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CAS No. : | 20357-21-5 | MDL No. : | MFCD09040530 |
Formula : | C7H4BrNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WRIAMYXQKSDDRP-UHFFFAOYSA-N |
M.W : | 230.02 | Pubchem ID : | 15063174 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 48.35 |
TPSA : | 62.89 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) : | -7.09 cm/s |
Log Po/w (iLOGP) : | 1.06 |
Log Po/w (XLOGP3) : | 0.87 |
Log Po/w (WLOGP) : | 2.17 |
Log Po/w (MLOGP) : | 1.02 |
Log Po/w (SILICOS-IT) : | 0.51 |
Consensus Log Po/w : | 1.13 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.05 |
Solubility : | 2.04 mg/ml ; 0.00887 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.77 |
Solubility : | 3.86 mg/ml ; 0.0168 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.59 |
Solubility : | 0.597 mg/ml ; 0.00259 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 3.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.89 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
24% | at 25℃; for 3 h; | Treatment of 1 (986 mg, 6.53 mmol) with NBS (878 mg, 4.93 mmol) in H2SO4 (conc. 5.0 mL), as described in the paper gave after chromatography (hexanes/EtOAc, 8:2) the following fractions in order of elution: (I) 4-bromo-2-nitrobenzaldehyde (2)1 (216 mg, 19percent), 5-bromo-2-nitrobenzaldehyde (4)2 (134 mg, 12percent), and 4,5-dibromo-2-nitrobenzaldehyde (7) (18 mg, 1percent) as a yellow solid; (II) 6-bromo-2-nitrobenzaldehyde (5) (268 mg, 24percent),3 3,6-dibromo-2-nitrobenzaldehyde (8) (25 mg, 2percent),4 and 1 (409 mg, 41percent) as a yellow oil; (III) 3-bromo-2-nitrobenzaldehyde (3)5 as a yellow solid (60 mg, 0.26 mmol, 4percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | at 25℃; for 3 h; | N-Bromosuccinimide (NBS) (1.48 g, 8.32 mmol) was added to a solution of 1 (1.01 g, 6.71 mmol) in H2SO4 (concentrated 5.0 mL). The resulting mixture was stirred at ambient temperature (3 h). The reaction was quenched with ice and extracted with ethyl acetate (320mL). The combined organic phases were washed with saturated NaCl (aqueous, 30 mL), dried (MgSO4), and filtered through a silica gel plug, and the solvents were evaporated under reduced pressure. The resulting brown oil was purified by column chromatography (hexanes=EtOAc, 8:2) to afford the following fractions in order of elution: (I) 7 (28 mg, 0.09 mmol, 1percent) as an off-white solid; (II) 2 (328 mg, 21percent), 4 (140 mg, 9percent), and 3,4-dibromo-2-nitrobenzaldehyde (6) (94 mg, 5percent); (III) 5 (310 mg, 20percent), 8 (65 mg, 3percent), 1 (168 mg, 17percent); (IV) 3 (54 mg, 0.23 mmol, 4percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10% | at 60℃; for 3 h; | Treatment of 1 (459 mg, 3.03 mmol) and NBS (677 mg, 3.80 mmol) in H2SO4 (3.0 mL) at 60 oC as described above afforded the following fractions in order of elution: (I) 7 (21 mg, 0.07 mmol, 2percent); (II) 2 (66 mg, 9percent) and 4 (24 mg, 3percent); (III): 2 (5 mg, 0.7percent) and 3,4-dibromo-2-nitrobenzaldehyde 6 (85 mg, 9percent); (IV) 5 (59 mg, 8percent), 8 (13 mg, 1percent), and 1 (18 mg, 4percent); (V) 3 (20 mg, 0.09 mmol, 3percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | at 25℃; for 3 h; | Treatment of 1 (504 mg, 3.33 mmol) and NBS (1.48 g, 8.30 mmol) in H2SO4 (3.0 mL) as described above provided after purification by chromatography (hexanes/EtOAc, 85:15) the following fractions in order of elution: (I) 7 (65 mg, 0.21 mmol, 9percent); (II) 2 (153 mg, 20percent), 4 (58 mg, 8percent), and 6 (128 mg, 12percent); (III) 5 (108 mg, 14percent), 8 (129 mg, 13percent), and 1 (17 mg, 3percent); (IV) 3 (57 mg, 0.25 mmol, 8percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | at 25℃; for 3 h; | Treatment of 1 (986 mg, 6.53 mmol) with NBS (878 mg, 4.93 mmol) in H2SO4 (conc. 5.0 mL), as described in the paper gave after chromatography (hexanes/EtOAc, 8:2) the following fractions in order of elution: (I) 4-bromo-2-nitrobenzaldehyde (2)1 (216 mg, 19percent), 5-bromo-2-nitrobenzaldehyde (4)2 (134 mg, 12percent), and 4,5-dibromo-2-nitrobenzaldehyde (7) (18 mg, 1percent) as a yellow solid; (II) 6-bromo-2-nitrobenzaldehyde (5) (268 mg, 24percent),3 3,6-dibromo-2-nitrobenzaldehyde (8) (25 mg, 2percent),4 and 1 (409 mg, 41percent) as a yellow oil; (III) 3-bromo-2-nitrobenzaldehyde (3)5 as a yellow solid (60 mg, 0.26 mmol, 4percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | at 25℃; for 3 h; | N-Bromosuccinimide (NBS) (1.48 g, 8.32 mmol) was added to a solution of 1 (1.01 g, 6.71 mmol) in H2SO4 (concentrated 5.0 mL). The resulting mixture was stirred at ambient temperature (3 h). The reaction was quenched with ice and extracted with ethyl acetate (320mL). The combined organic phases were washed with saturated NaCl (aqueous, 30 mL), dried (MgSO4), and filtered through a silica gel plug, and the solvents were evaporated under reduced pressure. The resulting brown oil was purified by column chromatography (hexanes=EtOAc, 8:2) to afford the following fractions in order of elution: (I) 7 (28 mg, 0.09 mmol, 1percent) as an off-white solid; (II) 2 (328 mg, 21percent), 4 (140 mg, 9percent), and 3,4-dibromo-2-nitrobenzaldehyde (6) (94 mg, 5percent); (III) 5 (310 mg, 20percent), 8 (65 mg, 3percent), 1 (168 mg, 17percent); (IV) 3 (54 mg, 0.23 mmol, 4percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | at 25℃; for 3 h; | Treatment of 1 (504 mg, 3.33 mmol) and NBS (1.48 g, 8.30 mmol) in H2SO4 (3.0 mL) as described above provided after purification by chromatography (hexanes/EtOAc, 85:15) the following fractions in order of elution: (I) 7 (65 mg, 0.21 mmol, 9percent); (II) 2 (153 mg, 20percent), 4 (58 mg, 8percent), and 6 (128 mg, 12percent); (III) 5 (108 mg, 14percent), 8 (129 mg, 13percent), and 1 (17 mg, 3percent); (IV) 3 (57 mg, 0.25 mmol, 8percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | Stage #1: at 135℃; for 16 h; Stage #2: With sodium periodate In water; N,N-dimethyl-formamide at 0 - 20℃; for 22 h; |
Example 35; This example describes the synthesis of Aldehyde 10: To a stirred solution of 9 (4.94 g, 22.3 mmol) and DMF (22.3 mL) was added DMF'DMA (8.18 g, 9.59 mL, 68.6 mmol). After heating at 135°C for 16 h, the dark red solution was cooled to 0°C and added to a rapidly stirred solution OfNaIO4 (14.7 g, 68.6 mmol) in H2O (46 mL) and DMF (23 mL) at 0°C. The reaction flask was washed with DMF (23 mL) at 0°C and added to NaIO4 mixture. The reaction was stirred at O0C for 4 h then allowed to warm to rt. After an additional 18 h, the orange solution was filtered over a pad of celite-.(R). and rinsed with EtOAc (200 mL) to remove precipitate. The filtrate was then washed with H2O (3 x 150 mL) and sat. aq. NaCl (3 x 150 mL). The dried extract (MgSO4) was concentrated in vacuo and purified by chromatography over silica gel, eluting with 40percent EtOAc / Hexanes to give the known aldehyde 10 (3.44 g, 14.8 mmol, 67percent). 1H NMR (400 MHz, CDCl3) δ 10.3 (s, IH), 8.04 (dd, J= 1.0, 8.2 Hz, IH), 7.95 (dd, J= 1.0, 8.0 Hz, IH), 7.55 (t, J= 8.0 Hz, IH); 13C NMR (100 MHz, CDCl3) δ 188.6, 148.4, 138.6, 132.9, 132.4, 123.4, 121.9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | Stage #1: for 0.166667 h; Cooling; Green chemistry Stage #2: at 45℃; for 0.833333 h; Irradiation; Green chemistry |
The compound (II) o-nitrobenzaldehyde (0.80 g, 5.30 mmol) and concentrated sulfuric acid (98 wtpercent, 6.4 ml) were placed in a reaction flask and stirred under a cold well for 10 minutes.Then, NBS (1.13 g, 6.36 mmol) was slowly added and stirred for 5 minutes, and finally transferred to an oil bath at 45 ° C and allowed to react under light for 45 minutes.After the reaction was completed, it was cooled to room temperature, and the reaction mixture was poured into crushed ice and quenched, and then extracted with ethyl acetate (50 ml).Wash with saturated aqueous sodium hydrogencarbonate (50 ml), dry over anhydrous sodiumdry,Obtained 281 mg of bromo o-nitrobenzaldehyde (III) as a brownish yellow solid, yield 92.0percent, purity ≥98percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With N-Bromosuccinimide; NaH In tetrahydrofuran; tetrachloromethane; water; toluene | (28-6) To a solution of the compound of Example 28-5 (194 mg) in carbon tetrachloride (5.0 mL) were added N-bromosuccinimide (156 mg) and 2,2'-azobis(isobutyronitrile) (16.3 mg) under nitrogen atmosphere, and the mixture was heated under reflux for 2 hours. The reaction solution was cooled to room temperature, and the insoluble materials were removed by filtration. The solvent was evaporated under reduced pressure to about 3 ml. Further, toluene was added thereto, and the mixture was evaporated under reduced pressure to about 3 mL. This procedure was repeated five times to give a solution of a crude bromo compound in toluene. Under nitrogen atmosphere, a solution of the compound of Reference Example 1 (158 mg) in THF (5.0 mL) was cooled to 0°C, and thereto was added 60 percent NaH (37.06 mg). Further, thereto was added the solution of the crude bromo compound in toluene, and the mixture was stirred at 50°C for 2 hours. The reaction solution was cooled to room temperature, and water was added to the mixture, and further extracted twice with ethyl acetate. The extract was washed with water and a saturated brine, dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column (hexane / ethyl acetate =3/ 1 --> 1/1) to give the title compound (90.9 mg, 26 percent). 1H NMR (CDCl3, 400MHz) δ 8.79 (d, 1H, J=2.1Hz), 8.20 (d, 1H, J=2.1Hz), 8.04 (d, 1H, J=8.4Hz), 7.80 (d, 1H, J=7.5Hz), 7.70 (d, 2H, J=8.0Hz), 7.53 (dd, 1H, J=7.5, 8.4Hz), 7.23 (d, 2H, J=8.0Hz), 7.11 (dd, 1H, J=1.7, 2.5Hz), 6.86 (dd, 1H, J=1.7, 4.0Hz), 6.31 (dd, 1H, J=2.5, 4.0Hz), 5.91 (s, 2H), 2.41 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With N-Bromosuccinimide; NaH In tetrahydrofuran; tetrachloromethane; water; toluene | (28-6) To a solution of the compound of Example 28-5 (194 mg) in carbon tetrachloride (5.0 mL) were added N-bromosuccinimide (156 mg) and 2,2'-azobis(isobutyronitrile) (16.3 mg) under nitrogen atmosphere, and the mixture was heated under reflux for 2 hours. The reaction solution was cooled to room temperature, and the insoluble materials were removed by filtration. The solvent was evaporated under reduced pressure to about 3 ml. Further, toluene was added thereto, and the mixture was evaporated under reduced pressure to about 3 mL. This procedure was repeated five times to give a solution of a crude bromo compound in toluene. Under nitrogen atmosphere, a solution of the compound of Reference Example 1 (158 mg) in THF (5.0 mL) was cooled to 0° C., and thereto was added 60percent NaH (37.06 mg). Further, thereto was added the solution of the crude bromo compound in toluene, and the mixture was stirred at 50° C. for 2 hours. The reaction solution was cooled to room temperature, and water was added to the mixture, and further extracted twice with ethyl acetate. The extract was washed with water and a saturated brine, dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column (hexane/ethyl acetate=3/1-->1/1) to give the title compound (90.9 mg, 26percent). 1H NMR (CDCl3, 400 MHz) δ 8.79 (d, 1H, J=2.1 Hz), 8.20 (d, 1H, J=2.1 Hz), 8.04 (d, 1H, J=8.4 Hz), 7.80 (d, 1H, J=7.5 Hz), 7.70 (d, 2H, J=8.0 Hz), 7.53 (dd, 1H, J=7.5, 8.4 Hz), 7.23 (d, 2H, J=8.0 Hz), 7.11 (dd, 1H, J=1.7, 2.5 Hz), 6.86 (dd, 1H, J=1.7, 4.0 Hz), 6.31 (dd, 1H, J=2.5, 4.0 Hz), 5.91 (s, 2H), 2.41 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | at 25℃; for 3 h; | Treatment of 1 (986 mg, 6.53 mmol) with NBS (878 mg, 4.93 mmol) in H2SO4 (conc. 5.0 mL), as described in the paper gave after chromatography (hexanes/EtOAc, 8:2) the following fractions in order of elution: (I) 4-bromo-2-nitrobenzaldehyde (2)1 (216 mg, 19percent), 5-bromo-2-nitrobenzaldehyde (4)2 (134 mg, 12percent), and 4,5-dibromo-2-nitrobenzaldehyde (7) (18 mg, 1percent) as a yellow solid; (II) 6-bromo-2-nitrobenzaldehyde (5) (268 mg, 24percent),3 3,6-dibromo-2-nitrobenzaldehyde (8) (25 mg, 2percent),4 and 1 (409 mg, 41percent) as a yellow oil; (III) 3-bromo-2-nitrobenzaldehyde (3)5 as a yellow solid (60 mg, 0.26 mmol, 4percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | at 25℃; for 3 h; | N-Bromosuccinimide (NBS) (1.48 g, 8.32 mmol) was added to a solution of 1 (1.01 g, 6.71 mmol) in H2SO4 (concentrated 5.0 mL). The resulting mixture was stirred at ambient temperature (3 h). The reaction was quenched with ice and extracted with ethyl acetate (320mL). The combined organic phases were washed with saturated NaCl (aqueous, 30 mL), dried (MgSO4), and filtered through a silica gel plug, and the solvents were evaporated under reduced pressure. The resulting brown oil was purified by column chromatography (hexanes=EtOAc, 8:2) to afford the following fractions in order of elution: (I) 7 (28 mg, 0.09 mmol, 1percent) as an off-white solid; (II) 2 (328 mg, 21percent), 4 (140 mg, 9percent), and 3,4-dibromo-2-nitrobenzaldehyde (6) (94 mg, 5percent); (III) 5 (310 mg, 20percent), 8 (65 mg, 3percent), 1 (168 mg, 17percent); (IV) 3 (54 mg, 0.23 mmol, 4percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10% | at 60℃; for 3 h; | Treatment of 1 (459 mg, 3.03 mmol) and NBS (677 mg, 3.80 mmol) in H2SO4 (3.0 mL) at 60 oC as described above afforded the following fractions in order of elution: (I) 7 (21 mg, 0.07 mmol, 2percent); (II) 2 (66 mg, 9percent) and 4 (24 mg, 3percent); (III): 2 (5 mg, 0.7percent) and 3,4-dibromo-2-nitrobenzaldehyde 6 (85 mg, 9percent); (IV) 5 (59 mg, 8percent), 8 (13 mg, 1percent), and 1 (18 mg, 4percent); (V) 3 (20 mg, 0.09 mmol, 3percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | at 25℃; for 3 h; | Treatment of 1 (504 mg, 3.33 mmol) and NBS (1.48 g, 8.30 mmol) in H2SO4 (3.0 mL) as described above provided after purification by chromatography (hexanes/EtOAc, 85:15) the following fractions in order of elution: (I) 7 (65 mg, 0.21 mmol, 9percent); (II) 2 (153 mg, 20percent), 4 (58 mg, 8percent), and 6 (128 mg, 12percent); (III) 5 (108 mg, 14percent), 8 (129 mg, 13percent), and 1 (17 mg, 3percent); (IV) 3 (57 mg, 0.25 mmol, 8percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | at 25℃; for 3 h; | Treatment of 1 (504 mg, 3.33 mmol) and NBS (1.48 g, 8.30 mmol) in H2SO4 (3.0 mL) as described above provided after purification by chromatography (hexanes/EtOAc, 85:15) the following fractions in order of elution: (I) 7 (65 mg, 0.21 mmol, 9percent); (II) 2 (153 mg, 20percent), 4 (58 mg, 8percent), and 6 (128 mg, 12percent); (III) 5 (108 mg, 14percent), 8 (129 mg, 13percent), and 1 (17 mg, 3percent); (IV) 3 (57 mg, 0.25 mmol, 8percent). |
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