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CAS No. : | 40106-98-7 | MDL No. : | MFCD09261099 |
Formula : | C9H5ClN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DWKLLQSQXXCSEW-UHFFFAOYSA-N |
M.W : | 208.60 | Pubchem ID : | 12582845 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 55.58 |
TPSA : | 58.71 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) : | -5.69 cm/s |
Log Po/w (iLOGP) : | 1.61 |
Log Po/w (XLOGP3) : | 2.65 |
Log Po/w (WLOGP) : | 2.8 |
Log Po/w (MLOGP) : | 2.04 |
Log Po/w (SILICOS-IT) : | 0.86 |
Consensus Log Po/w : | 1.99 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.27 |
Solubility : | 0.113 mg/ml ; 0.000543 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.53 |
Solubility : | 0.061 mg/ml ; 0.000292 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.7 |
Solubility : | 0.0412 mg/ml ; 0.000198 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.95 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
59% | at -15 - 20℃; for 3 h; | a. 4-Chloro-8-nitroquinoline (6a) and 4-chloro-5-nitroquinoline (6d). 4-Chloroquinoline (10.0 g, 61.3 mmol) was added in small portions to sulfuric acid (45 mL) taking care to maintain the temperature at or below [15 °C.] Then the solution was cooled and maintained at-5 °C during the addition of fuming nitric acid (9 mL). The mixture was allowed to warm to room temperature and stirred for an additional 3 h. The reaction mix was poured on ice and basified (pH 9) with NH40H. The resulting precipitate was filtered, washed well with water, dried, and recrystallized from methanol to provide 7.5 g (59percent) [OF 6A] as golden-brown needles; mp [128-129 °C] (lit. 32 mp [129-130 °C) ; IH NMR (CDC13)] [6] 7.67 (d, 1H, [J=4.] 5), 7.75 (dd, 1H, [J=8.] 6,. [J=7.] 6), 8.10 (dd, 1H, [J=7.] 6, [J=1.] 3), 8. 48 (dd, 1H, [J=8.] 6, J=1. 3), 8.94 (d, 1H, J=4. 5); [13C] NMR (CDC13) [6] 123.0, 124.4, 126.5, 127.5, 128.3, 140.6, 143.2, 148.7, 152.1. The mother liquor was evaporated and chromatographed in 19: 1 hexanes-ethyl acetate, to provide 2.05 g (16percent) of the 5-nitro isomer 6d as a very light yellow solid; mp [144-146 °C] (lit. 31 mp [150 °C) ; IH] NMR (CDCl3) [6] 7.65 (d, 1H, J=4. 7), 7. 82 [(M,] 2H), 8.35 (dd, [1H,] [J=2.] 5, J=7. 3), 8.90 (d, 1H, J=4. 7); [13C] NMR [(CDC13)] 8 118.2, 123.4, 125.1, 128.8, 134.2, 135.6, 139.1, 149.7, 151.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | at -15 - 20℃; for 3 h; | a. 4-Chloro-8-nitroquinoline (6a) and 4-chloro-5-nitroquinoline (6d). 4-Chloroquinoline (10.0 g, 61.3 mmol) was added in small portions to sulfuric acid (45 mL) taking care to maintain the temperature at or below [15 °C.] Then the solution was cooled and maintained at-5 °C during the addition of fuming nitric acid (9 mL). The mixture was allowed to warm to room temperature and stirred for an additional 3 h. The reaction mix was poured on ice and basified (pH 9) with NH40H. The resulting precipitate was filtered, washed well with water, dried, and recrystallized from methanol to provide 7.5 g (59percent) [OF 6A] as golden-brown needles; mp [128-129 °C] (lit. 32 mp [129-130 °C) ; IH NMR (CDC13)] [6] 7.67 (d, 1H, [J=4.] 5), 7.75 (dd, 1H, [J=8.] 6,. [J=7.] 6), 8.10 (dd, 1H, [J=7.] 6, [J=1.] 3), 8. 48 (dd, 1H, [J=8.] 6, J=1. 3), 8.94 (d, 1H, J=4. 5); [13C] NMR (CDC13) [6] 123.0, 124.4, 126.5, 127.5, 128.3, 140.6, 143.2, 148.7, 152.1. The mother liquor was evaporated and chromatographed in 19: 1 hexanes-ethyl acetate, to provide 2.05 g (16percent) of the 5-nitro isomer 6d as a very light yellow solid; mp [144-146 °C] (lit. 31 mp [150 °C) ; IH] NMR (CDCl3) [6] 7.65 (d, 1H, J=4. 7), 7. 82 [(M,] 2H), 8.35 (dd, [1H,] [J=2.] 5, J=7. 3), 8.90 (d, 1H, J=4. 7); [13C] NMR [(CDC13)] 8 118.2, 123.4, 125.1, 128.8, 134.2, 135.6, 139.1, 149.7, 151.2. |