182056-39-9

Usage

Uses

Used in Organic Synthesis:
2-Bromo-4-iodoanisole is used as an intermediate in organic synthesis for the production of various pharmaceuticals, agrochemicals, and other organic compounds. Its strong halogenation properties allow for the introduction of bromine and iodine atoms into other molecules, facilitating the synthesis of complex organic structures.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-Bromo-4-iodoanisole is utilized as a key component in the development of new therapeutic agents. Its unique structure and reactivity make it a valuable tool for medicinal chemists in designing and synthesizing novel drug candidates with potential applications in various therapeutic areas.
Used in the Preparation of Biologically Active Compounds:
2-Bromo-4-iodoanisole is also employed in the preparation of biologically active compounds for research purposes. Its ability to introduce halogens into molecular structures can enhance the biological activity of certain compounds, making it a useful building block in the synthesis of bioactive molecules.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-Bromo-4-iodoanisole has potential applications in the development of new therapeutic agents. Its strong halogenation properties can be harnessed to create molecules with improved pharmacological properties, such as increased potency, selectivity, and bioavailability. This makes it a valuable resource for the discovery and optimization of novel drug candidates.

InChI:InChI=1S/C7H6BrIO/c1-10-7-3-2-5(9)4-6(7)8/h2-4H,1H3

Upstream product

• 696-62-8 para-iodoanisole 
• 19056-41-8 3-bromo-p-anisidine 
• 540-38-5 p-Iodophenol 
• 133430-98-5 2-bromo-4-iodo-phenol 
• 74-88-4 methyl iodide 
• 104-94-9 4-methoxy-aniline 
• 578-57-4 2-bromoanisole 

Downstream Products

• 1373873-52-9 1-bromo-3-chloro-5-iodo-2-methoxybenzene 
• 56341-31-2 2-bromo-9H-xanthene-9-one 
• 1431304-49-2 N-(3-bromo-4-methoxyphenyl)methanesulfonamide 
• 1070195-91-3 C₁₉H₁₉O₆^(1-)*Na⁽¹⁺⁾ 
• 1070195-95-7 C₁₈H₂₁BO₆ 
• 1070195-87-7 2-methoxy-5-(1-(3,4,5-trimethoxyphenyl)vinyl)benzoic acid 
• 1067880-44-7 5-(1-(3-bromo-4-methoxyphenyl)vinyl)-1,2,3-trimethoxybenzene 

Relevant academic research and scientific papers

Progress Toward a Semi-Synthetic Organism with an Unrestricted Expanded Genetic Alphabet

We have developed a family of unnatural base pairs (UBPs), exemplified by the pair formed between dNaM and dTPT3, for which pairing is mediated not by complementary hydrogen bonding but by hydrophobic and packing forces. These UBPs enabled the creation of

Structure-Activity-Relationship-Aided Design and Synthesis of xCT Antiporter Inhibitors

The xCT antiporter is a cell membrane protein involved in active counter-transportation of glutamate (outflux) with cystine (influx) over the human cell membrane. This feature makes the xCT antiporter a crucial element of the biosynthesis of the vital free radical scavenger glutathione. The prodrug sulfasalazine, a medication for the treatment of ulcerative colitis, was previously proven to inhibit the xCT antiporter. Starting from sulfasalazine, a molecular scaffold jumping followed by SAR-assisted design and synthesis provided a series of styryl hydroxy-benzoic acid analogues that were biologically tested in vitro for their ability to decrease intracellular glutathione levels using four different cancer cell lines: A172 (glioma), A375 (melanoma), U87 (glioma) and MCF7 (breast carcinoma). Depletion of glutathione levels varied among the compounds as well as among the cell lines. Flow cytometry using propidium iodide and the annexin V marker demonstrated minimal toxicity in normal human astrocytes for a promising candidate molecule (E)-5-(2-([1,1′-biphenyl]-4-yl)vinyl)-2-hydroxybenzoic acid.

Air-Stable Blue Phosphorescent Tetradentate Platinum(II) Complexes as Strong Photo-Reductant

Strong photo-reductants have applications in photo-redox organic synthesis involving reductive activation of C?X(halide) and C=O bonds. We report herein air-stable PtII complexes supported by tetradentate bis(phenolate-NHC) ligands having peripheral electron-donating N-carbazolyl groups. Photo-physical, electrochemical, and computational studies reveal that the presence of N-carbazolyl groups enhances the light absorption and redox reversibility because of its involvement into the frontier MOs in both ground and excited states, making the complexes robust strong photo-reductant with E([Pt]+/*) over ?2.6 V vs. Cp2Fe+/0. The one-electron reduced [Pt]? species are stronger reductants with EPC([Pt]0/?) up to ?3.1 V vs. Cp2Fe+/0. By virtue of the strong reducing nature of these species generated upon light excitation, they can be used in light-driven reductive coupling of carbonyl compounds and reductive debromination of a wide range of unactivated aryl bromides.

An alternative to the Sandmeyer approach to aryl iodides

Iodoarenes are important synthons for a wide range of organic transformations. Here we report a general strategy to prepare singly iodinated electron-rich aromatic compounds through the intermediacy of diaryliodonium salts. This process, which incorporates a phase separation that greatly simplifies product purification, is an attractive replacement for the Sandmeyer approach to iodoarenes that are otherwise difficult to access.

Gold(I)-catalyzed iodination of arenes

A wide variety of electron-rich arenes were efficiently converted into the corresponding iodinated compounds via a gold(I)-catalyzed reaction under mild conditions. Georg Thieme Verlag Stuttgart. New York.

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.

Dual selectivity: Electrophile and nucleophile selective cross-coupling reactions on a single aromatic substrate

The development of a high yielding, both nucleophile and electrophile selective cross-coupling reaction with aromatic rings is presented. The reaction is general with respect to functional groups. Furthermore, the products still contain a boronic ester and a bromide. These two functional groups allow them to be easy-to-prepare, highly complex starting materials for further reactions, avoiding protecting group transformations.

Regioselective heterohalogenation of 4-halo-anisoles via a series of sequential ortho-aluminations and electrophilic halogenations

As the aluminate base [LiAl(TMP)2(iBu)2] 1 displays halogen tolerance towards substituted aromatics, 4-halo-anisoles have been ortho-aluminated and electrophilically quenched to form synthetically useful multi-heterohalogenated aniso

Solvent-free iodination of arenes using iodine-silver nitrate combination

A simple and environmentally safe general method of iodination of aromatic substrates under sovent-free conditions using the I2/AgNO3 combination in a solid state is reported. Both activated and deactivated aromatic compounds afford the respective aryl iodides in generally high yields (80-90%). Copyright Taylor & Francis Group, LLC.