| Identification | More | [Name]
2-Chloro-4-bromopyridine | [CAS]
73583-37-6 | [Synonyms]
2-CHLORO-4-BROMOPYRIDINE
4-BROMO-2-CHLOROPYRIDINE
PYRIDINE, 4-BROMO-2-CHLORO-
4-Bromo-2-chloropyridine 98%
2-chloro-4-bromopyridne
2-CHLORO-4-FLUOROYRIDINE
4-Bromo-2-chloropyridine ,98%
2-Bromo-2-chloropyridine | [EINECS(EC#)]
629-180-4 | [Molecular Formula]
C5H3BrClN | [MDL Number]
MFCD03840756 | [Molecular Weight]
192.44 | [MOL File]
73583-37-6.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-white Cryst | [Melting point ]
27 C | [Boiling point ]
70 °C / 3mmHg | [density ]
1.7336 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.5900(lit.)
| [Fp ]
225 °F
| [storage temp. ]
Inert atmosphere,2-8°C | [form ]
Powder | [pka]
0.24±0.10(Predicted) | [color ]
Yellow | [Specific Gravity]
1.7336 | [Water Solubility ]
Not miscible or difficult to mix in water. | [Detection Methods]
HPLC,NMR | [InChI]
InChI=1S/C5H3BrClN/c6-4-1-2-8-5(7)3-4/h1-3H | [InChIKey]
ONHMWUXYIFULDO-UHFFFAOYSA-N | [SMILES]
C1(Cl)=NC=CC(Br)=C1 | [CAS DataBase Reference]
73583-37-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes.
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 .
S36:Wear suitable protective clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white Cryst | [Uses]
It is used in the synthesis of quaterpyridine nemertelline. | [Synthesis]
Step a: Synthesis of 2-chloro-4-bromopyridine
To 8.9 g (69.2 mmol) of 2-chloro-4-aminopyridine was added 81.5 mL of 48% aqueous hydrobromic acid at 0 °C. Subsequently, 33.4 g (208.75 mmol) of bromine monomer was slowly added over 10 min. The reaction mixture was cooled to -10°C and 10.65 g (154 mmol) of sodium nitrite dissolved in 20 mL of water was added dropwise over 30 min. After the dropwise addition was completed, stirring was continued at -10°C for 10 minutes and then brought to room temperature and stirred for 1.5 hours. Upon completion of the reaction, the mixture was cooled to 5°C and saturated aqueous sodium sulfite solution was added until the reaction solution was colorless. The reaction solution was adjusted to alkaline with 35% sodium hydroxide aqueous solution. The basic aqueous phase was extracted twice with diethyl ether, the organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated. The yellow oil obtained (13 g) was purified by silica gel column chromatography (eluent: ethyl acetate/heptane=1/9). The product was a light-colored oily substance in 52% yield.
1H NMR (CDCl3): δ 8.25 (d, 1H, J = 5Hz), 7.55 (s, 1H), 7.4 (d, 1H, J = 5Hz). | [References]
[1] Journal of Organic Chemistry, 2006, vol. 71, # 22, p. 8602 - 8609
[2] Synlett, 2016, vol. 27, # 1, p. 67 - 69
[3] Patent: US2006/89364, 2006, A1. Location in patent: Page/Page column 22
[4] Roczniki Chemii, 1955, vol. 29, p. 1019,1025
[5] Chem.Abstr., 1956, p. 12045 |
|
|