| Identification | More | [Name]
2-Bromopyridine-5-carbaldehyde | [CAS]
149806-06-4 | [Synonyms]
2-BROMO-5-FORMYLPYRIDINE
2-BROMO-5-PYRIDINECARBOXALDEHYDE
2-BROMOPYRIDINE-5-CARBALDEHYDE
2-BROMOPYRIDINE-5-CARBOXALDEHYDE
6-BROMO-3-PYRIDINECARBOXALDEHYDE
6-BROMONICOTINALDEHYDE
6-BROMO-PYRIDINE-3-CARBALDEHYDE
6-BROMOPYRIDINE-3-CARBOXALDEHYDE
2-BROMO-5-FORMYLPYRIDINE97+% | [EINECS(EC#)]
629-088-4 | [Molecular Formula]
C6H4BrNO | [MDL Number]
MFCD04115419 | [Molecular Weight]
186.01 | [MOL File]
149806-06-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Light yellow Cryst | [Melting point ]
104-110 °C(lit.)
| [Boiling point ]
284° | [density ]
1.683 | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
Soluble in dichloromethane, ether, ethyl acetate and methanol. | [form ]
Solid | [pka]
-1.01±0.10(Predicted) | [color ]
Pale yellow | [Sensitive ]
Air Sensitive | [Usage]
A useful synthetic intermediate | [InChI]
InChI=1S/C6H4BrNO/c7-6-2-1-5(4-9)3-8-6/h1-4H | [InChIKey]
PVUKGNBRJFTFNJ-UHFFFAOYSA-N | [SMILES]
C1=NC(Br)=CC=C1C=O | [CAS DataBase Reference]
149806-06-4(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 .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Chemical Properties]
Light yellow Cryst | [Uses]
2-Bromopyridine-5-carbaldehyde can be a useful synthetic intermediate
| [Synthesis]
General procedure for the synthesis of 2-bromo-5-formylpyridine (Intermediate 1b) from 2-bromo-5-(dibromomethyl)pyridine (Intermediate Ia, 3.650 g, 11.07 mmol): a mixture of Intermediate Ia with calcium carbonate (2.437 g, 24.35 mmol) in water (80 ml) was stirred and reacted for 16 hours at 105 °C. After completion of the reaction, the mixture was cooled to room temperature, diluted with water and extracted twice with ethyl acetate (EtOAc). The organic phases were combined, washed sequentially with water and saturated sodium chloride (NaCl) solution, dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to give Intermediate 1b (1.890 g, 92% yield). The product was characterized by 1H NMR (500 MHz, CDCl3): δ 10.05 (s, 1H), 8.78 (d, J = 2.2 Hz, 1H), 7.98 (dd, J = 8.2,2.4 Hz, 1H), 7.65 (d, J = 8.2 Hz, 1H). | [References]
[1] Patent: WO2016/124747, 2016, A1. Location in patent: Page/Page column 58; 59
[2] Patent: US2018/202388, 2018, A1
[3] Tetrahedron Letters, 2005, vol. 46, # 36, p. 6033 - 6036
[4] Synthesis, 1994, # 1, p. 87 - 92 |
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