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17402-78-7

17402-78-7

Identification

  • Product Name:Benzo[b]thiophene,3-bromo-2-nitro-

  • CAS Number: 17402-78-7

  • EINECS:

  • Molecular Weight:258.095

  • Molecular Formula: C8H4BrNO2S

  • HS Code:2934999090

  • Mol File:17402-78-7.mol

Synonyms:3-Bromo-2-nitrobenzo[b]thiophene;NSC 167741;

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Safety information and MSDS view more

  • Signal Word:Danger

  • Hazard Statement:H301 Toxic if swallowedH319 Causes serious eye irritation

  • 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

Supplier and reference price

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  • Manufacture/Brand:Matrix Scientific
  • Product Description:3-Bromo-2-nitrobenzo[b]thiophene 95%+
  • Packaging:1g
  • Price:$ 877
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  • Manufacture/Brand:Chemenu
  • Product Description:3-Bromo-2-nitro-1-benzothiophene 95%+
  • Packaging:5g
  • Price:$ 4573
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:3-BROMO-2-NITRO-BENZO[B]THIOPHENE 95.00%
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  • Price:$ 3091.6
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:3-BROMO-2-NITRO-BENZO[B]THIOPHENE 95.00%
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:3-BROMO-2-NITRO-BENZO[B]THIOPHENE 95.00%
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  • Manufacture/Brand:AK Scientific
  • Product Description:3-Bromo-2-nitro-benzo[b]thiophene
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  • Manufacture/Brand:Advanced Chemicals Intermediatesced Chemicals Intermediates
  • Product Description:3-Bromo-2-nitro-benzo[b]thiophene 95%+
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  • Manufacture/Brand:Advanced Chemicals Intermediatesced Chemicals Intermediates
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  • Manufacture/Brand:Acints
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Relevant articles and documentsAll total 15 Articles be found

-

van Zyl et al.

, p. 2283,2286 (1966)

-

Phosphine-catalyzed dearomative (3 + 2) annulation of 2-nitrobenzofurans and nitrobenzothiophenes with allenoates

Zhao, Jian-Qiang,Yang, Lei,You, Yong,Wang, Zhen-Hua,Xie, Ke-Xin,Zhang, Xiao-Mei,Xu, Xiao-Ying,Yuan, Wei-Cheng

, p. 5294 - 5304 (2019)

An efficient Ph2PMe-catalyzed dearomative (3 + 2) annulation of 2-nitrobenzofurans, 2-nitrobenzothiophenes, and 3-nitrobenzothiophenes with allenoates has been developed. With the developed protocol, a series of structurally important cyclopenta[b]benzofurans and cyclopenta[b]benzothiophenes were obtained in good to excellent yields (up to 98%) under mild conditions. In addition, preparative-scale experiments and transformations were conducted to exemplify the synthetic utility. The asymmetric version of this dearomative (3 + 2) annulation reaction was tentatively investigated by using chiral phosphine catalysts.

Regio- and Stereoselective Cascade of β,γ-Unsaturated Ketones by Dipeptided Phosphonium Salt Catalysis: Stereospecific Construction of Dihydrofuro-Fused [2,3-b] Skeletons

Chen, Yayun,He, Jiajia,Jiang, Chunhui,Ren, Xiaoyu,Su, Zhishan,Wang, Tianli,Xiao, Kai,Zhang, Hongkui,Zhuang, Cheng

, p. 19860 - 19870 (2021/08/06)

Chiral (dihydro)furo-fused heterocycles are significant structural motifs in numerous natural products, functional materials and pharmaceuticals. Therefore, developing efficient methods for preparing compounds with these privileged scaffolds is an important endeavor in synthetic chemistry. Herein, we develop an effective, modular method by a dipeptide-phosphonium salt-catalyzed regio- and stereoselective cascade reaction of readily available linear β,γ-unsaturated ketones with aromatic alkenes, affording a wide variety of structurally fused heterocyclic molecules in high yields with excellent stereoselectivities. Moreover, mechanistic investigations revealed that the bifunctional phosphonium salt controlled the regio- and stereoselectivities of this cascade reaction, particularly proceeding through the initial ketone α-addition followed by O-participated substitution; and the multiple hydrogen-bonding interactions between Br?nsted acid moieties of catalyst and nitro group of aromatic alkene were crucial in asymmetric induction. Given the generality, versatility, and high efficiency of this method, we anticipate that it will have broad synthetic utilities.

Catalytic Asymmetric Dearomative 1,3-Dipolar Cycloaddition of 2-Nitrobenzothiophenes and Isatin-Derived Azomethine Ylides

Zhao, Jian-Qiang,Zhou, Shun,Yang, Lei,Du, Hong-Yan,You, Yong,Wang, Zhen-Hua,Zhou, Ming-Qiang,Yuan, Wei-Cheng

, p. 8600 - 8605 (2021/11/13)

An enantioselective dearomative 1,3-dipolar cycloaddition of 2-nitrobenzothiophenes and isatin-derived azomethine ylides with a bifunctional hydrogen-bonding thiourea catalyst was established, giving polyheterocyclic compounds in excellent results (up to 99% yield, >20:1 dr for all cases and up to 99% ee). The enantioselectivity could be reversed by the bifunctional hydrogen-bonding squaramide catalyst containing the same chiral source as in the thiourea catalyst. DFT calculations revealed the origin of the observed stereochemistry and the reversal of enantioselectivity.

Palladium-Catalyzed Highly Stereoselective Dearomative [3 + 2] Cycloaddition of Nitrobenzofurans

Cheng, Qiang,Zhang, Hui-Jun,Yue, Wen-Jun,You, Shu-Li

, p. 428 - 436 (2017/09/22)

Stereoselective construction of highly functionalized heterocyclic molecules is an ongoing concern for the chemical community. Among the various strategies developed with this goal, catalytic asymmetric dearomatization, an attractive method for constucting cyclic molecules with multiple stereocenters from readily available aromatic compounds, has received extensive attention in recent years. Here, we report a highly stereoselective construction of tetrahydrofurobenzofurans and tetrahydrofurobenzothiophenes via palladium-catalyzed dearomative [3 + 2] cycloaddition of nitrobenzofurans and nitrobenzothiophenes, respectively. Good to excellent yields (63%–92%), diastereoselectivity (13/1 → >20/1 dr), and enantioselectivity (75%–95% ee) were obtained, leading to products with vicinal stereogenic carbon centers. The reaction features wide substrate scope and diverse transformations of the products.

Substituted imidazole as a ligand containing transition metal complex and their use in OLED

-

Paragraph 0106-0108, (2017/12/15)

Compounds having a metal M complexed to a ligand L containing a substituted imidazole carbene group, which is represented Formula (I), below: wherein ring B is a 5-member aromatic heterocyclic ring containing at least one heteroatom selected from the grou

Process route upstream and downstream products

Process route

3-Bromothianaphthene
7342-82-7

3-Bromothianaphthene

3-bromo-2-nitro-1-benzothiophene
17402-78-7

3-bromo-2-nitro-1-benzothiophene

Conditions
Conditions Yield
With nitric acid; acetic acid; at 60 ℃; for 0.5h;
97%
With nitric acid; acetic acid; at 20 ℃; for 1h;
77%
With nitric acid; In dichloromethane; trifluoroacetic acid; at 0 ℃; for 0.5h;
73%
With nitric acid; acetic acid; at 20 ℃; for 5.75h;
72%
3-Bromothianaphthene; With trifluoroacetic anhydride; In dichloromethane; at 0 ℃; for 0.166667h;
With nitric acid; In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; at 0 ℃; for 0.5h;
60%
With nitric acid; acetic acid; at 20 ℃; for 24h;
55%
With nitric acid; trifluoroacetic acid; In dichloromethane; at 0 ℃; Reagent/catalyst;
41%
With nitric acid; In acetic anhydride; at 20 - 30 ℃; for 15h;
39%
With nitric acid; acetic anhydride; acetic acid; at 0 - 20 ℃; for 2h; Inert atmosphere;
32%
With nitronium tetrafluoborate; In dichloromethane; at 0 ℃; for 2.16667h;
23%
With nitronium tetrafluoborate; In dichloromethane; at 10 - 25 ℃; for 5h;
With nitric acid; acetic anhydride; acetic acid; at 0 - 20 ℃; for 2h; Inert atmosphere;
0.7 g
With nitric acid; acetic acid;
With nitric acid; acetic anhydride; acetic acid; at 0 - 20 ℃; for 2h;
With nitric acid; acetic anhydride; acetic acid; at 0 - 20 ℃; for 2h;
Benzo[b]thiophene
95-15-8,11095-43-5

Benzo[b]thiophene

3-bromo-2-nitro-1-benzothiophene
17402-78-7

3-bromo-2-nitro-1-benzothiophene

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: N-Bromosuccinimide; acetic acid / chloroform / 52 h / 0 - 20 °C
2: nitric acid; trifluoroacetic acid / dichloromethane / 0 °C
With N-Bromosuccinimide; nitric acid; acetic acid; trifluoroacetic acid; In dichloromethane; chloroform;
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / tetrahydrofuran / 48.5 h / 0 - 20 °C / Inert atmosphere
2: acetic anhydride; nitric acid; acetic acid / 2 h / 0 - 20 °C / Inert atmosphere
With N-Bromosuccinimide; nitric acid; acetic anhydride; acetic acid; In tetrahydrofuran;
Multi-step reaction with 2 steps
1.1: acetic acid; N-Bromosuccinimide / chloroform / 3 h / Reflux
2.1: trifluoroacetic anhydride / dichloromethane / 0.17 h / 0 °C
2.2: 0.5 h / 0 °C
With N-Bromosuccinimide; acetic acid; trifluoroacetic anhydride; In dichloromethane; chloroform;
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / tetrahydrofuran / 48.5 h / 0 - 20 °C / Inert atmosphere
2: nitric acid; acetic acid; acetic anhydride / 2 h / 0 - 20 °C / Inert atmosphere
With N-Bromosuccinimide; nitric acid; acetic anhydride; acetic acid; In tetrahydrofuran;
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / tetrahydrofuran / 48.5 h / 0 - 20 °C
2: nitric acid; acetic acid; acetic anhydride / 2 h / 0 - 20 °C
With N-Bromosuccinimide; nitric acid; acetic anhydride; acetic acid; In tetrahydrofuran;
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / tetrahydrofuran / 48.5 h / 0 - 20 °C
2: acetic anhydride; acetic acid; nitric acid / 2 h / 0 - 20 °C
With N-Bromosuccinimide; nitric acid; acetic anhydride; acetic acid; In tetrahydrofuran;
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / tetrahydrofuran / 48 h / 0 - 20 °C
2: acetic anhydride; nitric acid; acetic acid / 2 h / 0 - 20 °C
With N-Bromosuccinimide; nitric acid; acetic anhydride; acetic acid; In tetrahydrofuran;
3-bromo-2-nitro-1-benzothiophene
17402-78-7

3-bromo-2-nitro-1-benzothiophene

Conditions
Conditions Yield
3-Bromothianaphthene
7342-82-7

3-Bromothianaphthene

3-bromo-2-nitro-1-benzothiophene
17402-78-7

3-bromo-2-nitro-1-benzothiophene

Conditions
Conditions Yield
With nitric acid; acetic acid; at 60 ℃; for 0.5h;
97%
With nitric acid; acetic acid; at 20 ℃; for 1h;
77%
With nitric acid; In dichloromethane; trifluoroacetic acid; at 0 ℃; for 0.5h;
73%
With nitric acid; acetic acid; at 20 ℃; for 5.75h;
72%
3-Bromothianaphthene; With trifluoroacetic anhydride; In dichloromethane; at 0 ℃; for 0.166667h;
With nitric acid; In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; at 0 ℃; for 0.5h;
60%
With nitric acid; acetic acid; at 20 ℃; for 24h;
55%
With nitric acid; trifluoroacetic acid; In dichloromethane; at 0 ℃; Reagent/catalyst;
41%
With nitric acid; In acetic anhydride; at 20 - 30 ℃; for 15h;
39%
With nitric acid; acetic anhydride; acetic acid; at 0 - 20 ℃; for 2h; Inert atmosphere;
32%
With nitronium tetrafluoborate; In dichloromethane; at 0 ℃; for 2.16667h;
23%
With nitronium tetrafluoborate; In dichloromethane; at 10 - 25 ℃; for 5h;
With nitric acid; acetic anhydride; acetic acid; at 0 - 20 ℃; for 2h; Inert atmosphere;
0.7 g
With nitric acid; acetic acid;
With nitric acid; acetic anhydride; acetic acid; at 0 - 20 ℃; for 2h;
With nitric acid; acetic anhydride; acetic acid; at 0 - 20 ℃; for 2h;
Benzo[b]thiophene
95-15-8,11095-43-5

Benzo[b]thiophene

3-bromo-2-nitro-1-benzothiophene
17402-78-7

3-bromo-2-nitro-1-benzothiophene

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: N-Bromosuccinimide; acetic acid / chloroform / 52 h / 0 - 20 °C
2: nitric acid; trifluoroacetic acid / dichloromethane / 0 °C
With N-Bromosuccinimide; nitric acid; acetic acid; trifluoroacetic acid; In dichloromethane; chloroform;
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / tetrahydrofuran / 48.5 h / 0 - 20 °C / Inert atmosphere
2: acetic anhydride; nitric acid; acetic acid / 2 h / 0 - 20 °C / Inert atmosphere
With N-Bromosuccinimide; nitric acid; acetic anhydride; acetic acid; In tetrahydrofuran;
Multi-step reaction with 2 steps
1.1: acetic acid; N-Bromosuccinimide / chloroform / 3 h / Reflux
2.1: trifluoroacetic anhydride / dichloromethane / 0.17 h / 0 °C
2.2: 0.5 h / 0 °C
With N-Bromosuccinimide; acetic acid; trifluoroacetic anhydride; In dichloromethane; chloroform;
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / tetrahydrofuran / 48.5 h / 0 - 20 °C / Inert atmosphere
2: nitric acid; acetic acid; acetic anhydride / 2 h / 0 - 20 °C / Inert atmosphere
With N-Bromosuccinimide; nitric acid; acetic anhydride; acetic acid; In tetrahydrofuran;
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / tetrahydrofuran / 48.5 h / 0 - 20 °C
2: nitric acid; acetic acid; acetic anhydride / 2 h / 0 - 20 °C
With N-Bromosuccinimide; nitric acid; acetic anhydride; acetic acid; In tetrahydrofuran;
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / tetrahydrofuran / 48.5 h / 0 - 20 °C
2: acetic anhydride; acetic acid; nitric acid / 2 h / 0 - 20 °C
With N-Bromosuccinimide; nitric acid; acetic anhydride; acetic acid; In tetrahydrofuran;
Multi-step reaction with 2 steps
1: N-Bromosuccinimide / tetrahydrofuran / 48 h / 0 - 20 °C
2: acetic anhydride; nitric acid; acetic acid / 2 h / 0 - 20 °C
With N-Bromosuccinimide; nitric acid; acetic anhydride; acetic acid; In tetrahydrofuran;
3-bromo-2-nitro-1-benzothiophene
17402-78-7

3-bromo-2-nitro-1-benzothiophene

Conditions
Conditions Yield

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