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Cas Database

137-07-5

137-07-5

Identification

  • Product Name:2-Aminobenzenethiol

  • CAS Number: 137-07-5

  • EINECS:205-277-3

  • Molecular Weight:125.194

  • Molecular Formula: C6H7NS

  • HS Code:2930.90

  • Mol File:137-07-5.mol

Synonyms:NSC 106635;o-Aminobenzenethiol;o-Aminophenyl mercaptan;o-Aminothiophenol;o-Mercaptoaniline;a-Aminothiophenol;Benzenethiol,2-amino-;Benzenethiol,o-amino- (6CI,8CI);1-Amino-2-mercaptobenzene;2-Amino-1-mercaptobenzene;2-Aminophenyl mercaptan;2-Mercaptoaniline;2-Thioaniline;

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Safety information and MSDS view more

  • Pictogram(s):CorrosiveC,DangerousN

  • Hazard Codes:C,N

  • Signal Word:No signal word.

  • Hazard Statement:none

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:2-Aminothiophenol90%
  • Packaging:50g
  • Price:$ 60
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Aminobenzenethiol >97.0%(T)
  • Packaging:100mL
  • Price:$ 48
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Aminobenzenethiol >97.0%(T)
  • Packaging:25mL
  • Price:$ 24
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Aminobenzenethiol >97.0%(T)
  • Packaging:500mL
  • Price:$ 166
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2-Aminothiophenol 98%
  • Packaging:500 g
  • Price:$ 352
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2-Aminothiophenol 98%
  • Packaging:100 g
  • Price:$ 141
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2-Aminothiophenol for synthesis. CAS 137-07-5, chemical formula 2-(NH )C H SH., for synthesis
  • Packaging:8013350100
  • Price:$ 125
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2-Aminothiophenol for synthesis. CAS 137-07-5, chemical formula 2-(NH )C H SH., for synthesis
  • Packaging:8013350025
  • Price:$ 56.8
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2-Aminothiophenol for synthesis
  • Packaging:25 mL
  • Price:$ 54.39
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2-Aminothiophenol 99%
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Relevant articles and documentsAll total 53 Articles be found

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.

-

Knowles,Watt

, p. 56,58 (1942)

-

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.

Natural Product-Mimetic Scaffolds with Privileged Heterocyclic Systems: Design, Synthesis, and Evaluation of Antioxidant Activity of Quinazoquinobenzothiazinones

Sharma, Kshitija,Khandelwal, Sarita,Samarth,Kumar, Mahendra

, p. 220 - 228 (2016)

(Chemical Equation Presented) Structurally diverse quinazolinoquinolinobenzothiazinones based on rutaecarpine structural framework with hybrid structural features of three medicinally privileged heterocyclic systems has been synthesized as natural product-mimetic scaffolds involving the use of multi-step reaction sequences. The synthesized quinazolinoquinolinobenzothiazinones have been evaluated for their antioxidant and radical scavenging activities.

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.

Facile syntheses of 3-trifluoromethylthio substituted thioflavones and benzothiophenes via the radical cyclization

Wang, Lu,Wang, Huaiyu,Meng, Weidong,Xu, Xiu-Hua,Huang, Yangen

supporting information, p. 389 - 392 (2020/03/04)

3-CF3S substituted thioflavones and benzothiophenes were achieved via the reactions of AgSCF3 with methylthiolated alkynones and alkynylthioanisoles, respectively, promoted by persulfate. This protocol possesses good functional group tolerance and high yields. Mechanistic studies suggested that a classic two-step radical process was involved, which includes addition of CF3S radical to triple bond and cyclization with SMe moiety.

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.

Iodine- And TBHP-Promoted Acylation of Benzothiazoles under Metal-Free Conditions

Wang, Bin,Zhang, Qianwei,Guo, Zhongqi,Ablajan, Keyume

, p. 3058 - 3064 (2020/08/28)

A simple protocol for the synthesis of 2-acylbenzothiazoles using aryl ketones and benzothiazoles in the presence of I 2and TBHP is described. Acylation of the benzothiazoles is achieved through a sequence involving oxidation of the aryl ketone to an aryl glyoxal, ring-opening of the benzothiazole followed by condensation of the amino group with the aryl glyoxal, cyclization and oxidation. The method avoids the use of metals and toxic solvents. In addition, this protocol has the advantage of broad scope and provides good to excellent product yields.

Aerobic Dehydrogenation of N-Heterocycles with Grubbs Catalyst: Its Application to Assisted-Tandem Catalysis to Construct N-Containing Fused Heteroarenes

Kawauchi, Daichi,Noda, Kenta,Komatsu, Yoshiyuki,Yoshida, Kei,Ueda, Hirofumi,Tokuyama, Hidetoshi

supporting information, p. 15793 - 15798 (2020/10/12)

An aerobic dehydrogenation of nitrogen-containing heterocycles catalyzed by Grubbs catalyst is developed. The reaction is applicable to various nitrogen-containing heterocycles. The exceptionally high functional group compatibility of this method was confirmed by the oxidation of an unprotected dihydroindolactam V to indolactam V. Furthermore, by taking advantage of the oxygen-mediated structural change of the Grubbs catalyst, we integrated ring-closing metathesis and subsequent aerobic dehydrogenation to develop the novel assisted-tandem catalysis using molecular oxygen as a chemical trigger. The utility of the assisted-tandem catalysis was demonstrated by the concise synthesis of N-containing fused heteroarenes including a natural antibiotic, pyocyanine.

Process route upstream and downstream products

Process route

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

2-Phenylquinoline
612-96-4

2-Phenylquinoline

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

Conditions
Conditions Yield
In toluene; for 4h; Heating;
95%
2-iodophenylamine
615-43-0

2-iodophenylamine

dimethyl sulfoxide
67-68-5,8070-53-9

dimethyl sulfoxide

1,3-Benzothiazole
95-16-9

1,3-Benzothiazole

2-Methylbenzothiazole
120-75-2

2-Methylbenzothiazole

dimethyltrisulfane
3658-80-8

dimethyltrisulfane

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
Conditions Yield
With copper(l) iodide; potassium sulfide; ammonium acetate; water; at 140 ℃; for 1.5h; Inert atmosphere; Schlenk technique;
1,3-Benzothiazole
95-16-9

1,3-Benzothiazole

formic acid
64-18-6

formic acid

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
Conditions Yield
bei der Kalischmelze;
2-(benzothiazol-2-yl)phenol
3411-95-8

2-(benzothiazol-2-yl)phenol

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
Conditions Yield
beim Schmelzen;
bis(2-nitrophenyl)disulfide
1155-00-6

bis(2-nitrophenyl)disulfide

o-nitrothiophenol
4875-10-9

o-nitrothiophenol

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
Conditions Yield
With sodium tetrahydroborate; zirconium(IV) chloride; In tetrahydrofuran; at 35 ℃; for 0.5h;
90%
10%
With sodium tetrahydroborate; zirconium(IV) chloride; In tetrahydrofuran; at 35 ℃; for 0.166667h;
80%
20%
water
7732-18-5

water

2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

bis-(2-nitro-phenyl)-sulfide
22100-66-9

bis-(2-nitro-phenyl)-sulfide

o-nitrothiophenol
4875-10-9

o-nitrothiophenol

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

o-chloroaniline
95-51-2

o-chloroaniline

Conditions
Conditions Yield
2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

bis-(2-nitro-phenyl)-sulfide
22100-66-9

bis-(2-nitro-phenyl)-sulfide

o-nitrothiophenol
4875-10-9

o-nitrothiophenol

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

o-chloroaniline
95-51-2

o-chloroaniline

Conditions
Conditions Yield
water
7732-18-5

water

2-amino-thiophenol; phosphate

2-amino-thiophenol; phosphate

phosphoric acid
86119-84-8,7664-38-2

phosphoric acid

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
Conditions Yield
beim Kochen;
2-benzylbenzothiazole
6265-94-7

2-benzylbenzothiazole

phenylacetic acid
103-82-2

phenylacetic acid

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

Conditions
Conditions Yield
beim Schmelzen;
1,3-Benzothiazole
95-16-9

1,3-Benzothiazole

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

2-Aminophenyl disulfide
1141-88-4

2-Aminophenyl disulfide

Conditions
Conditions Yield
With di-isopropyl azodicarboxylate; In water; at 100 ℃;
63%
33%

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