823-86-9

Basic information

• Product Name: 4-chlorophenylhydroxylamine
• Synonyms: 4-chlorophenylhydroxylamine;4-Chloro-N-hydroxyaniline;N-(4-chlorophenyl)hydroxylamine
• CAS NO: 823-86-9
• Molecular Formula: C₆H₆ClNO
• Molecular Weight: 143.57
• Mol File: 823-86-9.mol
• Article Data: 84

Chemical Properties

• Melting Point: 86 °C
• Boiling Point: 251.7 °C at 760 mmHg
• Flash Point: 106 °C
• Appearance: /
• Density: 1.409
• Vapor Pressure: 0.0106mmHg at 25°C
• Refractive Index: 1.661
• PKA: 8.30±0.70(Predicted)
• CAS DataBase Reference: 4-chlorophenylhydroxylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chlorophenylhydroxylamine(823-86-9)
• EPA Substance Registry System: 4-chlorophenylhydroxylamine(823-86-9)

Safety Data

• Hazardous Substances Data: 823-86-9(Hazardous Substances Data)

Usage

General Description

4-chlorophenylhydroxylamine is a chemical compound with the formula C6H6ClNO. It is a derivative of phenylhydroxylamine with the addition of a chlorine atom. 4-chlorophenylhydroxylamine is a white to light yellow solid with a melting point of 60-63°C. It is soluble in organic solvents and exhibits reactivity in various chemical reactions. 4-chlorophenylhydroxylamine is commonly used in the synthesis of pharmaceuticals and agrochemicals. It is also utilized in the preparation of other organic compounds and as a reagent in organic chemistry reactions. Additionally, it has been studied for its potential biological activity and has been found to have antimicrobial and antiviral properties.

InChI:InChI=1/C6H6ClNO/c7-5-1-3-6(8-9)4-2-5/h1-4,8-9H

Upstream product

• 100-00-5 4-chlorobenzonitrile 
• 51639-68-0 N-(p-chlorophenyl)-2-furohydroxamic acid 
• 932-98-9 1-chloro-4-nitroso-benzene 
• 33175-34-7 N-(3,4-dichlorophenyl)-hydroxylamine 
• 116278-63-8 N-(4-chlorophenyl)-O-pivaloylhydroxylamine 
• 1503-91-9 N-(4-chlorophenyl)-N-hydroxyacetamide 
• 109-89-7 diethylamine 
• 106-47-8 4-chloro-aniline 
• 1303610-38-9 4-ClC₆H₄-N(Teoc)OTBS 
• 163188-54-3 N-p-chlorophenyl-α-p-chlorophenylstyrylacrylohydroxamic acid 
• 163188-50-9 N-p-chlorophenyl-α-phenylstyrylacrylohydroxamic acid 
• 131303-56-5 N-p-chlorophenylquinaldinohydroxamic acid 
• 131303-55-4 N-p-chlorophenylpicolinohydroxamic acid 
• 68166-12-1 N-p-chlorophenyl-2-thenohydroxamic acid 

Downstream Products

• 19865-58-8 N-(4-chlorophenyl)-α-phenylnitrone 
• 19865-61-3 N-(salicylidene)-4-chlorophenylamine-N-oxide 
• 109399-98-6 N,O-dibenzoyl-N-(4-chloro-phenyl)-hydroxylamine 
• 614-26-6 4,4'-bis(chloro)azoxybenzene 
• 1070874-61-1 cinnamaldehyde-[N-(4-chloro-phenyl)-oxime ] 
• 1602-00-2 bis-(4-chloro-phenyl)-diazene 
• 932-98-9 1-chloro-4-nitroso-benzene 
• 873-38-1 4-chloro-2-bromoaniline 
• 874-17-9 4-chloro-2,6-dibromoaniline 
• 554-00-7 2,4-Dichloroaniline 
• 61563-93-7 2-(4-chlorophenyl)-5-methylisoxazole-3(2H)-one 
• 27546-29-8 N'-Tosyloxy-N-<4-chlor-phenyl>-diimid-N-oxid 
• 3170-87-4 Iminokohlensaeure-<3-chlor-phenylester>-<4-chlor-phenylhydroxylamid> 
• 3170-86-3 Iminokohlensaeure-<2,4-dimethyl-phenylester>-<4-chlor-phenylhydroxylamid> 

Relevant articles and documents

Electrochemically Tuned Oxidative [4+2] Annulation and Dioxygenation of Olefins with Hydroxamic Acids

This work represents the first [4+2] annulation of hydroxamic acids with olefins for the synthesis of benzo[c][1,2]oxazines scaffold via anode-selective electrochemical oxidation. This protocol features mild conditions, is oxidant free, shows high regioselectivity and stereoselectivity, broad substrate scope of both alkenes and hydroxamic acids, and is compatible with terpenes, peptides, and steroids. Significantly, the dioxygenation of olefins employing hydroxamic acid is also successfully achieved by switching the anode material under the same reaction conditions. The study not only reveals a new reactivity of hydroxamic acids and its first application in electrosynthesis but also provides a successful example of anode material-tuned product selectivity.

Synthesis, anti-microbial, toxicity and molecular docking studies of N-nitroso-N-phenylhydroxylamine (cupferron) and its derivatives

Bacterial resistance to antimicrobial agents is increasing at an alarming rate globally and requires new lead compounds for antibiotics. In this study, N-phenyl-N-nitroso hydroxylamine (cupferron) and its derivatives have been synthesised using readily available starting materials. The compounds were obtained in high yield and purity. They show activity towards a range of Gram-positive and Gram-negative pathogenic bacteria, with minimum inhibitory concentration (MIC) values as low as 2 μg.mL?1 against the tested organisms, especially for Gram-positive species. Toxicity studies on the lead compound 3b indicate insignificant effects on healthy cell lines. Molecular docking studies on the lead compound identify possible binding modes of the compound, and the results obtained correlate with those of in vitro and MIC studies. The lead compound shows excellent drug-likeness properties.

Selective Photoinduced Reduction of Nitroarenes to N-Arylhydroxylamines

We report the selective photoinduced reduction of nitroarenes to N-arylhydroxylamines. The present methodology facilitates this transformation in the absence of catalyst or additives and uses only light and methylhydrazine. This noncatalytic photoinduced transformation proceeds with a broad scope, excellent functional-group tolerance, and high yields. The potential of this protocol reflects on the selective and straightforward conversion of two general antibiotics, azomycin and chloramphenicol, to the bioactive hydroxylamine species.