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2-(4-Methoxyphenyl)benzothiazole is a chemical compound that belongs to the benzothiazole family. It is characterized by its distinctive yellow-green fluorescence and is commonly used as a fluorescent dye in various fields such as polymer science, biochemistry, and organic synthesis. 2-(4-METHOXYPHENYL)BENZOTHIAZOLE is also recognized for its potential applications in medical imaging, diagnostics, and as a building block in the synthesis of other organic compounds. Furthermore, it has been studied for its possible anti-inflammatory and antioxidant properties.

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  • 6265-92-5 Structure
  • Basic information

    1. Product Name: 2-(4-METHOXYPHENYL)BENZOTHIAZOLE
    2. Synonyms: 2-(4-methoxyphenyl)-benzothiazol;2-(p-methoxyphenyl)benzothiazole;2-(4-METHOXYPHENYL)BENZOTHIAZOLE;1-(2-BENZOTHIAZOLYL)-4-METHOXYBENZENE;4-(2-BENZOTHIAZOLYL)ANISOLE;AKOS BBS-00007335;Benzothiazole, 2-(4-methoxyphenyl)-;Benzothiazole, 2-(p-methoxyphenyl)- (6ci,7ci,8ci)
    3. CAS NO:6265-92-5
    4. Molecular Formula: C14H11NOS
    5. Molecular Weight: 241.31
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 6265-92-5.mol
  • Chemical Properties

    1. Melting Point: 120.0 to 124.0 °C
    2. Boiling Point: 392.5 °C at 760 mmHg
    3. Flash Point: 191.2 °C
    4. Appearance: /
    5. Density: 1.234 g/cm3
    6. Vapor Pressure: 5.16E-06mmHg at 25°C
    7. Refractive Index: 1.656
    8. Storage Temp.: N/A
    9. Solubility: soluble in Toluene
    10. CAS DataBase Reference: 2-(4-METHOXYPHENYL)BENZOTHIAZOLE(CAS DataBase Reference)
    11. NIST Chemistry Reference: 2-(4-METHOXYPHENYL)BENZOTHIAZOLE(6265-92-5)
    12. EPA Substance Registry System: 2-(4-METHOXYPHENYL)BENZOTHIAZOLE(6265-92-5)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS: DL5330000
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 6265-92-5(Hazardous Substances Data)

6265-92-5 Usage

Uses

Used in Research and Development:
2-(4-Methoxyphenyl)benzothiazole is used as a fluorescent dye for its yellow-green fluorescence, which aids in the visualization and tracking of molecules in biological and environmental studies.
Used in Polymer Science:
In the polymer industry, 2-(4-Methoxyphenyl)benzothiazole is used as a building block in the synthesis of other organic compounds, contributing to the development of new materials with specific properties.
Used in Biochemistry:
2-(4-Methoxyphenyl)benzothiazole serves as a fluorescent tracer in biochemistry, enabling researchers to study molecular interactions and processes within biological systems.
Used in Organic Synthesis:
As a key component in organic synthesis, 2-(4-Methoxyphenyl)benzothiazole is utilized to create a variety of organic compounds with diverse applications.
Used in Medical Imaging and Diagnostics:
2-(4-Methoxyphenyl)benzothiazole is being investigated for its potential use in medical imaging and diagnostics, where its fluorescent properties could enhance the detection and monitoring of diseases.
Used in Pharmaceutical Development:
2-(4-METHOXYPHENYL)BENZOTHIAZOLE has been studied for its potential anti-inflammatory and antioxidant properties, indicating its possible use in the development of pharmaceuticals for treating inflammation and oxidative stress-related conditions.

Check Digit Verification of cas no

The CAS Registry Mumber 6265-92-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,2,6 and 5 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 6265-92:
(6*6)+(5*2)+(4*6)+(3*5)+(2*9)+(1*2)=105
105 % 10 = 5
So 6265-92-5 is a valid CAS Registry Number.
InChI:InChI=1/C14H11NOS/c1-16-11-8-6-10(7-9-11)14-15-12-4-2-3-5-13(12)17-14/h2-9H,1H3

6265-92-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(4-Methoxyphenyl)benzothiazole

1.2 Other means of identification

Product number -
Other names 2-(4-methoxyphenyl)-1,3-benzothiazole

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:6265-92-5 SDS

6265-92-5Relevant articles and documents

Novel synthesis of 2-arylbenzothiazoles mediated by ceric ammonium nitrate (CAN).

Tale

, p. 1641 - 1642 (2002)

[reaction: see text] Cyclization of the intermediate radical formed after initial oxidative coupling between thiophenols and aromatic nitriles leads to the synthesis of a wide range of 2-arylbenzothiazoles.

Room temperature HFIP/Ag-promoted palladium-catalyzed C–H functionalization of benzothiazole with iodoarenes

Bhujbal, Yuvraj,Gharpure, Santosh J.,Kapdi, Anant R.,Kommyreddy, Saidurga Prasad,Kori, Santosh,Vadagaonkar, Kamlesh

supporting information, p. 847 - 850 (2022/02/01)

A versatile synthetic protocol involving the room temperature direct arylation of benzothiazole with a wide variety of iodoarenes under Ag-promoted Pd-catalyzed conditions in HFIP as the reaction solvent has been presented. A sequential HFIP-promoted sele

A biomass-derived N-doped porous carbon catalyst for the aerobic dehydrogenation of nitrogen heterocycles

Cui, Fu-Jun,Guo, Fu-Hu,Liu, Jing-Jiang,Liu, Xiao-Yu,Quan, Zheng-Jun,Ullah, Arif,Wang, Xi-Cun,Zhu, Ji-Hua

supporting information, p. 1791 - 1799 (2022/01/31)

N-doped porous carbon (NC) was synthesized from sugar cane bagasse, which is a sustainable and widely available biomass waste. The preferred NC sample had a well-developed porous structure, a graphene-like surface morphology and different N species. More

Recyclable copper-catalyzed cyclization of o-haloanilides and metal sulfides: An efficient and practical access to substituted benzothiazoles

Cai, Mingzhong,Hao, Wenyan,Huang, Wencheng,Ye, Qian

, (2022/01/19)

An efficient heterogeneous copper-catalyzed cyclization of o-haloanilides and metal sulfides has been achieved via the C–S coupling in DMF at 80 or 140 °C in the existence of an MCM-41-bound NHC-Cu(I) catalyst and then intramolecular condensation, delivering a wide range of substituted benzothiazoles in mostly good to high yields. This new MCM-41-NHC-CuI complex can facilely be obtained by a two-step procedure starting from easily accessible and inexpensive reagents and reused more than seven times without any significant loss of its catalytic efficiency. The present protocol has been successfully applied to the gram-scale synthesis of two antitumor agents 5F203 and PMX 610.

RADIOLABELED COMPOUNDS

-

Page/Page column 24; 26; 28, (2022/02/09)

This invention relates to radiolabelled compounds as described herein, precursor compounds and reference compounds, as well as pharmaceutical compositions comprising the radiolabelled compounds, which are for use in a diagnostic method practised on the hu

Photocatalytic green synthesis of benzazoles from alcohol oxidation/toluene sp3C-H activation over metal-free BCN: effect of crystallinity and N-B pair exposure

Cheng, Hongmei,Gao, Xue,Jiang, Heyan,Sun, Bin,Zang, Cuicui

, p. 7955 - 7962 (2021/12/27)

Porous borocarbonitride (P-BCN), with the characteristics of enhanced crystallinity and improved N-B pair exposure, was prepared with a simple KCl-assisted molten salt strategy. Efficient heterogeneous photocatalytic tandem synthesis of benzazoles from alcohol oxidation/toluene sp3C-H activation was achieved firstly over the metal-free P-BCN using visible light and the green oxidant O2, with only water as a by-product. Variouso-thio/hydroxy/aminoanilines and alcohols or toluenes could be converted to the corresponding 2-substituted benzothiazoles, benzoxazoles and benzimidazoles with good to excellent photocatalytic performance. The improved photocatalytic performance in comparison to bulk BCN should be due to the crystallinity-enhancement-induced improvement in charge separation and transmission. The increased N-B pair exposure promoted superoxide radical generation due to the electron-enriched N atoms, as well as improved oxidation ability due to the valence band constructed by the B 2p orbital. This work presents a green and efficient synthetic strategy towards benzazoles and other fine chemicalsviametal-free heterogeneous photocatalysis.

Visible-Light Carbon Nitride-Catalyzed Aerobic Cyclization of Thiobenzanilides under Ambient Air Conditions

Bai, Jin,Yan, Sijia,Zhang, Zhuxia,Guo, Zhen,Zhou, Cong-Ying

, p. 4843 - 4848 (2021/06/28)

A metal-free heterogeneous photocatalysis has been developed for the synthesis of benzothiazoles via intramolecular C-H functionalization/C-S bond formation of thiobenzanilides by inexpensive graphitic carbon nitride (g-C3N4) under visible-light irradiation. This reaction provides access to a broad range of 2-substituted benzothiazoles in high yields under an air atmosphere at room temperature without addition of a strong base or organic oxidizing reagents. In addition, the catalyst was found to be stable and reusable after five reaction cycles.

Improved, gram-scale synthesis of sildenafil in water using arylacetic acid as the acyl source in the pyrazolo[4,3-d]pyrimidin-7-one ring formation

Laha, Joydev K.,Gulati, Upma,Saima,Gupta, Anjali,Indurthi, Harish Kumar

supporting information, p. 2643 - 2648 (2021/02/16)

An improved, gram-scale synthesis of the blockbuster drug sildenafil, used for the treatment of male erectile dysfunction, has been developed. Unlike the previous literature, the current method demonstrates the use of arylacetic acid as an acyl source, a cheap oxidant K2S2O8, and water as the reaction medium in the key step of pyrrazolo[4,3-d]pyrimidin-7-one ring formation. As well as being a green and benign approach, the current method reduces the cost by half compared to our previous strategy. In addition, the general relevance of the method has been demonstrated in the synthesis of a variety of quinazolinone and benzothiazole derivatives with excellent functional group tolerance.

KOtBu-Promoted Halogen-Bond-Assisted Intramolecular C-S Cross-Coupling of o-Iodothioanilides for the Synthesis of 2-Substituted Benzothiazoles

Nandy, Anuradha,Sekar, Govindasamy

, p. 15825 - 15834 (2021/11/01)

An efficacious and mild KOtBu-promoted intramolecular C-S cross-coupling of ortho-iodothioanilides in conjunction with a catalytic quantity of phenanthroline as an additive has been described for the convenient synthesis of 2-substituted benzothiazoles. The methodology is suitable for attaining a wide variety of 2-alkyl- and 2-aryl-substituted benzothiazoles. Single-crystal XRD, DFT calculations, NMR, and UV studies suggest that halogen bonds between the units of ortho-iodothioanilides may assist in the electron transfer process.

Ionic-Liquid-Catalyzed Synthesis of Imines, Benzimidazoles, Benzothiazoles, Quinoxalines and Quinolines through C?N, C?S, and C?C Bond Formation

Adimurthy, Subbarayappa,Badhani, Gaurav,Joshi, Abhisek

, p. 6705 - 6716 (2021/12/31)

We report the tetramethyl ammonium hydroxide catalyzed oxidative coupling of amines and alcohols for the synthesis of imines under metal-free conditions by utilizing oxygen from air as the terminal oxidant. Under the same conditions, with ortho-phenylene diamines and 2-aminobenzenethiols the corresponding benzimidazoles and benzothiazoles were obtained. Quinoxalines were obtained from ortho-phenylene diamines and 1-phenylethane-1,2-diol, the conditions were then extended to the synthesis of quinoline building blocks by reaction of 2-amino benzyl alcohols either with 1-phenylethan-1-ol or acetophenone derivatives. The formation of C?N, C?S and C?C bonds was achieved under metal-free conditions. A broad range of amines (aromatic, aliphatic, cyclic and heteroaromatic) as well as benzylic alcohols including heteroaryl alcohols reacted smoothly and provided the desired products. The mild reaction conditions, commercially available catalyst, metal-free, good functional-group tolerance, broad range of products (imines, benzimidazoles, benzothiazoles, quinoxalines and quinolines) and applicability at gram scale reactions are the advantages of the present strategy.

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