25324-52-1

Basic information

• Product Name: 1-(10-methyl-10H-phenothiazin-2-yl)ethan-1-one
• Synonyms: 1-(10-methyl-10H-phenothiazin-2-yl)ethan-1-one;2-Acetyl-10-methyl-10H-phenothiazine;Einecs 246-847-1
• CAS NO: 25324-52-1
• Molecular Formula: C₁₅H₁₃NOS
• Molecular Weight: 255.33482
• EINECS: 246-847-1
• Mol File: 25324-52-1.mol

Chemical Properties

• Boiling Point: 444.1°Cat760mmHg
• Flash Point: 222.4°C
• Appearance: /
• Density: 1.226g/cm³
• Vapor Pressure: 4.39E-08mmHg at 25°C
• Refractive Index: 1.647
• CAS DataBase Reference: 1-(10-methyl-10H-phenothiazin-2-yl)ethan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(10-methyl-10H-phenothiazin-2-yl)ethan-1-one(25324-52-1)
• EPA Substance Registry System: 1-(10-methyl-10H-phenothiazin-2-yl)ethan-1-one(25324-52-1)

Safety Data

• Hazardous Substances Data: 25324-52-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(10-methyl-10H-phenothiazin-2-yl)ethan-1-one is used as a precursor for the synthesis of pharmacologically active compounds due to its phenothiazine core structure and ketone functional group, which contribute to its potential antipsychotic and antiemetic properties.
Used in Chemical Industry:
1-(10-methyl-10H-phenothiazin-2-yl)ethan-1-one is used as a building block in organic synthesis for creating more complex molecules, leveraging its ketone group's reactivity and the phenothiazine structure's potential for medicinal properties.

InChI:InChI=1/C15H13NOS/c1-10(17)11-7-8-15-13(9-11)16(2)12-5-3-4-6-14(12)18-15/h3-9H,1-2H3

Upstream product

• 50971-92-1 2-(2-methyl-1,3-dioxolan-2-yl)-10H-phenothiazine 
• 74-88-4 methyl iodide 
• 6632-11-7 1-(2-acetyl-10H-phenothiazin-10-yl)ethan-1-one 
• 1628-29-1 10-acetyl-10H-phenothiazine 
• 6631-94-3 2-acetylphenothiazine 
• 723249-76-1 10-methyl-2-(2-methyl-[1,3]dioxolan-2-yl)-10H-phenothiazine 

Downstream Products

• 13611-85-3 4-[(10-methyl-10H-phenothiazin-2-yl)-thioacetyl]-morpholine 
• 13993-65-2 Metiazinic acid 
• 381165-06-6 2,7-bis(2'-iodoethyl)-N-methylphenothiazine 
• 381165-15-7 2,7-bis(2'-bromoethyl)-N-methylphenothiazine 
• 155130-13-5 N-methyl-2,7-bis[17'-(p-toluenesulfonyl)-3',6',9',12',15'-pentaoxaheptadecyloxycarbonylmethyl]phenothiazine 
• 155130-12-4 N-methyl-2,7-bis[14'-(p-toluenesulfonyl)-3',6',9',12'-tetraoxatetradecyloxycarbonylmethyl]phenothiazine 

Relevant articles and documents

A benzopyrylium-phenothiazine conjugate of a flavylium derivative as a fluorescent chemosensor for cyanide in aqueous media and its bioimaging

A new benzopyrylium-phenothiazine conjugate (BP) of a flavylium derivative was synthesized and characterized. The probe BP was shown to be selective and sensitive for CN- among the 17 anions and biothiols studied in HEPES buffer medium by fluorescence, absorption, and visual color change. The colorimetric and fluorescence response of the probe BP to cyanide ions is due to the Michael addition of cyanide to the activated Michael receptor of the probe which blocks an intramolecular charge transfer process. The probe displays a fast response to cyanide ions at room temperature, and a maximal fluorescence signal is achieved in the presence of only 2 equivalents of cyanide ions. Moreover, the probe BP could be used as a practical, visible colorimetric test strip for CN- in an aqueous environment. TDDFT calculations were performed in order to demonstrate the electronic properties of the probe and its cyanide product. Density functional reactivity theory (DFRT) calculation also exhibits the characterisation of the most electrophilic and nucleophilic centres of the molecule. The probe could be applied for imaging cyanide in live cells by fluorescence imaging.

Ni-Catalyzed Reductive Allylation of α-Chloroboronates to Access Homoallylic Boronates

The transition-metal-catalyzed allylation reaction is an efficient strategy for the construction of new carbon-carbon bonds alongside allyl or homoallylic functionalization. Herein we describe a Ni-catalyzed reductive allylation of α-chloroboronates to efficiently render the corresponding homoallylic boronates, which could be readily converted into valuable homoallylic alcohols or amines or 1,4-diboronates. This reaction features a broad substrate scope with good functional group compatibility that is complementary to the existing methods for the preparation of homoallylic boronates.

Design of novel potent antihyperlipidemic agents with antioxidant/anti- inflammatory properties: Exploiting phenothiazine's strong antioxidant activity

Because atherosclerosis is an inflammatory process involving a series of pathological events such as dyslipidemia, oxidative stress, and blood clotting mechanisms, we hereby report the synthesis and evaluation of novel compounds in which antioxidant, anti-inflammatory, and squalene synthase (SQS) inhibitory/hypolipidemic activities are combined in simple molecules through design. The coupling of two different pharmacophores afforded compounds 1-12, whose biological profile was markedly improved compared to those of parent lead structures (i.e., the hypolipidemic 2-hydroxy-2-aryl-(benzo)oxa(or thia)zine and the antioxidant phenothiazine). Most derivatives strongly inhibited in vitro microsomal lipid and LDL peroxidation, exhibiting potent free-radical scavenging activity. They further significantly inhibited SQS activity and showed remarkable antidyslipidemic activity in vivo in animal models of acute and high-fat-induced hyperlipidemia. Finally, several compounds showed anti-inflammatory activity in vitro, inhibiting cycloxygenase (COX-1/2) activity. The multimodal properties of the new compounds and especially their combined antioxidant/SQS/COX inhibitory activity render them interesting lead compounds for further evaluation against atherosclerosis.

Phenothiazine - Bipyridinium cyclophanes

The syntheses of oligooxa[8.8]-, -[11.11]-, -[14,14]-, -[17.17]and -[20.20]cyclophanes with phenothiazine as donor and bipyridinium dication as acceptor are described, together with preparations of the corresponding oligomethylene-[3.3]and -[4.4]cyclophanes. While the large [8.8]-, [11.11]- and [14.14]cyclophanes in particular show well-defined charge-transfer (CT) absorption maxima, the smallest [3.3]cyclophane does not exhibit any CT effect. For the large cyclophanes, a preferred conformation with crossed donor and acceptor units is proposed. The fluorescence quenching and electrochemical behaviour of all phenothiazine - bipyridinium cyclophanes is discussed.

DIBENZOHETEROCYCLIC HYDROXAMIC ACIDS AND HYDROXY UREAS AS INHIBITORS OF 5-LIPOXYGENASE

Compounds having the formula I: are inhibitors of the 5-lipoxygenase enzyme. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating diarrhea, hypertension, angina, platelet aggregation, cerebral spasm, premature labor, spontaneous abortion, dysmenorrhea, and migraine.