50638-47-6

Basic information

• Product Name: 4-BROMO-2-CHLOROANISOLE
• Synonyms: 4-BROMO-2-CHLOROANISOLE;1-Bromo-3-chloro-4-methoxybenzene;2-Chloro-4-bromoanisole;Methyl(2-chloro-4-bromophenyl) ether;3-Chloro-4-methoxyphenyl bromide;2-chloro-4-Bromo-1-methoxy-benzene;Chloro-4-bromoanisole;Benzene,4-bromo-2-chloro-1-methoxy-
• CAS NO: 50638-47-6
• Molecular Formula: C₇H₆BrClO
• Molecular Weight: 221.48
• EINECS: 256-672-2
• Product Categories: Anisole;Anisoles, Alkyloxy Compounds & Phenylacetates;Bromine Compounds;Chlorine Compounds
• Mol File: 50638-47-6.mol

Chemical Properties

• Melting Point: 68.5-70.5°C
• Boiling Point: 242℃
• Flash Point: 100℃
• Appearance: /
• Density: 1.564
• Vapor Pressure: 0.0538mmHg at 25°C
• Refractive Index: 1.556
• Storage Temp.: Room temperature.
• CAS DataBase Reference: 4-BROMO-2-CHLOROANISOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-2-CHLOROANISOLE(50638-47-6)
• EPA Substance Registry System: 4-BROMO-2-CHLOROANISOLE(50638-47-6)

Safety Data

• Hazardous Substances Data: 50638-47-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Bromo-2-chloroanisole is used as a key intermediate in the synthesis of various pharmaceuticals and organic compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Flavor and Fragrance Industry:
4-Bromo-2-chloroanisole is used as a flavor and fragrance ingredient in the production of perfumes and other consumer products. Its strong, sweet, and floral odor makes it a valuable component in creating appealing scents for a wide range of applications.
Used in Agricultural Chemicals Production:
4-Bromo-2-chloroanisole serves as an intermediate in the production of agricultural chemicals. Its chemical properties enable the development of effective and innovative agrochemicals for various agricultural applications.
Used in Specialty Chemicals Production:
4-Bromo-2-chloroanisole is also utilized as an intermediate in the production of specialty chemicals. Its unique structure and properties contribute to the creation of specialized chemical products for various industries, including coatings, adhesives, and plastics.

InChI:InChI=1/C7H6BrClO/c1-10-7-3-2-5(8)4-6(7)9/h2-4H,1H3

Upstream product

• 473-34-7 N,N-dichloro-p-toluenesulfonamide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 766-51-8 2-Chloroanisole 
• 3964-56-5 4-bromo-2-chlorophenol 
• 77-78-1 dimethyl sulfate 
• 7789-69-7 phosphorus pentabromide 
• 67-68-5 dimethyl sulfoxide 
• 67-56-1 methanol 
• 4903-09-7 3-chloro-4-methoxy-benzaldehyde 
• 60811-21-4 1-bromo-3-chloro-4-fluorobenzene 
• 865-33-8 potassium methanolate 
• 50638-51-2 4-bromo-2-chloro-N,N-dimethylaniline 
• 100-66-3 methoxybenzene 
• 74-88-4 methyl iodide 

Downstream Products

• 103978-44-5 ethyl 1-ethyl-7-(3-chloro-4-methoxyphenyl)-6,8-difluoro-1,4-dihydroquinol-4-one 3-carboxylate 
• 117896-21-6 (S)-3-{4-[3-(3-Chloro-4-methoxy-benzyl)-4-methoxy-phenoxy]-3,5-dinitro-phenyl}-2-(2,2,2-trifluoro-acetylamino)-propionic acid ethyl ester 
• 117896-29-4 (S)-3-{4-[3-(3-Chloro-4-methoxy-benzyl)-4-methoxy-phenoxy]-3,5-diiodo-phenyl}-2-(2,2,2-trifluoro-acetylamino)-propionic acid ethyl ester 
• 117653-16-4 (S)-2-Amino-3-{4-[3-(3-chloro-4-hydroxy-benzyl)-4-hydroxy-phenoxy]-3,5-diiodo-phenyl}-propionic acid 
• 117653-34-6 (5-acetoxy-2-methoxyphenyl)(3-chloro-4-methoxyphenyl)methyl acetate 
• 117653-33-5 (5-acetoxy-2-methoxyphenyl)(3-chloro-4-methoxyphenyl)methane 
• 117653-31-3 3-(3-chloro-4-methoxybenzyl)-4-methoxyphenol 
• 146558-40-9 2-Chloro-4-(2,2-dimethyl-1-methylene-propyl)-1-methoxy-benzene 
• 157932-58-6 2-Chloro-4-(1-chloro-1,2,2-trimethyl-propyl)-1-methoxy-benzene 
• 261381-36-6 3-[(m-chloro-p-methoxyphenyl)dimethylsilyl]propyl tosylate 
• 261381-42-4 3-[(m-chloro-p-methoxyphenyl)dimethylsilyl]-1-propanol 
• 460742-61-4 4-nitro-benzoic acid 1-(3-chloro-4-methoxy-phenyl)-1-phenyl-ethyl ester 
• 625446-79-9 3-chloro-6-[2-(3-chloro-4-methoxy-phenyl)-ethyl]-6-cyclopentyl-4-hydroxy-5,6-dihydro-pyran-2-one 

Relevant articles and documents

Organophotochemical SNAr Reactions of Mildly Electron-Poor Fluoroarenes

C–F functionalization of arenes with a range of alcohol and pyrazole nucleophiles has been achieved without the need for metal catalysts or highly electron-poor substrates. Treatment of fluoroarenes with alcohols or pyrazoles and DDQ under irradiation by blue LED light provides the corresponding substituted products. The procedure is complementary to classical SNAr chemistry which generally requires basic reaction conditions and high temperatures, and provides products under non-basic conditions at ≈ 40 °C.

Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation

Herein, we report a Ni-catalyzed reductive coupling for the synthesis of benzonitriles from aryl (pseudo)halides and an electrophilic cyanating reagent, 2-methyl-2-phenyl malononitrile (MPMN). MPMN is a bench-stable, carbon-bound electrophilic CN reagent that does not release cyanide under the reaction conditions. A variety of medicinally relevant benzonitriles can be made in good yields. Addition of NaBr to the reaction mixture allows for the use of more challenging aryl electrophiles such as aryl chlorides, tosylates, and triflates. Mechanistic investigations suggest that NaBr plays a role in facilitating oxidative addition with these substrates.

Amplification of Trichloroisocyanuric Acid (TCCA) Reactivity for Chlorination of Arenes and Heteroarenes via Catalytic Organic Dye Activation

Heteroarenes and arenes that contain electron-withdrawing groups are chlorinated in good to excellent yields (scalable to gram scale) using trichloroisocyanuric acid (TCCA) and catalytic Brilliant Green (BG). Visible-light activation of BG serves to amplify the electrophilic nature of TCCA, providing a mild alternative approach to acid-promoted chlorination of deactivated (hetero)aromatic substrates. The utility of the TCCA/BG system is demonstrated through comparison to other chlorinating reagents and by the chlorination of pharmaceuticals including caffeine, lidocaine, and phenazone.

Visible-light photocatalytic activation of N-chlorosuccinimide by organic dyes for the chlorination of arenes and heteroarenes

A variety of arenes and heteroarenes are chlorinated in moderate to excellent yields using N-chlorosuccinimide (NCS) under visible-light activated conditions. A screening of known organic dye photocatalysts resulted in the identification of methylene green as the most efficient catalyst to use with NCS. According to mechanistic studies described within, the reaction is speculated to proceed via a single electron oxidation of NCS utilizing methylene green under visible-light photoredox pathway. The photo-oxidation of NCS amplifies the electrophilicity of the chlorine atom of the NCS, thus leading to enhanced reactivity as a chlorinating reagent with aromatic substrates.

In situ Generation of Hypervalent Iodine Reagents for the Electrophilic Chlorination of Arenes

Efficient metal-free methods for the electrophilic chlorination of arenes using PIFA and simple chlorine sources are reported. The in situ formation of PhI(Cl)OCOCF3 from PIFA and KCl is proposed, which resulted in a chlorinating species for moderately activated arenes. Moreover, the in situ formation of PhICl2 from PIFA and TMSCl resulted in an excellent approach for the chlorination of a great variety of arenes (20 examples) in high yields, even when working on a multigram scale.

From Anilines to Aryl Ethers: A Facile, Efficient, and Versatile Synthetic Method Employing Mild Conditions

We have developed a simple and direct method for the synthesis of aryl ethers by reacting alcohols/phenols (ROH) with aryl ammonium salts (ArNMe3+), which are readily prepared from anilines (ArNR′2, R′=H or Me). This reaction proceeds smoothly and rapidly (within a few hours) at room temperature in the presence of a commercially available base, such as KOtBu or KHMDS, and has a broad substrate scope with respect to both ROH and ArNR′2. It is scalable and compatible with a wide range of functional groups.

Mechanistic study on iodine-catalyzed aromatic bromination of aryl ethers by N-Bromosuccinimide

Although iodine-catalyzed reaction has rapid advances in recent years, examples on iodine-catalyzed bromination are rare and the mechanism of these reactions remains unclear. Herein, we reported an I2-catalyzed aromatic bromination of aryl ethers by NBS and presented the details of the mechanistic study including kinetic study and the study of kinetic isotope effects. The study revealed that the reaction was actually catalyzed by IBr formed in the induction period, and the rate-determining step was the HBr-elimination of the Wheland intermediate assisted by IBr.

Iron(III)-Catalyzed Chlorination of Activated Arenes

A general and regioselective method for the chlorination of activated arenes has been developed. The transformation uses iron(III) triflimide as a powerful Lewis acid for the activation of N-chlorosuccinimide and the subsequent chlorination of a wide range of anisole, aniline, acetanilide, and phenol derivatives. The reaction was utilized for the late-stage mono- and dichlorination of a range of target compounds such as the natural product nitrofungin, the antibacterial agent chloroxylenol, and the herbicide chloroxynil. The facile nature of this transformation was demonstrated with the development of one-pot, tandem, iron-catalyzed dihalogenation processes allowing highly regioselective formation of different carbon-halogen bonds. The synthetic utility of the resulting dihalogenated aryl compounds as building blocks was established with the synthesis of natural products and pharmaceutically relevant targets.

AMINE COMPOUND AND USE THEREOF FOR MEDICAL PURPOSES

The present invention provides a compound represented by the following formula (I): wherein each symbol is as described in the DESCRIPTION, which has a superior peripheral blood lymphocyte decreasing action, and is useful for the treatment or prophylaxis of autoimmune diseases; prophylaxis or suppression of resistance or acute rejection or chronic rejection of transplantation of organ or tissue; treatment or prophylaxis of graft-versus-host (GvH) disease due to bone marrow transplantation; or treatment or prophylaxis of allergic diseases.

Practical and metal-free electrophilic aromatic halogenation by interhalogen compounds generated in situ from N-halosuccinimide and catalytic TMSCL

Halomonochloride compounds (ClCl, BrCl, ICl) generated in situ from N-halosuccinimide and catalytic chlorotrimethylsilane (TMSCl, 0.1 equiv) can efficiently halogenate aromatic compounds to give halogenated products in good to excellent yields and selectivities. The reaction can be carried out at room temperature or at lower temperatures, requires only one hour, is practical to apply to a wide range of substrates, and provides a simple access to a variety of haloarene compounds. Georg Thieme Verlag Stuttgart New York.