What is 4-Bromopyridine Hydrochloride CAS 19524-06-2
4-Bromopyridine hydrochloride CAS 19524-06-2 is used as a useful synthetic intermediate. It is also used as an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff. Soluble in DMSO, Methanol and Water. Store at -20°C.
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Aminopyridines are a group of monoamino and diamino derivatives of pyridine, which inhibit voltage-gated potassium (Kv) channels. Especially, the 2 broad-spectrum potassium channel blockers 4-Bromopyridine hydrochloride CAS 19524-06-2 (4-Bromopyridine hydrochloride CAS 19524-06-2) and 3,4-diaminopyridine (3,4-DAP) have been used as investigational new substances in various neurologic diseases. Despite the fact that 3,4-DAP is a more potent antagonist of potassium channels, 4-Bromopyridine hydrochloride CAS 19524-06-2 crosses the blood-brain barrier more readily1 and was clinically superior in patients with MS, particularly for improving visual function,2 fatigue,3 cognition,4 and walking speed.1 In addition, 4-Bromopyridine hydrochloride CAS 19524-06-2 has been reported to facilitate neural conduction in neurologic diseases other than MS.
In healthy axons, the channels Kv1.1 and Kv1.2 are clustered near the nodes of Ranvier.These channels become exposed after demyelination and migrate through the demyelinated segment. At the same time, expression of these channels is increased several fold.8 This misdirected redistribution of the Kv channels impairs the transmission of action potentials, leading to permanent disability. 4-Bromopyridine hydrochloride CAS 19524-06-2 blocks these exposed potassium channels and therefore enhances signal transduction.9,10 The Kv1.3 channel was discovered in human T-cells, was found to be highly expressed on inflammatory infiltrates in the MS brain,and is expressed on macrophages, microglia, and effector memory T cells.13 Selective and nonselective Kv1.3 channel blockers might thereby provide immunomodulatory properties by inhibiting cell proliferation and proinflammatory cytokine secretion.14 Studies before 2009 failed to establish 4-Bromopyridine hydrochloride CAS 19524-06-2 as a symptomatic treatment for MS because drug blood levels in patients were unpredictable, with excessive doses being associated with the risk of epileptic seizures and impaired consciousness.Therefore, fampridine, the prolonged release formulation of 4-Bromopyridine hydrochloride CAS 19524-06-2 was developed and has subsequently been approved for the symptomatic treatment of walking disability in MS.Interestingly, more recently, an increasing body of evidence suggests that besides these widely acknowledged symptomatic effects, 4-Bromopyridine hydrochloride CAS 19524-06-2 may have additional protective properties.
Reaction Of 4-Bromopyridine Hydrochloride CAS 19524-06-2
Because of the electronegative nitrogen in the 4-Bromopyridine hydrochloride CAS 19524-06-2 ring, 4-Bromopyridine hydrochloride CAS 19524-06-2 enters less readily into electrophilic aromatic substitution reactions than benzene derivatives.Instead, in terms of its reactivity, 4-Bromopyridine hydrochloride CAS 19524-06-2 resembles nitrobenzene.
Correspondingly 4-Bromopyridine hydrochloride CAS 19524-06-2 is more prone to nucleophilic substitution, as evidenced by the ease of metalation by strong organometallic bases.The reactivity of 4-Bromopyridine hydrochloride CAS 19524-06-2 can be distinguished for three chemical groups. With electrophiles, electrophilic substitution takes place where 4-Bromopyridine hydrochloride CAS 19524-06-2 expresses aromatic properties. With nucleophiles, 4-Bromopyridine hydrochloride CAS 19524-06-2 reacts at positions 2 and 4 and thus behaves similar to imines and carbonyls. The reaction with many Lewis acids results in the addition to the nitrogen atom of 4-Bromopyridine hydrochloride CAS 19524-06-2, which is similar to the reactivity of tertiary amines. The ability of 4-Bromopyridine hydrochloride CAS 19524-06-2 and its derivatives to oxidize, forming amine oxides (N-oxides), is also a feature of tertiary amines.
The nitrogen center of 4-Bromopyridine hydrochloride CAS 19524-06-2 features a basic lone pair of electrons. This lone pair does not overlap with the aromatic π-system ring, consequently 4-Bromopyridine hydrochloride CAS 19524-06-2 is basic, having chemical properties similar to those of tertiary amines. Protonation gives pyridinium, C5H5NH+.The pKa of the conjugate acid (the pyridinium cation) is 5.25. The structures of 4-Bromopyridine hydrochloride CAS 19524-06-2 and pyridinium are almost identical. The pyridinium cation is isoelectronic with benzene. Pyridinium p-toluenesulfonate (PPTS) is an illustrative pyridinium salt; it is produced by treating 4-Bromopyridine hydrochloride CAS 19524-06-2 with p-toluenesulfonic acid. In addition to protonation, 4-Bromopyridine hydrochloride CAS 19524-06-2 undergoes N-centred alkylation, acylation, and N-oxidation. 4-Bromopyridine hydrochloride CAS 19524-06-2 and poly(4-vinyl) 4-Bromopyridine hydrochloride CAS 19524-06-2 have been shown to form conducting molecular wires with remarkable polyenimine structure on UV irradiation, a process which accounts for at least some of the visible light absorption by aged 4-Bromopyridine hydrochloride CAS 19524-06-2 samples. These wires have been theoretically predicted to be both highly efficient electron donors and acceptors, and yet are resistant to air oxidation.
Properties of 4-Bromopyridine Hydrochloride CAS 19524-06-2
Physical Properties
Crystal structure of 4-Bromopyridine hydrochloride CAS 19524-06-2
4-Bromopyridine hydrochloride CAS 19524-06-2 is diamagnetic. Its critical parameters are: pressure 5.63 MPa, temperature 619 K and volume 248 cm3/mol.
Structure
4-Bromopyridine hydrochloride CAS 19524-06-2 forms a C5N hexagon. Slight variations of the C−C and C−N distances as well as the bond angles are observed.
Crystallography
4-Bromopyridine hydrochloride CAS 19524-06-2 crystallizes in an orthorhombic crystal system with space group Pna21 and lattice parameters a = 1752 pm, b = 897 pm, c = 1135 pm, and 16 formula units per unit cell (measured at 153 K). For comparison, crystalline benzene is also orthorhombic, with space group Pbca, a = 729.2 pm, b = 947.1 pm, c = 674.2 pm (at 78 K), but the number of molecules per cell is only 4.[18] This difference is partly related to the lower symmetry of the individual 4-Bromopyridine hydrochloride CAS 19524-06-2 molecule (C2v vs D6h for benzene). A trihydrate (4-Bromopyridine hydrochloride CAS 19524-06-2·3H2O) is known; it also crystallizes in an orthorhombic system in the space group Pbca, lattice parameters a = 1244 pm, b = 1783 pm, c = 679 pm and eight formula units per unit cell (measured at 223 K).[21]
Spectroscopy
The optical absorption spectrum of 4-Bromopyridine hydrochloride CAS 19524-06-2 in hexane consists of bands at the wavelengths of 195, 251, and 270 nm. With respective extinction coefficients (ε) of 7500, 2000, and 450 L·mol−1·cm−1, these bands are assigned to π → π*, π → π*, and n → π* transitions. The compound displays very low fluorescence.
The 1H nuclear magnetic resonance (NMR) spectrum shows signals for α-(δ 8.5), γ-(δ7.5) and β-protons (δ7). By contrast, the proton signal for benzene is found at δ7.27. The larger chemical shifts of the α- and γ-protons in comparison to benzene result from the lower electron density in the α- and γ-positions, which can be derived from the resonance structures. The situation is rather similar for the 13C NMR spectra of 4-Bromopyridine hydrochloride CAS 19524-06-2 and benzene: 4-Bromopyridine hydrochloride CAS 19524-06-2 shows a triplet at δ(α-C) = 150 ppm, δ(β-C) = 124 ppm and δ(γ-C) = 136 ppm, whereas benzene has a single line at 129 ppm. All shifts are quoted for the solvent-free substances.4-Bromopyridine hydrochloride CAS 19524-06-2 is conventionally detected by the gas chromatography and mass spectrometry methods.
Bonding
4-Bromopyridine hydrochloride CAS 19524-06-2 with its free electron pair
4-Bromopyridine hydrochloride CAS 19524-06-2 has a conjugated system of six π electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. In contrast to benzene, the electron density is not evenly distributed over the ring, reflecting the negative inductive effect of the nitrogen atom. For this reason, 4-Bromopyridine hydrochloride CAS 19524-06-2 has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ/mol in 4-Bromopyridine hydrochloride CAS 19524-06-2 vs. 150 kJ/mol in benzene).
The ring atoms in the 4-Bromopyridine hydrochloride CAS 19524-06-2 molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. As a result, the lone pair does not contribute to the aromatic system but importantly influences the chemical properties of 4-Bromopyridine hydrochloride CAS 19524-06-2, as it easily supports bond formation via an electrophilic attack.However, because of the separation of the lone pair from the aromatic ring system, the nitrogen atom cannot exhibit a positive mesomeric effect.
Many analogues of 4-Bromopyridine hydrochloride CAS 19524-06-2 are known where N is replaced by other heteroatoms from the same column of the Periodic Table of Elements . Substitution of one C–H in 4-Bromopyridine hydrochloride CAS 19524-06-2 with a second N gives rise to the diazine heterocycles (C4H4N2), with the names pyridazine, pyrimidine, and pyrazine.
What is 4-Bromopyridine Hydrochloride CAS 19524-06-2 Used for in Organic Synthesis?
4-Bromopyridine hydrochloride CAS 19524-06-2, also known as 4-Bromopyridine hydrochloride CAS 19524-06-2, is a white crystalline solid at room temperature and pressure. It has a certain hygroscopicity and is easily deliquescent when exposed to water. 4-Bromopyridine hydrochloride CAS 19524-06-2 is a pyridine salt commonly used as a coupling reagent and precursor molecule for pyridine derivatives in organic synthesis chemistry. It is often treated with a base to release 4-bromopyridine. Due to the coordinating properties of pyridine, this substance is commonly used as an assembly material for the preparation of supramolecular compounds.
Properties
Neutralization reaction of 4-Bromopyridine hydrochloride CAS 19524-06-2
In a dry reaction flask, 4-Bromopyridine hydrochloride CAS 19524-06-2 (1 equivalent) and anhydrous potassium carbonate (10 equivalents) are mixed and stirred in acetonitrile as a solvent at room temperature for 6 hours. After the reaction is complete, the resulting reaction mixture is filtered through anhydrous magnesium sulfate to remove salts from the reaction system. The resulting reaction filtrate is concentrated at room temperature to evaporate the solvent in the reaction system, and the residue obtained is the target product molecule, which can be used for the next reaction without further separation and purification.
Applications
4-Bromopyridine hydrochloride CAS 19524-06-2 is a pyridine salt commonly used as a coupling reagent and precursor molecule for pyridine derivatives in organic synthesis chemistry. It is often treated with a base to release 4-bromopyridine. The coupling reaction of 4-Bromopyridine hydrochloride CAS 19524-06-2 is commonly used to construct C-C, C-N, C-O, and other bonds. Common reactions include Suzuki coupling reaction, Stille coupling reaction, Heck coupling reaction, etc. 4-Bromopyridine hydrochloride CAS 19524-06-2 can also be used to synthesize various pyridine derivatives, such as heterocyclic compounds, pyridinylamide compounds, etc. In these reactions, 4-Bromopyridine hydrochloride CAS 19524-06-2 can serve as a precursor molecule for pyridine, which is converted into the target product through substitution reactions, condensation reactions, and other reaction steps. Pyridine has strong coordinating ability and hydrogen bonding ability, so it can assemble into various supramolecular structures with other molecules through non-covalent interactions. 4-Bromopyridine hydrochloride CAS 19524-06-2, as a derivative of pyridine, also has similar coordinating properties and hydrogen bonding ability, making it one of the assembly materials for supramolecular compounds.
Company Introduction
Huarong (Guangdong) Pharmaceutical Co., Ltd. is a pharmaceutical intermediate manufacturing and production company, based on the synthesis of DPP-4 inhibitor intermediates. It comprehensively constructs a production line for active ingredients of bisamide insecticides, as well as a multifunctional production line for chiral synthesis and enzymatic synthesis of compound intermediates. Build an advanced and green comprehensive production base for pharmaceutical and pesticide intermediates.
The company was established on November 8, 2023, with a type of other limited liability company and registered in Nanxiong City, Shaoguan City. The company's project plan covers an area of 53406.97 square meters. The main building includes 5 Class A multifunctional workshops, 1 Class C workshop, 1 comprehensive building, 1 quality inspection and research and development building, as well as supporting power and environmental protection facilities. The construction of the project covers an area of 19042 square meters, with a building area of 50137 square meters and a plot ratio of 0.94.
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