5197-28-4

Basic information

• Product Name: 2-Bromo-4-nitroanisole
• Synonyms: 3-BROMO-4-METHOXYNITROBENZENE;2-BROMO-4-NITROANISOLE;2-BROMO-4-NITROANISOLE 95%;1-Methoxy-2-bromo-4-nitrobenzene;Benzene,2-broMo-1-Methoxy-4-nitro-;2-Bromo-1-methoxy-4-nitrobenzene, 2-Bromo-4-nitrophenyl methyl ether
• CAS NO: 5197-28-4
• Molecular Formula: C₇H₆BrNO₃
• Molecular Weight: 232.03
• EINECS: 225-983-5
• Product Categories: Aromatic Halides (substituted);Halides;Phenyls & Phenyl-Het;Anisoles, Alkyloxy Compounds & Phenylacetates;Bromine Compounds;Nitro Compounds;Phenyls & Phenyl-Het;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 5197-28-4.mol

Chemical Properties

• Melting Point: 104-106 °C(lit.)
• Boiling Point: 306.315 °C at 760 mmHg
• Flash Point: 139.055 °C
• Appearance: /
• Density: 1.64 g/cm³
• Vapor Pressure: 0.00141mmHg at 25°C
• Refractive Index: 1.581
• Storage Temp.: Room temperature.
• BRN: 2556372
• CAS DataBase Reference: 2-Bromo-4-nitroanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-4-nitroanisole(5197-28-4)
• EPA Substance Registry System: 2-Bromo-4-nitroanisole(5197-28-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 5197-28-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromo-4-nitroanisole is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structure allows for the creation of a range of medicinal compounds, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Bromo-4-nitroanisole serves as a starting material for the production of agrochemicals. Its properties make it suitable for the synthesis of compounds that can be used in pest control and crop protection, enhancing agricultural productivity.
Used in Organic Synthesis:
2-Bromo-4-nitroanisole is used as a starting material for the synthesis of various substituted anisoles and other aromatic compounds. Its reactivity and functional groups make it a valuable component in organic chemistry for creating diverse chemical entities with potential applications in different industries.
Safety Note:
Given its moderate acute toxicity, 2-Bromo-4-nitroanisole should be handled with care in laboratory or industrial settings to ensure the safety of personnel and the environment. Proper safety measures and protocols should be followed during its use and disposal.

InChI:InChI=1/C7H6BrNO3/c1-12-7-3-2-5(9(10)11)4-6(7)8/h2-4H,1H3

Upstream product

• 578-57-4 2-bromoanisole 
• 100-17-4 para-methoxynitrobenzene 
• 5411-50-7 3,4-dibromonitrobenzene 
• 124-41-4 sodium methylate 
• 99-59-2 3-amino-4-methoxynitrobenzene 
• 186581-53-3 diazomethane 
• 5847-59-6 2-bromo-4-nitrophenol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 74-88-4 methyl iodide 
• 7726-95-6 bromine 
• 110-86-1 pyridine 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 99-58-1 3-bromo-4-methoxybenzoic acid 

Downstream Products

• 14064-93-8 1-methoxy-2-phenoxy-4-nitrobenzene 
• 19056-41-8 3-bromo-p-anisidine 
• 36324-64-8 2-Bromo-4,6-dinitroanisole 
• 79807-63-9 1-methoxy-2-(4-methylphenoxy)-4-nitrobenzene 
• 15854-75-8 2-methoxy-5-nitro-1,1’-biphenyl 
• 205192-98-9 1-methoxy-4-nitro-2-(perfluoroethyl)benzene 
• 462652-21-7 3-(2-methoxy-5-nitro-phenyl)-pyridine 
• 677746-34-8 2-(2-methoxy-5-nitrophenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane 
• 10496-75-0 2-methoxy-5-nitrobenzylnitrile 
• 117572-79-9 3-bromo-4-methoxybenzonitrile 
• 677746-35-9 2-methoxy-5-nitrophenylboronic acid 
• 677746-32-6 (2-hydroxy-5-nitrophenyl)boronic acid 
• 181633-31-8 4-methoxy-3-(3-pyridyl)aniline 
• 264617-19-8 (4-methoxy-3-pyridin-3-yl-phenyl)-carbamic acid phenyl ester 

Relevant articles and documents

Bromination of Anisoles Using N-Bromophthalimide: A Synthetic and Kinetic Approach

N-Bromophthalimide (NBP)-triggered bromination of aromatic compounds has been studied in the presence of aqueous acetic acid. Reaction Kinetics indicated first order in [NBP] and zero order in [Anisole]. The reactions afforded very good yields of corresponding bromo derivatives under kinetic conditions. The mechanism of the reaction is explained through the formation of acetyl hypobromite due to the interaction of NBP and acetic acid, which in turn reacts with anisole to afford a bromo derivative of anisole.

Electrophilic aryl-halogenation using N-halosuccinimides under ball-milling

We report here a methodology of chemo- and regio-selective aryl bromination and iodination using respective N-halosuccinimides at room temperature in the absence of any solvents, catalyst/additives under ball-milling condition. However, for chlorination ceric ammonium nitrate was used as additive. The coupled product succinimide, produced from the reactions, was recycled via regeneration of NBS. This methodology works with the electron-donor substituted or unsubstituted arenes.

Electrophilic aryl-halogenation using N-halosuccinimides under ball-milling

We report here a methodology of chemo- and regio-selective aryl bromination and iodination using respective N-halosuccinimides at room temperature in the absence of any solvents, catalyst/additives under ball-milling condition. However, for chlorination ceric ammonium nitrate was used as additive. The coupled product succinimide, produced from the reactions, was recycled via regeneration of NBS. This methodology works with the electron-donor substituted or unsubstituted arenes.

Metal and H2O2 free aerobic oxidative aromatic halogenation with [RNH3+] [NO3-]/HX and [BMIM(SO3H)][NO3)x(X)y] (X = Br, Cl) as multifunctional ionic liquids

Novel multifunctional ionic liquids (ILs) are generated by addition of HBr or HCl to alkylammonium nitrates ([RNH3+] [NO 3-]) and to 3-methyl-1-(butyl-4-sulfonyl)imidazolium nitrate ([BMIM(SO3H)][NO3]). The resulting [RNH 3+] [NO3-]/HX and mono (3-methyl-1-(butyl-4-sulfonyl)imidazolium) monohalogenide mononitrate ([BMIM(SO3H)][NO3)x(X)y] (X = Br, Cl)) systems act as solvent and promoter for aerobic oxidative halogenation of arenes under mild conditions in high yields that can be repeated over several cycles.

Regioselective bromination of organic substrates by LDH-CO3 2--Br- promoted by V2O5-H 2O2

An efficient, fast, simple, mild, and selective monobromination of aromatic compounds, with high para-selectivity, is reported. The catalytic system is readily prepared from a Mg-Al-layered double hydroxide-CO3 2--Br- (LDH-CO32--Br-) as the source of bromide, V2O5 as a promoter and hydrogen peroxide as the oxidant. The use of hydrogen peroxide as a synthetically useful oxidizing agent is reported for generating electrophilic bromine in situ from easily available KBr as a bromine source, to brominate electron rich aromatic compounds, employing LDH-CO32--Br3- as the phase-transfer catalyst. The phase-transfer catalyst leads to nearly complete bromination in 3 h at room temperature with high selectivity. The reaction rate of p-bromoanisole and p-bromotoluene formation by LDH-CO 32--Br3- in a triphasic system was studied. The heterogeneity of the reaction system facilitates the recovery and recycling of the catalyst, and the reagent components are environmentally acceptable. The catalyst, LDH-CO32--Br3 -, and its precursors, LDH-CO32--Br- and LDH-CO32-, were characterized by powder XRD, FT-IR and UV-vis spectroscopy.

Regiospecific oxyhalogenation of aromatics over SBA-15-supported nanoparticle group IV-VI metal oxides

TiOx, VOx, MoOx and WOx supported on SBA-15 exhibit efficient catalytic activity for oxyhalogenation of aromatics with the H2O2-halide ion system. Unlike the hitherto known solid catalysts, these reusable catalysts yield the para-halogenated product with 100% selectivity at 298 K and moderate acidic pH (3-5). The catalytic activity was enhanced by five orders of magnitude when supported on SBA-15. Springer Science+Business Media, LLC 2010.

Efficient one-pot transformation of aminoarenes to haloarenes using halodimethylisulfonium halides generated in situ

Halodimethylsulfonium halide 1, which is readily formed in situ from hydrohaloic acid and DMSO, is a good nucleophilic halide. This activated nucleophilic halide rapidly converts aryldiazonium salt prepared in situ by the same hydrohaloic acid and nitrite ion to aryl chlorides, bromides, or iodides in good yield. The combined action of nitrite ion and hydrohaloic acid in DMSO is required for the direct transformation of aromatic amines, which results in the production of aryl halides within 1 h. Substituted compounds with electron-donating or -withdrawing groups or sterically hindered aromatic amines are also smoothly transformed to the corresponding aromatic halides. The only observed by-product is the deaminated arene (usually 7%). The isolated aryldiazonium salts can also be converted to the corresponding aryl halides using 1. The present method offers a facile, one-step procedure for transforming aminoarenes to haloarenes and lacks the environmental pollutants that usually accompany the Sandmeyer reaction using copper halides.

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.

ipso Nitration in p-halophenyl ethers

Addition of nitronium ion ipso to halogen occurs on nitration of the p-haloanisoles in acetic anhydride at -60 deg C.In the cases of p-fluoro- and p-chloro-anisole, addition of the nitronium ion is reversible and only small amounts of ipso products are obtained.With p-bromoanisole nitrodebromination occurs.When p-halophenyl ethers containing a trapping substituent, e.g., 2-(4-chlorophenoxy)-2-methylpropanoic acid, are used as substrates, substantial amounts of the spiro diene with nitro ipso to halogen, e.g., 3,3-dimethyl-8-chloro-8-nitro-1,4-dioxaspirodeca-6,9-dien-2-one, can be isolated.The results demonstrate that extensive ipso attack at the halogen-substituted position is general in the nitration of p-halophenyl ethers.Key words: ipso nitration, ether, diene, p-haloanisole.

N-Bromosuccinimide (NBS) Bromination of Anisole and p-Substituted Anisoles in 50percent Aqueous Acetic Acid

The kinetics of bromination of anisole and p-substituted anisoles by NBS was investigated in the presence of HClO4/NaOAc and Hg(OAc)2 in 50percent aq.HOAc.Pure NBS bromination can be followed by initial addition of Hg(OAc)2, which prevents accumulation of bromine in the system.The reaction is catalysed by AgClO4.Based on Hammett plot, the reaction constant is -7.85 for Ag+-catalysed bromination.As the water content in aq.HOAc is increased from 0-60percent (v/v), the rate constant is found to increase 20 fold for PNA-NBS reaction.The product analysis of the PNA-NBS reaction catalysed by Ag+ was done by glc which gave 2-bromo-4-nitroanisole as the only product.