3,5-Dibromopyridine, 98+%, Thermo Scientific Chemicals
3,5-Dibromopyridine, 98+%, Thermo Scientific Chemicals
Thermo Scientific Chemicals

3,5-Dibromopyridine, 98+%, Thermo Scientific Chemicals

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Catalog number A10875.06
also known as A10875-06
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5 g
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3,5-Dibromopyridine, 98+%, Thermo Scientific Chemicals
Catalog numberA10875.06
Price (USD)/ Each
72.60
-
Add to cart
Chemical Identifiers
CAS625-92-3
IUPAC Name3,5-dibromopyridine
Molecular FormulaC5H3Br2N
InChI KeySOSPMXMEOFGPIM-UHFFFAOYSA-N
SMILESBrC1=CC(Br)=CN=C1
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SpecificationsSpecification SheetSpecification Sheet
Appearance (Color)White to pale cream
Assay (GC)≥98.0%
FormCrystals or powder or crystalline powder or fused solid or flakes
Water Content (Karl Fischer Titration)≤1%
Melting Point (clear melt)107.0-114.0?C
3-Acetylamino-5-ethoxypyridine was prepared by converting 3, 5-dibromopyridine with sodium ethylate into 3-bromo-5-ethoxypyridine, allowing this substance to interact with ammonia and acetylating the aminoethoxypyridine thus formed with acetic anhydride. Lithiation of 3, 5-dibromopyridine with LDA and subsequent reaction with electrophiles provided 4-alkyl-3, 5-dibromopyridines 2 in high yield. Ligand was prepared by a Pd(0)-catalyzed cross-coupling reaction of 3,5-dibromopyridine and 5-tributylstannyl-3,3?-bipyridine. The synthesis of 3, 5-bis (2-indolyl) pyridine and 3-[(2-indolyl)-5-phenyl] pyridine derivatives as includes Stille or Suzuki type reactions, which were realized on the 3,5-dibromopyridine.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
3-Acetylamino-5-ethoxypyridine was prepared by converting 3, 5-dibromopyridine with sodium ethylate into 3-bromo-5-ethoxypyridine, allowing this substance to interact with ammonia and acetylating the aminoethoxypyridine thus formed with acetic anhydride. Lithiation of 3, 5-dibromopyridine with LDA and subsequent reaction with electrophiles provided 4-alkyl-3, 5-dibromopyridines 2 in high yield. Ligand was prepared by a Pd(0)-catalyzed cross-coupling reaction of 3,5-dibromopyridine and 5-tributylstannyl-3,3′-bipyridine. The synthesis of 3, 5-bis (2-indolyl) pyridine and 3-[(2-indolyl)-5-phenyl] pyridine derivatives as includes Stille or Suzuki type reactions, which were realized on the 3,5-dibromopyridine.

Solubility
Soluble in Chloroform and Methanol. Insoluble in water.

Notes
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store away from strong oxidizing agents, alkali metals, moisture.
RUO – Research Use Only

General References:

  1. V. Krishnakumar,; R.John Xavier. Density functional theory calculations and vibrational spectra of 3,5-dibromopyridine and 3,5-dichloro-2,4,6-trifluoropyridine. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2005, 61(1-2), 253-260.
  2. Alexandre Bouillon,; Jean-Charles Lancelot,; Valérie Collot,; Philippe R Bovy,; Sylvain Rault. Synthesis of novel halopyridinylboronic acids and esters. Part 2: 2,4, or 5-Halopyridin-3-yl-boronic acids and esters . Tetrahedron. 2002 , 58(17), 3323-3328.
  3. With n-BuLi at -30 °, selective metallation occurs by exchange with one Br atom: J. Org. Chem., 16,1485 (1951). In contrast, using LDA in THF at -100 °, lithiation can be accomplished at the 4-position. Subsequent reaction with an electrophile can be followed by lithiation with n-BuLi to give 3-bromo-4,5-disubstituted pyridines: Tetrahedron Lett ., 37, 2565 (1996):