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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.

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  • 16611-15-7 Structure
  • Basic information

    1. Product Name: 4-chloro-2-nitro-N-phenylaniline
    2. Synonyms: 4-chloro-2-nitro-N-phenylaniline;C.I.10348;C.I.Disperse Yellow 26;SRA Fast Golden Yellow X
    3. CAS NO:16611-15-7
    4. Molecular Formula: C12H9ClN2O2
    5. Molecular Weight: 248.66506
    6. EINECS: 240-660-9
    7. Product Categories: N/A
    8. Mol File: 16611-15-7.mol
  • Chemical Properties

    1. Melting Point: 59-61 °C
    2. Boiling Point: 366.4°Cat760mmHg
    3. Flash Point: 175.4°C
    4. Appearance: /
    5. Density: 1.387g/cm3
    6. Vapor Pressure: 1.47E-05mmHg at 25°C
    7. Refractive Index: 1.671
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: -3.90±0.40(Predicted)
    11. CAS DataBase Reference: 4-chloro-2-nitro-N-phenylaniline(CAS DataBase Reference)
    12. NIST Chemistry Reference: 4-chloro-2-nitro-N-phenylaniline(16611-15-7)
    13. EPA Substance Registry System: 4-chloro-2-nitro-N-phenylaniline(16611-15-7)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 16611-15-7(Hazardous Substances Data)

16611-15-7 Usage

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

Check Digit Verification of cas no

The CAS Registry Mumber 16611-15-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,6,1 and 1 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 16611-15:
(7*1)+(6*6)+(5*6)+(4*1)+(3*1)+(2*1)+(1*5)=87
87 % 10 = 7
So 16611-15-7 is a valid CAS Registry Number.
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

16611-15-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-chloro-2-nitro-N-phenylaniline

1.2 Other means of identification

Product number -
Other names 4-Chlor-2-nitro-diphenylamin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:16611-15-7 SDS

16611-15-7Relevant articles and documents

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

Zhou, Hang,Gao, Juanhong,Chen, Zhaohang,Duan, Shan,Li, Chao,Qiao, Renzhong

, p. 284 - 288 (2018)

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.

COMPOUND FOR ORGANIC OPTOELECTRONIC DEVICE, COMPOSITION FOR ORGANIC OPTOELECTRONIC DEVICE, ORGANIC OPTOELECTRONIC DEVICE AND DISPLAY DEVICE

-

Paragraph 0348-0352, (2021/11/09)

The compound according to claim 1, wherein the compound is represented by the following Formula. The present invention relates to a composition for an organic optoelectric device, an organic optoelectric device, and a display device. The details of Formula 1 are as defined in the specification.

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

Gao, Yuqi,Guo, Lei,Huang, Yi-You,Lai, Zengwei,Li, Xiangmin,Li, Zhe,Luo, Hai-Bin,Wu, Deyan,Wu, Yinuo,Yu, Yan-Fa,Zhang, Chen,Zhang, Sirui,Zhou, Qian

, (2020/03/24)

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.

Organic photoelectric material containing ring-like urea structure and preparation method and application thereof

-

Paragraph 0058-0061; 0080-0083; 0109-0111, (2019/07/29)

The invention relates to an organic photoelectric material containing a ring-like urea structure and a preparation method and application thereof. The structure of the organic photoelectric material is as shown in the general formula (I). In the general formula (I), A is selected from one of the following structural groups: R1-R3 are separately selected from any one of hydrogen, methyl, ethyl, C6-C30 polycyclic aromatic group conjugated structural group or C4-C30 polycyclic aromatic group conjugated structural group containing hetero atoms such as N, S, O, etc. The organic photoelectric material containing a ring-like urea structure is applied to a CPL layer of an organic light-emitting device. The organic photoelectric material containing the ring-like urea structure has high glass-transition temperature and molecular heat stability, has low absorption and high refractive index in the field of visible light, can help promote light extraction efficiency of an organic light-emitting device effectively after being applied to the CPL layer of the organic light-emitting device, and has a good application effect and industrial prospects.

NOVEL and IMPROVED SYNTHESIS OF ANTIPSYCHOTIC DRUG

-

Page/Page column 13, (2020/01/08)

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.

Construction of Druglike 2-Amido Benzo[ d]imidazole Analogues via Desulfurative Cyclization of Thiourea Intermediate Resin on Solid-Phase

Ryu, Hyun-Jeong,Yang, Seung-Ju,Lee, Gee-Hyung,Gong, Young-Dae

supporting information, p. 282 - 291 (2018/05/24)

A 2-amido benzo[d]imidazole library has been constructed by solid-phase synthesis. The key step of this solid-phase synthesis involves the preparation of polymer-bound 2-amino benzo[d]imidazole resin through desulfurative cyclization of thiourea resin using 2-chloro-1,3-dimethylimidazolinium chloride and N,N-diisopropylethylamine in dichloromethane (DCM), and the resin is then functionalized by acylation at the 2-amine position to afford 2-amidobenzo[d]imidazole resin. In the case of 2-amidobenzo[d]imidazole resin having a p-I or m-NO2, the resin was further functionalized by Suzuki/Sonogashira-coupling (p-I) and reduction to the primary amine (m-NO2) followed by acylation. Finally, the functionalized 2-amido-benzo[d]imidazole resin was cleaved from the polymer support by treatment with a cocktail of trifluoroacetic acid and DCM. As a result, we obtained 2-amidobenzo[d]imidazole analogues in high yield and good purities.

Synthesis and biological evaluation of novel pyrazole carboxamide with diarylamine-modi?ed scaffold as potent antifungal agents

Zhang, Xiao-Xiao,Jin, Hong,Deng, Yuan-Jie,Gao, Xu-Heng,Li, Yong,Zhao, Yong-Tian,Tao, Ke,Hou, Tai-Ping

, p. 1731 - 1736 (2017/07/27)

Twenty-seven novel pyrazole carboxamides with diarylamine-modi?ed scaffold were designed, synthesized and characterized in detail via 1H NMR, 13C NMR, IR and ESI-HRMS. Preliminary bioassays showed that some of the target compounds exhibited good antifungal activity against Rhizoctonia solani, Rhizoctonia cerealis and Sclerotinia sclerotiorum. Among them, compound 9c-7 exhibited the highest antifungal activities against R. solani, R. cerealis and S. sclerotiorum in vitro with IC50 values of 0.013, 1.608 and 1.874?μg/mL, respectively. Notably, compound 9c-7 still presented the highest fungicidal activities against R. solani in vivo with an IC50 value of 22.21?μg/mL. Molecular docking simulation results reveal that compound 9c-7 binds well to the hydrophobic pockets of the receptor protein succinate dehydrogenase. This study suggests that compound 9c-7 could act as a potential fungicide to be used for further optimization.

Chan-Evans-Lam Amination of Boronic Acid Pinacol (BPin) Esters: Overcoming the Aryl Amine Problem

Vantourout, Julien C.,Law, Robert P.,Isidro-Llobet, Albert,Atkinson, Stephen J.,Watson, Allan J. B.

, p. 3942 - 3950 (2016/05/24)

The Chan-Evans-Lam reaction is a valuable C-N bond forming process. However, aryl boronic acid pinacol (BPin) ester reagents can be difficult coupling partners that often deliver low yields, in particular in reactions with aryl amines. Herein, we report effective reaction conditions for the Chan-Evans-Lam amination of aryl BPin with alkyl and aryl amines. A mixed MeCN/EtOH solvent system was found to enable effective C-N bond formation using aryl amines while EtOH is not required for the coupling of alkyl amines.

Steric-Hindrance-Induced Regio- and Chemoselective Oxidation of Aromatic Amines

Patil, Vilas Venunath,Shankarling, Ganapati Subray

, p. 7876 - 7883 (2015/09/01)

Unusual regio- and chemoselective oxidation of aromatic amines hindered with ortho substituents (except -NH2, -NHCH3, and -OH) to the corresponding nitro compounds is described by use of nonanebis(peroxoic acid). The mechanistic investigation for selective oxidation of amines ortho-substituted with -NH2 or -OH showed the involvement of H-bonding between the ortho hydrogen of the adjacent -XH group (where X = NH, NR, or O) and an oxygen atom from the diperoxy acid. Various mono- and diamines are oxidized into corresponding mononitro derivatives in high yield and purity without employing any protection strategies. The protocol was also found to successful on the gram scale.

NOVEL AZA-OXO-INDOLES FOR THE TREATMENT AND PROPHYLAXIS OF RESPIRATORY SYNCYTIAL VIRUS INFECTION

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Page/Page column 35; 36, (2015/02/25)

The invention provides novel compounds having the general formula: wherein R1, R2, R3, R4, R5, W and X are as described herein, compositions including the compounds and methods of using the compounds.

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