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CAS No. : | 4965-34-8 | MDL No. : | MFCD09787847 |
Formula : | C10H8BrN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VEKOCCXFMXGRTF-UHFFFAOYSA-N |
M.W : | 222.08 | Pubchem ID : | 12332896 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 54.41 |
TPSA : | 12.89 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.33 cm/s |
Log Po/w (iLOGP) : | 2.39 |
Log Po/w (XLOGP3) : | 3.28 |
Log Po/w (WLOGP) : | 3.31 |
Log Po/w (MLOGP) : | 2.85 |
Log Po/w (SILICOS-IT) : | 3.6 |
Consensus Log Po/w : | 3.08 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.9 |
Solubility : | 0.028 mg/ml ; 0.000126 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.23 |
Solubility : | 0.132 mg/ml ; 0.000595 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.95 |
Solubility : | 0.00251 mg/ml ; 0.0000113 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.46 |
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 |
---|---|---|
46% | Stage #1: With hydrogenchloride In water at 0 - 20℃; for 4 h; Reflux Stage #2: With sodium hydroxide In water at 0℃; |
Doebner Miller synthesis: 3-Bromoaniline (10 mL, 92 mmol) was added to a solution of 37 percent HCl at 0 °C (200 mL). Paraldehyde (11 mL, 0.8 mol, 9 eq) was then introduced and the mixture was left to react at room temperature for 1 hour, and then heated to reflux temperature for 3 hours. After cooling to 0 °C, a saturated aquous solution of sodium hydroxide (200 mL) was slowly added and the mixture was extracted with dichloromethane. The organic layer was washed with water and brine, then dried over MgSO4, and concentrated under reduced pressure. The crude product was obtained as a mixture of 5-bromoquinaldine and 7-bromoquinaldine that were separated by column chromatography (SiO2, cyclohexane-AcOEt 9:1). The 7-bromoquinaldine regioisomer was obtained as a sand yellow solid (9,3 g, 46 percent). Molecular formula: C10H8BrN. Molecular weight: 222.08 g.mol-1. IR (film): 1610, 1494, 1264, 841, 736 cm-1. Tfusion: 57 °C. 1H NMR: δ 8.09 (s, 1H, H8), 7.80 (d, J = 8.2 Hz, 1H, H4), 7.39 (m, 2H, H5 et H7), 7.12 (d, J = 8.2 Hz, 1H, H3), 2.61 (s, 3H, H9). 13C NMR: δ 160.3 (s, C2), 148.6 (s, C8a), 136.2 (s, C4), 131.2 (s, C8), 129.4 (s, C5), 128.9 (s, C6), 125.3 (s, C4a), 123.7 (s, C7), 122.6 (s, C3), 25.7 (s, C9). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | Stage #1: With hydrogenchloride In water at 0℃; for 4 h; Reflux Stage #2: With sodium hydroxide In water at 0℃; |
1) Preparation of 7-bromo-2-methyl-quinolineDoebner-Miller synthesis:3-bromoaniline (3 mL, 27 mmol), was added to a solution of 37percent HC1 at 0°C (24 mL). Paraldehyde (8 mL, 83 mmol, 3 eq) was then introduced and the mixture was left to react at room temperature for 1 hour, then refluxed for 3 hours. After cooling to 0°C, sodium hydroxide (25 mL) was added dropwise and the mixture was extracted with dichloromethane. The organic layer was washed twice with water and brine, then dried over MgS04, and concentrated under reduced pressure. The product was purified by column chromatography (Si02, Cyclohexane-AcOEt 9/1) and obtained as a white solid (2.8 g, 46percent).Molecular formula: Ci0HgBrNMolecular weight: 222.08 g.mol"1 IR (film): 1610, 1494, 1264, 841, 736 cm-1 Melting point: 57°C1H NMR: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | Stage #1: With hydrogenchloride In water at 0℃; for 4 h; Reflux Stage #2: With sodium hydroxide In water at 0℃; |
3-Bromoaniline (10 mL, 92 mmol) was added to a solution of 37 percent HC1 at 0 °C (200 mL). Paraldehyde (1 1 mL, 0.8 mol, 9 eq) was then introduced and the mixture was left to react at room temperature for 1 hour, and then heated to reflux temperature for 3 hours. After cooling to 0 °C, a saturated aquous solution of sodium hydroxide (200 mL) was slowly added and the mixture was extracted with dichloromethane. The organic layer was washed with water and brine, then dried over MgS04, and concentrated under reduced pressure. The crude product was obtained as a mixture of 5-bromoquinaldine and 7-bromoquinaldine that were separated by column chromatography (Si02, cyclohexane- AcOEt 9: 1). The 7-bromoquinaldine regioisomer was obtained as a sand yellow solid (9,3 g, 46 percent).Molecular formula: CioH8BrN.Molecular weight: 222.08 g.mol"s.IR (film): 1610, 1494, 1264, 841, 736 cm"1.Tfusion: 57 °C.1H NMR: δ 8.09 (s, 1H, H8), 7.80 (d, J = 8.2 Hz, 1H, H4), 7.39 (m, 2H, H5 et H7), 7.12 (d, J= 8.2 Hz, 1H, H3), 2.61 (s, 3H, H9).13C NMR: δ 160.3 (s, C2), 148.6 (s, C8a), 136.2 (s, C4), 131.2 (s, C8), 129.4 (s, C5), 128.9(s, C6), 125.3 (s, C4a), 123.7 (s, C7), 122.6 (s, C3), 25.7 (s, C9). |