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| 2-Chloropyridine-5-sulfonyl chloride Basic information |
| 2-Chloropyridine-5-sulfonyl chloride Chemical Properties |
Melting point | 51 °C | Boiling point | 132 °C(Press: 8 Torr) | density | 1.615±0.06 g/cm3(Predicted) | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | form | solid | pka | -5.29±0.10(Predicted) | Appearance | White to light yellow Solid | InChI | InChI=1S/C5H3Cl2NO2S/c6-5-2-1-4(3-8-5)11(7,9)10/h1-3H | InChIKey | QXZKKHONVQGXAK-UHFFFAOYSA-N | SMILES | C1=NC(Cl)=CC=C1S(Cl)(=O)=O | CAS DataBase Reference | 6684-39-5(CAS DataBase Reference) |
Hazard Codes | Xi | Risk Statements | 36 | Safety Statements | 26 | HS Code | 2933399990 |
| 2-Chloropyridine-5-sulfonyl chloride Usage And Synthesis |
Uses | 6-Chloro-3-pyridinesulfonyl Chloride, is a heterocylic building block used for chemical synthesis. It is also an intermediate in the synthesis of 6-Aminopyridine-3-sulfonamide (A628835), that can be used as anticoccidial agents. | Synthesis | General procedure for the synthesis of 2-chloropyridine-5-sulfonyl chloride from 2-chloro-5-aminopyridine: 10 g (79.2 mmol) of 2-chloro-5-aminopyridine was dissolved in a mixture of concentrated hydrochloric acid (16 mL) and glacial acetic acid (89 mL), and cooled to 10 °C in an ice bath. 5.46 g (79.2 mmol) of sodium nitrite was added in batches and the reaction temperature was controlled to be below 15 °C. After stirring the reaction mixture for 1 hour, it was slowly added dropwise to a solution containing sulfur dioxide (carrier 27 mL), 2.77 g (16.2 mmol) of sulfur dioxide, copper(II) chloride dihydrate, and a solution consisting of acetic acid (59 mL) and water (11 mL), with the dropwise addition time being controlled to be between 5 and 10 minutes. The reaction mixture was gradually warmed to room temperature and subsequently poured into an ice-water mixture (300 mL) and stirring was continued for 15 minutes. The precipitate was isolated by filtration, washed with water (2 x 100 mL) and dried under reduced pressure to give 12.99 g of 2-chloropyridine-5-sulfonyl chloride. The product was characterized by 1H NMR (400 MHz, chloroform-d): δ 7.62 (1H, d, J = 8.31 Hz), 8.26 (1H, dd, J = 8.56,2.69 Hz), 9.04 (1H, d, J = 2.69 Hz). | References | [1] Patent: US2008/39464, 2008, A1. Location in patent: Page/Page column 30-31 [2] Organic Process Research and Development, 2009, vol. 13, # 5, p. 875 - 879 [3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 13, p. 3947 - 3953 [4] Patent: WO2009/39328, 2009, A1. Location in patent: Page/Page column 54 [5] Patent: EP1144368, 2004, B1. Location in patent: Page 64 |
| 2-Chloropyridine-5-sulfonyl chloride Preparation Products And Raw materials |
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