1022128-96-6

Basic information

• Product Name: 2-Bromo-6-iodo-benzoic acid
• Synonyms: 2-Bromo-6-iodo-benzoic acid
• CAS NO: 1022128-96-6
• Molecular Formula: C₇H₄BrIO₂
• Molecular Weight: 326.91393
• EINECS: 604-604-1
• Mol File: 1022128-96-6.mol

Chemical Properties

• Boiling Point: 352.7±37.0 °C(Predicted)
• Appearance: /
• Density: 2.331±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C(protect from light)
• PKA: 1.51±0.10(Predicted)
• CAS DataBase Reference: 2-Bromo-6-iodo-benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-6-iodo-benzoic acid(1022128-96-6)
• EPA Substance Registry System: 2-Bromo-6-iodo-benzoic acid(1022128-96-6)

Safety Data

• Hazardous Substances Data: 1022128-96-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromo-6-iodo-benzoic acid is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with specific therapeutic properties, such as antibacterial, antifungal, and antiviral agents. The presence of halogen substituents on the benzene ring can influence the drug's activity, selectivity, and pharmacokinetics.
Used in Agrochemical Industry:
In the agrochemical industry, 2-Bromo-6-iodo-benzoic acid serves as a precursor for the synthesis of various agrochemicals, including herbicides, insecticides, and fungicides. Its versatile chemical properties enable the creation of compounds with targeted pest control capabilities, contributing to more effective and environmentally friendly agricultural practices.
Used in Organic Synthesis:
2-Bromo-6-iodo-benzoic acid is utilized as a building block in organic synthesis for the preparation of a wide range of organic compounds. Its reactivity and the presence of bromine and iodine atoms make it a valuable component in the synthesis of complex organic molecules, such as dyes, polymers, and specialty chemicals.
Used as a Reagent in Chemical Reactions:
2-Bromo-6-iodo-benzoic acid is employed as a reagent in various chemical reactions, including substitution, addition, and coupling reactions. Its unique properties allow for the preparation of diverse compounds with specific functional groups, which can be further utilized in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.

Upstream product

• 88-65-3 2-bromobenzoic-acid 
• 591-18-4 1-Bromo-3-iodobenzene 
• 124-38-9 carbon dioxide 

Downstream Products

• 84483-27-2 2-bromo-6-iodobenzenamine 
• 1421275-50-4 tert-butyl 4-[1-(2-bromo-6-iodobenzoyl)-2-(ethoxycarbonyl)hydrazinyl]piperidine-1-carboxylate 
• 1421274-73-8 C₁₉H₂₄F₂N₄O₂ 
• 1421274-84-1 C₂₀H₂₆F₂N₄O₂ 
• 1261552-99-1 2-bromo-6-iodobenzoyl chloride 
• 1245648-93-4 2-bromo-6-iodobenzonitrile 

Relevant articles and documents

Synthesis of novel natural product-like diaryl acetylenes as hypoxia inducible factor-1 inhibitors and antiproliferative agents

The selaginellin derivatives are a type of novel natural pigments with an unusual alkynyl phenol skeleton from the genus Selaginella. Some of these natural compounds were previously reported to show important bioactivities, including anticancer activity, cardiovascular protection and phosphodiesterase-4 inhibition. We designed and synthesized fifteen biphenyl-containing diaryl acetylene derivatives mimicking the skeleton of natural alkynyl phenols. In MTT assay in cancer cells, compounds 1c, 2d, 2g, 2h, 2i and 2j exhibited potent antiproliferative activity. The evaluation of Hypoxia Inducible Factor-1 (HIF-1) pathway inhibitory activity in dual luciferase assay demonstrated that most tested compounds exhibited moderate to good activities. Compounds 1a, 2f and 2h displayed high HIF-1 inhibitory activities and relatively low cytotoxicity, demonstrating great potential as HIF-1 inhibitors. These results afford a new strategy for the discovery of new HIF-1 inhibitors and anti-proliferative agents from natural or synthetic diaryl acetylene derivatives.

Synthesis and evaluation of 3-(phenylethynyl)-1,1′-biphenyl-2-carboxylate derivatives as new HIF-1 inhibitors

Selaginellins are a type of rare natural products from the genus Selaginella with unusual alkynyl phenol skeletons and extensive biological activities. Previous structural simplification of these natural compounds afforded a series of diaryl acetylene derivatives with hypoxia-inducible factor 1 (HIF-1) inhibitory activity. In this study, we synthesized thirty compounds by stepwise optimization using methyl 3-(4-methoxylphenyl ethynyl)-[4′-methoxyl-1,1′-biphenyl]-2-carboxylate (1a) as a lead compound and evaluated their HIF-1 inhibitory activity by dual luciferase reporter assay. Among them, compound 9i displayed the most potent HIF-1 inhibitory activity (IC50 = 1.5 ± 0.03 μM) with relatively low cytotoxicity. Under hypoxia, compound 9i showed no effect on the accumulation of HIF-1α protein in western blot analysis, but could down-regulate the expression of VEGF mRNA, the downstream target gene of HIF-1 pathway. Cell-based activity assay demonstrated that compound 9i could inhibit the hypoxia-induced migration, invasion and proliferation of HeLa cells at the concentrations of 1 ~ 5 μM. In mouse breast cancer xenograft model, compound 9i exhibited obvious tumor growth inhibition and very low toxicity at a dose of 15 mg/kg. The results suggested that compound 9i would be a potential antitumor agent via HIF-1 pathway inhibition.

Analogues of acetylene phenolic natural product as well as preparation method and application of analogues

The invention belongs to the technical field of drugs and chemical engineering, and discloses analogues of an acetylene phenolic natural product as well as a preparation method and application of theanalogues. The analogues of the acetylene phenolic natural product prepared by the invention have remarkable inhibiting effect on a hypoxia-inducible factor HIF-1, and partial chemical compounds showsremarkable anti-proliferation effect to cancer cells; the chemical compounds and pharmaceutically acceptable salts thereof have wide application space in preparing anti-tumor drugs and HIF-1 inhibitors.

Isothiazolinone compound and corresponding application

The invention provides an isothiazolinone compound with an IDO inhibitory activity, and a preparing method and pharmaceutical application thereof. The invention particularly relates to a compound shown in a formula I, pharmaceutically acceptable salts thereof, isomers and prodrugs, wherein definitions of all groups are shown in the description. The invention further relates to compound drug preparations, drug compositions and the application of the compound drug preparations and the drug compositions in treating, relieving and/or preventing various relevant diseases caused by immunosuppressionsuch as tumors, virus infection or autoimmune diseases. The isothiazolinone compound has the excellent IDO inhibitory activity.

Base- and Additive-Free Ir-Catalyzed ortho-Iodination of Benzoic Acids: Scope and Mechanistic Investigations

A protocol for the C-H activation/iodination of benzoic acids catalyzed by a simple iridium complex has been developed. The method described in this paper allows the ortho-selective iodination of a variety of benzoic acids under extraordinarily mild conditions in the absence of any additive or base in 1,1,1,3,3,3-hexafluoroisopropanol as the solvent. The iridium catalyst used tolerates air and moisture, and selectively gives ortho-iodobenzoic acids with high conversions. Mechanistic investigations revealed that an Ir(III)/Ir(V) catalytic cycle operates, and that the unique properties of HFIP enables the C-H iodination using the carboxylic moiety as a directing group.

A simple and efficient two-step synthesis of 1,2,3-triiodoarenes via consecutive C-H iodination/ipso-Iododecarboxylation strategy: A potential application towards Ortho-diiodoarenes by Regioselective metal-iodine exchange reaction

A general, robust, and efficient method for the conversion of benzoic acids to 1,2,3-triiodoarenes and 1,2,3-trihaloarenes via a two-step synthesis is reported. Commercially available benzoic acids were used that can allow the reactions to be performed on multi-gram scales with good-to-excellent yields. This report discloses a practical method for the synthesis of 1,2,3-triiodoarenes and 1,2,3-trihaloarenes that is general in scope, scalable, and easy to workup and purify. A potential application of the target compounds as precursors for novel regioselective metal-iodine exchange reaction of 1,2,3-triiodoarenes was also demonstrated. It provided ortho-diiodoaryl derivatives in a high regioselective fashion that are useful intermediates in synthesis and indeed are hard to synthesize by any other means.

3-OXO-2,3-DIHYDRO-1H-INDAZOLE-4-CARBOXAMIDE DERIVATIVES AS PARP-1 INHIBITORS

There are provided 3-oxo-2,3-dihydro-lH-indazole-4-carboxamide derivatives which selectively inhibit the activity of poly (ADP-ribose) polymerase PARP-1 with respect to poly (ADP-ribose) polymerase PARP-2. The compounds of this invention are therefore useful in treating diseases such as cancer, cardiovascular diseases, central nervous system injury and different forms of inflammation. The present invention also provides methods for preparing these compounds, pharmaceutical compositions comprising these compounds, and methods of treating diseases utilizing pharmaceutical compositions comprising these compounds.

Synthesis of pyrrolnitrin and related halogenated phenylpyrroles

A general approach to halogenated arylpyrroles, including the antifungal natural product pyrrolnitrin, is described using newly synthesized halogenated pyrroles and 2,6-disubstituted nitrobenzenes or 2,6-disubstituted anilines.

PdII-catalyzed monoselective ortho halogenation of C-H bonds assisted by counter cations: A complementary method to directed ortho lithiation

(Chemical Equation Presented) When the counterion counts: The yield and selectivity of the title transformation of benzoic acid derivatives were improved greatly by using tetraalkyl ammonium salts as additives (see scheme; monoselectivity: 5:1-18:1). These effects are attributed to the influence of counter cations. The halogenated products are versatile intermediates for the construction of substituted aromatic compounds. DMF=N,N-dimethylformamide.