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CAS No. : | 214614-81-0 | MDL No. : | MFCD06804929 |
Formula : | C5H7BrN2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | REUWXYIZJBMWPB-UHFFFAOYSA-N |
M.W : | 191.03 | Pubchem ID : | 16640642 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 37.16 |
TPSA : | 38.05 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.34 cm/s |
Log Po/w (iLOGP) : | 1.38 |
Log Po/w (XLOGP3) : | 0.17 |
Log Po/w (WLOGP) : | 0.64 |
Log Po/w (MLOGP) : | 0.29 |
Log Po/w (SILICOS-IT) : | 0.74 |
Consensus Log Po/w : | 0.64 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.41 |
Solubility : | 7.42 mg/ml ; 0.0389 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.53 |
Solubility : | 56.8 mg/ml ; 0.297 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.5 |
Solubility : | 6.05 mg/ml ; 0.0317 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.8 |
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 |
---|---|---|
86% | With potassium hydroxide; potassium iodide In ethanol at 155℃; for 8 h; microwave | The mixture of 8d (400mg, 2.72mmol), KI (671mg, 4.04mmol), KOH (290mg, 5.2mmol) and 22a (625mg, 5.0mmol) in EtOH (1OmL) were reacted under microwave condition at 1550C for 8h. After the reaction was complete, the mixture was cooled, filtered and evaporated. The residue was dissolved in 2OmL of EtOAc 15 and washed with 2OmL of water, dried over Na2SO4 and concentrated to give 22b (0.45g, 86percent yield) as yellow oil. |
65% | With tetra-(n-butyl)ammonium iodide; caesium carbonate In N,N-dimethyl-formamide at 90℃; for 2 h; | To a solution of 4-bromo-1H-pyrazole (1.00 g, 6.80 mmol) in 20 mL of DMF was successively added 2-bromoethanol (0.53 mL, 7.48 mmol), Cs2CO3 (2.66 g, 8.16 mmol) and TBAI (503 mg, 1.36 mmol). The resulting mixture was heated at 90 °C for 2 h and diluted with 60 mL of water. The mixture was extracted with EA (3 × 100 mL). The combined organic layer was washed with water (3 × 50 mL), brine (60 mL), dried over anhydrous Na2SO4 and concentrated under vacuum. The crude product was purified by flash column chromatography (0-30percent EA/PE gradient) to afford 27 as light yellow oil in 65percent yield. 1H NMR (300 MHz, CDCl3) δ 7.49 (s, 1H), 7.48 (s, 1H), 4.23 (t, J = 4.8 Hz, 2H), 3.99 (t, J = 4.8 Hz, 2H), 2.73 (br, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | Stage #1: With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5 h; Stage #2: at 20℃; |
General Procedure 77 To a stirred solution of 4-bromo-1H-pyrazole in DMF was added sodium hydride at room temperature. The mixture was stirred for 30 minutes, [1,3]dioxolan-2-one was added, the mixture was stirred and slowly warmed to room temperature. The reaction was monitored by TLC. After the reaction was done, EtOAc was added, washed with saturated NaHCO3, water and brine, dried with Na2SO4, filtered and concentrated. The residue was purified by silica gel, eluants EtOAc and DCM 10percent, to give 2-(4-Bromo-pyrazol-1-yl)-ethanol 0.22 g, yield 34percent. 1H NMR (400 MHz, chloroform-D) δ ppm 7.49 (s, 1H) 7.46 (s, 1H) 4.18-4.23 (m, 2H) 3.93-3.98 (m, 2H) 3.09 (s, 1H). |
34% | Stage #1: With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5 h; Stage #2: at 20℃; |
To a stirred solution of 4-bromo-1 H-pyrazole in DMF was added sodium hydride at room temperature. The mixture was stirred for 30 minutes, [1,3]dioxolan-2-one was added, the mixture was stirred and slowly warmed to room temperature. The reaction was monitored by TLC. After the reaction was done, EtOAc was added, washed with saturated NaHCO3, water and brine, dried with Na2SO4, filtered and concentrated. The residue was purified by silica gel, eluants EtOAc and DCM 10percent, to give 2-(4-Bromo-pyrazol-1-yl)-ethanol 0.22 g, yield 34percent. 1H NMR (400 MHz, chloroform-D) 6 ppm 7.49 (s, 1 H) 7.46 (s, 1 H) 4.18 - 4.23 (m, 2 H) 3.93 - 3.98 (m, 2 H) 3.09 (s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26.6% | Stage #1: With potassium acetate In N,N-dimethyl-formamide for 0.166667 h; Stage #2: at 80℃; |
To a solution of 22b (0.45g, 2.36mmol) and bis(pinacolato)diboron (0.718g, 2.83mmol) in DMF (2OmL), was added KOAc (0.694g, 7.08mmol). The mixture was 0 degassed with N2, stirred for 1 Omin and added Pd(dppf)Cl2 (58mg, 0.071 mmol). The mixture was degassed with N2 and stirred at 8O0C overnight. DMF was removed and the residue was purified by column chromatography (EA:PE=1 :10) to afford of 22c (149mg, 26.6percent yield). |
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