2-Chlorophenothiazine
[CAS# 92-39-7]

Identification

• Classification: Chemical pesticide >> Insecticide intermediate
• Name: 2-Chlorophenothiazine
• Molecular Formula: C₁₂H₈ClNS
• Molecular Weight: 233.71
• CAS Registry Number: 92-39-7
• EC Number: 202-152-5
• SMILES: C1=CC=C2C(=C1)NC3=C(S2)C=CC(=C3)Cl

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Melting point: 195-200 ºC (Expl.)
• Index of Refraction: 1.680, Calc.^*
• Boiling Point: 395.7±31.0 ºC (760 mmHg), Calc.^*
• Flash Point: 193.1±24.8 ºC, Calc.^*

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Warning
• Hazard Statements: H315-H317-H319-H335-H341-H411
• Precautionary Statements: P203-P261-P264-P264+P265-P271-P272-P273-P280-P302+P352-P304+P340-P305+P351+P338-P318-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin sensitization	Skin Sens.	1	H317
Germ cell mutagenicity	Muta.	2	H341

Discovory and Applicatios

2-Chlorophenothiazine is an organic compound belonging to the phenothiazine class, which is known for its diverse biological activities. The chemical structure of 2-chlorophenothiazine consists of a phenothiazine core, which features a sulfur atom and a nitrogen atom within its three-ring structure, and a chlorine atom attached to the second position of the phenyl ring. This compound has the molecular formula C12H9ClN2S and is often used as an intermediate in the synthesis of various pharmaceuticals, particularly those with antipsychotic and antimicrobial properties.

The discovery of phenothiazine and its derivatives dates back to the early 19th century, when the compound was first synthesized by the German chemist August Wilhelm von Hofmann. However, it wasn’t until the mid-20th century that phenothiazine derivatives gained significant attention for their biological effects. The development of 2-chlorophenothiazine, specifically, emerged as part of a broader effort to design and synthesize compounds with enhanced pharmacological activity. The introduction of the chlorine atom at the 2-position of the phenothiazine ring system was found to affect the compound's electronic properties, contributing to its unique reactivity and increasing its biological effectiveness in certain applications.

2-chlorophenothiazine has been widely studied for its potential as a precursor in the synthesis of antipsychotic and anti-anxiety medications. Phenothiazine derivatives, such as chlorpromazine, have had a profound impact on psychiatry since their introduction in the 1950s as one of the first classes of antipsychotic drugs. While 2-chlorophenothiazine itself is not used directly in clinical applications, it serves as an important intermediate in the preparation of phenothiazine-based drugs, which are used to treat schizophrenia, bipolar disorder, and other mental health conditions. The chlorine substitution at the second position plays a significant role in modulating the drug's pharmacological properties, including its potency and selectivity for certain neurotransmitter receptors in the brain.

In addition to its applications in the pharmaceutical industry, 2-chlorophenothiazine has been investigated for its antimicrobial properties. Phenothiazine derivatives have been found to exhibit activity against a range of pathogens, including bacteria and fungi. This has led to their incorporation into various formulations aimed at combating infections. As a precursor, 2-chlorophenothiazine can be used in the development of new antimicrobial agents with enhanced efficacy and reduced side effects.

Furthermore, 2-chlorophenothiazine has applications in materials science, where it has been studied for its role in the development of organic semiconductors. Phenothiazine derivatives, including 2-chlorophenothiazine, have shown promise in organic light-emitting diodes (OLEDs) and organic solar cells. The compound’s ability to absorb light and its electronic properties make it a candidate for use in these energy-efficient technologies.

In conclusion, 2-chlorophenothiazine is a versatile chemical with significant applications in pharmaceuticals, antimicrobial research, and materials science. Its role as a key intermediate in the synthesis of biologically active compounds has contributed to the development of important therapeutic agents, and its potential in advanced materials makes it a subject of ongoing research.

References

2019. Recent Progress in Synthesis, Structure and Biological Activities of Phenothiazine Derivatives. Reviews and Advances in Chemistry, 9(2).
DOI: 10.1134/s2079978019020018

2018. Synthesis and Anticancer Evaluation of Some Phenothiazine Derivatives. Russian Journal of General Chemistry, 88(11).
DOI: 10.1134/s1070363218110269

2014. A Catalyst System, Copper/N-Methoxy-1H-pyrrole-2-carboxamide, for the Synthesis of Phenothiazines in Poly(ethylene glycol). Synthesis, 46(9).
DOI: 10.1055/s-0034-1379045