| Identification | Back Directory | [Name]
3,5-Dibromopyridine-4-carboxaldehyde | [CAS]
70201-42-2 | [Synonyms]
3,5-DibromoisonicotinaL
3,5-Dibromo-4-formylpyridine
3,5-Dibromoisonicotinaldehyde
3,5-Dibromopyridine-4-carbaldehyde
3,5-Dibromo-4-pyridinecarbaldehyde
5-Dibromo-4-pyridinecarboxaldehyde
3,5-Dibromo-4-pyridinecarboxaldehyde
3,5-Dibromopyridine-4-carboxaldehyde
4-PYRIDINECARBOXALDEHYDE, 3,5-DIBROMO-
3,5-DibroMo-4-pyridinecarboxaldehyde 97%
3,5-Dibromopyridine-4-carboxaldehyde ISO 9001：2015 REACH
3,5-Dibromopyridine-4-carboxaldehyde, 3,5-Dibromo-4-formylpyridine | [Molecular Formula]
C6H4BrNO | [MDL Number]
MFCD06410681 | [MOL File]
70201-42-2.mol | [Molecular Weight]
186.01 |
| Chemical Properties | Back Directory | [Melting point ]
118-122 °C(lit.)
| [Boiling point ]
278.1±35.0 °C(Predicted) | [density ]
2.090±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [solubility ]
Choroform (Slightly), Methanol (Slightly, Sonicated) | [form ]
Solid | [pka]
-1.47±0.28(Predicted) | [color ]
Pale Yellow to Light Yellow | [InChI]
InChI=1S/C6H3Br2NO/c7-5-1-9-2-6(8)4(5)3-10/h1-3H | [InChIKey]
WPBYVMDYYFWYAY-UHFFFAOYSA-N | [SMILES]
C1=NC=C(Br)C(C=O)=C1Br |
| Hazard Information | Back Directory | [Uses]
3,5-Dibromo-4-pyridinecarboxaldehyde is easily soluble in water and miscible with organic solvents. It is used as an intermediate for synthesising the insecticide pyrazinone and in textiles to improve the stiffness of cotton fabrics.
| [Synthesis]
Step 1: Diisopropylamine (2.4 g, 24.0 mmol) was dissolved in anhydrous tetrahydrofuran (20 mL) under nitrogen protection and cooled to 0 °C. A n-butyllithium solution (9.6 mL, 24.0 mmol) in hexane was slowly added dropwise and stirred continuously for 30 min at this temperature. Subsequently, additional anhydrous tetrahydrofuran (30 mL) was added and the reaction mixture was further cooled to -78 °C. To this low-temperature solution, dry 3,5-dibromopyridine (4.7 g, 20 mmol) was added, diluted dropwise with tetrahydrofuran (50 mL), and stirring was continued for 30 minutes. Next, methyl formate (2.4 g, 40 mmol) was added and the reaction mixture was continued stirring at -78 °C for 30 min. After slowly warming to room temperature, the reaction was quenched with saturated sodium bicarbonate solution (100 mL) and extracted with ethyl acetate (50 mL × 3). The organic phases were combined, dried over anhydrous sodium sulfate, concentrated and purified by column chromatography to afford the target product 3,5-dibromopyridine-4-carbaldehyde (26-b) as a light yellow solid (4.0 g, 75% yield).1H NMR (300 MHz, DMSO-d6) δ: 10.06 (s, 1H), 8.87 (s, 2H). | [References]
[1] Patent: US2017/158680, 2017, A1. Location in patent: Paragraph 0418; 0419; 0420
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 10, p. 2789 - 2794
[3] Journal of Fluorine Chemistry, 2006, vol. 127, # 6, p. 755 - 759
[4] Patent: US6232320, 2001, B1 |
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