1771-19-3

Basic information

• Product Name: 3-methoxy-10H-phenothiazine
• Synonyms: 3-methoxy-10H-phenothiazine;3-Methoxyphenothiazine;10H-Phenothiazine, 3-Methoxy-
• CAS NO: 1771-19-3
• Molecular Formula: C₁₃H₁₁NOS
• Molecular Weight: 229.29754
• EINECS: 217-196-0
• Mol File: 1771-19-3.mol

Chemical Properties

• Boiling Point: 410.1°Cat760mmHg
• Flash Point: 201.9°C
• Appearance: /
• Density: 1.235g/cm³
• Vapor Pressure: 6.16E-07mmHg at 25°C
• Refractive Index: 1.646
• CAS DataBase Reference: 3-methoxy-10H-phenothiazine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methoxy-10H-phenothiazine(1771-19-3)
• EPA Substance Registry System: 3-methoxy-10H-phenothiazine(1771-19-3)

Safety Data

• Hazardous Substances Data: 1771-19-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Methoxy-10H-phenothiazine is used as an intermediate in the synthesis of various pharmaceutical compounds. One of its significant applications is in the synthesis of 10-Dechlorovancomycin (D226740), which is an impurity of Vancomycin (V096500, HCl salt). Vancomycin is an amphoteric glycopeptide antibiotic produced by Streptomyces orientalis, a bacterium found in soil. This antibiotic works by inhibiting bacterial cell wall synthesis through its binding to peptidoglycan, thus playing a crucial role in treating bacterial infections.

InChI:InChI=1/C13H11NOS/c1-15-9-6-7-11-13(8-9)16-12-5-3-2-4-10(12)14-11/h2-8,14H,1H3

Upstream product

• 104-94-9 4-methoxy-aniline 
• 2942-13-4 6-methoxy-1,3-benzothiazole 
• 583-55-1 1-Bromo-2-iodobenzene 
• 95-16-9 1,3-Benzothiazole 
• 4897-68-1 2-iodo-4-methoxybromobenzene 
• 108-94-1 cyclohexanone 
• 6274-29-9 2-amino-5-methoxy-thiophenol 
• 1747-60-0 6-methoxybenzothiazol-2-ylamine 
• 583-53-9 2,3-dibromobenzene 
• 2732-80-1 2-bromo-1-chloro-4-methoxybenzene 
• 137-07-5 2-amino-benzenethiol 
• 13623-26-2 1-(7-methoxy-10H-phenothiazin-2-yl)-ethanone 
• 19688-68-7 1-[3-azido-4-(4-methoxy-phenylsulfanyl)-phenyl]-ethanone 
• 19693-21-1 2,10-diacetyl-7-methoxy-10H-phenothiazine 

Downstream Products

• 1927-44-2 3-hydroxyphenothiazine 
• 19555-64-7 10-(2-Chlor-ethyl)-3-methoxyphenothiazin 
• 69625-66-7 N-(7-methoxy-phenothiazin-3-ylidene)-benzenesulfonamide 
• 69625-67-8 N-(7-methoxy-phenothiazin-3-ylidene)-benzamide 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 67-64-1 acetone 

Relevant articles and documents

Tuning Electron-Withdrawing Strength on Phenothiazine Derivatives: Achieving 100 % Photoluminescence Quantum Yield by NO2 Substitution

The weak fluorescence (quantum yield 2) is a well-known fluorescence quencher. Interestingly, we obtained a highly fluorescent chromophore by combining these two moieties, forming 3-nitrophenothiazine (PTZ-NO2). For comparison, a series of PTZ derivatives bearing electron-withdrawing groups (EWGs; CN and CHO) or electron-donating groups (EDGs; OMe) at the 3-position have been designed and synthesized. The phenothiazines bearing EWGs exhibited enhanced emission compared with the parent PTZ or EDG derivatives. Computational approaches unveiled that for PTZ and PTZ-OMe, the transitions are from HOMOs dominated by π orbitals to LUMOs of mixed sulfur nonbonding–π* orbitals, and hence are partially forbidden. In contrast, the EWGs lower the energy level of the lone-pair electrons on the sulfur atom, thereby suppressing the mixing of the nonbonding orbital with the π* orbital in the LUMO, such that the allowed ππ* transition becomes dominant. This work thus demonstrates a judicious chemical design to fine-tune the transition character in PTZ analogues, with PTZ-NO2 attaining 100 % emission quantum yields in nonpolar solvent.

A method of synthesizing phenoxthine compounds

The invention develops a method for synthesizing phenothiazine compounds by using benzothiazole and derivatives thereof as well as 1-bromo-2-iodobenzene and derivatives thereof as raw materials and copper or copper salt/N-alkoxy-1H-pyrrolic amide system as a copper catalyst. The method is a brand-new method for synthesizing phenothiazine compounds. The method has the characteristics of low temperature, short reaction time, low solvent toxicity and wide substrate adaptability, and has wide application prospects in the aspect of preparation of medicines, pesticides and materials.

Copper-Catalyzed Domino Reactions for the Synthesis of Phenothiazines

A method for the one-pot synthesis of phenothiazines from benzothiazoles and aryl ortho-dihalides was explored. Preliminary work on the mechanism of the reaction suggested that it follows a domino process, including the hydrolysis of benzothiazoles followed by C-S coupling and C-N coupling. The low loading of the catalyst system (5 mol-% for both copper and ligand), the mild experimental conditions (90 °C, 12 h), and the use of a green reaction medium make this synthesis very attractive to academia and industry. A copper-catalyzed domino reaction consisting of the hydrolysis of benzothiazoles followed by C-S and C-N couplings for the synthesis of phenothiazines from benzothiazoles and aryl ortho-dihalides is described. The low loading of the catalyst system, mild experimental conditions, and the use of polyethylene glycol as the solvent make this synthetic approach very attractive to academia and industry.

Synthesis of phenothiazines from cyclohexanones and 2-aminobenzenethiols under transition-metal-free conditions

A convenient method for the synthesis of various substituted phenothiazines from cyclohexanones and 2-aminobenzenethiols using molecular oxygen as hydrogen acceptor in the absence of transition-metals is described. For the first time cyclohexanones were used as coupling partners for the construction of phenothiazines.

Synthesis of phenothiazines via ligand-free CuI-catalyzed cascade C-S and C-N coupling of aryl ortho-dihalides and ortho-aminobenzenethiols

A ligand-free CuI-catalyzed cascade C-S and C-N cross coupling of (hetero)aryl ortho-dihalides and ortho-aminobenzenethiols has been developed, and various phenothiazines were synthesized with excellent regioselectivity. A possible mechanism is proposed for the cascade coupling.

Assembly of substituted phenothiazines by a sequentially controlled CuI/L-proline-catalyzed cascade C-S and C-N bond formation

(Chemical equation presented) In the pro-line of fire: A general and efficient cascade reaction approach to substituted phenothiazines, which relies on controlled sequential Cul/L-prolinecatalyzed C-S and C-N bond formations, is described. DMSO = dimethylsulfoxide.

Synthesis and antitubercular activity of phenothiazines with reduced binding to dopamine and serotonin receptors

Analogs of the psychotropic phenothiazines were synthesized and examined as antitubercular agents against Mycobacterium tuberculosis H37Rv. The compounds were subsequently counter-screened for binding to the dopaminergic-receptor subtypes D1, D2, D3 and the serotonergic-receptor subtypes 5-HT1A, 5-HT2A, and 5-HT2C. The most active compounds showed MICs from 2 to 4 μg/mL and had overall reduced binding to the dopamine and serotonin receptors compared to chlorpromazine and trifluoperazine.

Antioxidant activities of phenothiazines and related compounds: Correlation between the antioxidant activities and dissociation energies of O-H or N-H bonds

The antioxidant activities of phenothiazines, carbazoles, and related diphenylamines were evaluated in the oxidation of tetralin at 60°C and linoleic acid micelles in aqueous dispersion at 37°C induced by an azo initiator. Phenothiazines were highly antioxidant in both systems. Although diphenylamine and carbazole were not good antioxidants, those having a hydroxy group as a substituent at the ortho or para position to the amino group were potently antioxidant. The antioxidant activity of o-hydroxydiphenylamine was much greater than that of other compounds in both systems due to a stabilization of the phenoxyl radical by delocalization of the unpaired electron to the p-type lone pair of the amino group. A semiempirical MNDO-AM1 calculation was applied to study hydrogen abstractions of antioxidants in the chain process of autoxidation. These results indicated that the rates of oxidation during the induction period correlated with the dissociation energies of the O-H or N-H bonds.