4920-79-0

Basic information

• Product Name: 2-Chloro-4-nitoranisole
• Synonyms: 3-CHLORO-4-METHOXYNITROBENZENE;2-chloro-4-nitoranisole;2-CHLORO-4-NITROANISOLE;2-CHLORO-1-METHOXY-4-NITROBENZENE;2-chloro-1-methoxy-4-nitro-benzen;2-chloro-4-nitro-anisol;Anisole, 2-chloro-4-nitro-;Chloronitroanisole
• CAS NO: 4920-79-0
• Molecular Formula: C₇H₆ClNO₃
• Molecular Weight: 187.58
• EINECS: 225-547-4
• Product Categories: Anisoles, Alkyloxy Compounds & Phenylacetates;Chlorine Compounds;Nitro Compounds
• Mol File: 4920-79-0.mol

Chemical Properties

• Melting Point: 94 °C
• Boiling Point: 286.598 °C at 760 mmHg
• Flash Point: 127.13 °C
• Appearance: /
• Density: 1.367 g/cm³
• Vapor Pressure: 0.00451mmHg at 25°C
• Refractive Index: 1.559
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-Chloro-4-nitoranisole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4-nitoranisole(4920-79-0)
• EPA Substance Registry System: 2-Chloro-4-nitoranisole(4920-79-0)

Safety Data

• Hazard Codes: Xi
• RTECS: BZ8578000
• HazardClass: IRRITANT
• Hazardous Substances Data: 4920-79-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Chloro-4-nitroanisole is used as a precursor in the synthesis of various complex organic compounds. Its presence as a nitroaromatic compound allows for further chemical reactions and modifications, making it a valuable component in the creation of new molecules.
Used in Pharmaceutical Industry:
2-Chloro-4-nitroanisole is used as an intermediate in the development of pharmaceutical compounds. Its unique structure and functional groups enable it to be a key component in the synthesis of potential drug candidates, contributing to the advancement of new treatments and therapies.
Used in Research and Development:
2-Chloro-4-nitroanisole is used as a research compound in academic and industrial laboratories. Its properties and reactivity make it an interesting subject for studying chemical reactions, mechanisms, and the development of new synthetic methods.
Used in Material Science:
2-Chloro-4-nitroanisole is used as a component in the synthesis of new materials with potential applications in various industries. Its incorporation into the molecular structure of these materials can lead to the discovery of novel properties and uses.
Note: The exact applications and industries may vary, and the information provided is based on the general description of 2-Chloro-4-nitroanisole as a synthetic compound with potential uses in chemical synthesis and related fields.

InChI:InChI=1/C7H6ClNO3/c1-12-7-3-2-5(9(10)11)4-6(7)8/h2-4H,1H3

Upstream product

• 67-56-1 methanol 
• 99-54-7 3,4-dichloronitrobenzene 
• 124-41-4 sodium methylate 
• 619-16-9 1-chloro-2,5-dinitrobenzene 
• 766-51-8 2-Chloroanisole 
• 108-24-7 acetic anhydride 
• 619-08-9 2-chloro-4-nitrophenol 
• 77-78-1 dimethyl sulfate 
• 99-59-2 3-amino-4-methoxynitrobenzene 
• 74-88-4 methyl iodide 
• 89975-38-2 2-chloro-3-methoxy-6-nitroaniline 
• 100-17-4 para-methoxynitrobenzene 
• 7697-37-2 nitric acid 
• 619-18-1 2,5-dinitroaniline 

Downstream Products

• 23789-10-8 5-chloro-4-methoxy-1,3-dinitrobenzene 
• 5345-54-0 3-chloro-4-methoxyaniline 
• 139-24-2 3,3'-dichloroazoxybenzene 
• 15854-75-8 2-methoxy-5-nitro-1,1’-biphenyl 
• 10496-75-0 2-methoxy-5-nitrobenzylnitrile 
• 102151-33-7 3-Chloro-4-methoxybenzonitrile 
• 38608-06-9 5-chloro-4-methoxy-o-phenylenediamine 
• 7073-42-9 N-(3-chloro-4-methoxyphenyl)acetamide 
• 160088-54-0 5-Chloro-4-methoxy-2-nitroaniline 
• 160088-53-9 N-(5-chloro-4-methoxy-2-nitrophenyl)-acetamide 
• 95220-18-1 N-(3-chloro-4-methoxy-phenyl)-N'-[1]naphthyl-thiourea 
• 23165-42-6 3-chloro-4-methoxyphenyl isothiocyanate 
• 90234-41-6 3-chloro-4-methoxy-N-methylaniline 
• 858244-81-2 formic acid-(3-chloro-4-methoxy-N-methyl-anilide) 

Relevant articles and documents

Room temperature C(sp2)-H oxidative chlorination: Via photoredox catalysis

Photoredox catalysis has been developed to achieve oxidative C-H chlorination of aromatic compounds using NaCl as the chlorine source and Na2S2O8 as the oxidant. The reactions occur at room temperature and exhibit exclusive selectivity for C(sp2)-H bonds over C(sp3)-H bonds. The method has been used for the chlorination of a diverse set of substrates, including the expedited synthesis of key intermediates to bioactive compounds and a drug.

4′-Alkoxyl substitution enhancing the anti-mitotic effect of 5-(3′,4′,5′-substituted)anilino-4-hydroxy-8-nitroquinazolines as a novel class of anti-microtubule agents

Mitosis inhibitors are powerful anticancer drugs. Based on a novel anti-microtubule agent of 5-(4′-methoxy)anilino-4-hydroxy-8-nitroquinazoline, a series of 5-(3′,4′,5′-substituted)anilino-4-hydroxy-8- nitroquinazolines were designed and synthesized to investigate the effect of the substitution on the inhibitory activity against mitotic progression of tumor cells. The large alkoxyl substitution on the 4′-position of 5-anilino ring is beneficial for the potency. The 5-(3′,4′,5′-trimethoxy)anilino-8-nitroquinazoline (1h) displays an overwhelming activity in arresting the cells at the G2/M phase, providing a promising new template for further development of potent microtubule-targeted anti-mitotic drugs.

Selective nitration of aromatic compounds with bismuth subnitrate and thionyl chloride

Bismuth subnitrate/thionyl chloride have been found to be an efficient combination of reagents for nitration of a wide range of aromatic compounds in dichloromethane. Phenols, in particular, were easily mononitrated and dinitrated with the reagents by controlling the stoichiometry.

Oxidative chlorination of various lodoarenes to (dichloroiodo)arenes with chromium(vi) oxide as the oxidant j

Chromium(vi) oxide dissolved in a mixture of acetic acid with concentrated hydrochloric acid converts, at or near room temperature, iodoarenes to (dichloroiodo)arenes, in a very simple and efficient procedure.

Chemoselective O-methylation of phenols under non-aqueous condition

Chemoselective O-methylation of substituted phenols takes place in dry. tetrahydrofuran (THF) in the presence of LiOH.H2O and dimethylsulfate (DMS). Quantitative methyl transfer from DMS preserves the atom economy.

Multinuclear Magnetic Resonance Spectroscopic and Semiempirical Molecular Orbital (AM1) Studies of Substituted Anisoles

13C, 15N, and 17O NMR spectra have been recorded for 4-nitroanisole (1), its 2-methyl-, 2-chloro-, 2-bromo-, 2-iodo-, 2,6-diamethyl-, 2,6-dichloro, 2,6-dibromo-, and 2,6-diiodo-derivatives 2-9, also nitrobenzene (1a), its 3-methyl-, 3-chloro-, 3-bromo-, and 3-iodo-derivatives 2a-5a and 3,5-dichloro- and 3,5-dibromo-derivatives 7a and 8a.Analysis of the chemical shifts of carbon bearing nitro group and nitro oxygens in these compounds suggests that presence of one substituent ortho- to the methoxyl group enhances its resonance interaction with the benzene ring whereas presence of two ortho-substituents inhibits this resonance.However, in no case the resonance is completely inhibited.The extent of enhancement or inhibition is almost independent of the nature of the ortho-substituent.This conclusion has also been arrived by analyzing the reported chemical shifts of the para-carbons in anisoles 1b-9b and the corresponding carbons in benzene derivatives 1c-9c.Though evidence could not be obtained for steric enhancement of resonance using methoxyl oxygen chemical shifts, analysis of these chemical shifts in di-ortho-substituted anisoles 6-9 and 6a furnishes evidence for steric inhibition of resonance.However, 15N chemical shifts are of no use in studying these phenomena.Semiempirical molecular orbital calculations using AM1 Hamiltonian suggest that the methoxyl group is coplanar with the benzene ring in anisole, 4-nitroanisole and 2-substituted-4-nitroanisoles but is perpendicular to the benzene ring in 2,6-disubstituted-4-nitroanisoles.Moreover, in 2-substituted-4-nitroanisoles the O-methyl group is anti to the 2-substituent.

Polyaza Heterocycles. Part 2. Nucleophilic Substitution of Halogens in Halogenoquinoxalinocinnolines

10-Chloroquinoxalinocinnoline readily undergoes methoxydechlorination when treated with sodium methoxide.The 1-, 2-, 3-, 4- and 9-chloro isomers are unreactive towards this reagent, but the 9,10-dichloro derivative undergoes substitution of both chlorines (the 10-position being much the more reactive).The 9- and 10-bromo analogues are both unreactive towards sodium methoxide, but the 9- and 10-fluoro analogues are both highly reactive, to the extent that it has not been possible even to isolate the 10-fluoro compound.Routes to 9- and 10-piperidinoquinoxalinocinnolines are described.

FORMATION OF METHOXY-SUBSTITUTED AZOXYBENZENES IN THE REDUCTION OF NITROARENES IN BASIC METHANOL-TOLUENE SOLUTIONS

The reduction of nitroarenes in boiling methanol-toluene containing KOH affords high yields of the corresponding azoxy derivative and small amounts of other azoxy compounds containing one or more OCH3 groups linked to the aromatic rings.It has been proved that the reaction does not occur via formation of methoxy-nitroarenes and their further reduction.The reaction is proposed to involve: a) formation of a Meisenheimer complex by attack of the methoxide ion on the nitroarene; b) abstraction of a proton from the Meisenheimer complex by a methoxide ion to form a dianion; c) protonation of the dianion with concurrent elimination of OH to form the nitroso-methoxy arene which is finally reduced to the methoxy-azoxy derivative.It is proposed that the dianion is the electron-donating species to start the reduction of nitro- and nitrosoarenes.

STUDIES OF METHOXYLATION OF 3,4-DICHLORONITROBENZENE.

The authors report the results of studies of methoxylation of 3,4-dichloronitrobenzene (3,4-DCNB), carried out in order to find the optimal conditions for production of highly pure 3-chloromethoxynitrobenzene. Experiments indicate that the optimal conditions of methoxylation of 3,4-dichloronitrobenzene in alkaline aqueous alcohol solutions are: 3,4-DCNB:methanol:NaOH molar ratio 1:15:1. 1, temperature 72 degree , time 5 h, alkali concentration 15%. The reaction of 3,4-DCNB methoxylation under the above optimal conditions is described by a second-order equation.