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INTATRADE GmbH |
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+49 3493/605464 |
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sales@intatrade.de |
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Ark Pharm, Inc. |
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847-367-3680 |
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| | 3-Bromo-4-formylpyridine Basic information |
| | 3-Bromo-4-formylpyridine Chemical Properties |
| Melting point | 81-82 °C(lit.) | | Boiling point | 246.2±20.0 °C(Predicted) | | density | 1.683±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | Acetonitrile (Slightly), Chloroform (Slightly) | | form | Solid | | pka | 0.90±0.18(Predicted) | | color | Light Brown | | InChI | 1S/C6H4BrNO/c7-6-3-8-2-1-5(6)4-9/h1-4H | | InChIKey | NOBDKWLIAQKADB-UHFFFAOYSA-N | | SMILES | [H]C(=O)c1ccncc1Br |
| Hazard Codes | Xn,Xi | | Risk Statements | 22-36/38-43 | | Safety Statements | 26-36/37 | | WGK Germany | 3 | | Hazard Note | Irritant | | HS Code | 29333990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
Skin Sens. 1 |
| | 3-Bromo-4-formylpyridine Usage And Synthesis |
| Chemical Properties | Off-white solid | | Uses | 3-Bromo-4-pyridinecarboxaldehyde acts as a reagent in the synthesis of 3,4,5-trisubstituted 4,5-dihydro-1,2,4-oxadiazoles agonists which interact with the G-protein-coupled bile acid receptor 1 (TGR5) inducing insulin secretion which may be used as a potential treatment for diabetus mellitus. | | Synthesis | Diisopropylamine (27.6 g, 273.0 mmol) was dissolved in tetrahydrofuran (300 mL) under nitrogen protection and cooled to -78 °C. A tetrahydrofuran solution of n-butyllithium (91 mL, 228.0 mmol, 2.5 M) was slowly added dropwise and stirred at -78 °C for 1 hour. Subsequently, 3-bromopyridine (30.0 g, 190.0 mmol) was added dropwise and stirring was continued at -78 °C for 20 min. Next, N,N-dimethylformamide (55.0 g, 760.0 mmol) was added dropwise and stirred at -78 °C for 1 hour. After completion of the reaction, the mixture was slowly warmed to room temperature and the reaction was quenched with saturated aqueous ammonium chloride solution (150 mL). The aqueous layer was extracted with ethyl acetate (200 mL x 3), and the organic layers were combined and concentrated in vacuum. The residue was purified by silica gel column chromatography to afford 3-bromopyridine-4-aldehyde (12.0 g, 34.0% yield). The product was confirmed by 1H NMR (400 MHz, CD3OD): δ 10.37 (s, 1H), 8.91 (s, 1H), 8.80-8.61 (m, 1H), 7.78-7.63 (m, 1H).LCMS (m/z): 187.0 (M + 1). | | References | [1] Tetrahedron, 2000, vol. 56, # 3, p. 397 - 406
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3146 - 3151
[3] Patent: WO2015/200677, 2015, A2. Location in patent: Paragraph 00504; 00505
[4] Tetrahedron Letters, 1983, vol. 24, # 32, p. 3291 - 3294
[5] Synthesis, 1999, # 2, p. 306 - 311 |
| | 3-Bromo-4-formylpyridine Preparation Products And Raw materials |
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