Structure of 320-47-8
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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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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 320-47-8 |
Formula : | C8H3F3N2O2 |
M.W : | 216.12 |
SMILES Code : | [O-][N+](=O)C1=CC(=C(C=C1)C#N)C(F)(F)F |
MDL No. : | MFCD01075729 |
InChI Key : | AGKQJEFSEQHGTA-UHFFFAOYSA-N |
Pubchem ID : | 2775783 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 15 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.12 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 6.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 44.98 |
TPSA ? Topological Polar Surface Area: Calculated from |
69.61 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.13 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.35 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.64 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.14 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.72 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.0 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.82 |
Solubility | 0.324 mg/ml ; 0.0015 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.45 |
Solubility | 0.0764 mg/ml ; 0.000354 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.76 |
Solubility | 0.377 mg/ml ; 0.00175 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 |
Yes |
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) |
Yes |
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 |
-5.95 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 |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
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) |
2.11 |
* 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 |
---|---|---|
With water; sodium hydroxide; In ethanol; at 80℃; | First, NaOH (5.88 g, 0.147 mol) was dissolved in ethanol/DI water (1:1) 400 ml in a 3-neck reaction flask, and then the <strong>[320-47-8]2-cyano-5-nitrobenzotrifluoride</strong> (9.34 g, 0.0368 mol) synthesized above was added thereto. The resulting solution was refluxed at 80 C. overnight to synthesize 4-nitro-2-(trifluoromethyl)benzoic acid (B). After the reaction, the solution was cooled again to room temperature and then ethanol was evaporated followed by neutralizing thereof with 1N aqueous HCl solution. Then, the precipitated solid was filtered through a filter paper. The solid was washed with a small amount of DI water to obtain 4-nitro-2-(trifluoromethyl)benzoic acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6.8 g (65%) | With hydrogenchloride; sodium nitrite; In water; sodium hydrogencarbonate; acetic acid; | a. 2-Cyano-5-nitrobenzotrifluoride A solution of 10.0 g (48.5 mmol) 2-amino-5-nitrobenzotrifluoride in 60 ml glacial acetic acid was added 200 ml 2N hydrochloric acid, and then at 0 C. diazotized with a solution of 3.36 g (48.6 mmol) sodium nitrite in 100 ml water. Stirring was continued at 0 C. for 1 h, and then at 25 C. a solution of 18 g (75 mmol) potassium tetracyanonickelate (K2 NiCN4) in 500 ml saturated sodium hydrogencarbonate was added dropwise. Extraction with ethyl acetate followed by distillation (95-100 C./0.5 mmHg) of the crude oil gave 6.8 g (65%) of 2-cyano-5-nitrobenzotrifluoride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; In acetic acid; | The diethyl glutamate used as starting material was obtained as follows:- A mixture of <strong>[320-47-8]4-nitro-2-trifluoromethylbenzonitrile</strong> (J.Amer.Chem.Soc. 1954, 76 , 1051; 5.6 g), glacial acetic acid (20 ml) and sulphuric acid (concentrated, 30 ml) was stirred and heated to 130C for 45 minutes. The mixture was cooled, poured onto ice (100 ml) and extracted with ethyl acetate (3 x 150 ml). The combined extracts were washed with aqueous 0.05N-hydrochloric acid solution, dried over sodium sulphate, filtered and evaporated. The residue was purified by chromatography on a silica gel column using ethyl acetate as eluent. There was thus obtained 4-nitro-2-trifluoromethylbenzamide (5.16 g), m.p. 192C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4-Nitro-2-(trifluoromethyl) benzaldehyde (D30) To <strong>[320-47-8]4-nitro-2-(trifluoromethyl)benzonitrile</strong> (100 mg, 0.463 mmol) in toluene (3 ml.) at 0 0C under argon was added DIBAL-H (0.51 ml_, 1 M in toluene, 0.51 mmol) and the reaction stirred for 3.75 h. MeOH and sulphuric acid were added and the reaction mixture was warmed to room temperature and stirred for 1 h. The mixture was concentrated and the residue was portioned between EtOAc (10 ml.) and water (10 ml_). The organic phase was dried and concentrated to give the crude product which was purified by column chromatography eluting with 0-15% EtOAc/petroleum ether to give the title compound as a yellow oil (91 mg), deltaH (CDCI3, 400MHz) 10.47 (1 H, s), 8.66 (1 H, d), 8.56 (1 H, dd), 8.33 (1 H, d). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; at 160℃; for 18h;Inert atmosphere; | 2-Bromo-5-nitrobenzo trifluoride (20 g, 0.111 mol) and CuCN (12 g, 0.134 mol) were dissolved in a 250 ml 3-neck reaction flask containing DMF (90 ml), respectively. Then, the solution was refluxed at 160 C. for 18 hours at nitrogen atmosphere to synthesize 2-cyano-5-nitrobenzotrifluoride (A). Then, the reactant was cooled to room temperature and homogeneously mixed with a pre-made workup solution (FeCl3 50 g, conc. HCl 30 ml, DI water 500 ml). The mixture was extracted with ethyl acetate and subjected to fractional washing with 10% (v/v) aqueous HCl solution followed by evaporating the ethyl acetated by using a rotary evaporator. Finally, dark brown liquid was obtained, and the solvent remained in the brown liquid was evaporated and removed in a 80 C. vacuum oven to obtain 2-cyano-5-nitrobenzotrifluoride. |