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CAS No. : | 474706-74-6 | MDL No. : | MFCD18800553 |
Formula : | C7H4BrIN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VADGFPDSVWQCHR-UHFFFAOYSA-N |
M.W : | 322.93 | Pubchem ID : | 22031632 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 55.61 |
TPSA : | 17.3 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.04 cm/s |
Log Po/w (iLOGP) : | 2.37 |
Log Po/w (XLOGP3) : | 3.14 |
Log Po/w (WLOGP) : | 2.7 |
Log Po/w (MLOGP) : | 2.35 |
Log Po/w (SILICOS-IT) : | 2.59 |
Consensus Log Po/w : | 2.63 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.43 |
Solubility : | 0.0121 mg/ml ; 0.0000375 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.17 |
Solubility : | 0.217 mg/ml ; 0.000672 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.87 |
Solubility : | 0.0441 mg/ml ; 0.000136 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.28 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With N-iodo-succinimide In acetonitrile at 20℃; for 1 h; | To a solution of 6-bromoimidazo[1,2-a]pyridine (721 mg 3.66 mmol) in 20 mL ACN were added 988 mg (4.39 mmol) of N-iodosuccinimide. The reaction was stirred at room temperature for 1 h. Solvent was removed in vacuo then residue was diluted with CH2Cl2 and washed successively with 10percent NaOH aqueous solution, saturated thiosulfate solution and then with water. The organic layer was dried over magnesium sulfate and concentrated in vacuo to afford the desired product as a white solid (1.18 g), 96percent yield, mp 209 °C; IR (ATR) ν (cm-1) 3024. 1516. 711. 698. 1H NMR (400 MHz, CDCl3) δ 7.29 (dd, J=9.6, 1.8 Hz, 1H), 7.51 (d, J=9.6 Hz, 1H), 7.70 (s, 1H), 8.26-8.28 (m, 1H). 13C NMR (100.6 MHz, CDCl3) δ 61.4, 108.4, 118.6, 126.4, 128.6, 128.6, 141.1, 146.5. HRMS (EI) m/z calcd for C7H4BrIN2 [M+H]+: 322.8675, found: 322.8678. |
77% | With N-iodo-succinimide In acetonitrile for 16.0833 h; | To a slightly cloudy mixture of 6-bromoimidazo[l,2-α]pyridine (15.4 g, 78.0 mmol) in dry MeCN (500 mL) was added jV-iodosuccinimide (17.6 g, 78.0 mmol) portionwise over ~5 min (a precipitate immediately formed). After 16 h, the crude product was collected by filtration and triturated with boiling MeCN to provide 19.56 g (77percent) of the title compound as an off-white solid. MS(ES)+ m/e 198.7 [M+H]+. |
67% | With N-iodo-succinimide In acetonitrile at 20℃; for 5 h; | Step: 1 To a solution of 6-bromoimidazo [l ,2-a]pyridine (20 g, 101.5 mmol) in ACN (300 mL) was added N-iodosuccinimide (22.8 g, 101.5 mmol) at rt and stirred for 5 h. The reaction mixture was filtered and washed with hot acetonitrile to afford 6-bromo-3-iodoimidazo[l,2- ajpyridine (22 g, 67percent) as a pale yellow solid. 1H NMR (400 MHz, CDC13) δ 8.29 (s, 1H), 7.58 (d, J= 9.2 Hz, 1H), 7.35 (d, J= 7.6 Hz, 1H), 7.27 (s, 1H). |
67% | With N-iodo-succinimide In acetonitrile at 20℃; for 5 h; | To a solution of 6-bromoimidazo[1,2-a]pyridine (20 g, 101.5 mmol) in ACN (300 mL) was added N-iodosuccinimide (22.8 g, 101.5 mmol) at rt and stirred for 5 h. The reaction mixture was filtered and washed with hot acetonitrile to afford 6-bromo-3-iodoimidazo[1,2-a]pyridine (22 g, 67percent) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.29 (s, 1H), 7.58 (d, J=9.2 Hz, 1H), 7.35 (d, J=7.6 Hz, 1H), 7.27 (s, 1H). |
51% | With N-iodo-succinimide In acetonitrile at 20℃; for 1 h; | To a solution of 6-bromoimidazo[1,2-a]pyridine (5 g, 25.4 mmol) in CH3CN (139 mL) was added NIS (6.85 g, 30.5 mmol). The reaction was stirred at r.t. for 1 hour and the reaction was concentrated. The residue was diluted with DCM (140 mL) and washed with 100 mL of 10 percent NaOH, 100 mL of saturated thiosulfate solution, and then 100 mL of water. The organic layer was dried over MgSO4, filtered and concentrated. The material was isolated as a beige solid (4.163 g, 51 percent yield).1H NMR (400 MHz, CDCl3) δ 8.28– 8.27 (m, 1H), 7.69 (s, 1H), 7.51 (dd, J = 1.2, 12.8 Hz, 1H), 7.29 (dd, J = 2.8, 12.8 Hz, 1H). This material had spectra that were indistinguishable from the literature. |
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