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;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;2,6-Dibromopyridine, 98%, for synthesis
- CBNumber:
- CB2299002
- Molecular Formula:
- C5H3Br2N
- Molecular Weight:
- 236.89
- MOL File:
- 626-05-1.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/4/8 9:37:31
| 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) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  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 |
|
2,6-Dibromopyridine price More Price(4)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | D43115 | 2,6-Dibromopyridine 98% | 626-05-1 | 25G | ₹4557.33 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | D43115 | 2,6-Dibromopyridine 98% | 626-05-1 | 100G | ₹12578.65 | 2022-06-14 | Buy |
| TCI Chemicals (India) | D1555 | 2,6-Dibromopyridine min. 98.0 % | 626-05-1 | 25G | ₹4000 | 2022-05-26 | Buy |
| TCI Chemicals (India) | D1555 | 2,6-Dibromopyridine min. 98.0 % | 626-05-1 | 250G | ₹18300 | 2022-05-26 | 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)CBr 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.
2,6-Dibromopyridine Preparation Products And Raw materials
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| SVS INTERCHEM | +91-91-40-27171109 +91-9311580480 | Telangana, India | 55 | 58 | Inquiry |
| Supplier | Advantage |
|---|---|
| BTC pharm India | 58 |
| GLR Innovations | 58 |
| Terma Medicare India Pvt.,Ltd | 58 |
| Madin Life Sciences Pvt Ltd | 58 |
| Jubilant Ingrevia | 58 |
| Vital synthetics | 58 |
| RPN ORGANICS PVT LTD | 58 |
| ALTRAKEM PHARMA LIFE SCIENCES PRIVATE LIMITED | 58 |
| ANJI BIOSCIENCES | 58 |
| SVS INTERCHEM | 58 |
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