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2-Amino-4-chlorophenol is a grayish to light brown crystalline solid or powder that is a widely used reagent in the synthesis of various drugs, dyes, and pesticides. It is also known as 5-chloro-2-hydroxyaniline and may be toxic by ingestion. However, it is insoluble in water.

95-85-2

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95-85-2 Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-4-chlorophenol is used as an intermediate in the synthesis of various drugs. It is particularly used in the synthesis of aggrecanase-2 inhibitors based on acylthiosemicarbazide zinc-binding, which are used in the treatment of osteoarthritis.
Used in Chemical Industry:
2-Amino-4-chlorophenol is used as a reagent in the synthesis of various dyes and pesticides. It is a key component in the production of these chemicals, contributing to their color and effectiveness.
Used in Research and Development:
2-Amino-4-chlorophenol is also used in research and development for the discovery and development of new drugs and chemicals. Its unique properties make it a valuable tool in the lab for creating new compounds and testing their efficacy.

Air & Water Reactions

5-Chloro-2-hydroxyaniline may be sensitive to prolonged exposure to air and/or light. Insoluble in water.

Reactivity Profile

5-Chloro-2-hydroxyaniline may react with strong oxidizing agents.

Health Hazard

Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Containers may explode when heated. Runoff may pollute waterways.

Safety Profile

A poison. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits very toxic fumes of Cland NOx. See also AROMATIC MINES and CHLORIDES.

Potential Exposure

Used as a chemical raw material, especially in dye manufacture

Shipping

UN2673 2-Amino-4-chlorophenol, Hazard Class: 6.1; Labels: 6.1-Poisonous materials

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, iron, moisture and temperatures .43 C.

Check Digit Verification of cas no

The CAS Registry Mumber 95-85-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 5 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 95-85:
(4*9)+(3*5)+(2*8)+(1*5)=72
72 % 10 = 2
So 95-85-2 is a valid CAS Registry Number.
InChI:InChI=1/C6H6ClNO/c7-4-1-2-6(9)5(8)3-4/h1-3,9H,8H2

95-85-2 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Alfa Aesar

  • (A10135)  2-Amino-4-chlorophenol, 98%   

  • 95-85-2

  • 100g

  • 329.0CNY

  • Detail
  • Alfa Aesar

  • (A10135)  2-Amino-4-chlorophenol, 98%   

  • 95-85-2

  • 500g

  • 635.0CNY

  • Detail
  • USP

  • (1130527)  ChlorzoxazoneRelatedCompoundA  United States Pharmacopeia (USP) Reference Standard

  • 95-85-2

  • 1130527-50MG

  • 14,500.98CNY

  • Detail

95-85-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Amino-4-chlorophenol

1.2 Other means of identification

Product number -
Other names 5-Chloro-2-hydroxyaniline

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:95-85-2 SDS

95-85-2Relevant academic research and scientific papers

Kinetics of liquid-phase catalytic hydrogenation of 4-chioro-2-nitrophenol

Mukhopadhyay, Sudip,Gandi, Ganesh K.,Chandalia, Sampatraj B.

, p. 201 - 205 (1999)

Process parameters were studied to increase the selectivity of the haloamino compound by preventing the formation of dehalogenated product for the selective hydrogenation of 4-chloro-2-nitrophenol on 5% Pd/C catalyst. At a conversion ratio of 87%, 96% selectivity was achieved in 5 h. Kinetic interpretations have been made for this liquid-phase hydrogenation reaction.

Kinetic study of alkaline induced hydrolysis of the skeletal muscle relaxant chlorzoxazone using ratio spectra first derivative spectrophotometry

Ellaithy,El-Ragehy,El-Ghobashy

, p. 337 - 342 (2003)

2-Amino-4-chlorophenol was found to be the alkaline induced degradation product and the synthetic precursor of chlorzoxazone. The aim of this work is to study different factors affecting the degradation process due to the high toxicity of 2-amino-4-chloro

Highly porous copper-supported magnetic nanocatalysts: made of volcanic pumice textured by cellulose and applied for the reduction of nitrobenzene derivatives

Fazeli, Atefeh,Maleki, Ali,Qazi, Fateme Sadat,Saeidirad, Mahdi,Shalan, Ahmed Esmail,Taheri-Ledari, Reza

, p. 25284 - 25295 (2021/08/05)

Herein, a novel designed heterogeneous catalytic system constructed of volcanic pumice magnetic particles (VPMPs), cellulose (CLS) as a natural polymeric matrix, and copper nanoparticles (Cu NPs) is presented. Also, to enhance the inherent magnetic property of VPMP, iron oxide (Fe3O4) nanoparticles have been prepared and incorporated in the structureviaanin situprocess. As its first and foremost excellent property, the designed composite is in great accordance with green chemistry principles because it contains natural ingredients. Another brilliant point in the architecture of the designed composite is the noticeable porosity of VPMP as the core of the composite structure (surface area: 84.473 m2g?1). This great porosity leads to the use of a small amount (0.05 g) of the particles for catalytic purposes. However, the main characterization methods, such as Fourier-transform infrared and energy-dispersive X-ray spectroscopy, thermogravimetric analysis, and electron microscopy, revealed that the spherical metallic particles (Fe and Cu oxides) were successfully distributed onto the surface of the VPMP and CLS matrices. Further, vibrating-sample magnetometer analysis confirmed the enhancement of the magnetic property (1.5 emu g?1) of the composite through the addition of Fe3O4nanoparticles. Further, the prepared (Fe3O4@VPMP/CLS-Cu) nanocomposite has been applied to facilitate the reduction reaction of hazardous nitrobenzene derivatives (NBDs) to their aniline analogs, with 98% conversion efficiency in eight minutes under mild conditions. Moreover, the good reusability of the catalytic system has been verified after recycling it ten times without any significant decrease in the performance.

Convenient conversion of hazardous nitrobenzene derivatives to aniline analogues by Ag nanoparticles, stabilized on a naturally magnetic pumice/chitosan substrate

Taheri-Ledari, Reza,Mirmohammadi, Seyedeh Shadi,Valadi, Kobra,Maleki, Ali,Shalan, Ahmed Esmail

, p. 43670 - 43681 (2020/12/25)

Herein, silver nanoparticles (Ag NPs), as an effective catalyst for the reduction process of nitrobenzene derivatives to non-hazardous and useful aniline derivatives, are conveniently synthesized on an inherently magnetic substrate. For this purpose, an efficient combination of volcanic pumice (VP), which is an extremely porous igneous rock, and a chitosan (CTS) polymeric network is prepared and suitably used for the stabilization of the Ag NPs. High magnetic properties of the fabricated Ag@VP/CTS composite, which have been confirmed via vibrating-sample magnetometer (VSM) analysis, are the first and foremost advantage of the introduced catalytic system since it gives us the opportunity to easily separate the particles and perform purification processes. Briefly, higher yields were obtained in the reduction reactions of nitrobenzenes (NBs) under very mild conditions in a short reaction time. Also, along with the natural biocompatible ingredients (VP and CTS) in the structure, excellent recyclability has been observed for the fabricated Ag@VP/CTS catalytic system, which convinces us to do scaling-up and suggests the presented system can be used for industrial applications. This journal is

Enhanced reduction of nitrobenzene derivatives: Effective strategy executed by Fe3O4/PVA-10%Ag as a versatile hybrid nanocatalyst

Rahimi, Jamal,Taheri-Ledari, Reza,Niksefat, Maryam,Maleki, Ali

, (2019/11/02)

Herein, we present an organic–inorganic hybrid nanocomposite constructed of polyvinyl alcohol (PVA), iron oxide (Fe3O4), and 10% of silver nanoparticles (Ag NPs). First, a convenient in situ method is introduced for the preparation of this efficient catalytic system (Fe3O4/PVA-10%Ag). Further, we study the high catalytic performance for the reduction of nitrobenzene (NB) derivatives as a hazardous species of chemicals and the significant biological activity (antibacterial effects) of the nanocomposite. However, high reaction yields (99%) have been obtained in short reaction times (~15 min). A plausible mechanism is suggested, and all the required characterizations of the presented nanocatalyst are investigated in this study.

Synthesis, docking, 3-D-qsar, and biological assays of novel indole derivatives targeting serotonin transporter, dopamine D2 receptor, and mao-a enzyme: In the pursuit for potential multitarget directed ligands

Alarcón-Espósito, Jazmín,Araya-Maturana, Ramiro,Cabezas, David,Cerda-Cavieres, Christopher,Chung, Hery,Iturriaga-Vásquez, Patricio,Mella-Raipán, Jaime,Ojeda-Gómez, Claudia,Pessoa-Mahana, Carlos D.,Pessoa-Mahana, Hernán,Quiroz, Gabriel,Reyes-Parada, Miguel,Rodríguez-Lavado, Julio,Saitz, Claudio

, (2020/10/18)

A series of 27 compounds of general structure 2,3-dihydro-benzo[1,4]oxazin-4-yl)-2-{4-[3-(1H-3indolyl)-propyl]-1-piperazinyl}-ethanamides, Series I: 7(a-o) and (2-{4-[3-(1H-3-indolyl) -propyl]-1-piperazinyl}-acetylamine)-N-(2-morfolin-4-yl-ethyl)-fluorinated benzamides Series II: 13(a-l) were synthesized and evaluated as novel multitarget ligands towards dopamine D2 receptor, serotonin transporter (SERT), and monoamine oxidase-A (MAO-A) directed to the management of major depressive disorder (MDD). All the assayed compounds showed affinity for SERT in the nanomolar range, with five of them displaying Ki values from 5 to 10 nM. Compounds 7k, Ki = 5.63 ± 0.82 nM, and 13c, Ki = 6.85 ± 0.19 nM, showed the highest potencies. The affinities for D2 ranged from micro to nanomolar, while MAO-A inhibition was more discrete. Nevertheless, compounds 7m and 7n showed affinities for the D2 receptor in the nanomolar range (7n: Ki = 307 ± 6 nM and 7m: Ki = 593 ± 62 nM). Compound 7n was the only derivative displaying comparable affinities for SERT and D2 receptor (D2/SERT ratio = 3.6) and could be considered as a multitarget lead for further optimization. In addition, docking studies aimed to rationalize the molecular interactions and binding modes of the designed compounds in the most relevant protein targets were carried out. Furthermore, in order to obtain information on the structure-activity relationship of the synthesized series, a 3-D-QSAR CoMFA and CoMSIA study was conducted and validated internally and externally (q2 = 0.625, 0.523 for CoMFA and CoMSIA and r2ncv = 0.967, 0.959 for CoMFA and CoMSIA, respectively).

Hydroxyl Assisted Rhodium Catalyst Supported on Goethite Nanoflower for Chemoselective Catalytic Transfer Hydrogenation of Fully Converted Nitrostyrenes

Hu, Zenan,Ai, Yongjian,Liu, Lei,Zhou, Junjie,Zhang, Gang,Liu, Hongqi,Liu, Xiangyu,Liu, Zhibo,Hu, Jianshe,Sun, Hong-bin,Liang, Qionglin

supporting information, p. 3146 - 3154 (2019/05/10)

Control of chemoselectivity is a special challenge for the reduction of nitroarenes bearing one or more unsaturated groups. Here, we report a flower-like Rh/α-FeOOH catalyst for the chemoselective hydrogenation of nitrostyrene to vinylaniline over full conversion, which benefits the new functionalized aminostyrene because the multisubstituted aminostyrenes are usually commercially unavailable. This catalyst does not only show desirable selectivity for the vinylanilines, but also exhibits the inertness to various other reducible groups over wide reaction duration. The catalytic selectivity for the reduction of the nitro group towards vinyl group was investigated by the control experiments and FT-IR analysis. We have found that the abundant hydroxyl groups in the α-FeOOH may contribute to the improvement of catalytic activity and selectivity. Furthermore, the catalyst exhibits excellent stability and keeps its catalytic performance even after 6 cycles. (Figure presented.).

Directed Structural Transformations of Coordination Polymers Supported Single-Site Cu(II) Catalysts to Control the Site Selectivity of C-H Halogenation

Huang, Chao,Zhu, Kaifang,Zhang, Yingying,Shao, Zhichao,Wang, Dandan,Mi, Liwei,Hou, Hongwei

supporting information, p. 12933 - 12942 (2019/10/11)

A main difficulty in C-H bond functionalization is to undertake the catalyst control accurately where the reaction takes place. In this work, to achieve highly effective and regioselective single-site catalysts, a three-dimensional (3D) rhombus-like framework of {[Mn(Hidbt)DMF]·H2O}n (1) [H3idbt = 5,5′-(1H-imidazole-4,5-diyl)-bis(2H-tetrazole)] containing coordinated DMF molecules was constructed. For the dissolution-recrystallization structural transformation process, attractive structural transformations proceeded from 1 to a new crystalline species formulated as {[Mn3(idbt)2(H2O)2]·3H2O}n (2) with a 3D windowlike architecture, and then the Mn ions in 2 could be exchanged with Cu ions through cation exchange in a single-crystal to single-crystal fashion to produce the Cu-exchanged product {[Mn2Cu(idbt)2(H2O)2]·3H2O}n (2a), which had a windowlike framework like that of 2. Furthermore, 2 and 2a were used as heterogeneous catalysts for the regioselective C-H halogenation of phenols with N-halosuccinimides (NCS and NBS) to produce the site selective single monohalogenated products. It was found that the catalytic activity and site selectivity of 2a were much higher than those of 2, because the unique structural features of 2a with the uniformly dispersed CuII active centers served as a single-site catalyst with a site-isolated and well-defined platform to promote the C-H halogenation reaction in regiocontrol and guide an orientation that favored the para selectivity during the reaction process.

Catalytic applications of β-cyclodextrin/palladium nanoparticle thin film obtained from oil/water interface in the reduction of toxic nitrophenol compounds and the degradation of azo dyes

Zare Asadabadi, Azam,Hoseini, S. Jafar,Bahrami, Mehrangiz,Nabavizadeh, S. Masoud

, p. 6513 - 6522 (2019/05/10)

A supramolecular catalyst of Pd/β-cyclodextrin thin film is synthesized via a facile and one-pot procedure at an oil-water interface. Macrocyclic oligosaccharides of cyclodextrins with glucose units have a wide range of applications due to their hydrophobic and chiral interior. Due to the ability of this supramolecular catalyst to form inclusion complexes with small organic molecules, the as-synthesized catalyst was applied for the reduction of toxic nitroaromatic compounds (p, o, m-nitrophenol and 4-Cl-2-nitrophenol) and the degradation of harmful azo dyes (methyl orange and bismarck brown) with considerable results. This investigation illustrates the change of the catalyst properties in the presence of molecular receptors attached to the catalyst surface.

Application of Silicon-Initiated Water Splitting for the Reduction of Organic Substrates

Gevorgyan, Ashot,Mkrtchyan, Satenik,Grigoryan, Tatevik,Iaroshenko, Viktor O.

, p. 375 - 382 (2018/06/04)

The use of water as a donor for hydrogen suitable for the reduction of several important classes of organic compounds is described. It is found that the reductive water splitting can be promoted by several metalloids among which silicon shows the best efficiency. The developed methodologies were applied for the reduction of nitro compounds, N-oxides, sulfoxides, alkenes, alkynes, hydrodehalogenation as well as for the gram-scale synthesis of several substrates of industrial importance.

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