Structure of 3-Nitrobenzoic acid
CAS No.: 121-92-6
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 121-92-6 |
Formula : | C7H5NO4 |
M.W : | 167.12 |
SMILES Code : | O=C(O)C1=CC=CC([N+]([O-])=O)=C1 |
MDL No. : | MFCD00007251 |
InChI Key : | AFPHTEQTJZKQAQ-UHFFFAOYSA-N |
Pubchem ID : | 8497 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335-H412 |
Precautionary Statements: | P261-P273-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 42.22 |
TPSA ? Topological Polar Surface Area: Calculated from |
83.12 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.77 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.83 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.29 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.51 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-0.93 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.69 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.27 |
Solubility | 0.904 mg/ml ; 0.00541 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.2 |
Solubility | 0.106 mg/ml ; 0.000637 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.15 |
Solubility | 12.0 mg/ml ; 0.0716 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.02 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.56 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
2.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.62 |
* 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 |
---|---|---|
76% | With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 20℃; for 3h;Inert atmosphere; | To the suspension of 3-nitrobenzoic acid ( 1 g, 5.98 mmol) in pyridine ( 10ml) <strong>[42303-42-4]ethyl <strong>[42303-42-4]1-aminocyclopropanecarboxylate hydrochloride</strong></strong> ( 1.090 g, 6.58 mmol) was added followed by EDC.HC1 (1.721 g, 8.98 mmol) under nitrogen. Reaction mixture was stirred at room temperature for 3hrs. Reaction mixture was diluted with cold water ( 100ml) and extracted with ethyl acetate (2X25ml). Separated organic layer was washed with brine and water, dried over sodium sulfate and concentrated under vacuum till dryness to obtain product ( 1.26g, 76%). NMR (400 MHz, CDC13) 8 (ppm): 8.59 (bs, 1H), 8.41-8.38 (m, 1H), 8.20-8. 18(m, 1H), 7.68 (t, 1H, J=8Hz), 6.82 (bs, 1H), 4.19 (q, 2H, J=7.2Hz), 1.70- 1.34 (m, 2H), 1.37- 1.33 (m, 2H), 1.26(t,3H,J=7.2Hz). ESI- MS (m/z): 279.58 (M+l) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
240 mg | With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 22 - 26℃; for 10h;Inert atmosphere; | Step-a: Synthesis of 3-Nitro-N-(tetrahydrofuran-3-yl)benzamide Tetrahydrofuran-3-amine (0.1 g, 1.148 mmol) and 3-nitrobenzoic acid (0.192 g, 1.148 mmol) were taken in pyridine (2 ml), to the mixture EDC.HCl (0.220 g, 1.148 mmol) was added, the reaction mixture was stirred under nitrogen for 10 hrs at room temperature. The reaction mixture was diluted with cold water (15 ml), extracted with ethyl acetate (2*10 ml). Combined organic layer was washed with satd. aq. sod bicarbonate and dil HCl, the organic layer was dried over sodium sulfate and concentrated under vacuum to afford the title product (240 mg). 1HNMR (400 MHz, CDCl3): delta 8.62-8.61 (m, 1H), 8.39-8.36 (m, 1H), 8.19-8.17 (m, 1H), 7.67 (t, 1H, J=8 Hz), 6.62 (d, 1H, J=6 Hz), 4.79-4.75 (m, 1H), 4.08-4.00 (m, 1H), 3.93-3.83 (m, 3H), 2.44-2.37 (m, 1H), 2.01-1.98 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 22 - 26℃; for 3h;Inert atmosphere; | Step-a: Synthesis of Ethyl 1-(3-nitrobenzamido)cyclopropanecarboxylate To the suspension of 3-nitrobenzoic acid (1 g, 5.98 mmol) in pyridine (10 ml) <strong>[42303-42-4]ethyl <strong>[42303-42-4]1-aminocyclopropanecarboxylate hydrochloride</strong></strong> (1.090 g, 6.58 mmol) was added followed by EDC.HCl (1.721 g, 8.98 mmol) under nitrogen. Reaction mixture was stirred at room temperature for 3 hrs. Reaction mixture was diluted with cold water (100 ml) and extracted with ethyl acetate (2*25 ml). Separated organic layer was washed with brine and water, dried over sodium sulfate and concentrated under vacuum till dryness to obtain product (1.26 g, 76%). 1H NMR (400 MHz, CDCl3) delta (ppm): 8.59 (bs, 1H), 8.41-8.38 (m, 1H), 8.20-8.18 (m, 1H), 7.68 (t, 1H, J=8 Hz), 6.82 (bs, 1H), 4.19 (q, 2H, J=7.2 Hz), 1.70-1.34 (m, 2H), 1.37-1.33 (m, 2H), 1.26 (t, 3H, J=7.2 Hz). ESI-MS (m/z): 279.58 (M+1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77.1% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 2 - 20℃; for 2.25h; | 7-Et-CPT (0.75?g, 2?mmol), EDCI (1.53g, 8?mmol) and DMAP (1.47?g, 12?mmol) were added to a solution of m-nitrobenzoic acid (1.00?g, 6?mmol) in 100?mL of CH2Cl2 with stirring at 2?°C for 15?min. The mixture was stirred at room temperature for 2?h and was poured onto 100?ml ice water. The obtained organic layer was washed with dilute hydrochloric acid and saturated salt water in turn, and concentrated. The crude product was chromatographically separated with CH2Cl2-THF as eluent. The pure product 3g (0.81?g) was obtained as almost white powder, yield 77.1percent, purity 98.97percent (HPLC), mp 272-274?°C. 1H NMR (CDCl3, 500?MHz) delta: 1.11 (t, J?=?7.5?Hz, 3H, 19-H), 1.40 (t, J?=?7.8?Hz, 3H, 30-H), 2.37-2.49 (m, 2H, 18-H), 3.20 (q, 2H, 29-H), 5.25 (d, J?=?18.5?Hz, 1H, 5-H), 5.29 (d, J?=?19.0?Hz, 1H, 5-H), 5.49 (d, J?=?17.0?Hz, 1H, 17-H), 5.79 (d, J?=?17.0?Hz, 1H, 17-H), 7.25 (s, 1H, 14-H), 7.68 (m, 2H, 10, 27-H), 7.77 (t, J?=?7.5?Hz, 1H, 11-H), 8.13 (t, J?=?9.8?Hz, 2H, 9,12-H), 8.40 (d, J?=?7.5?Hz, 1H, 24-H), 8.46 (m, 1H, 26-H), 8.93 (s, 1H, 28-H). ESI-MS m/z: 526.2 (M?+?1)+. |
A151989 [3807-81-6]
5-Nitrobenzene-1,2,3-tricarboxylic acid
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