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| | 3,5-Dibromopyridine-4-carboxaldehyde Basic information |
| Product Name: | 3,5-Dibromopyridine-4-carboxaldehyde | | Synonyms: | 3,5-Dibromopyridine-4-carboxaldehyde;4-PYRIDINECARBOXALDEHYDE, 3,5-DIBROMO-;3,5-Dibromopyridine-4-carbaldehyde;3,5-Dibromo-4-pyridinecarboxaldehyde;5-Dibromo-4-pyridinecarboxaldehyde;3,5-Dibromopyridine-4-carboxaldehyde, 3,5-Dibromo-4-formylpyridine;3,5-DibroMo-4-pyridinecarboxaldehyde 97%;3,5-Dibromo-4-formylpyridine | | CAS: | 70201-42-2 | | MF: | C6H3Br2NO | | MW: | 264.9 | | EINECS: | | | Product Categories: | Heterocycle-Pyridine series;Carbonyl Compounds;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Organic Building Blocks;C6Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyridines;Pyridine series;Aldehydes;Building Blocks;C1 to C6;C5 to C6;C6 to C7 | | Mol File: | 70201-42-2.mol |  |
| | 3,5-Dibromopyridine-4-carboxaldehyde Chemical Properties |
| Melting point | 118-122 °C (lit.) | | Boiling point | 278.1±35.0 °C(Predicted) | | density | 2.090±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 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 Codes | Xn | | Risk Statements | 22-36/37/38-43 | | Safety Statements | 26-36/37 | | RIDADR | UN 2811 6.1/PG 3 | | WGK Germany | 3 | | HazardClass | 6.1 | | PackingGroup | Ⅲ | | HS Code | 2933399990 | | Storage Class | 6.1D - Non-combustible acute toxic Cat.3
toxic hazardous materials or hazardous materials causing chronic effects | | Hazard Classifications | Acute Tox. 3 Oral
Eye Irrit. 2
Skin Irrit. 2
Skin Sens. 1
STOT SE 3 |
| | 3,5-Dibromopyridine-4-carboxaldehyde Usage And Synthesis |
| 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 |
| | 3,5-Dibromopyridine-4-carboxaldehyde Preparation Products And Raw materials |
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