396092-82-3

Basic information

• Product Name: 2-Bromo-4-dimethylaminopyridine
• Synonyms: 2-Bromo-4-dimethylaminopyridine;2-BroMo-N,N-diMethylpyridine-4-aMine;2-Bromo-N,N-dimethylpyridin-4-amine
• CAS NO: 396092-82-3
• Molecular Formula: C₇H₉BrN₂
• Molecular Weight: 201.06
• Product Categories: Heterocycle-Pyridine series
• Mol File: 396092-82-3.mol

Chemical Properties

• Boiling Point: 285.734°C at 760 mmHg
• Flash Point: 126.608°C
• Appearance: /
• Density: 1.469g/cm³
• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.593
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-Bromo-4-dimethylaminopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-4-dimethylaminopyridine(396092-82-3)
• EPA Substance Registry System: 2-Bromo-4-dimethylaminopyridine(396092-82-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 396092-82-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-Bromo-4-dimethylaminopyridine is used as a reagent for activating carboxylic acids, facilitating amide bond formation. Its unique structure with bromine and dimethylamino groups provides a strong nucleophilic catalyst, enhancing the efficiency of organic synthesis processes.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 2-Bromo-4-dimethylaminopyridine is utilized as a catalyst in the synthesis of various drugs. Its catalytic properties enable the efficient production of pharmaceutical compounds, contributing to the development of new medications and therapies.
Used in Agrochemical Synthesis:
Similarly, in agrochemical synthesis, 2-Bromo-4-dimethylaminopyridine serves as a catalyst, aiding in the production of agrochemicals such as pesticides and herbicides. Its application ensures the efficient synthesis of these compounds, supporting agricultural productivity and crop protection.
Used in Materials Science:
2-Bromo-4-dimethylaminopyridine is also explored for its potential applications in materials science. It has been studied for the preparation of functionalized polymers and advanced materials, contributing to the development of innovative materials with diverse properties and applications.

InChI:InChI=1/C7H9BrN2/c1-10(2)6-3-4-9-7(8)5-6/h3-5H,1-2H3

Upstream product

• 1122-58-3 dmap 
• 58530-53-3 2,4-dibromopyridine 
• 124-40-3 dimethyl amine 
• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 7598-35-8 2-bromo-4-aminopyridine 
• 74-88-4 methyl iodide 
• 22918-01-0 2-bromo-4-chloropyridine 

Downstream Products

• 441072-26-0 2-(2,4-difluorophenyl)-4-N,N-dimethylaminopyridine 
• 37941-27-8 N,N-dimethyl-2-phenylpyridin-4-amine 
• 1421748-75-5 C₂₇H₄₂N₄O₃S 
• 1421748-74-4 C₂₃H₃₈N₄O₃S 
• 1421748-73-3 C₂₃H₃₆N₄O₃S 
• 1421748-72-2 C₂₈H₄₃N₅O₄S 
• 1421748-71-1 C₂₂H₃₁N₅O₄S 
• 1421748-70-0 C₂₈H₄₄N₄O₂S 
• 1421748-69-7 C₂₂H₃₂N₄O₂S 
• 1421748-68-6 C₂₀H₂₈N₄O₂S 
• 1421748-67-5 C₁₄H₂₁F₃N₄O₂S 
• 1421748-66-4 C₁₄H₂₄N₄O₂S 
• 1416450-11-7 N²,N²'-((1R,2R)-cyclohexane-1,2-diyl)bis(N⁴,N⁴-dimethylpyridine-2,4-diamine) 
• 1421748-76-6 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1R,2R)-2-((4-(dimethylamino)pyridin-2-yl)amino)cyclohexyl)thiourea 

Relevant articles and documents

Photophysical and electroluminescence properties of bis(2′,6′-difluoro-2,3′-bipyridinato-N,C4′)iridium(picolinate) complexes: effect of electron-withdrawing and electron-donating group substituents at the 4′ position of the pyridyl moiety of the cyclometalated ligand

Herein, we have synthesized a series of 2′,6′-difluoro-2,3′-bipyridine cyclometalating ligands by substituting electron-withdrawing (-CHO, -CF3, and -CN) and electron-donating (-OMe and -NMe2) groups at the 4′ position of the pyridyl moiety and utilized them for the construction of five new iridium(iii) complexes (Ir1-Ir5) in the presence of picolinate as an ancillary ligand. The photophysical properties of the developed iridium(iii) compounds were investigated with a view to understand the substituent effects. The strong electron-withdrawing (-CN) group containing the iridium(iii) compound (Ir3) exhibits highly efficient genuine green phosphorescence (λmax = 508 nm) at room temperature in solution and in thin film, with an excellent quantum efficiency (ΦPL) of 0.90 and 0.98, respectively. On the other hand, the -CF3 group substituted iridium(iii) compound (Ir2) displays a sky-blue emission (λmax = 468 nm) with a promising quantum efficiency (ΦPL = 0.88 and 0.84 in solution and in thin film, respectively). The -CHO substituted iridium(iii) complex (Ir1) showed greenish-yellow emission (λmax = 542 nm). Most importantly, the strong electron-donating -NMe2 substituted iridium(iii) complex (Ir5) gives a structureless and a broad emission profile in the wavelength region 450 to 700 nm (λmax = 520 nm) with a poor quantum efficiency. An intense blue phosphorescence with impressive quantum efficiency, especially in thin-film noted in the case of the -OMe substituted iridium(iii) complex (Ir4). Comprehensive density functional theory (DFT) and time-dependent DFT (TD-DFT) approaches have been performed on the ground and excited states of the synthesized iridium(iii) complexes, in order to obtain information about the absorption and emission processes and to gain deeper insights into the photophysical properties. The combinations of a smaller ΔES1-T1 and higher contribution of 3MLCT in the emission process result in the higher quantum yields and lifetime values for complexes Ir1-Ir3. Multi-layered Phosphorescent Organic Light Emitting Diodes (PhOLEDs) were designed using the phosphorescent dopants Ir2, Ir3 and Ir4 and their elecroluminescence properties were evaluated. Compound Ir4 at a doping level of 5 wt% shows the best performance with an external quantum efficiency of 4.7%, in the nonoptimized device, and a power efficiency of 5.8 lm W-1, together with a true-blue chromacity CIEx,y = 0.15, 0.17 recorded at the maximum brightness of 33 180 cd m-2.

Rationally Designed Blue Triplet Emitting Gold(III) Complexes Based on a Phenylpyridine-Derived Framework

A series of blue-emitting phosphorescent mono-cyclometalated AuIII complexes have been successfully synthesized. Tailoring the substitutions on the phenylpyridine (ppy) ligand scaffold with electron-withdrawing fluorine groups on the phenyl ring to achieve stabilization of the HOMO and an electron-donating dimethylamino group on the pyridine ring to destabilize the LUMO resulted in a large energy gap and bestowed on the gold(III) complexes high-energy emission and high quantum efficiencies. The results of cyclic voltammetry studies suggested a predominantly redox event localized on the cyclometalated ligand. Thermogravimetric analysis of selected complexes revealed a high stability up to 280 °C, thus the complexes are suitable for device fabrication through vacuum-deposition. Photophysical investigations performed on all the derivatives revealed phosphorescence emission in neat solid, solution, doped in poly(methyl methacrylate) (PMMA) films at room temperature as well as in rigidified glass media (2-MeTHF) at 77 K. A high photoluminescent quantum efficiency of 28 % was obtained for a complex in PMMA, the highest quantum yield reported for a blue-emitting gold(III) complex.

First direct C-2-lithiation of 4-DMAP. Convenient access to reactive functional derivatives and ligands

The first direct α-lithiation of 4-DMAP has been peformed via reaction with the BuLi-Me2N(CH2)2-OLi (BuLi-LiDMAE) reagent. This new methodology avoids the use of a activation-lithiation-regeneration sequence or halogen-met

High Triplet Energy Iridium(III) Isocyanoborato Complex for Photochemical Upconversion, Photoredox and Energy Transfer Catalysis

Cyclometalated Ir(III) complexes are often chosen as catalysts for challenging photoredox and triplet–triplet-energy-transfer (TTET) catalyzed reactions, and they are of interest for upconversion into the ultraviolet spectral range. However, the triplet e

Structure-Activity Relationships of Radioiodinated 6,5,6-Tricyclic Compounds for the Development of Tau Imaging Probes

Tau aggregate, which is the main component of the neurofibrillary tangle, is an attractive imaging target for diagnosing and monitoring the progression of Alzheimer's disease (AD). In this study, we designed and synthesized six radioiodinated 6,5,6-tricyc

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Modifying Emission Spectral Bandwidth of Phosphorescent Platinum(II) Complexes Through Synthetic Control

The design, synthesis, and characterization of a series of tetradentate cyclometalated Pt(II) complexes are reported. The platinum complexes have the general structure Pt(ppz-O-CbPy-R), where a tetradentate cyclometalating ligand is consisting of ppz (3,5

Nucleophilic Aromatic Substitution Reactions in Water Enabled by Micellar Catalysis

Given the huge dependence on dipolar, aprotic solvents such as DMF, DMSO, DMAc, and NMP in nucleophilic aromatic substitution reactions (SNAr), a simple and environmentally friendly alternative is reported. Use of a "benign-by-design" nonionic surfactant, TPGS-750-M, in water enables nitrogen, oxygen, and sulfur nucleophiles to participate in SNAr reactions. Aromatic and heteroaromatic substrates readily participate in this micellar catalysis, which takes place at or near ambient temperatures.

A novel neutral organic electron donor with record half-wave potential

Tricyclic donor 26 has been prepared and is the most reducing neutral ground-state organic molecule known, with an oxidation potential 260 mV more negative than the previous record. Cyclic voltammetry shows that a 2-electron reversible redox process occurs in DMF as solvent at -1.46 V vs. Ag/AgCl.

Phosphorescent light-emitting iridium complex containing pyridyltriazole ligand

An Ir complex having a pyridyl triazole ligand substituted with at least one substituent on its pyridyl ring, and a light emitting material comprising such Ir complex. Such light emitting material was found to have a significantly enhanced photophosphorescence quantum yield and hypsochromic blue shifted photophosphorescent emission over other Ir complexes with a pyridyl triazole ligand having no substituent in its pyridine ring. Use of such light emitting material and an organic light emitting device including the same.