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A10875 3,5-Dibromopyridine, 98+%

CAS Number
625-92-3
Synonyms

Stock No. Size Price ($) Quantity Availability
A10875-06 5g 59.60
A10875-14 25g 247.00
A10875-22 100g 866.00
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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°
Storage & Sensitivity
Ambient temperatures.
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: H302-H312-H315-H319-H332-H335

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

Precautionary Statements: P261-P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Rinse mouth. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
108477
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2933.39
TSCA
No

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