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CAS No. : | 5926-51-2 | MDL No. : | MFCD00005519 |
Formula : | C4HBrO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YPRMWCKXOZFJGF-UHFFFAOYSA-N |
M.W : | 176.95 | Pubchem ID : | 80027 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 28.11 |
TPSA : | 43.37 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.83 cm/s |
Log Po/w (iLOGP) : | 0.8 |
Log Po/w (XLOGP3) : | 0.77 |
Log Po/w (WLOGP) : | 0.35 |
Log Po/w (MLOGP) : | 0.42 |
Log Po/w (SILICOS-IT) : | 1.32 |
Consensus Log Po/w : | 0.73 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.42 |
Solubility : | 6.69 mg/ml ; 0.0378 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.26 |
Solubility : | 9.7 mg/ml ; 0.0548 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.11 |
Solubility : | 13.8 mg/ml ; 0.078 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.41 |
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 |
---|---|---|
87% | With hydrazinium sulfate In water at 100℃; for 19 h; | Hydrazine sulfate (2.25 g. 17,2 mmol) was dissolved in boiling water (20 ml.) with stirring. To this solution, bromomaieic anhydride (2.6mL, 28.2 mmol) was added dropwise via addition funnel, the mixture heated ( 100 °C) under reflux for 19 h, then cooled to ambient temperature. The resulting white precipitate was filtered on a medium frit sintered glass funnel, washed with acetone (3 x 5ml), and air dried in vacuo to give the desired product 4-bromo-l,2- dihydropyridazine--3,6-dione (2.85 g) as a white powder in 87percent yield (gravimetric) with a melting point of 262 °C. |
83% | With hydrazinium sulfate In water at 90℃; for 4 h; | To a solution of N2H4·H2SO4 (3.7 g, 28.3 mmol) in H2O (50 mL) was added dropwise compound 1 (5 g, 28.3 mmol), and the mixture was stirred at 90 °C for 4 h. After the reaction, it was filtered to get compound 2 (4.5 g, yield: 83percent). 1H-NMR (DMSO-d6, 400 MHz,) δ 12.47 (s, 1H), 11.17 (s, 1H), 7.62 (s, 1H). |
77% | With hydrazine hydrate In tetrahydrofuran | a 4-Bromo-1,2-dihydropyridazine-3,6-dione Hydrazine hydrate (28 ml, 576 mmol) was added dropwise to a stirred solution of bromomaleic anhydride (100 g, 565 mmol) in THF (1l) cooled in an ice-bath so that the internal temperature did not exceed 10° C. After complete addition of the hydrazine the mixture was refluxed for 18 h. Solvent was removed by evaporation and the residues were dried by azeotroping with toluene. The residue was triturated and washed with diethyl ether to give the title compound as an orange solid (83 g, 77percent). 1H NMR (250 MHz, d6-DMSO) δ7.68 (1H, br s). MS (ES+) m/e 193 [MH]+, 191 [MH]+. This material was used without further purification. |
77% | With hydrazine hydrate In tetrahydrofuran | a 4-Bromo-1,2-dihydropyridazine-3,6-dione Hydrazine hydrate (28 ml, 576 mmol) was added dropwise to a stirred solution of bromomaleic anhydride (100 g, 565 mmol) in THF (1 l) cooled in an ice-bath so that the internal temperature did not exceed 10° C. After complete addition of the hydrazine the mixture was refluxed for 18 h. Solvent was removed by evaporation and the residues were dried by azeotroping with toluene. The residue was triturated and washed with diethyl ether to give the title compound as an orange solid (83 g, 77percent). 1H NMR (250 MHz, d6-DMSO) δ 7.68 (1H, br s). MS (ES+) m/e 193 [MH]+, 191 [MH]+. This material was used without further purification. |
56% | With (x)H2O4S*H4N2 In water at 90℃; for 4 h; | To a solution of NH2NH2•H2504 (362 mg, 2.8 mmol) in H20 (5 mL) was added dropwise 3-bromofuran-2,5-dione (500 mg, 2.8 mmol), and the mixture was stirred at 90 °C for 4hours. After the reaction, the mixture was filtered to get 4-bromo-1,2-dihydropyridazine-3,6- dione (300 mg, yield: 56percent). ‘H-NMR (DMSO-d6, 400 MHz) 12.47 (s, 1H), 11.17 (s, 1H), 7.62 (s, 1H). MS (M+H): 191 / 193. |
56% | With hydrazinium sulfate In water at 90℃; for 4 h; | To a solution ofNH2NH2•H2S04 (362 mg, 2.8 mmol) in H20 (5 mL) was addeddropwise 3-bromofuran-2,5-dione (500 mg, 2.8 mmol), and the mixture was stirred at 90 °C for 410 hours. After the reaction, the mixture was filtered to get 4-bromo-1,2-dihydropyridazine-3,6-dione (300 mg, yield: 56percent). 1H-NMR (DMSO-d6, 400 MHz) 8 12.47 (s, 1H), 11.17 (s, 1H),7.62 (s, 1H). MS (M+Ht: 191 I 193. |
37% | With sodium acetate; hydrazine hydrate In water; acetic acid | a) 4-Bromo-1,2-dihydropyridazine-3,6-dione A mixture of bromomaleic anhydride (50 g, 283 mmol) and sodium acetate (76.5 g, 562 mmol) in 40percent acetic acid/water (750 ml) was treated with hydrazine monohydrate (16.5 ml, 339 mmol) at room temperature under nitrogen. The brown solution was stirred and heated at 100° C. for 18 hours. Upon cooling the mixture was poured into water (1 l) and extracted with ethyl acetate (6*500 ml). The combined extracts were dried (MgSO4), filtered and evaporated to afford the title pyridazine (20 g, 37percent) as an orange solid. 1H NMR (250 MHz, d6-DMSO) 7.68 (br s). MS (ES+) 193 [MH]+, 191 [MH]+. This material was used without further purification. |
37% | With sodium acetate; hydrazine hydrate In water; acetic acid | a 4Bromo-1,2-dihydropyridazine-3,6-dione A mixture of bromomaleic anhydride (50 g, 283 mmol) and sodium acetate (76.5 g, 562 mmol) in 40percent acetic acid/water (750 ml) was treated with hydrazine monohydrate (16.5 ml, 339 mmol) at room temperature under nitrogen. The brown solution was stirred and heated at 100° C. for 18 hours. Upon cooling the mixture was poured into water (1 l) and extracted with ethyl acetate (6*500 ml). The combined extracts were dried (MgSO4), filtered and evaporated to afford the title compound (20 g, 37percent) as an orange solid. 1H NMR (250 MHz, d6-DMSO) δ 7.68 (1H, br s). MS (ES+) m/e 193 [MH]+, 191 [MH]+. This material was used without further purification. |
37% | With sodium acetate; hydrazine hydrate In water; acetic acid | a 4-Bromo-1,2-dihydropyridazine-3,6-dione A mixture of bromomaleic anhydride (50 g, 283 mmol) and sodium acetate (76.5 g, 562 mmol) in 40percent acetic acid/water (750 ml) was treated with hydrazine monohydrate (16.5 ml, 339 mmol) at room temperature under nitrogen. The brown solution was stirred and heated at 100° C. for 18 hours. Upon cooling the mixture was poured into water (11) and extracted with ethyl acetate (6*500 ml). The combined extracts were dried (MgSO4), filtered and evaporated to afford the title compound (20 g, 37percent) as an orange solid. 1H NMR (250 MHz, d6-DMSO) δ7.68 (1H, br s). MS (ES+) m/e 193 [MH]+, 191 [MH]+. This material was used without further purification. |
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