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CAS No. : | 19064-73-4 | MDL No. : | MFCD11101043 |
Formula : | C8H5BrN2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DHXVJJHOVGTNDK-UHFFFAOYSA-N |
M.W : | 225.04 | Pubchem ID : | 614310 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 50.06 |
TPSA : | 45.75 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) : | -6.38 cm/s |
Log Po/w (iLOGP) : | 1.53 |
Log Po/w (XLOGP3) : | 1.82 |
Log Po/w (WLOGP) : | 1.69 |
Log Po/w (MLOGP) : | 2.27 |
Log Po/w (SILICOS-IT) : | 2.75 |
Consensus Log Po/w : | 2.01 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.0 |
Solubility : | 0.226 mg/ml ; 0.001 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.4 |
Solubility : | 0.895 mg/ml ; 0.00398 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.09 |
Solubility : | 0.0181 mg/ml ; 0.0000804 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.12 |
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 |
---|---|---|
60% | Stage #1: With phosphorus pentabromide In dichloromethane for 24 h; Heating / reflux Stage #2: at 120℃; for 2 h; |
4-Bromo-2H-phthalazin-1-one: 2,3-Dihydro-1,4-phthalazinedione (12.5 g, 78 mmol) was suspended in DCE (200 ml) and phosphorous pentabromide (50.0 g, 116 mmol) was added in one portion and the reaction heated to reflux for 24 hours. A further portion of phosphorous pentabromide (20.0 g, 70 mol) was added and the reaction heated for a further 24 hours. The reaction was cooled to RT and poured into ice water. The resulting precipitate was filtered and washed with water to give a crude mixture of mono and dibrominated product (22.8 g). This crude material was suspended in HOAc (230.0 mL) and heated to 120° C. for 2 hrs. The reaction was cooled to RT and poured into ice water and the resulting precipitate filtered. The solid was washed with water and dried to give the title compound (10.4 g, 60percent yield) as a white solid. 1H-NMR: (400 MHz, D6-DMSO), 12.95 (1H, s), 8.25 (1H, dd), 8.03 (1H, ddd), 7.96-7.90-(2H, m); MS (ESI+)=(M+H)+ 225 227 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With bromine; potassium bromide In water at 20℃; for 31 h; Heating | The reaction was carried out in a round-bottom flask fitted with a magnetic stirrer bar. To a suspension of phthalazin-1(2H)-one (2) or 2-methylphthalazin-1(2H)-one (5) or pyridopyridazinone 8 (6.84mmol) in water (55mL) (Method A) or in the acetate buffer solution pH=5.8 (55mL) (Method B), was added potassium bromide (8.44mmol) and bromine (8.44mmol) at an ambient temperature. The mixture was then stirred for 6h at an ambient temperature, and next the whole was heated to boiling and stirred for 25h until the bromine colour entirely disappeared. After cooling to an ambient temperature (in the case of 9 the mixture was adjusted to pH 7 with saturated NaHCO3) the separated solid was collected by filtration and washed with water (5mL). The crude product was purified by flash chromatography. 4.4.1 4-Bromophthalazin-1(2H)-one (3) (Path A) White solid; Yield: 693 mg, 45percent (Method A), 1.02 g, 66percent (Method B); Mp: 279-281 °C, (lit. 277-279 °C;273 °C ); Rf (DCM/AcOEt/Hex 6:1:1)=0.24; FTIR (KBr): ν=3022, 2931, 2892, 1671, 1659 (C=O), 1581 cm-1; 1H NMR (600 MHz, DMSO-d6): δ=12.94 (s, 1H, NH), 8.26 (d, J=7.9 Hz, 1H, 8 Ar-H), 8.06-8.01 (m, 1H, Ar-H), 7.97-7.91 (m, 2H, Ar-H); 13C NMR (150 MHz, DMSO-d6): δ=159.1 (C=O), 134.8, 133.1, 129.9, 129.4, 128.2, 127.6, 126.5 ppm; HRMS (ESI) m/z: calcd for C8H6BrN2O [M+H]+ 224.9658, found 224.9658. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: at 120℃; for 2 h; Stage #2: at 0 - 20℃; |
This crude material was suspended in acetic acid (230.OmL) and heated to 12O0C for 2 hrs. The reaction was cooled to room temperature and poured into ice water EPO <DP n="156"/>and the resulting precipitate filtered. The solid was washed with water and dried to give the title compound (10.4g, 60percent yield) as a white solid. 1H-NMR: (400 MHz, D6-DMSO), 12.95 (IH, s), 8.25 (IH, dd), 8.03 (IH, ddd), 7.96-7.90-(2H, m); MS (ESI+) = (M+H)+ 225 227 |
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