| Identification | More | [Name]
2,6-Dibromopyridine | [CAS]
626-05-1 | [Synonyms]
2,6-DIBROMOPYRIDINE
2,6-dibromo-pyridin
2,6-Dibromopyridine,98%
Pyridine, 2,6-dibromo- | [EINECS(EC#)]
210-926-9 | [Molecular Formula]
C5H3Br2N | [MDL Number]
MFCD00006223 | [Molecular Weight]
236.89 | [MOL File]
626-05-1.mol |
| Chemical Properties | Back Directory | [Appearance]
White to light yellow crystalline powder | [Melting point ]
117-119 °C (lit.) | [Boiling point ]
255°C | [density ]
2.0383 (rough estimate) | [refractive index ]
1.5800 (estimate) | [Fp ]
213 °C
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Crystalline Powder | [pka]
-3.65±0.10(Predicted) | [color ]
White to gray or buff | [Water Solubility ]
insoluble | [Detection Methods]
HPLC | [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 Data | Back Directory | [Hazard Codes ]
Xi,T | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R25:Toxic if swallowed.
R20/21:Harmful by inhalation and in contact with skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S36:Wear suitable protective clothing . | [RIDADR ]
2811 | [WGK Germany ]
3
| [RTECS ]
US7883000
| [Hazard Note ]
Irritant | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29333999 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
2,3,4,5,6-PENTABROMOPYRIDINE-->6-BROMO-1-METHYLPYRIDIN-2(1H)-ONE-->2,6-Dibromopyridine oxide-->3-Aminopyridine-->2,6-Dibromopyridin-3-amine-->2,6-Dichloropyridine | [Preparation Products]
6-Bromopyridine-2-carbaldehyde-->6-Methoxypyridine-2-carbaldehyde-->6-TERT-BUTOXYPYRIDINE-2-CARBOXALDEHYDE-->2-Bromo-6-methoxypyridine-->2-Amino-6-methoxypyridine-->2,6-Dihydroxypyridine-->4-AMINO-2,6-DIBROMOPYRIDINE-->Acrivastine-->2-Amino-6-bromopyridine-->2-BROMO-6-(1H-PYRAZOL-1-YL)PYRIDINE-->6-ETHOXY-2-PYRIDINAMINE-->(6-BROMO-2-PYRIDINYL)-CARBAMIC ACID,1,1-DIMETHYLETHYL ESTER-->2,6-DIETHYNYLPYRIDINE |
| Hazard Information | Back Directory | [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.
|
|
|