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
• Article Data: 13

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

General Description

2-Bromo-4-nitroanisole is a chemical compound that is classified as a halogenated nitroaromatic compound. It is a yellow crystalline solid with the molecular formula C7H6BrNO3. 2-Bromo-4-nitroanisole is commonly used as a chemical intermediate in the production of pharmaceuticals, agrochemicals, and other organic compounds. It is also used as a starting material for the synthesis of various substituted anisoles and other aromatic compounds. 2-Bromo-4-nitroanisole is known to have moderate acute toxicity and should be handled with care in a laboratory or industrial setting.

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

Upstream product

• 99-59-2 3-amino-4-methoxynitrobenzene 
• 186581-53-3 diazomethane 
• 5847-59-6 2-bromo-4-nitrophenol 
• 100-17-4 para-methoxynitrobenzene 
• 7726-95-6 bromine 
• 110-86-1 pyridine 
• 578-57-4 2-bromoanisole 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 18771-85-2 4-nitrobenzofuroxan 
• 21678-94-4 4-bromo-5-methoxy-benzo[1,2,5]oxadiazole 1-oxide 
• 74-88-4 methyl iodide 
• 99-58-1 3-bromo-4-methoxybenzoic acid 
• 90150-94-0 2-bromo-3-methoxy-6-nitroaniline 

Downstream Products

• 462652-21-7 3-(2-methoxy-5-nitro-phenyl)-pyridine 
• 10496-75-0 2-methoxy-5-nitrobenzylnitrile 
• 117572-79-9 3-bromo-4-methoxybenzonitrile 
• 181633-31-8 4-methoxy-3-(3-pyridyl)aniline 
• 264617-19-8 (4-methoxy-3-pyridin-3-yl-phenyl)-carbamic acid phenyl ester 
• 70995-08-3 Phenyl-(5-nitro-2-hydroxy-phenyl)-aether 
• 17419-02-2 4-methoxy-3-phenoxy-aniline 
• 14064-98-3 acetic acid-(4-methoxy-3-phenoxy-anilide) 
• 158430-73-0 4-amino-5-nitro-2-phenyloxyanisole 
• 158430-70-7 4-acetamino-5-nitro-2-phenyloxyanisole 
• 5847-59-6 2-bromo-4-nitrophenol 
• 874959-37-2 cis-3,5-dimethyl-1-[2-(methyloxy)-5-nitrophenyl]piperazine 
• 6943-73-3 N-(3-bromo-4-methoxyphenyl)acetamide 
• 1265153-58-9 7-(4-(trifluoromethyl)phenyl)-1,2-dihydro-6-methoxy-2,2,4-trimethylquinoline 

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.

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.