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CAS No. : | 552331-30-3 | MDL No. : | MFCD12028623 |
Formula : | C9H9BrN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FMYUTSXDZFFESE-UHFFFAOYSA-N |
M.W : | 225.09 | Pubchem ID : | 22607588 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 53.66 |
TPSA : | 17.82 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) : | -5.78 cm/s |
Log Po/w (iLOGP) : | 2.23 |
Log Po/w (XLOGP3) : | 2.66 |
Log Po/w (WLOGP) : | 2.64 |
Log Po/w (MLOGP) : | 2.49 |
Log Po/w (SILICOS-IT) : | 2.54 |
Consensus Log Po/w : | 2.51 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.47 |
Solubility : | 0.0769 mg/ml ; 0.000342 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.69 |
Solubility : | 0.464 mg/ml ; 0.00206 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.72 |
Solubility : | 0.0429 mg/ml ; 0.000191 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.58 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
67% | With NaH In N,N-dimethyl-formamide | Example 112A 5-Bromo-1,3-dimethyl-1H-indazole Example 102C (500 mg; 2.37 mmol) was added to a mixture of 60percent NaH (115 mg; 2.84 mmol) in DMF (10 mL). After 15 min. at r.t. iodomethane (456 mg; 3.21 mmol) was added, the reaction was stirred for 2 hrs then diluted with water and extracted with EtOAc. The extracts were rinsed with water and brine, dried (MgSO4), evaporated, and isolated by flash chromatography (1:1 Et2O:hexane) to give the desired product (360 mg; 67percent). |
67% | Stage #1: With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.25 h; Stage #2: at 20℃; for 2 h; |
Example 112A 5-Bromo-1,3-dimethyl-1H-indazole Example 102C (500 mg; 2.37 mmol) was added to a mixture of 60percent NaH (115 mg; 2.84 mmol) in DMF (10 mL). After 15 min. at r.t. iodomethane (456 mg; 3.21 mmol) was added, the reaction was stirred for 2 hrs then diluted with water and extracted with EtOAc. The extracts were rinsed with water and brine, dried (MgSO4), evaporated, and isolated by flash chromatography (1:1 Et2O:hexane) to give the desired product (360 mg; 67percent). |
67% | With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.25 h; Inert atmosphere | To a stirred solution of 5-bromo-3-methyl- 1H-indazole (2.51 g, 11.6 mmol), dissolved in N,N-dimethylformamide (30 mL) and cooled to 0°C under nitrogen, was added portionwise sodium hydride (60percent dispersion in mineral oil; 596 mg, 14.9 mmol).The dark brown, effervescing solution was stirred for 70 minutes prior to addition of iodomethane (0.87 mL, 14 mmol). The reaction mixture was stirred at 0°C for 15 minutes before warming to r.t. A brown-orange solid was formed and the mixture was stirred for 3 h prior to the addition of water (30 mL) and EtOAc (30 mL). The mixture was stirred for 40 minutes before leaving to stand overnight. Further EtOAc (20 mL) andwater (20 mL) were added, then the organic layer was separated. The aqueous layer was re-extracted with further EtOAc (2 x 50 mL). The organic layers were combined, dried with anhydrous sodium sulfate and filtered under reduced pressure, then the solvent was removed in vacuo. The resulting brown oil was purified by flash column chromatography on silica (gradient elution with 0-100percent EtOAc/isohexane) to afford the title compound (1.75 g, 67percent) as an orange oil. oH (DMSO-d6, 300 MHz) 7.94 (dd, J 1.7, 0.7 Hz, 1H), 7.55 (dd,J8.8, 0.7 Hz, 1H), 7.46 (dd,J8.9, 1.8 Hz, 1H), 3.95 (s, 3H), 2.45 (s, 3H). LCMS (ES+) [M+H] 227.0, RT 2.00 minutes (method 3). |
39% | Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5 h; Stage #2: at 0℃; for 4 h; |
To a stirred suspension of NaH (60percent oil dispersion, 136 mg,2.83 mmol) in DMF (10 mL) was added a solution of 24 (400 mg,1.89 mmol) in DMF (2 mL) at 0 C, and the mixture was stirred atthe same temperature for 30 min. MeI (400 lL, 2.83 mmol) wasadded and the resulting mixture was stirred at 0 C for 4 h. Thereaction mixture was quenched with water and extracted withEtOAc. The combined EtOAc layers were washed with brine, driedover Na2SO4, and concentrated. The residue was purified by columnchromatography (silica gel, hexane/EtOAc = 80/20) to givethe title compound (200 mg, 39percent) as a yellow oil. 1H NMR(400 MHz, DMSO-d6) d 2.45 (3H, s), 3.95 (3H, s), 7.46 (1H, dd,J = 8.9, 1.8 Hz), 7.54 (1H, d, J = 8.9 Hz), 7.94 (1H, d, J = 1.5 Hz). MS(ESI/APCI) m/z = 225.0 [M+H]+. |
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