16611-15-7

Basic information

• Product Name: 4-chloro-2-nitro-N-phenylaniline
• Synonyms: 4-chloro-2-nitro-N-phenylaniline;C.I.10348;C.I.Disperse Yellow 26;SRA Fast Golden Yellow X
• CAS NO: 16611-15-7
• Molecular Formula: C₁₂H₉ClN₂O₂
• Molecular Weight: 248.66506
• EINECS: 240-660-9
• Mol File: 16611-15-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 59-61 °C
• Boiling Point: 366.4°Cat760mmHg
• Flash Point: 175.4°C
• Appearance: /
• Density: 1.387g/cm³
• Vapor Pressure: 1.47E-05mmHg at 25°C
• Refractive Index: 1.671
• PKA: -3.90±0.40(Predicted)
• CAS DataBase Reference: 4-chloro-2-nitro-N-phenylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-2-nitro-N-phenylaniline(16611-15-7)
• EPA Substance Registry System: 4-chloro-2-nitro-N-phenylaniline(16611-15-7)

Safety Data

• Hazardous Substances Data: 16611-15-7(Hazardous Substances Data)

Usage

Description

4-chloro-2-nitro-N-phenylaniline is an organic compound with the molecular formula C12H9ClN2O2. It is characterized by its reddish-yellow color and is known for its use in various applications, particularly in the dyeing industry.

Uses

Used in Dye Industry:
4-chloro-2-nitro-N-phenylaniline is used as a dyestuff for coloring vinegar and polyamide fibers. It provides good colorfastness properties, making it suitable for various applications.
Used in Vinegar Dyeing:
4-chloro-2-nitro-N-phenylaniline is used as a coloring agent for vinegar, offering good light fastness (ISO 5) and ironing fastness (ISO 4). This ensures that the color remains vibrant and resistant to fading and staining during use.
Used in Polyamide Fiber Dyeing:
In the polyamide fiber industry, 4-chloro-2-nitro-N-phenylaniline is used as a dyestuff that provides excellent colorfastness properties. It has a light fastness rating of ISO 7 and perspiration fastness rating of ISO 3, making it ideal for use in fabrics that may be exposed to sunlight and sweat.
Overall, 4-chloro-2-nitro-N-phenylaniline is a versatile compound with significant applications in the dyeing industry, particularly for vinegar and polyamide fibers, due to its colorfastness properties and ability to provide vibrant, long-lasting colors.

Preparation

Aniline?and 2, 5 – Dichloronitrobenzene condensation

StandardVinegar fiber

Ironing Fastness

Fading

Stain

InChI:InChI=1/C12H9ClN2O2/c13-9-6-7-11(12(8-9)15(16)17)14-10-4-2-1-3-5-10/h1-8,14H

Upstream product

• 127-09-3 sodium acetate 
• 62-53-3 aniline 
• 89-61-2 2,5-dichloronitrobenzene 
• 108-86-1 bromobenzene 
• 89-63-4 4-Chloro-2-nitroaniline 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 42837-74-1 4-chloro-N¹-phenylbenzene-1,2-diamine 
• 591-50-4 iodobenzene 
• 345-18-6 2-fluoro-5-chloronitrobenzene 

Downstream Products

• 5786-21-0 clozaril 
• 303-79-7 2-chlorophenazine 5,10-di-N-oxide 
• 151385-84-1 7-Chloro-5-(3-methyl-butyl)-1-phenyl-3-(phenyl-hydrazono)-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione 
• 151620-79-0 3-Amino-7-chloro-5-(3-methyl-butyl)-1-phenyl-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione 
• 151620-92-7 4-Chloro-N²-(3-methyl-butyl)-N¹-phenyl-benzene-1,2-diamine 
• 42837-74-1 4-chloro-N¹-phenylbenzene-1,2-diamine 
• 64794-94-1 (4-chloro-2-nitro-phenyl)-methyl-phenyl-amine 
• 1137-69-5 2-chlorophenazine 

Relevant articles and documents

Double-strand cleavage of DNA by a polyamide-phenazine-di-N-oxide conjugate

Phenazine and its derivatives have been widely applied as nucleic acid cleavage agents due to active oxygen activating the C–H bond of the substrate. However, diffusion of oxygen radicals limits their potential applications in the DNA-targeted metal-free drug. Introduction of groove binder moiety such as polyamide enhanced the regional stability of radical molecules and reduced cytotoxicity of the drugs. In this work, we described the design and synthesis of a polyamide-modified phenazine-di-N-oxide as a DNA double-strand cleavage agent. The gel assays showed the hybrid conjugates can effectively break DNA double strands in a non-random manner under physiological conditions. The probable binding mode to DNA was investigated by sufficient spectral experiments, revealing weak interaction between hybrid ligand and nucleic acid molecules. The results of our study have implications on the design of groove-binding hybrid molecules as new artificial nucleases and may provide a strategy for developing efficient and safe DNA cleavage reagents.

Discovery and Optimization of Chromone Derivatives as Novel Selective Phosphodiesterase 10 Inhibitors

Phosphodiesterase 10 (PDE10) inhibitors have received much attention as promising therapeutic agents for central nervous system (CNS) disorders such as schizophrenia and Huntington's disease. Recently, a hit compound 1 with a novel chromone scaffold has shown moderate inhibitory activity against PDE10A (IC50 = 500 nM). Hit-to-lead optimization has resulted in compound 3e with an improved inhibitory activity (IC50 = 6.5 nM), remarkable selectivity (>95-fold over other PDEs), and good metabolic stability (RLM t1/2 = 105 min) by using an integrated strategy (molecular modeling, chemical synthesis, bioassay, and cocrystal structure). The cocrystal structural information provides insights into the binding pattern of 3e in the PDE10A catalytic domain to highlight the key role of the halogen and hydrogen bonds toward Tyr524 and Tyr693, respectively, thereby resulting in high selectivity against other PDEs. These new observations are of benefit for the rational design of the next generation PDE10 inhibitors for CNS disorders.

NOVEL and IMPROVED SYNTHESIS OF ANTIPSYCHOTIC DRUG

The present invention relates to novel as well as improved process for the preparation of Clozapine of Formula I which involves anti-narcotic and highly cost effective raw materials.