| Identification | More | [Name]
2-Bromo-3,5-dichloropyridine | [CAS]
14482-51-0 | [Synonyms]
2-BROMO-3,5-DICHLOROPYRIDINE
3,5-DICHLORO-2-BROMOPYRIDINE
3,5-DICHLOROPYRIDIN-2-YL-BORONIC ACID
AKOS BBS-00001365
PYRIDINE, 2-BROMO-3,5-DICHLORO-
2-BROMO-3,5-DICHLOROPYRIDUNE
3,5-DICHLORO-2-BROMOPYRIDINE 98+% | [EINECS(EC#)]
672-535-3 | [Molecular Formula]
C5H2BrCl2N | [MDL Number]
MFCD00233990 | [Molecular Weight]
226.89 | [MOL File]
14482-51-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
40-42 | [Boiling point ]
243.3±35.0 °C(Predicted) | [density ]
1.848±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
Solid | [pka]
-2.37±0.10(Predicted) | [color ]
Pale brown | [InChI]
InChI=1S/C5H2BrCl2N/c6-5-4(8)1-3(7)2-9-5/h1-2H | [InChIKey]
QCKPJWDIDCGQRB-UHFFFAOYSA-N | [SMILES]
C1(Br)=NC=C(Cl)C=C1Cl | [CAS DataBase Reference]
14482-51-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [Hazard Note ]
Irritant | [HazardClass ]
6.1 | [HazardClass ]
IRRITANT | [HS Code ]
2933399990 |
| Hazard Information | Back Directory | [Uses]
2-Bromo-3,5-dichloropyridine is used in various fields, including pharmaceuticals, agrochemicals, and materials science. It is an essential intermediate for the synthesis of different chemical compounds, such as fungicides, herbicides, and insecticides. | [Synthesis]
Step 1: Synthesis of 2-bromo-3,5-dichloropyridine
To a solution of 3,5-dichloropyridin-2-amine (1.0 g, 6.2 mmol) dissolved in 40% aqueous hydrobromic acid (8 mL), bromine (2.8 g, 17 mmol) was slowly added dropwise at -20 °C. The resulting orange-colored suspension was stirred continuously for 2 hours at -20 °C. Subsequently, aqueous sodium nitrite (1.1 g, 17 mmol) was added at the same temperature. The reaction mixture was warmed up to ambient temperature and stirring was continued for 2 hours. Upon completion of the reaction, the mixture was cooled to 0 °C and the pH was adjusted with 30% aqueous sodium hydroxide solution to about 12. The reaction mixture was extracted with ether to give a light yellow organic phase. The organic phases were combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound 2-bromo-3,5-dichloropyridine as a yellow solid (730 mg, 52% yield).
1H NMR (400MHz, CDCl3) δ 8.27 (d, J=2.3Hz, 1H). | [References]
[1] Patent: US4510148, 1985, A
[2] Patent: WO2008/70908, 2008, A1. Location in patent: Page/Page column 71-72
[3] Patent: WO2015/187845, 2015, A1. Location in patent: Paragraph 0239
[4] European Journal of Medicinal Chemistry, 1989, vol. 24, # 3, p. 249 - 258
[5] Phosphorus and Sulfur and the Related Elements, 1987, vol. 34, p. 123 - 132 |
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