4225-26-7

Basic information

• Product Name: 2-MORPHOLINOBENZOTHIAZOLE
• Synonyms: 2-MORPHOLINOBENZOTHIAZOLE;Benzothiazole, 2-(4-morpholinyl)- (9CI)
• CAS NO: 4225-26-7
• Molecular Formula: C₁₁H₁₂N₂OS
• Molecular Weight: 220.29
• Product Categories: BENZOTHIAZOLE
• Mol File: 4225-26-7.mol
• Article Data: 48

Chemical Properties

• Melting Point: 112-113 °C
• Boiling Point: 315°Cat760mmHg
• Flash Point: 160.8°C
• Appearance: /
• Density: 1.228g/cm³
• Vapor Pressure: 1.25E-05mmHg at 25°C
• Refractive Index: 1.657
• PKA: 3.19±0.10(Predicted)
• CAS DataBase Reference: 2-MORPHOLINOBENZOTHIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-MORPHOLINOBENZOTHIAZOLE(4225-26-7)
• EPA Substance Registry System: 2-MORPHOLINOBENZOTHIAZOLE(4225-26-7)

Safety Data

• Hazardous Substances Data: 4225-26-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H12N2OS/c1-2-4-10-9(3-1)12-11(15-10)13-5-7-14-8-6-13/h1-4H,5-8H2

Upstream product

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• 121-44-8 triethylamine 
• 273-53-0 benzoxazole 
• 98041-44-2 2-iodophenyl isothiocyanate 

Relevant articles and documents

Ionic Reactivity of 2-Isocyanoaryl Thioethers: Access to 2-Halo and 2-Aminobenzothia/Selenazoles

An ionic cascade insertion/cyclization reaction of thia-/selena-functionalized arylisocyanides has been successfully developed for the efficient and practical synthesis of 2-halobenzothiazole/benzoselenazole derivatives. This synthetic protocol, incorporating a halogen atom when forming the five-membered ring of benzothia/selenazoles, is different from the existing ones, where halogenation of the preformed benzothia/selenazole precursors happens. Additionally, a facile access to 2-aminobenzothiazoles is also achieved by the one-pot cascade reaction of 2-isocyanoaryl thioethers, iodine, and amines.

Room-Temperature Amination of Chloroheteroarenes in Water by a Recyclable Copper(II)-Phosphaadamantanium Sulfonate System

Buchwald-Hartwig amination of chloroheteroarenes has been a challenging synthetic process, with very few protocols promoting this important transformation at ambient temperature. The current report discusses about an efficient copper-based catalytic system (Cu/PTABS) for the amination of chloroheteroarenes at ambient temperature in water as the sole reaction solvent, a combination that is first to be reported. A wide variety of chloroheteroarenes could be coupled efficiently with primary and secondary amines as well as selected amino acid esters under mild reaction conditions. Catalytic efficiency of the developed protocol also promotes late-stage functionalization of active pharmaceutical ingredients (APIs) such as antibiotics (floxacins) and anticancer drugs. The catalytic system also performs efficiently at a very low concentration of 0.0001 mol % (TON = 980,000) and can be recycled 12 times without any appreciable loss in activity. Theoretical calculations reveal that the π-acceptor ability of the ligand PTABS is the main reason for the appreciably high reactivity of the catalytic system. Preliminary characterization of the catalytic species in the reaction was carried out using UV-VIS and ESR spectroscopy, providing evidence for the Cu(II) oxidation state.

Visible-Light-Mediated Aerobic Oxidative C(sp3)?C(sp3) Bond Cleavage of Morpholine Derivatives Using 4CzIPN as a Photocatalyst

Herein, a metal-free strategy for the aerobic oxidative cleavage of the inert C(sp3)?C(sp3) bond was developed. Deconstruction of morpholine derivatives was conducted using visible light as an energy source and O2 as an oxidant under mild conditions. This procedure demonstrated suitable selectivity and functional group tolerance. Moreover, a possible mechanism involving a radical process was proposed based on a series of mechanism exploration and control experiments. (Figure presented.).