)-1 3-diphenylpropan-3-one
Conditions | Yield |
---|---|
With piperidine In ethanol Heating; | 100% |
3-chloro-2-phenyl-but-2-enal
2-amino-benzenethiol
2-Methyl-3-phenyl-benzo[b][1,4]thiazepine
Conditions | Yield |
---|---|
100% |
bis(2-chloroethyl)disulfide
2-amino-benzenethiol
1,8-Bis(2-aminophenyl)-1,4,5,8-tetrathiaoctane
Conditions | Yield |
---|---|
With potassium hydroxide In methanol for 2h; Heating; | 100% |
2-naphthyl benzoate
2-amino-benzenethiol
A
2-Phenylbenzothiazole
B
β-naphthol
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; potassium carbonate at 100℃; for 0.75h; Hydrolysis; cyclization; debenzoylation; | A n/a B 100% |
2-naphthyl pivalate
2-amino-benzenethiol
A
2-(tert-butyl)benzo[d]thiazole
B
β-naphthol
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; potassium carbonate at 100℃; for 2h; Hydrolysis; cyclization; | A n/a B 100% |
4-cyanophenyl acetate
2-amino-benzenethiol
A
2-Methylbenzothiazole
B
4-cyanophenol
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; potassium carbonate at 100℃; for 0.5h; Hydrolysis; cyclization; | A n/a B 100% |
2-amino-benzenethiol
4-cyanophenyl pivalate
A
2-(tert-butyl)benzo[d]thiazole
B
4-cyanophenol
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; potassium carbonate at 100℃; for 1.5h; Hydrolysis; cyclization; | A n/a B 100% |
Conditions | Yield |
---|---|
copper(II) bis(tetrafluoroborate) at 30 - 33℃; for 1h; | 100% |
Lawessons reagent
2-amino-benzenethiol
2-(4-methoxyphenyl)-2,3-dihydro-1,3,2-benzothiazaphosphole 2-sulfide
Conditions | Yield |
---|---|
at 190℃; for 0.0166667h; Neat (no solvent); Microwave irradiation; | 100% |
Conditions | Yield |
---|---|
With copper(ll) sulfate pentahydrate; ethane-1,2-dithiol; potassium hydroxide In water; dimethyl sulfoxide at 90℃; for 20h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; iodine In water; dimethyl sulfoxide at 60℃; | 98% |
With potassium hydroxide at 110℃; for 24h; Reagent/catalyst; | 87% |
With iodine; potassium hydroxide In water; dimethyl sulfoxide at 100℃; | 82% |
Conditions | Yield |
---|---|
With indium; ammonium chloride In ethanol for 2h; Reduction; Heating; | 96% |
With sodium tetrahydroborate; lithium chloride In tetrahydrofuran at 0 - 35℃; | 93% |
With magnesium In methanol for 2h; Ambient temperature; | 85% |
2-(2-aminophenylthio)-4-phenyl-2,3-dihydro-1,5-benzothiazepine
A
2-Phenylquinoline
B
2-amino-benzenethiol
C
2-Aminophenyl disulfide
Conditions | Yield |
---|---|
In toluene for 4h; Heating; | A 95% B n/a C n/a |
Conditions | Yield |
---|---|
With hydrogen bromide In water at 30℃; for 2h; Temperature; Inert atmosphere; | 92.7% |
2-Aminophenyl disulfide
ethyl 2-(4-fluorophenyl)acetate
A
2-(4-fluorophenyl)-3-oxo-3,4-dihydro-2H-1,4-benzothiazine
B
2-amino-benzenethiol
Conditions | Yield |
---|---|
With sodium hydride In dimethyl sulfoxide; N,N-dimethyl-formamide at 100℃; for 0.333333h; | A 92% B n/a |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; zirconium(IV) chloride In tetrahydrofuran at 35℃; for 0.5h; Reduction; | A 10% B 90% |
With sodium tetrahydroborate; zirconium(IV) chloride In tetrahydrofuran at 35℃; for 0.166667h; Reduction; | A 80% B 20% |
4-methoxy-phenyl acetic acid methyl ester
2-Aminophenyl disulfide
A
2-(4-methoxy-phenyl)-4H-benzo[1,4]thiazin-3-one
B
2-amino-benzenethiol
Conditions | Yield |
---|---|
With sodium hydride In dimethyl sulfoxide; N,N-dimethyl-formamide at 100℃; for 0.333333h; | A 88% B n/a |
benzeneacetic acid methyl ester
2-Aminophenyl disulfide
A
3,4-dihydro-2-phenyl-2H-1,4-benzothiazin-3-one
B
2-amino-benzenethiol
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h; | A 86% B n/a |
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h; other methyl or ethyl aryl- or pyridylacetates; |
2-amino-benzenethiol
Conditions | Yield |
---|---|
With sodium tetrahydroborate; zirconium(IV) chloride In tetrahydrofuran at 35℃; for 0.25h; Reduction; | 85% |
methyl 1-naphthylacetate
2-Aminophenyl disulfide
A
2-Naphthalen-1-yl-4H-benzo[1,4]thiazin-3-one
B
2-amino-benzenethiol
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h; | A 82% B n/a |
Conditions | Yield |
---|---|
With potassium hydroxide at 110℃; for 24h; Reagent/catalyst; | 82% |
(4-chloro-phenyl)-acetic acid methyl ester
2-Aminophenyl disulfide
A
2-amino-benzenethiol
B
2-(4-chlorophenyl)-1,4-benzothiazin-3-one
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h; | A n/a B 81% |
methyl 2-(3-bromo-4-methoxyphenyl)acetate
2-Aminophenyl disulfide
A
2-(3-Bromo-4-methoxy-phenyl)-4H-benzo[1,4]thiazin-3-one
B
2-amino-benzenethiol
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h; | A 80% B n/a |
IUPAC Name: 2-Aminobenzenethiol
Canonical SMILES: C1=CC=C(C(=C1)N)S
InChI: InChI=1S/C6H7NS/c7-5-3-1-2-4-6(5)8/h1-4,8H,7H2
InChIKey: VRVRGVPWCUEOGV-UHFFFAOYSA-N
Molecular Weight: 125.19148 [g/mol]
Molecular Formula: C6H7NS
XLogP3-AA: 1.4
H-Bond Donor: 1
H-Bond Acceptor: 1
EINECS: 205-277-3
Water Solubility: INSOLUBLE
Sensitive: Stench
Appearance: clear yellow to amber liquid
Melting Point: 23 °C
Index of Refraction: 1.663
Molar Refractivity: 38.66 cm3
Molar Volume: 104.3 cm3
Surface Tension: 53 dyne/cm
Density: 1.2 g/cm3
Flash Point: 95.8 °C
Enthalpy of Vaporization: 47.16 kJ/mol
Boiling Point: 234.9 °C at 760 mmHg
Vapour Pressure: 0.0517 mmHg at 25 °C
Product Categories of 2-Aminobenzenethiol (CAS NO.137-07-5): Phenol & Thiophenol & Mercaptan; Phenoles and thiophenoles; Carbonyl Group Labeling Reagents for Fluorescence HPLC; Fluorescence Detection (HPLC Labeling Reagents); HPLC Labeling Reagents; Analytical Chemistry
2-Aminobenzenethiol (CAS NO.137-07-5) is used as an antinematodal agent, as well as an intermediate of belfosdil.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 25mg/kg (25mg/kg) | National Technical Information Service. Vol. AD277-689, | |
mouse | LD50 | intravenous | 100mg/kg (100mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02532, | |
rat | LDLo | oral | 500mg/kg (500mg/kg) | BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN | "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 90, 1969. |
Reported in EPA TSCA Inventory.
Hazard Codes: C,N
Risk Statements: 22-34-50/53-37-20/21/22
R22:Harmful if swallowed.
R34:Causes burns.
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
R37:Irritating to respiratory system
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-36/37/39-45-60-61-25-27
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S60:This material and its container must be disposed of as hazardous waste.
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
S25:Avoid contact with eyes.
S27:Take off immediately all contaminated clothing.
RIDADR: UN 1760 8/PG 3
WGK Germany: 3
RTECS: DC0600000
Hazard Note: Corrosive/Stench
HazardClass: 8
PackingGroup of 2-Aminobenzenethiol (CAS NO.137-07-5): III
2-Aminobenzenethiol (CAS NO.137-07-5), its Synonyms are 1-Amino-2-mercaptobenzene ; 2-Aminothiophenol ; 2-Mercaptaniline ; 2-Mercaptoaniline ; o-Aminobenzenethiol ; o-Aminothiophenol ; o-Mercaptoaniline ; Benzenethiol, 2-amino- ; Benzenethiol, o-amino- .
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