408502-43-2

Basic information

• Product Name: 3-Bromo-2-iodopyridine
• Synonyms: 3-BROMO-2-IODOPYRIDINE;2-iodo-3-bromopyridine
• CAS NO: 408502-43-2
• Molecular Formula: C₅H₃BrIN
• Molecular Weight: 283.89
• Product Categories: Pyridine series;Halides;Pyridines
• Mol File: 408502-43-2.mol

Chemical Properties

• Boiling Point: 264°Cat760mmHg
• Flash Point: 113.5°C
• Appearance: /
• Density: 2.347g/cm³
• Refractive Index: 1.665
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 3-Bromo-2-iodopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-2-iodopyridine(408502-43-2)
• EPA Substance Registry System: 3-Bromo-2-iodopyridine(408502-43-2)

Safety Data

• Hazardous Substances Data: 408502-43-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-Bromo-2-iodopyridine is used as a building block for the synthesis of various organic compounds. Its presence in the molecular structure allows for the formation of new chemical bonds and the creation of diverse molecules with specific properties.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 3-Bromo-2-iodopyridine is used as a reagent in cross-coupling reactions, which are crucial for the synthesis of pharmaceuticals and agrochemicals. Its ability to participate in these reactions contributes to the development of new drugs with potential therapeutic applications.
Used in Material Science:
3-Bromo-2-iodopyridine is utilized in the development of new materials, such as organic light-emitting diodes (OLEDs) and liquid crystal displays (LCDs). Its unique electronic properties make it a valuable component in the design and fabrication of advanced electronic devices.
Safety Considerations:
It is important to handle 3-Bromo-2-iodopyridine with caution, as it is potentially hazardous. It should be used in a controlled laboratory environment to minimize risks associated with its chemical properties. Proper safety measures, including the use of personal protective equipment and adherence to laboratory safety protocols, are essential when working with 3-Bromo-2-iodopyridine.

InChI:InChI=1/C5H3BrIN/c6-4-2-1-3-8-5(4)7/h1-3H

Upstream product

• 626-55-1 3-Bromopyridine 
• 52200-48-3 3-bromo-2-chloropyridine 
• 13534-89-9 2,3-dibromopyridine 
• 77332-76-4 2-chloro-3-(trimethylsilyl)pyridine 
• 7553-56-2 iodine 

Downstream Products

• 922501-62-0 dimethyl(phenylethynyl)[2-(phenylethynyl)pyridin-3-yl]silane 
• 131747-43-8 2-(trifluoromethyl)nicotinic acid 
• 1392013-91-0 2,3-bis(phenylethynyl)pyridine 

Relevant articles and documents

AROMATIC FUSED RING COMPOUND AND ORGANIC LIGHT EMITTING DEVICE USING THE SAME

The present invention relates to an aromatic condensed-ring compound and an organic light-emitting device using the same. In the present invention, provided is the compound represented by chemical formula 1. The compound described in the present specifica

Modular Construction of Fluoroarenes from a New Difluorinated Building Block by Cross-Coupling/Electrocyclisation/Dehydrofluorination Reactions

Palladium-catalysed coupling reactions based on a novel and easy-to-synthesise difluorinated organotrifluoroborate were used to assemble precursors to 6π-electrocyclisations of three different types. Electrocyclisations took place at temperatures between 90 and 240 °C, depending on the central component of the π-system; nonaromatic trienes were most reactive, but even systems that required the temporary dearomatisation of two arenyl subunits underwent electrocyclisation, albeit at elevated temperatures. Photochemical conditions were effective for these more demanding reactions. The package of methods delivered a structurally diverse set of fluorinated arenes, spanning a 20 kcal mol?1range of reactivity, by a flexible route.

Continuous flow magnesiation of functionalized heterocycles and acrylates with TMPMgCl·LiCl

A flow procedure for the metalation of functionalized heterocycles (pyridines, pyrimidines, thiophenes, and thiazoles) and various acrylates using the strong, non-nucleophilic base TMPMgCl·LiCl is reported. The flow conditions allow the magnesiations to be performed under more convenient conditions than the comparable batch reactions, which often require cryogenic temperatures and long reaction times. Moreover, the flow reactions are directly scalable without further optimization. Metalation under flow conditions also allows magnesiations that did not produce the desired products under batch conditions, such as the magnesiation of sensitive acrylic derivatives. The magnesiated species are subsequently quenched with various electrophiles, thereby introducing a broad range of functionalities. Go with the flow: Flow conditions allow a practical metalation of functionalized heterocycles and various acrylates in the presence of the base TMPMgCl·LiCl (TMP=2,2,6,6-tetramethylpiperidyl). More convenient temperatures and very fast reaction times can usually be achieved by applying the flow conditions. Sensitive acrylic derivatives can be magnesiated under flow conditions. Furthermore, the flow reactions are readily scalable without further optimization.

A study on the BF3 directed lithiation of 3-chloro- and 3-bromopyridine

The BF3-directed lithiation of 3-chloro- and 3-bromopyridine (1a and 1b, respectively) has been investigated. The reactions of 3-chloro- or 3-bromopyridine-BF3 adduct with LDA (1.3/1.1 equiv) followed by quenching with benzaldehyde or iodine exclusively gave the C-2 substituted products. However, when 2.2 equiv of LDA and dimethyl disulfide was used, a C-6 substituted product was obtained. Dilithiation of 1a and 1b has been studied with and without the involvement of BF3 complexation. The role of Lia?F(BF3) interactions has been investigated by experimental and DFT calculations.

Deprotonative metalation of chloro- and bromopyridines using amido-based bimetallic species and regioselectivity-computed CH acidity relationships

A series of chloro- and bromopyridines have been deprotometalated by using a range of 2,2,6,6-tetramethylpiperidino-based mixed lithium-metal combinations. Whereas lithium-zinc and lithium-cadmium bases afforded different mono- and diiodides after subsequent interception with iodine, complete regioselectivities were observed with the corresponding lithium-copper combination, as demonstrated by subsequent trapping with benzoyl chlorides. The obtained selectivities have been discussed in light of the CH acidities of the substrates, determined both in the gas phase and as a solution in THF by using the DFT B3LYP method.

Bromine-lithium exchange under non-cryogenic conditions: TMSCH 2Li-LiDMAE promoted C-2 lithiation of 2,3-dibromopyridine

The first C-2 selective bromine-lithium exchange in 2,3-dibromopyridine was performed at 0°C in toluene using the TMSCH2Li-LiDMAE reagent. The Royal Society of Chemistry.

Recommendable routes to trifluoromethyl-substituted pyridine- and quinolinecarboxylic acids

As part of a case study, rational strategies for the preparation of all ten 2-, 3-, or 4-pyridinecarboxylic acids and all nine 2-, 3-, 4-, or 8-quinolinecarboxylic acids bearing trifluoromethyl substituents at the 2-, 3-, or 4-position were elaborated. The trifluoromethyl group, if not already present in the precursor, was introduced either by the deoxygenative fluorination of suitable carboxylic acids with sulfur tetrafluoride or by the displacement of ring-bound bromine or iodine by trifluoromethylcopper generated in situ. The carboxy function was produced by treatment of organolithium or organomagnesium intermediates, products of halogen/metal or hydrogen/ metal permutation, with carbon dioxide. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

Regiocontrolled deprotonative-zincation of bromopyridines using aminozincates

Regiochemistry in the deprotonation of bromopyridines was found to be greatly influenced by the choice of metal amide base, and DA-zincate and TMP-zincate turned out to be excellent complementary practical agents for regioselective metalation of bromopyri