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CAS No. : | 367-30-6 | MDL No. : | MFCD00007651 |
Formula : | C6H5F2N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YNOOQIUSYGWMSS-UHFFFAOYSA-N |
M.W : | 129.11 | Pubchem ID : | 67775 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 30.76 |
TPSA : | 26.02 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.99 cm/s |
Log Po/w (iLOGP) : | 1.47 |
Log Po/w (XLOGP3) : | 1.54 |
Log Po/w (WLOGP) : | 2.4 |
Log Po/w (MLOGP) : | 2.34 |
Log Po/w (SILICOS-IT) : | 1.99 |
Consensus Log Po/w : | 1.95 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.1 |
Solubility : | 1.02 mg/ml ; 0.00787 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.7 |
Solubility : | 2.6 mg/ml ; 0.0202 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.56 |
Solubility : | 0.357 mg/ml ; 0.00277 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P270-P271-P272-P280-P301+P312+P330-P302+P352+P312-P304+P340+P312-P333+P313-P370+P378-P403+P235-P501 | UN#: | N/A |
Hazard Statements: | H302+H312+H332-H317-H227 | 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 |
---|---|---|
87% | With hydrogenchloride; acetic acid; sodium nitrite In ethanol; water | 12.9 g (99.9 mmol) of 2,5-difluoroaniline are added rapidly to a mixture, cooled to below -10° C. by a bath of cardice in ethanol, of 33 ml of concentrated hydrochloric acid and 10 ml of acetic acid, followed by dropwise addition of a solution of 7.4 g (107 mmol) of sodium nitrite in 15 ml of water. Stirring is continued for 45 min after the end of the addition, at a temperature between -10 and -25° C. This solution, maintained at about -25° C., is added portionwise to a mixture, cooled to 10° C. in an ice bath, obtained by saturation of 100 ml of acetic acid with sulphur dioxide and addition of 2.5 g (25.3 mmol) of cuprous chloride. Considerable evolution of nitrogen is produced. The reaction medium is allowed to return to room temperature and is maintained at that temperature for 2 h, after which it is poured into 450 ml of a mixture of water and ice; it is extracted with ethyl ether. The combined ether extracts are washed with saturated aqueous sodium bicarbonate solution, dried over sodium sulphate and concentrated. The oily residue obtained is distilled under reduced pressure to give 14.3 g (87percent) of a liquid consisting essentially of 2,5-difluorobenzenesulphonyl chloride, which is used in the next step without further purification. b.p.=65-70° C. at 0.5 mm of mercury |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | at 20℃; for 1 h; | To a solution of 1,4-difluoro-2-nitrobenzene (500 mg, 3.14 mmol) in MeOH (20 mL) was added Pd/C (66.9 mg, 0.629 mmol) in portions. Then the mixture was stirred under a H2 atmosphere at 20° C. for 1 h. After TLC (PE/EA=3/1) analysis showed the starting material had disappeared, the mixture was filtered. The filtrate was concentrated to give the desired product 2,5-difluoroaniline (338 mg, 2.61 mmol, 83percent yield). 1H NMR: (400 MHz, CDCl3) δ 6.94-6.88 (m, 1H), 6.50-6.46 (m, 1H), 6.40-6.31 (m, 1H), 3.82 (br. s., 2H). |
83% | With palladium on activated charcoal; hydrogen In methanol at 20℃; for 1 h; | To a solution of l,4-difluoro-2-nitrobenzene (500 mg, 3.14 mmol) in MeOH (20 mL) was added Pd/C (66.9 mg, 0.629 mmol) in portions. Then the mixture was stirred under a H2 atmosphere at 20 °C for 1 h. After TLC (PE/EA=3/1) analysis showed the starting material had disappeared, the mixture was filtered. The filtrate was concentrated to give the desired product 2,5-difluoroaniline (338 mg, 2.61 mmol, 83percent yield). lH NMR: (400 MHz, CDC13) δ 6.94-6.88 (m, 1H), 6.50-6.46 (m, 1H), 6.40-6.31 (m, 1H), 3.82 (br. s., 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.5% | With bromine In dichloromethane; water; acetic acid | Example 14 Preparation of 4-bromo-2,5-difluoroaniline To a stirred mixture of 100g of 2,5-difluoroaniline and 1150 mL, of AcOH is added over 1.3 hours a solution of 40.2 mL of Br2 in 350 mL of AcOH at a temperature of 15°-20°. The pink suspension is stirred 30 minutes longer and then evaporated in vacuo. The residue is basified with 50percent NaOH (ice is added to keep the temperature below 35°). Extraction of the free base with 1L of CH2Cl2 and washing of the extract with 2 x 100 mL of H2O, drying with Na2SO4 and evaporation in vacuo gives 157 g (97.5percent yield) of 4-bromo-2,5-difluoroaniline, m.p. 73°-75°. The mass spectrum had a M+1 ions at 208,210. |
200 g | With N-Bromosuccinimide In acetonitrile at 0 - 20℃; for 3.33333 h; | N-Bromosuccinimide (178 g, 1.0 mol) was added over 20 mm to a solution of 2,5-difluoroaniline (129 g, 1.0 mol) in acetonitrile (1 L) at 0 °C. The resulting mixture was stirred at room temperature for 3 h, concentrated in vacuo, and poured into water (2 L). The mixture was extracted with ethyl acetate (2x500 mL), washed (200 mL brine), dried (Na2SO4), and concentrated under reduced pressure. The residue was re-crystallized from PE (1 L) to afford the title compound as a gray solid (200 g). 1H NMR (400 MHz, DMSO-d6): ö 7.54-7.50 (m, 1H), 6.79-6.74 (m, 1H), 5.44 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.5% | With bromine In acetic acid | EXAMPLE 14 Preparation of 4-bromo-2,5-difluoroaniline To a stirred solution of 100 g of 2,5-difluoroaniline and 1150 mL of AcOH is added over 1.3 hours a solution of 40.2 mL of Br2 in 350 mL of AcOH at a temperature of 15°-20°. The pink suspension is stirred 30 minutes longer and then evaporated in vacuo. The residue is basified with 50percent NaOH (ice is added to keep the temperature below 35°). Extraction of the free base with 1 L of CH2 Cl2 and washing of the extract with 2*100 mL of H2 O, drying with Na2 SO4 and evaporation in vacuo gives 157 g (97.5percent yield) of 4-bromo-2,5-difluoroaniline, m.p. 73°-75°. The mass spectrum had a M+1 ions at 208,210. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With iodine; sodium hydrogencarbonate In water at 20℃; for 2 h; | A mixture of 2,5-difluoroaniline (0.5 g, 3.9 mmol), NaHCO3 (0.8 g, 9.8 mmol), I2 (2.5 g, 9.8 mmol) and H2O (50 mL) was stirred at r.t. for 2 h. Than Na2SO3 (1 g, 8 mmol) was added, and the reaction mixture was extracted with CH2Cl2 (2×50 mL). The combined organic layers were washed with H2O (50 mL), dried (MgSO4) and purified by flash chromatography on Al2O3. Evaporation of the solvent was performed in vacuo to obtain 6b (0.9 g, 91 percent) as brown solid (the 1H and 13C NMR spectra closely agree with the literature data [37]); νmax (KBr): 3464, 3379, 3042, 2926, 2855, 1632, 1501, 1414, 1323, 1298, 1234, 1184, 1167, 864, 837, 795, 733, 596, 444 cm−1; 1H NMR (500.13 MHz, CDCl3): δ=7.27 (dd, 1H, JH3,F2=9.9, JH3,F5=5.6 Hz, H3), 6.52 (d, 1H, JH6,F5=8.7, JH6,F2=7.7 Hz, H6), 3.91 (br s, 2H, NH2); 13C NMR (125.76 MHz, CDCl3): δ=158.0 (d, 1JC5,F5=239.1 Hz, C5), 147.4 (d, 1JC2,F2=239.6Hz, C2), 135.7 (dd, 2JC1,F2=14.7, 3JC1,F5=10.6 Hz, C1), 123.8 (dd, 2JC3,F2=22.8, 3JC3,F5=3.5Hz, C3), 102.7 (dd, 2JC6,F5=29.9, 3JC6,F2=3.7 Hz, C6), 62.8 (dd, 2JC4,F5=29.1, 3JC4,F2=8.1 Hz, C4); 19F NMR (282.37 MHz, CDCl3): δ=−101.5 (ddd, 1F, JF5,F2=13.4, JF5,H6=8.7, JF5,H3=5.6 Hz, F5), −140.0 (ddd, 1F, JF2,F5=13.4, JF2,H3=9.9, JF2,H6=7.7 Hz, F2); HRMS (EI): +, found 254.9356. C6H4F2IN requires 254.9351. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.5% | at 120℃; for 10 h; | Step 1) Synthesis of 5-fluorobenzo [d] thiazole-2-thiol 2, 5-Difluoroaniline (1.00 g, 7.75 mmol) and potassium ethylxanthate (2.73 g, 17.05 mmol) were added into N, N-dimethylformamide (50 mL) in turn, the mixture was heated at 120 ? for 10 h. After the reaction is complete, the mixture was cooled to rt and diluted with water (100 mL) . The resulting mixture was adjusted with hydrochloric acid (1 M) to pH 4 to 5. Some solid precipitated, the mixture was filtered by suction. The solid was dried at 50 ? under a vacuum to give the title compound as a white solid (1.11 g, 76.5percent) .MS (ESI, pos. ion) m/z: 185.00 [M+H] +; and1H NMR (DMSO-d6, 600 MHz) ? (ppm) : 13.98 (s, 1H) , 7.55 (d, J = 8.2 Hz, 1H) , 7.36~7.31 (m, 2H) . |
67% | at 120℃; for 0.25 h; microwave | A mixture of 2,5-difluoro-phenylamine (129 mg, 1 mmol) and potassium o-ethyl dithiocarbonate (352 mg, 2.2 mmol) in DMF (5 mL) was heated to 120°C for 15 min in microwave. The reaction mixture was cooled, diluted with 10 mL of ice water, and acidified with 3 mL of HCI solution (1 mol/L). Then the mixture was extracted with EtOAc (3 x 50 mL), washed with brine and dried over Na2SO/i. The dried organic layers were concentrated to give 5- fluorobenzo[d]thiazole-2-thiol (120 mg, 0.67 mmol, 67percent). ESI-MS (M+l): 185 calc. for |
40% | for 4 h; Inert atmosphere; Heating | General procedure: GP3-1: A solution of 2-halo substituted aniline (1.0 eq), potassium ethyl xanthate (1.2 eq or 2.2 eq,typically 2.2 eq) in 10 volume of anhydrous DMF was heated at 100 0Cor 120 0C for 4 hours under nitrogen. TLC monitored the progress ofreaction. After completion, the reaction mixture was cooled to room temperature,diluted with water (10 volume) and neutralized by 1 M HCl solution to pH 5. Theformed precipitate was collected by filtration, rinsed with water, firstlydried by rotavapor, and then dried by oil pump to afford 2-mercaptobenzothiazole.GP3-2: 2-mercaptobenzothiazole in 10 volume ofanhydrous DCM, was added by sulfuryl chloride (SO2Cl2, 1volume) under ice-cooled condition. The mixture was stirred at rt for 1 hour,which was monitored by TLC. After consumption of starting material, the mixturewas diluted by 30 volume of ether, following quenching carefully by addingwater. Stirring was kept for 1 hour to make sure the SO2Cl2was totally consumed and product was released. Organic layer was collected,neutralized by saturated NaHCO3, dried over Na2SO4and purified by silica gel chromatograph to give the pure product, which wasfinally characterized by LC-MS and NMR. |
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