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2,6-Dibromopyridine

CAS No.
626-05-1
Chemical Name:
2,6-Dibromopyridine
Synonyms
2,4-dibroMo-6-nitropyridine;2,6-dibromo-pyridin;2,6-DIBROMOPYRIDINE;Lasmiditan Impurity 46;Pyridine, 2,6-dibromo-;2,6-Dibromopyridine,98%;2,6-Dibromopyridine >2,6-DibroMopyridine, 98% 25GR;2,6-Dibromopyridine CAS 626-05-1;2,6-Dibromopyridine ISO 9001:2015 REACH
CBNumber:
CB2299002
Molecular Formula:
C5H3Br2N
Molecular Weight:
236.89
MDL Number:
MFCD00006223
MOL File:
626-05-1.mol
MSDS File:
SDS
Last updated:2024-11-13 18:13:23

2,6-Dibromopyridine Properties

Melting point 117-119 °C (lit.)
Boiling point 255°C
Density 2.0383 (rough estimate)
refractive index 1.5800 (estimate)
Flash point 213 °C
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility Chloroform (Slightly), Methanol (Slightly)
pka -3.65±0.10(Predicted)
form Crystalline Powder
color White to gray or buff
Water Solubility insoluble
BRN 108922
InChI InChI=1S/C5H3Br2N/c6-4-2-1-3-5(7)8-4/h1-3H
InChIKey FEYDZHNIIMENOB-UHFFFAOYSA-N
SMILES C1(Br)=NC(Br)=CC=C1
CAS DataBase Reference 626-05-1(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII D9SBA5R353

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H300-H312+H332-H315-H319-H335
Precautionary statements  P280-P301+P310+P330-P302+P352+P312-P304+P340+P312-P305+P351+P338
Hazard Codes  Xi,T,T+
Risk Statements  36/37/38-25-20/21-52-28-52/53-36/38
Safety Statements  26-37/39-45-36/37/39-36-36/37-28-61
RIDADR  2811
WGK Germany  3
RTECS  US7883000
Hazard Note  Irritant
HazardClass  6.1
PackingGroup  II
HS Code  29333999
NFPA 704
1
3 0

2,6-Dibromopyridine price More Price(50)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich D43115 2,6-Dibromopyridine 98% 626-05-1 25g $118 2024-03-01 Buy
Sigma-Aldrich D43115 2,6-Dibromopyridine 98% 626-05-1 100g $208 2024-03-01 Buy
TCI Chemical D1555 2,6-Dibromopyridine >98.0%(GC) 626-05-1 25g $34 2024-03-01 Buy
TCI Chemical D1555 2,6-Dibromopyridine >98.0%(GC) 626-05-1 250g $230 2024-03-01 Buy
Alfa Aesar A15397 2,6-Dibromopyridine, 98% 626-05-1 25g $72.6 2024-03-01 Buy
Product number Packaging Price Buy
D43115 25g $118 Buy
D43115 100g $208 Buy
D1555 25g $34 Buy
D1555 250g $230 Buy
A15397 25g $72.6 Buy

2,6-Dibromopyridine Chemical Properties,Uses,Production

Chemical Properties

White to light yellow crystalline powder

Uses

2,6-Dibromopyridine is used as a tridentate chelating ligand and in the formation of macrocycles containing the terpyridine moiety. It is also used to produce 6-bromo-2-methoxypyridine.

Application

2,6-Dibromopyridine is an important organic chemical reagent with a wide range of uses:
(1) Spectroscopic studies: There is a satisfactory correlation between the normal Raman spectra of 2,6-dibromopyridine in aqueous solution and the surface enhanced Raman (SER) spectra in silver-pure sols. In the SER spectra, the compounds are notable for the stretching of the vibrational modes of (py)CBr and (CC,CN)(py) in 2,6-dibromopyridine to give enhanced vibrational intensities at 1175 and 1369 cm-1 , respectively[1].
(2) Reaction reagent: Friedel–Crafts-type acylation of alkenes with acyl chlorides has been successfully conducted with a wide substrate scope by the combined use of AlCl3 and 2,6-dibromopyridine. Trisubstituted alkenes afford allylketones or vinylketones depending on the presence or absence of hydrogen atom(s) at the β-position to the acylation site, while monosubstituted alkenes exclusively afford vinylketones[2]. In addition, 2,6-Dibromopyridine can be brominated to form 2,4,6-tribromopyridine by reacting with a mixture of bromine at 450~ 550 °C[3]. It can also be lithiated with butyl lithium for the synthesis of L-739,010[4].
(3) A selective palladium-catalysed arylation of 2,6-dibromopyridine has been developed by employing N-heterocyclic carbene ligands. Selective mono-arylation was performed in water/acetonitrile solvent system at ambient temperature with catalyst loading of 0.1 mol%. This reaction was also found to proceed smoothly in water although at a slightly elevated temperature of 80 °C. 2,6-Disubstituted and diversely substituted 2,6-pyridines were also obtained in high yields which will be of importance to organic and medicinal chemists[5].

Purification Methods

Purify 2,6-dibromopyridine by steam distillation, then recrystallise it twice from EtOH. It does not form an HgCl2 salt. [den Hertog & Wibaut Recl Trav Chim Pays Bas 51 381 1932, Beilstein 20/5 V 435.]

References

[1] S. CHATTOPADHYAY S. K B. Surface-enhanced Raman spectroscopy of 2,5-dibromopyridine and 2,6-dibromopyridine[J]. Spectrochimica acta. Part A: Molecular spectroscopy, 1992. DOI:10.1016/0584-8539(92)80253-S.
[2] SHINYA TANAKA*. Acylation of Alkenes with the Aid of AlCl3 and 2,6-Dibromopyridine[J]. Organic Letters, 2019. DOI:10.1021/acs.orglett.9b02688.
[3] H. J. HERTOG C. R K ;W Combe. Substitution reactions in the pyridine nucleus at elevated temperatures (I). The bromination of 2,6‐dibromopyridine[J]. Recueil des Travaux Chimiques des Pays-Bas, 2010. DOI:10.1002/RECL.19580770109.
[4] D. CAI T. V D Hughes. A study of the lithiation of 2,6-dibromopyridine with butyllithium, and its application to synthesis of L-739,010[J]. Tetrahedron Letters, 1996. DOI:10.1016/0040-4039(96)00336-X.
[5] PRAJAPATI D, SCHULZKE C, KINDERMANN M K, et al. Selective palladium-catalysed arylation of 2,6-dibromopyridine using N-heterocyclic carbene ligands?[J]. RSC Advances, 2015. DOI:10.1039/C5RA10561G.

2402-78-0
626-05-1
Synthesis of 2,6-Dibromopyridine from 2,6-Dichloropyridine
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View Lastest Price from 2,6-Dibromopyridine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2,6-Dibromopyridine pictures 2024-12-27 2,6-Dibromopyridine
626-05-1
US $15.00-50.00 / kg 1kg NLT98% 5 ton per month Anhui Dexinjia Biopharm Co., Ltd
2,6-Dibromopyridine pictures 2024-11-13 2,6-Dibromopyridine
626-05-1
US $19.90 / kg 1kg 99% 10 mt Hebei Weibang Biotechnology Co., Ltd
2,6-Dibromopyridine pictures 2023-01-31 2,6-Dibromopyridine
626-05-1
US $100.00 / kg 1kg 99 300tons Hebei Mojin Biotechnology Co., Ltd
2,6-DIBROMOPYRIDINE 2,6-dibromo-pyridin 2,6-Dibromopyridine,98% Pyridine, 2,6-dibromo- 2,6-DibroMopyridine, 98% 25GR 2,4-dibroMo-6-nitropyridine 2,6-Dibromopyridine > 2,6-Dibromopyridine, 98%, for synthesis 2,6-Dibromopyridine ISO 9001:2015 REACH 2,6-Dibromopyridine CAS 626-05-1 Lasmiditan Impurity 46 626-05-1 626-89-3 626-05-3 625-05-1 626-06-1 C5H3BrN Building Blocks Pyridines Halogenated Heterocycles Heterocyclic Building Blocks Bromopyridines Halopyridines alkyl bromide Bromopyridines Halopyridines C5Heterocyclic Building Blocks Halogenated Heterocycles Heterocyclic Building Blocks Building Blocks C5 Chemical Synthesis Halogenated Heterocycles Heterocyclic Building Blocks Pyridines Pyridine Pyridine Series Pyridines, Pyrimidines, Purines and Pteredines bc0001