| Identification | Back Directory | [Name]
3H-Imidazo[4,5-b]pyridine, 5,7-dichloro- | [CAS]
24485-01-6 | [Synonyms]
Nsc264046
7-dichloro-1H-iMidazo[4
5,7-Dichloroimidazo[4,5-b]pyridine
5,7-dichloro-1H-imidazo[4,5-b]pyridine
5,7-dichloro-7aH-imidazo[4,5-b]pyridine
1H-IMidazo[4,5-b]pyridine, 5,7-dichloro-
3H-Imidazo[4,5-b]pyridine, 5,7-dichloro-
(1)5,7-dichloro-3H-imidazo[4,5-b]pyridine | [Molecular Formula]
C6H3Cl2N3 | [MDL Number]
MFCD13189664 | [MOL File]
24485-01-6.mol | [Molecular Weight]
188.01 |
| Chemical Properties | Back Directory | [Melting point ]
273-274 °C | [Boiling point ]
200.8±50.0 °C(Predicted) | [density ]
1.79±0.1 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [pka]
5.37±0.40(Predicted) | [Appearance]
Off-white to pink Solid | [InChI]
InChI=1S/C6H3Cl2N3/c7-3-1-4(8)11-6-5(3)9-2-10-6/h1-2H,(H,9,10,11) | [InChIKey]
IKJFWUNKUZVHGU-UHFFFAOYSA-N | [SMILES]
C12NC=NC1=C(Cl)C=C(Cl)N=2 |
| Questions And Answer | Back Directory | [Uses]
5,7-Dichloro-1H-imidazo[4,5-B]pyridine is an important type of imidazopyridine compound with good antimicrobial and bactericidal effects. |
| Hazard Information | Back Directory | [Synthesis]
General procedure for the synthesis of 5,7-dichloro-1H-imidazo[4,5-B]pyridine from 7-nitro-3H-imidazo[4,5-B]pyridine 4-oxide: 7-nitro-1H-imidazo[4,5-b]pyridine 4-oxide (2.0 g, 11.04 mmol) was added batchwise to a mixed solution of ice-bath-cooled (0 °C) phosphoryl chloride (POCl3, 30 mL , 322 mmol) and N,N-dimethylformamide (DMF, 15 mL) in a mixed solution. Subsequently, the reaction mixture was heated to 120°C and maintained for 3 hours. After completion of the reaction, it was cooled to room temperature, slowly poured into ice water and neutralized with 5 M sodium hydroxide solution. The reaction mixture was extracted with ethyl acetate (3 × 75 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford the crude product 5,7-dichloro-3H-imidazo[4,5-b]pyridine (1.86 g, 9.89 mmol, 90% yield), which was used directly in the next reaction without further purification. Mass spectrum (electrospray ionization) m/e 188 ([M+H]+). 1H NMR (400 MHz, methanol-d4) δ 8.45 (broad single peak, 1H), 7.46 (single peak, 1H). | [References]
[1] Patent: WO2013/95761, 2013, A1. Location in patent: Page/Page column 32; 33; 34
[2] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 8, p. 1757 - 1760
[3] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 8, p. 1757 - 1760 |
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