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625-92-3 - 3,5-Dibromopyridine, 98+% - A10875 - Alfa Aesar

A10875 3,5-Dibromopyridine, 98+%

CAS Number
625-92-3
Synonyms

Size Price ($) Quantity Availability
5g 59.12
25g 244.25
100g 686.40
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3,5-Dibromopyridine, 98+%

MDL
MFCD00014634
EINECS
210-916-4

Chemical Properties

Formula
C5H3Br2N
Formula Weight
236.90
Melting point
110-113°
Solubility
Soluble in Chloroform and Methanol. Insoluble in water.

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.

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.

Literature References

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.

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.

With n-BuLi at -30 o, selective metallation occurs by exchange with one Br atom: J. Org. Chem., 16,1485 (1951). In contrast, using LDA in THF at -100 o, 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):

GHS Hazard and Precautionary Statements

Hazard Statements: H301-H311-H332-H315-H319-H335

Toxic if swallowed. Toxic in contact with skin. Harmful if inhaled. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P280-P301+P310-P305+P351+P338-P361-P304+P340-P362-P312-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Remove/Take off immediately all contaminated clothing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
108477
Harmonized Tariff Code
2933.39
TSCA
No

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