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137-07-5

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137-07-5 Usage

Chemical Properties

clear yellow to amber liquid

Uses

Different sources of media describe the Uses of 137-07-5 differently. You can refer to the following data:
1. A multifunctional compound which shows antioxidant activity in a skin cell model of UVA-induced stress.
2. 2-Aminothiophenol was used in the synthesis of 1,5-benzothiazepines derivatives by reacting with 1,3-diphenylpropenone derivatives and using aluminosilicate solid catalysts. It was also used in the synthesis of benzothiazole2 and 3-(benzothiazol-2-yl)coumarin derivatives. The ternary complexes of copper (II) with salicylidene-2-aminothiophenol (L) and glycine, alanine, valine and histidene amino acids.
3. 2-Aminothiophenol was used in one-pot synthesis of stable phosphonium ylides. It was also used in the synthesis of 2-[(2-benzothiazolylmethyl)thio]-benzenamine. It was used to functionalize silver nano particles for biological pH sensing based on surface enhanced Raman scattering.

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 1514, 1946 DOI: 10.1021/ja01212a038

General Description

2-Aminothiophenol couples with Amberlite XAD by means of an N=N spacer to prepare a new functionalized resin for on-line preconcentration of copper and cadmium.

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion. Moderately flammable. Can react with oxilzing materials. To fight fire, use water, foam, CO2, mist or spray, dry chemical

Check Digit Verification of cas no

The CAS Registry Mumber 137-07-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 7 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 137-07:
(5*1)+(4*3)+(3*7)+(2*0)+(1*7)=45
45 % 10 = 5
So 137-07-5 is a valid CAS Registry Number.
InChI:InChI=1/C6H7NS/c7-5-3-1-2-4-6(5)8/h1-4,8H,7H2/p-1

137-07-5 Well-known Company Product Price

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  • Alfa Aesar

  • (A18952)  2-Aminothiophenol, 98%   

  • 137-07-5

  • 25g

  • 193.0CNY

  • Detail
  • Alfa Aesar

  • (A18952)  2-Aminothiophenol, 98%   

  • 137-07-5

  • 100g

  • 330.0CNY

  • Detail
  • Alfa Aesar

  • (A18952)  2-Aminothiophenol, 98%   

  • 137-07-5

  • 500g

  • 1283.0CNY

  • Detail
  • Aldrich

  • (274240)  2-Aminothiophenol  99%

  • 137-07-5

  • 274240-25G

  • 631.80CNY

  • Detail
  • Aldrich

  • (274240)  2-Aminothiophenol  99%

  • 137-07-5

  • 274240-100G

  • 1,528.02CNY

  • Detail
  • Aldrich

  • (123137)  2-Aminothiophenol  technical grade, 90%

  • 137-07-5

  • 123137-100G

  • 530.01CNY

  • Detail

137-07-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Aminobenzenethiol

1.2 Other means of identification

Product number -
Other names ortho-aminothiophenol

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:137-07-5 SDS

137-07-5Synthetic route

2-iodophenylamine
615-43-0

2-iodophenylamine

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; ethane-1,2-dithiol; potassium hydroxide In water; dimethyl sulfoxide at 90℃; for 20h; Inert atmosphere;99%
1,3-Benzothiazole
95-16-9

1,3-Benzothiazole

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
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%
2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
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
86333-20-2

2-(2-aminophenylthio)-4-phenyl-2,3-dihydro-1,5-benzothiazepine

A

2-Phenylquinoline
612-96-4

2-Phenylquinoline

B

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

C

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

Conditions
ConditionsYield
In toluene for 4h; Heating;A 95%
B n/a
C n/a
2-(Methylthio)aniline
2987-53-3

2-(Methylthio)aniline

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
With hydrogen bromide In water at 30℃; for 2h; Temperature; Inert atmosphere;92.7%
2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

ethyl 2-(4-fluorophenyl)acetate
587-88-2

ethyl 2-(4-fluorophenyl)acetate

A

2-(4-fluorophenyl)-3-oxo-3,4-dihydro-2H-1,4-benzothiazine
100638-27-5

2-(4-fluorophenyl)-3-oxo-3,4-dihydro-2H-1,4-benzothiazine

B

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
With sodium hydride In dimethyl sulfoxide; N,N-dimethyl-formamide at 100℃; for 0.333333h;A 92%
B n/a
bis(2-nitrophenyl)disulfide
1155-00-6

bis(2-nitrophenyl)disulfide

A

2-nitrothiophenol
4875-10-9

2-nitrothiophenol

B

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
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
23786-14-3

4-methoxy-phenyl acetic acid methyl ester

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

A

2-(4-methoxy-phenyl)-4H-benzo[1,4]thiazin-3-one
92552-87-9

2-(4-methoxy-phenyl)-4H-benzo[1,4]thiazin-3-one

B

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
With sodium hydride In dimethyl sulfoxide; N,N-dimethyl-formamide at 100℃; for 0.333333h;A 88%
B n/a
benzeneacetic acid methyl ester
101-41-7

benzeneacetic acid methyl ester

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

A

3,4-dihydro-2-phenyl-2H-1,4-benzothiazin-3-one
38533-19-6

3,4-dihydro-2-phenyl-2H-1,4-benzothiazin-3-one

B

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
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-(2-amino-phenyldisulfanyl)-pyridin-3-ylamine

2-(2-amino-phenyldisulfanyl)-pyridin-3-ylamine

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
With sodium tetrahydroborate; zirconium(IV) chloride In tetrahydrofuran at 35℃; for 0.25h; Reduction;85%
methyl 1-naphthylacetate
2876-78-0

methyl 1-naphthylacetate

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

A

2-Naphthalen-1-yl-4H-benzo[1,4]thiazin-3-one
131602-98-7

2-Naphthalen-1-yl-4H-benzo[1,4]thiazin-3-one

B

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h;A 82%
B n/a
2-Mercaptobenzothiazole
149-30-4

2-Mercaptobenzothiazole

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
With potassium hydroxide at 110℃; for 24h; Reagent/catalyst;82%
(4-chloro-phenyl)-acetic acid methyl ester
52449-43-1

(4-chloro-phenyl)-acetic acid methyl ester

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

A

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

B

2-(4-chlorophenyl)-1,4-benzothiazin-3-one
4652-24-8

2-(4-chlorophenyl)-1,4-benzothiazin-3-one

Conditions
ConditionsYield
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
19626-36-9

methyl 2-(3-bromo-4-methoxyphenyl)acetate

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

A

2-(3-Bromo-4-methoxy-phenyl)-4H-benzo[1,4]thiazin-3-one
131602-96-5

2-(3-Bromo-4-methoxy-phenyl)-4H-benzo[1,4]thiazin-3-one

B

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h;A 80%
B n/a
methyl (2-chlorophenyl)acetate
57486-68-7

methyl (2-chlorophenyl)acetate

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

A

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

B

2-(2-chloro-phenyl)-4H-benzo[1,4]thiazin-3-one
58553-47-2

2-(2-chloro-phenyl)-4H-benzo[1,4]thiazin-3-one

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h;A n/a
B 79%
2-amino-benzthiazole
136-95-8

2-amino-benzthiazole

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
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
14062-19-2

p-tolylacetic acid ethyl ester

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

A

2-(4-methylphenyl)-1,4-benzothiazin-3-one
131602-92-1

2-(4-methylphenyl)-1,4-benzothiazin-3-one

B

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
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
326-59-0

benzo[1,3]dioxol-5-yl-acetic acid methyl ester

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

A

2-Benzo[1,3]dioxol-5-yl-4H-benzo[1,4]thiazin-3-one
131602-97-6

2-Benzo[1,3]dioxol-5-yl-4H-benzo[1,4]thiazin-3-one

B

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
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
39931-77-6

pyridin-3-yl-acetic acid ethyl ester

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

A

2-(3-pyridyl)-3-oxo-3,4-dihydro-2H-1,4-benzothiazine
131603-00-4

2-(3-pyridyl)-3-oxo-3,4-dihydro-2H-1,4-benzothiazine

B

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h;A 72%
B n/a
ethyl 3,4-dimethoxyphenylacetate
18066-68-7

ethyl 3,4-dimethoxyphenylacetate

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

A

2-(3,4-Dimethoxy-phenyl)-4H-benzo[1,4]thiazin-3-one
117838-86-5

2-(3,4-Dimethoxy-phenyl)-4H-benzo[1,4]thiazin-3-one

B

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
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
113372-40-0

2,3-dihydro-3-methoxycarbonyl-2-benzothiazolecarbonitrile

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 2h; Heating;70%
With potassium hydroxide In ethanol for 2h; Heating;70%
2-Mercaptobenzothiazole
149-30-4

2-Mercaptobenzothiazole

A

N,N',N''-triaminoguanidine
2203-24-9

N,N',N''-triaminoguanidine

B

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

C

2-hydrazono-2,3-dihydro-1,3-benzothiazole
615-21-4

2-hydrazono-2,3-dihydro-1,3-benzothiazole

D

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

Conditions
ConditionsYield
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
2739-98-2

ethyl 2-(pyridinyl-2)acetate

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

A

2-(2-pyridyl)-3-oxo-3,4-dihydro-2H-1,4-benzothiazine
131602-99-8

2-(2-pyridyl)-3-oxo-3,4-dihydro-2H-1,4-benzothiazine

B

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h;A 69%
B n/a
methyl 2-(4-isopropylphenyl)acetate
16216-94-7

methyl 2-(4-isopropylphenyl)acetate

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

A

2-(4-Isopropyl-phenyl)-4H-benzo[1,4]thiazin-3-one
131602-93-2

2-(4-Isopropyl-phenyl)-4H-benzo[1,4]thiazin-3-one

B

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
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
62451-84-7

(3-trifluoromethyl-phenyl)-acetic acid methyl ester

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

A

2-(3-Trifluoromethyl-phenyl)-4H-benzo[1,4]thiazin-3-one
131602-94-3

2-(3-Trifluoromethyl-phenyl)-4H-benzo[1,4]thiazin-3-one

B

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h;A 65%
B n/a
1,3-Benzothiazole
95-16-9

1,3-Benzothiazole

A

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

B

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate In water at 100℃;A 63%
B 33%
2-(benzylsulfanyl)aniline
6325-92-4

2-(benzylsulfanyl)aniline

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
With titanium(III) chloride; lithium In tetrahydrofuran for 20h; Heating;55%
2-(2-propen-1-ylsulfanyl)aniline
77053-20-4

2-(2-propen-1-ylsulfanyl)aniline

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
With titanium(III) chloride; lithium In tetrahydrofuran at 25℃; for 2h;47%
2,3-dihydro-3-(4-methylbenzoyl)-2-benzothiazolecarbonitrile
95479-50-8

2,3-dihydro-3-(4-methylbenzoyl)-2-benzothiazolecarbonitrile

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 2h; Heating;46%
cyclohexanone
108-94-1

cyclohexanone

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

3H-spiro{benzothiazole-2,1'-cyclohexane}
182-53-6

3H-spiro{benzothiazole-2,1'-cyclohexane}

Conditions
ConditionsYield
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%
benzaldehyde
100-52-7

benzaldehyde

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

2-Phenylbenzothiazole
883-93-2

2-Phenylbenzothiazole

Conditions
ConditionsYield
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%
acetyl chloride
75-36-5

acetyl chloride

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

2-Methylbenzothiazole
120-75-2

2-Methylbenzothiazole

Conditions
ConditionsYield
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%
2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

acetone
67-64-1

acetone

2,2-dimethyl-2,3-dihydro-benzothiazole
25111-89-1

2,2-dimethyl-2,3-dihydro-benzothiazole

Conditions
ConditionsYield
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%
2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

Conditions
ConditionsYield
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%
benzaldehyde
100-52-7

benzaldehyde

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

2-Phenylbenzothiazolin
31230-83-8

2-Phenylbenzothiazolin

Conditions
ConditionsYield
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
104-88-1

4-chlorobenzaldehyde

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

2-(4-chlorophenyl)-2,3-dihydrobenzo[d]thiazole
56048-77-2

2-(4-chlorophenyl)-2,3-dihydrobenzo[d]thiazole

Conditions
ConditionsYield
In ethanol for 0.666667h; Ambient temperature;100%
ethyl iodide
75-03-6

ethyl iodide

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

2-(ethylthio)aniline
13920-91-7

2-(ethylthio)aniline

Conditions
ConditionsYield
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
120-46-7

1,3-diphenylpropanedione

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

1-(2-mercaptophenylimino)-1 3-diphenylpropan-3-one
131526-02-8

1-(2-mercaptophenylimino)-1 3-diphenylpropan-3-one

Conditions
ConditionsYield
With piperidine In ethanol Heating;100%
3-chloro-2-phenyl-but-2-enal
31357-83-2, 31357-84-3, 39831-17-9

3-chloro-2-phenyl-but-2-enal

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

2-Methyl-3-phenyl-benzo[b][1,4]thiazepine
133205-45-5

2-Methyl-3-phenyl-benzo[b][1,4]thiazepine

Conditions
ConditionsYield
100%
bis(2-chloroethyl)disulfide
1002-41-1

bis(2-chloroethyl)disulfide

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

1,8-Bis(2-aminophenyl)-1,4,5,8-tetrathiaoctane
220597-09-1

1,8-Bis(2-aminophenyl)-1,4,5,8-tetrathiaoctane

Conditions
ConditionsYield
With potassium hydroxide In methanol for 2h; Heating;100%
2-naphthyl benzoate
93-44-7

2-naphthyl benzoate

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

A

2-Phenylbenzothiazole
883-93-2

2-Phenylbenzothiazole

B

β-naphthol
135-19-3

β-naphthol

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; potassium carbonate at 100℃; for 0.75h; Hydrolysis; cyclization; debenzoylation;A n/a
B 100%
2-naphthyl pivalate
1503-86-2

2-naphthyl pivalate

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

A

2-(tert-butyl)benzo[d]thiazole
17626-88-9

2-(tert-butyl)benzo[d]thiazole

B

β-naphthol
135-19-3

β-naphthol

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; potassium carbonate at 100℃; for 2h; Hydrolysis; cyclization;A n/a
B 100%
4-cyanophenyl acetate
13031-41-9

4-cyanophenyl acetate

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

A

2-Methylbenzothiazole
120-75-2

2-Methylbenzothiazole

B

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; potassium carbonate at 100℃; for 0.5h; Hydrolysis; cyclization;A n/a
B 100%
2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

4-cyanophenyl pivalate
180143-65-1

4-cyanophenyl pivalate

A

2-(tert-butyl)benzo[d]thiazole
17626-88-9

2-(tert-butyl)benzo[d]thiazole

B

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; potassium carbonate at 100℃; for 1.5h; Hydrolysis; cyclization;A n/a
B 100%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

2-hydroxybenzothiazole

2-hydroxybenzothiazole

Conditions
ConditionsYield
copper(II) bis(tetrafluoroborate) at 30 - 33℃; for 1h;100%
Lawessons reagent
19172-47-5

Lawessons reagent

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

2-(4-methoxyphenyl)-2,3-dihydro-1,3,2-benzothiazaphosphole 2-sulfide
1253576-24-7

2-(4-methoxyphenyl)-2,3-dihydro-1,3,2-benzothiazaphosphole 2-sulfide

Conditions
ConditionsYield
at 190℃; for 0.0166667h; Neat (no solvent); Microwave irradiation;100%
2-iodophenylamine
615-43-0

2-iodophenylamine

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; ethane-1,2-dithiol; potassium hydroxide In water; dimethyl sulfoxide at 90℃; for 20h; Inert atmosphere;99%
1,3-Benzothiazole
95-16-9

1,3-Benzothiazole

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
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%
2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
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
86333-20-2

2-(2-aminophenylthio)-4-phenyl-2,3-dihydro-1,5-benzothiazepine

A

2-Phenylquinoline
612-96-4

2-Phenylquinoline

B

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

C

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

Conditions
ConditionsYield
In toluene for 4h; Heating;A 95%
B n/a
C n/a
2-(Methylthio)aniline
2987-53-3

2-(Methylthio)aniline

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
With hydrogen bromide In water at 30℃; for 2h; Temperature; Inert atmosphere;92.7%
2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

ethyl 2-(4-fluorophenyl)acetate
587-88-2

ethyl 2-(4-fluorophenyl)acetate

A

2-(4-fluorophenyl)-3-oxo-3,4-dihydro-2H-1,4-benzothiazine
100638-27-5

2-(4-fluorophenyl)-3-oxo-3,4-dihydro-2H-1,4-benzothiazine

B

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
With sodium hydride In dimethyl sulfoxide; N,N-dimethyl-formamide at 100℃; for 0.333333h;A 92%
B n/a
bis(2-nitrophenyl)disulfide
1155-00-6

bis(2-nitrophenyl)disulfide

A

2-nitrothiophenol
4875-10-9

2-nitrothiophenol

B

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
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
23786-14-3

4-methoxy-phenyl acetic acid methyl ester

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

A

2-(4-methoxy-phenyl)-4H-benzo[1,4]thiazin-3-one
92552-87-9

2-(4-methoxy-phenyl)-4H-benzo[1,4]thiazin-3-one

B

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
With sodium hydride In dimethyl sulfoxide; N,N-dimethyl-formamide at 100℃; for 0.333333h;A 88%
B n/a
benzeneacetic acid methyl ester
101-41-7

benzeneacetic acid methyl ester

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

A

3,4-dihydro-2-phenyl-2H-1,4-benzothiazin-3-one
38533-19-6

3,4-dihydro-2-phenyl-2H-1,4-benzothiazin-3-one

B

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
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-(2-amino-phenyldisulfanyl)-pyridin-3-ylamine

2-(2-amino-phenyldisulfanyl)-pyridin-3-ylamine

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
With sodium tetrahydroborate; zirconium(IV) chloride In tetrahydrofuran at 35℃; for 0.25h; Reduction;85%
methyl 1-naphthylacetate
2876-78-0

methyl 1-naphthylacetate

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

A

2-Naphthalen-1-yl-4H-benzo[1,4]thiazin-3-one
131602-98-7

2-Naphthalen-1-yl-4H-benzo[1,4]thiazin-3-one

B

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h;A 82%
B n/a
2-Mercaptobenzothiazole
149-30-4

2-Mercaptobenzothiazole

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
With potassium hydroxide at 110℃; for 24h; Reagent/catalyst;82%
(4-chloro-phenyl)-acetic acid methyl ester
52449-43-1

(4-chloro-phenyl)-acetic acid methyl ester

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

A

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

B

2-(4-chlorophenyl)-1,4-benzothiazin-3-one
4652-24-8

2-(4-chlorophenyl)-1,4-benzothiazin-3-one

Conditions
ConditionsYield
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
19626-36-9

methyl 2-(3-bromo-4-methoxyphenyl)acetate

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

A

2-(3-Bromo-4-methoxy-phenyl)-4H-benzo[1,4]thiazin-3-one
131602-96-5

2-(3-Bromo-4-methoxy-phenyl)-4H-benzo[1,4]thiazin-3-one

B

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h;A 80%
B n/a

137-07-5Related news

Copper-II mediated tandem reaction between aromatic ketones and 2-Aminobenzenethiol (cas 137-07-5) for the synthesis of 2-aroylbenzothiazoles09/29/2019

A novel copper(II) mediated tandem reaction was developed for the synthesis of 2-aroylbenzothiazoles from readily available aryl–alkyl ketones in the presence of oxygen in ethanol. This method is mild, operationally simple, makes the use of inexpensive CuBr2 as mediator, and affords the corresp...detailed

137-07-5Relevant articles and documents

Synthesis of 2H-1,4-benzothiazin-3(4H)-ones and 2H-1,4-benzoselenazin-3(4H)-ones with the aid of samarium(II) iodide

Zhong, Weihui,Zhang, Yongmin

, p. 3125 - 3127 (2001)

Bis(o-nitrophenyl) disulfides or diselenides were easy to reduce by samarium(II) iodide to produce the active intermediates 2 in situ, which readily react with α-halocarboxylic derivatives to yield the corresponding products 2H-1,4-benzothiazin-3(4H)-ones and 2H-1,4-benzoselenazin-3(4H)-ones, respectively, in moderate to high yields under mild conditions.

Iodine mediated oxidative cross-coupling of unprotected anilines and heteroarylation of benzothiazoles with 2-methylquinoline

Rahim, Abdul,Shaik, Siddiq Pasha,Baig, Mirza Feroz,Alarifi, Abdullah,Kamal, Ahmed

, p. 635 - 644 (2018)

Iodine-promoted oxidative C-H/C-H cross-coupling of unprotected anilines and 2-methylquinoline to furnish C4-carbonylated aniline (4-aminophenyl)(quinoline-2-yl) methanones in moderate to good yields has been demonstrated. This work provides the first site-selective approach for the synthesis of free amino groups containing methanones including unprecedented C-H functionalization rather than the N-H functionalization of unprotected anilines via the Kornblum oxidation of 2-methylquinoline. Furthermore, we noticed that the incorporation of KOH under standard conditions provides 2-heteroarylbenzothiazoles from benzothiazoles and 2-methylquinoline in good to excellent yields. These transformations do not require any transition metals or peroxides and tolerate various functional groups such as methoxy, hydroxy, bromo, chloro and nitro groups. Moreover, a plausible mechanistic pathway is proposed.

Novel synthesis of benzothiazole by self-redox tandem reaction of disulfide with aldehyde

Liu, Bo,Zhu, Ning,Hong, Hailong,Han, Limin

, p. 9287 - 9292 (2015)

A novel methodology for the preparation of benzothiazole derivatives via the reaction of ortho-anilino disulfides with aryl and heteroaryl aldehydes catalyzed by Na2S·9H2O has been developed. The reaction mechanism was investigated by LC-MS and 1H NMR. The disulfide was cleaved firstly by the interchange reaction of the disulfide and metal sulfide, and the resulting thiol reacted in situ with the aldehyde to form the corresponding benzothiazoline. Subsequently, the intermediate benzothiazoline reduced the disulfide to thiol and it was oxidized to benzothiazole. The excess benzothiazoline was oxidized by air and both halves of the disulfide were ultimately converted to the desired benzothiazole.

Iodine-catalyzed amination of benzothiazoles with KSeCN in water to access primary 2-aminobenzothiazoles

Chen, Xiran,Fu, Lianrong,Hao, Xin-Qi,Shi, Linlin,Song, Mao-Ping,Zhu, Xinju,Zhu, Yu-Shen

, (2021/09/09)

A facile and sustainable approach for the amination of benzothiazoles with KSeCN using iodine as the catalyst in water has been disclosed under transition-metal free conditions. The reaction proceeded smoothly to afford various primary 2-amino benzothiazoles in up to 96% yield. A series of control experiments were performed, suggesting a ring-opening mechanism was involved via a radical process. This protocol provides efficient synthesis of primary 2-aminobenzothiazoles

Rh-Catalyzed Asymmetric Hydrogenation of Unsaturated Medium-Ring NH Lactams: Highly Enantioselective Synthesis of N-Unprotected 2,3-Dihydro-1,5-benzothiazepinones

Yin, Congcong,Yang, Tao,Pan, Yingmin,Wen, Jialin,Zhang, Xumu

supporting information, p. 920 - 923 (2020/02/04)

A straightforward method to prepare 1,5-benzothiazepines was reported. Catalyzed by a Rh/Zhaophos complex, unsaturated cyclic NH lactams with a medium-size ring were hydrogenated smoothly, giving remarkably high enantioselectivities. The sulfur atom in the substrates did not bring an inhibition which was observed with commercially available bisphosphine ligands. This method was successfully applied in the scale-up synthesis of (R)-(-)-thiazesim.

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