103966-66-1

Basic information

• Product Name: 4-bromo-2-methoxy-1-nitrobenzene
• Synonyms: 4-bromo-2-methoxy-1-nitrobenzene;5-Bromo-2-nitroanisole;4-Bromo-2-methoxynitrobenzene;3-Methoxy-4-nitrobromobenzene;5-Bromo-1-methoxy-2-nitrobenzene;5-Bromo-2-nitrophenyl methyl ether;4-Bromo-2-methoxynitrobenzene, 5-Bromo-2-nitrophenyl methyl ether;Benzene, 4-broMo-2-Methoxy-1-nitro-
• CAS NO: 103966-66-1
• Molecular Formula: C₇H₆BrNO₃
• Molecular Weight: 232.04
• Mol File: 103966-66-1.mol

Chemical Properties

• Melting Point: 91-92℃
• Boiling Point: 298.7±20.0 °C(Predicted)
• Appearance: /
• Density: 1.640
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-bromo-2-methoxy-1-nitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-bromo-2-methoxy-1-nitrobenzene(103966-66-1)
• EPA Substance Registry System: 4-bromo-2-methoxy-1-nitrobenzene(103966-66-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 7/9-22-36/37/39-51
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 103966-66-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-bromo-2-methoxy-1-nitrobenzene is utilized as a precursor in organic synthesis for the production of a range of other organic compounds. Its unique structure allows for further functionalization and modification, making it a valuable building block in the synthesis of complex organic molecules.
Used in Pharmaceutical Research:
In pharmaceutical research, 4-bromo-2-methoxy-1-nitrobenzene serves as a key intermediate for the synthesis of pharmaceutical drugs. Its presence in the molecular structure can impart specific biological activities, contributing to the development of new therapeutic agents.
Used in Dye and Pigment Synthesis:
4-bromo-2-methoxy-1-nitrobenzene is employed as a building block in the synthesis of dyes and pigments. Its chemical properties enable the creation of a variety of colorants used in different industries, including textiles, plastics, and printing inks.
Used in Agrochemical Production:
4-bromo-2-methoxy-1-nitrobenzene also finds application in the agrochemical industry, where it is used as a starting material for the synthesis of various agrochemicals. Its role in the production of crop protection agents and other agricultural chemicals highlights its importance in this sector.
Environmental Considerations:
4-bromo-2-methoxy-1-nitrobenzene is recognized as a potential environmental pollutant. Therefore, it is crucial to handle and dispose of it with proper precautions to minimize the risk of harm to human health and the environment. This includes adhering to safety guidelines and regulations during its production, use, and disposal processes.

Upstream product

• 610-38-8 4-bromo-1,2-dinitrobenzene 
• 124-41-4 sodium methylate 
• 321-23-3 4-bromo-2-fluoronitrobenzene 
• 67-56-1 methanol 
• 27684-84-0 5-bromo-2-nitrophenol 
• 74-88-4 methyl iodide 
• 889849-21-2 (4-bromo-2-methoxyphenyl)boronic acid 
• 2398-37-0 3-methoxyphenyl bromide 

Downstream Products

• 883901-80-2 5-ethenyl-2-nitrophenyl methyl ether 
• 1089281-45-7 3-[3-(methyloxy)-4-nitrophenyl]-2-propyn-1-ol 
• 862855-85-4 2-methoxy-3-(3-methoxy-4-nitrophenyl)pyrazine 
• 59557-91-4 4-bromo-2-methoxyaniline 
• 1352448-58-8 1-(3-methoxy-4-nitrophenyl)-6-methylpiperidin-2-one 
• 1352448-42-0 1-(2-bromo-5-methoxy-4-nitrophenyl)-6-methylpiperidin-2-one 
• 5840-10-8 1-amino-2-methoxy-4-(N-phenylamino)benzene 
• 267416-80-8 2-methoxy-4-phenoxy-phenylamine 
• 126491-48-3 3'-methoxy-4'-nitrodihenylamine-2-carboxylic acid 
• 181995-71-1 5-bromo-2,4-dinitroanisole 
• 21212-69-1 1-bromo-3-methoxy-2,4,6-trinitrobenzene 
• 4920-84-7 2,4-dimethoxynitrobenzene 
• 875241-67-1 2-methoxy-1-nitro-4-phenoxy-benzene 

Relevant articles and documents

Palladium-catalyzed aromatic C-H bond nitration using removable directing groups: Regiospecific synthesis of substituted o -nitrophenols from related phenols

A general and regiospecific transformation of substituted phenols into the related o-nitrophenols has been achieved via a three-step process involving the palladium-catalyzed chelation-assisted ortho-C-H bond nitration as the key step. In the process, 2-pyridinyloxy groups act as removable directing groups for the palladium-catalyzed ortho-nitration of substituted 2-phenoxypridines, and they can be readily removed in the subsequent conversion of the resulting 2-(2-nitrophenoxy)pyridines into 2-nitrophenols.

Preparation method of 2-amino-3-methoxy-5-bromobenzonitrile

The invention discloses a preparation method of 2-amino-3-methoxy-5-bromobenzonitrile. The method comprises the following steps: (1) reacting a compound (II) with sodium methoxide to generate a compound (III); (2) carrying out reduction treatment on the compound (III) to obtain a compound (IV); (3) reacting the compound (IV) with trichloroacetaldehyde hydrate and hydroxylamine hydrochloride to generate a compound (V); (4) reacting the compound (V) with concentrated sulfuric acid to generate a compound (VI); (5) preparing a compound (VII) from the compound (VI) under the conditions of hydrogenperoxide and sodium hydroxide; (6) reacting the compound (VII) with acyl chloride to generate a compound (VIII); (7) reacting the compound (VIII) with ammonia water to generate a compound (IX); and (8) reacting the compound (IX) in the presence of phosphorus pentoxide to generate 2-amino-3-methoxy-5-bromobenzonitrile. The preparation method provided by the invention is higher in yield.

Novel PPARδ antagonist and Pharmaceutical composition for enhancing anti-cancer effect comprising the same

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Ipso Nitration of Aryl Boronic Acids Using Fuming Nitric Acid

The ipso nitration of aryl boronic acid derivatives has been developed using fuming nitric acid as the nitrating agent. This facile procedure provides efficient and chemoselective access to a variety of aromatic nitro compounds. While several activating agents and nitro sources have been reported in the literature for this synthetically useful transformation, this report demonstrates that these processes likely generate a common active reagent, anhydrous HNO3. Kinetic and mechanistic studies have revealed that the reaction order in HNO3 is >2 and indicate that the ?NO2 radical is the active species.

Nitration of deactivated aromatic compounds via mechanochemical reaction

A variety of deactivated arenes were nitrated to their corresponding nitro derivatives in excellent yields under high-speed ball milling condition using Fe(NO3)3·9H2O/P2O5 as nitrating reagent. A radical involved mechanism was proposed for this facial, eco-friendly, safe, and effective nitration reaction.

O-Anisidine Dimer, 2-Methoxy- N4-(2-methoxyphenyl) Benzene-1,4-diamine, in Rat Urine Associated with Urinary bladder Carcinogenesis

Monocyclic aromatic amines, o-toluidine (o-Tol) and its structural analog o-anisidine (o-Ans), are IARC Group 1 and Group 2A urinary bladder carcinogens, respectively, and are involved in metabolic activation and DNA damage. Our recent study revealed that 2-methyl-N4-(2-methylphenyl) benzene-1,4-diamine (MMBD), a p-semidine-type homodimer of o-Tol, was detected and identified in an in vitro reaction of o-Tol with S9 mix and in vivo urinary samples of o-Tol-exposed rats. Potent mutagenic, genotoxic, and cytotoxic activities were reported with MMBD, suggesting its involvement in urinary bladder carcinogenesis. However, it remains unknown whether o-Ans is converted to active metabolites to induce DNA damage in a similar manner as o-Tol. In this study, we report that a novel o-Ans metabolite, 2-methoxy-N4-(2-methoxyphenyl) benzene-1,4-diamine (MxMxBD), a dimer by head-to-tail binding (p-semidine form), was for the first time identified in o-Ans-exposed rat urine. MxMxBD induced a stronger mutagenicity in N-acetyltransferase overexpressed Salmonella typhimurium strains and potent genotoxicity and cytotoxicity in human bladder carcinoma T24 cells compared with o-Ans. These results suggest that MxMxBD may to some extent contribute toward urinary bladder carcinogenesis. In addition to homodimerization, such as MxMxBD, heterodimerizations were observed when o-Ans was coincubated with o-Tol or aniline (Ani) in in vitro reactions with S9 mix. This study highlights the important consideration of homodimerizations and heterodimerizations of monocyclic aromatic amines, including o-Ans, o-Tol, and Ani, in the evaluation of the combined exposure risk of bladder carcinogenesis.

Anaplastic lymphoma kinase (ALK) inhibitor, and preparation method and application thereof

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Transetherification of 2,4-dimethoxynitrobenzene by aromatic nucleophilic substitution

In view of the few reports concerning aromatic nucleophilic substitution reactions featuring an alkoxy group as a leaving group, the aromatic nucleophilic substitution of 2,4-dimethoxy-nitrobenzene was investigated with a bulky t-butoxide nucleophile under microwave irradiation. The transetherification of 2,4-dimethoxynitrobenezene with sodium t-butoxide under specific conditions, namely for 20 min at 110C in 10% dimethoxyethane in toluene, afforded the desired product in 87% yield with exclusive ortho-selectivity. A variety of reaction conditions were screened to obtain the maximum yield. The aromatic nucleophilic substitution of 2,4-dimethoxynitrobenzene with t-butoxide should be carried out under controlled conditions in order to avoid the formation of byproducts, unlike that of dihalogenated activated ben-zenes. Among the formed byproducts, a major compound was elucidated as 2,4-dimethoxy-N-(5-methoxy-2-nitrophenyl)aniline by X-ray crystallography.

2,4-DISUBSTITUTED PHENYLENE-1,5-DIAMINE DERIVATIVES AND APPLICATIONS THEREOF, AND PHARMACEUTICAL COMPOSITIONS AND PHARMACEUTICALLY ACCEPTABLE COMPOSITIONS PREPARED THEREFROM

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