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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. : | 76179-40-3 |
Formula : | C6H6F2N2 |
M.W : | 144.12 |
SMILES Code : | NC1=C(C=C(C(=C1)F)F)N |
MDL No. : | MFCD00061131 |
InChI Key : | PPWRHKISAQTCCG-UHFFFAOYSA-N |
Pubchem ID : | 2736755 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 35.17 |
TPSA ? Topological Polar Surface Area: Calculated from | 52.04 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 1.09 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 0.76 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 1.99 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | 1.68 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | 1.26 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 1.36 |
Log S (ESOL):? ESOL: Topological method implemented from | -1.66 |
Solubility | 3.18 mg/ml ; 0.0221 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (Ali)? Ali: Topological method implemented from | -1.43 |
Solubility | 5.32 mg/ml ; 0.0369 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -2.21 |
Solubility | 0.881 mg/ml ; 0.00611 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) | 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 | -6.64 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 | 0.55 |
PAINS? Pan Assay Interference Structures: implemented from | 0.0 alert |
Brenk? Structural Alert: implemented from | 1.0 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) | 1.08 |
* 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 |
---|---|---|
88% | at 80℃; for 12h; | A solution of 4,5-difluorobenzene-1 ,2-diamine (1.5 g, 10 mmol) in formic acid (20 mL) was heated at 80C for 12 hours. The reaction mixture was cooled to 25C and concentrated under reduced pressure. The residue was recrystallized form Petroleum ether:EtOAc (15: 1 ) to afford 5,6-difluoro- 1 H-benzo[d]imidazole as a yellow solid (1.4 g, 88%). MS (ESI) m/z: 155 [M+H]+. |
75% | With orthoformic acid triethyl ester; at 100℃; for 1h; | Step 2: A stirred mixture of 4,5-difluorobenzene-1,2-diamine (1.40 g, 9.7 mmol) from the previous step, formicacid (2.0 mL), and triethyl orthoformate (20 mL) was heated at 100 C for 1 h. The reaction mixture was cooled to rt andconcentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 5%MeOH in DCM to afford 5,6-difluoro-1H-benzo[d]imidazole as (1.12 g, 75%) as a white solid. 1H NMR (300 MHz, CDCl3) delta 8.07 (s, 1H), 7.44 (m, 2H); LCMS (ESI) m/z 155 (M + H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In isopropyl alcohol; for 16h;Heating / reflux; | Example 4: Synthesis of 5,6-Difluoro-lH-benzo[d]imidazole EPO <DP n="31"/>EtOCH=C(CN)2 iPrOH [0088] A solution of 4,5-difluoro-2-nitroaniline (6)(1.0 g) in 30 niL of THF was treated with a solution comprised of 6 g OfNa2S2O4 and 3 g NaHCO3 in 30 niL of water. Methanol (10 mL) was added after the addition of the aqueous solution so that the mixture remained homogeneous. The mixture was stirred for two hours and then diluted with 100 mL of ethyl acetate and 100 mL of water. The organic layer was separated and the aqueous layer was extracted again with 100 mL of methylene chloride. The combined organic layers were dried over sodium sulfate, filtered, and concentrated to provide the crude intermediate 4,5-difluorobenzene-l,2-diamine (7). The intermediate was refluxed with (ethoxymethylene)malononitrile (1.1 g) in 25 mL of isopropyl alcohol for 16 h. The mixture was concentrated in vacuo and the resulting crude product was suspended in water and filtered. The precipitate was washed with water and air-dried to provide 380 mg of 5,6-difluoro-lH-benzo[d]imidazole (8). | |
In isopropyl alcohol; for 16h;Heating / reflux; | Example 4 Synthesis of 5,6-Difluoro-1H-benzo[d]imidazole A solution of 4,5-difluoro-2-nitroaniline (6)(1.0 g) in 30 mL of THF was treated with a solution comprised of 6 g of Na2S2O4 and 3 g NaHCO3 in 30 mL of water. Methanol (10 mL) was added after the addition of the aqueous solution so that the mixture remained homogeneous. The mixture was stirred for two hours and then diluted with 100 mL of ethyl acetate and 100 mL of water. The organic layer was separated and the aqueous layer was extracted again with 100 mL of methylene chloride. The combined organic layers were dried over sodium sulfate, filtered, and concentrated to provide the crude intermediate 4,5-difluorobenzene-1,2-diamine (7). The intermediate was refluxed with (ethoxymethylene)malononitrile (1.1 g) in 25 mL of isopropyl alcohol for 16 h. The mixture was concentrated in vacuo and the resulting crude product was suspended in water and filtered. The precipitate was washed with water and air-dried to provide 380 mg of 5,6-difluoro-1H-benzo[d]imidazole (8). | |
In isopropyl alcohol; for 16h;Heating / reflux; | A solution of 4,5-difluoro-2-nitroaniline (6)(1.0 g) in 30 mL of THF was treated with a solution comprised of 6 g OfNa2SaO4 and 3 g NaHCC>3 in 30 mL of water. Methanol (10 mL) was added after the addition of the aqueous solution so that the mixture remained homogeneous. The mixture was stirred for two hours and then diluted with 100 mL of <n="29"/>ethyl acetate and 100 mL of water. The organic layer was separated and the aqueous layer was extracted again with 100 mL of methylene chloride. The combined organic layers were dried over sodium sulfate, filtered, and concentrated to provide the crude intermediate 4,5-difluorobenzene-l,2-diamine (7). The intermediate was refluxed with (ethoxymethylene)malononitrile (1.1 g) in 25 mL of isopropyl alcohol for 16 h. The mixture was concentrated in vacuo and the resulting crude product was suspended in water and filtered. The precipitate was washed with water and air-dried to provide 380 mg of 5,6- difluoro-lH-benzo[d]imidazole (8). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With phenylsilane; at 120℃; for 12h; | General procedure: A mixture of 1a (1b-1n, 0.4 mmol) and PhSiH3 (98 mL, 1.6 mmol)in N,N-dimethylformamide 2a (2b-2c, 1 mL) was stirred at 120 C for 12 h. When the reaction was completed, the resulting mixture was extracted with ethyl acetate three times. The combined organic layer was washed by NaCl aqueous solution and dried over anhydrous Na2SO4, after which the solvent was removed under reduced pressure. The residue was purified by column chromatography onsilica gel with petroleum ether and ethyl acetate (6:1-1:2) to give the corresponding product 3a (3b-3p). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tert.-butylhydroperoxide; In dimethyl sulfoxide; at 90℃; for 0.5h; | N-methyl indole (0.5 mmol), DMSO (5 ml) were added into reaction tube and stirred at 90 C. Then the I2 (0.6 mmol) and TBHP (2.5 mmol) were added into the reaction tube. After 24 h the o-benzenediamine (0.34 mmol) was added into the mixture. The reaction was stopped until the o-benzenediamine was completely consumed as monitored by TLC analysis. After the completion of reaction, 5% Na2S2O3 solution (30 mL) was added to the mixture. The mixture was extracted with EtOAc (3 * 20 ml) and the organic layer was dried by Na2SO4. Then the crude product was purified by silica gel chromatography (petroleum ether/ethyl acetate/dichloromethane 3/1/1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With sodium dithionite; In N,N-dimethyl-formamide; at 140℃; for 24h;Schlenk technique; Inert atmosphere; | Add 4,5-difluoro-o-phenylenediamine (290mg, 2mmol), <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> (540mg, 2mmol), Na2S2O4 (1050mg, 6mmol) into a 50ml Schleck tube, Add 6mL DMF and heat to reflux for 24 hours under nitrogen protection. Dilute the cooled reaction solution with 20mL saturated sodium chloride solution, extract with 3*25mL ethyl acetate, combine the organic phases, add anhydrous MgSO4 to dry, filter to remove anhydrous magnesium sulfate, evaporate the solvent under reduced pressure, petroleum ether: the target product separated by ethyl acetate (6:1) column chromatography, with a yield of 83%. |
Tags: 76179-40-3 synthesis path| 76179-40-3 SDS| 76179-40-3 COA| 76179-40-3 purity| 76179-40-3 application| 76179-40-3 NMR| 76179-40-3 COA| 76179-40-3 structure
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