3,5-Dibromopyridine

Base Information

• Chemical Name: 3,5-Dibromopyridine
• CAS No.: 625-92-3
• Molecular Formula: C5H3Br2N
• Molecular Weight: 236.894
• Hs Code.: 2933.39
• European Community (EC) Number: 210-916-4
• NSC Number: 6209
• DSSTox Substance ID: DTXSID3073921
• Nikkaji Number: J79.765K
• Wikipedia: 3,5-dibromopyridine
• Wikidata: Q27122668
• Metabolomics Workbench ID: 57797
• Mol file: 625-92-3.mol

Synonyms:3,5-dibromopyridine

Chemical Property of 3,5-Dibromopyridine

Chemical Property:

• Appearance/Colour: Light-Yellow Solid
• Vapor Pressure: 0.155mmHg at 25°C
• Melting Point: 110-115 °C(lit.)
• Refractive Index: 1.607
• Boiling Point: 222 °C at 760 mmHg
• PKA: 0.52±0.20(Predicted)
• Flash Point: 84.3 °C
• PSA: 12.89000
• Density: 2.059 g/cm³
• LogP: 2.60660
• Storage Temp.: Store below +30°C.
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly)
• Water Solubility.: Soluble in Chloroform and Methanol. Insoluble in water.
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 236.86117
• Heavy Atom Count: 8
• Complexity: 68.8

Purity/Quality:

99%, ^*data from raw suppliers

3,5-Dibromopyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C=NC=C1Br)Br
• General Description: 3,5-Dibromopyridine serves as a key precursor in the synthesis of κ³SCS pincer palladium complexes, where it undergoes Pd-catalyzed aryl phosphination and subsequent sulfurization to form ligands for complexation. Its 3,5-pyridinediyl unit facilitates cyclopalladation, forming stable pincer complexes with a Pd–C bond, while the pyridine nitrogen enables further quaternization and coordination to generate hetero-binuclear species. 3,5-Dibromopyridine's utility in constructing these complexes highlights its role as a versatile building block in organometallic chemistry.

Technology Process of 3,5-Dibromopyridine

There total 39 articles about 3,5-Dibromopyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

3,5-dibromopyridine-N-oxide (2402-99-5) → 3,5-dibromopyridine (625-92-3)

Guidance literature:

With titanium tetrachloride; sodium iodide; In acetonitrile; at 30 ℃; for 0.0833333h;

Reference yield: 82.0%

pyridine (110-86-1) → 3,5-dibromopyridine (625-92-3)

Guidance literature:

With thionyl chloride; sulfuric acid; bromine; at 130 ℃; for 10h; Temperature;

Reference yield: 78.0%

4-amino-3,5-dibromopyridine (84539-34-4) → 3,5-dibromopyridine (625-92-3)

Guidance literature:

With trifluoroacetic acid; isopentyl nitrite; In tetrahydrofuran; at 70 ℃; for 7h;

DOI:10.1002/chem.201605272

upstream raw materials:

pyridine

Pyridine-2,3-dicarboxylic acid

pyridinepentacarboxylic acid

piperidine hydrochloride

Downstream raw materials:

5-bromo-3-ethoxypyridine

3,5-dibromo-1-(2-[2]naphthyl-2-oxo-ethyl)-pyridinium; iodide

3,5-dibromo-1-[2-oxo-2-(5,6,7,8-tetrahydro-[2]naphthyl)-ethyl]-pyridinium; iodide

3,5-dimethoxypyridine

Refernces

Synthesis, structure, and quaternization and complexation reactions of κ³SCS pincer palladium complexes having 3,5-pyridinediyl unit

10.1016/j.jorganchem.2007.12.033

The research focuses on the synthesis, structure, and reactions of novel j3S,C,S-pincer palladium complexes containing a 3,5-pyridinediyl unit. The cyclopalladation of 3,5-bis(diphenylphosphinothioyl)pyridine led to the formation of new j3S,C,S-pincer palladium complexes with a p-bond between Pd and the 4C of the centered 3,5-pyridinediyl unit. The study utilized the quaternization and complexation ability of the pyridine imine nitrogen (Npy) atom to synthesize various new pincer-type complexes, including hetero-binuclear complexes. The experiments involved Pd-catalyzed aryl phosphination of 3,5-dibromopyridine with diphenylphosphine, followed by sulfurization to obtain the ligand. Further reactions with PdCl2(PhCN)2 and sodium acetate yielded the pincer palladium complex, which was then subjected to quaternization and complexation reactions. The chemical structures were confirmed using NMR, FAB-mass spectroscopy, elemental analysis, and X-ray crystallography. The study also investigated the UV–Vis absorption spectra of the complexes.

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