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CAS No. : | 99517-31-4 | MDL No. : | MFCD31380108 |
Formula : | C9H7NO5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HGZXANUIYKGGSW-UHFFFAOYSA-N |
M.W : | 209.16 | Pubchem ID : | 14838655 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 51.57 |
TPSA : | 92.35 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.67 cm/s |
Log Po/w (iLOGP) : | 1.14 |
Log Po/w (XLOGP3) : | 1.28 |
Log Po/w (WLOGP) : | 1.23 |
Log Po/w (MLOGP) : | 0.22 |
Log Po/w (SILICOS-IT) : | -0.34 |
Consensus Log Po/w : | 0.71 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.11 |
Solubility : | 1.63 mg/ml ; 0.00781 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.82 |
Solubility : | 0.317 mg/ml ; 0.00152 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.45 |
Solubility : | 7.42 mg/ml ; 0.0355 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.17 |
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 |
---|---|---|
21.4% | With nitric acid; In trifluoroacetic acid; | c. Preparation of 5-nitro-2,3-dihydrobenzo[b]furan-7-carboxylic acid (15k) Method A: To an ice-cooled solution of 2,3-dihydrobenzo[b]furan-7-carboxylic acid (15a) (0.33 g, 2.0 mmol) in 3 ml of TFA there was added dropwise 0.6 ml of HNO3. At the end of 1 hour, the cooling bath was removed. After an additional 3 hours of stirring, the mixture was poured into ice-water. The precipitate was collected on a filter to give 0.22 g (52.6%) of crude 15k. This was recrystallized from ethyl acetate to provide 88 mg of acid 15k (21.4%), mp 249-251.5 C. |
21.4% | With nitric acid; In trifluoroacetic acid; | Method A To an ice-cooled solution of 2,3-dihydrobenzo[b]furan-7-carboxylic acid (15a) (0.33 g, 2.0 mmol) in 3 ml of TFA there was added dropwise 0.6 ml of HNO3. At the end of 1 hour, the cooling bath was removed. After an additional 3 hours of stirring, the mixture was poured into ice-water. The precipitate was collected on a filter to give 0.22 g (52.6%) of crude 15k. This was recrystallized from ethyl acetate to provide 88 mg of acid 15k (21.4%), mp 249-251.5C. |
With nitric acid; In acetic acid; | To an ice-cooled solution of 2,3-dihydrobenzo[b]furan-7-carboxylic acid (15a) (0.33 g, 2.0 mmol) in 3 ml of acetic acid there was added dropwise 0.6 ml of HNO3. The mixture was stirred in a warm oil bath (70 C.) for 24 hours, and then poured into water. After cooling, the product was collected on a filter to give 0.21 g of solid (50.2%). This was recrystallized from ethyl acetate to afford 0.14 g (33.5%) of 15k, mp 249-251.5 C. |
With nitric acid; In acetic acid; | Method B To an ice-cooled solution of 2,3-dihydrobenzo[b]furan-7-carboxylic acid (15a) (0.33 g, 2.0 mmol) in 3 ml of acetic acid there was added dropwise 0.6 ml of HNO3. The mixture was stirred in a warm oil bath (70C) for 24 hours, and then poured into water. After cooling, the product was collected on a filter to give 0.21 g of solid (50.2%). This was recrystallized from ethyl acetate to afford 0.14 g (33.5%) of 15k , mp 249-251.5C. | |
With nitric acid; trifluoroacetic acid; In trifluoroacetic acid; at 0℃; for 4h; | Nitric acid (9 ml) was added to a cooled (ice bath) solution of 2,3-dihydrobenzo[b]furan-7-carboxylic acid (5.1 g, 31 mmol) in trifluoroacetic acid (45 ml). After 4 hours the mixture was quenched into ice-water (150 ml) and the mixture filtered to give 5-nitro-2,3-dihydrobenzo[b]furan-7-carboxylic acid, which was washed with water and used crude (wet) in the next stage. 1H NMR (delta, 250 MHz, CD3OD): 3.70 (2H, t, 8.7 Hz), 5.21 (2H, t, 8.9 Hz), 8.67 (1H, d, 2.7 Hz), 8.83 (1H, d, 2.4 Hz) | |
With nitric acid; trifluoroacetic acid; for 4h; | Nitric acid (9ml) was added to a cooled (ice bath) solution of 2,3-dihydrobenzo[b]furan-7-carboxylic acid (5.1g, 31mmol) in trifluoroacetic acid (45ml). After 4 hours the mixture was quenched into ice-water (150ml) and the mixture filtered to give 5-nitro-2,3-dihydrobenzo[b]furan-7-carboxylic acid, which was washed with water and used crude (wet) in the next stage.1H NMR (delta, 250MHz, CD3OD): 3.70 (2H, t, 8.7Hz), 5.21 (2H, t, 8.9Hz), 8.67 (1H, d, 2.7Hz), 8.83 (1H, d, 2.4Hz) The crude 5-nitro-2,3-dihydrobenzo[b]furan-7-carboxylic acid was dissolved in the minimum amount of methanol (1.3L) and nitrogen was bubbled through the solution for 20 minutes. A mixture of 5% palladium on charcoal (1.0g) in water (20ml) was added and the mixture loaded into a 2L autoclave. After 2 sequential evacuation-N2 purges the vessel was charged to 5 bar H2 and stirred for 4 days. The mixture was flushed with nitrogen, filtered through celite and concentrated to give 5-amino-2,3-dihydrobenzo[b]furan-7-carboxylic acid (3.5g, 19.5mmol, 63% over 2 steps)1H NMR (delta, 250MHz, CD3OD): 3.46 (2H, t, 8.5Hz), 4.85 (2H, t, 8.7Hz), 7.19 (1H, br s), 7.27 (1 H, br s) . |