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CAS No. : | 69518-17-8 | MDL No. : | MFCD01863730 |
Formula : | C8H3IN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OOHQHYJZUSXMFD-UHFFFAOYSA-N |
M.W : | 254.03 | Pubchem ID : | 4120024 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 48.59 |
TPSA : | 47.58 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.42 cm/s |
Log Po/w (iLOGP) : | 1.67 |
Log Po/w (XLOGP3) : | 2.01 |
Log Po/w (WLOGP) : | 2.03 |
Log Po/w (MLOGP) : | 1.66 |
Log Po/w (SILICOS-IT) : | 2.73 |
Consensus Log Po/w : | 2.02 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.08 |
Solubility : | 0.209 mg/ml ; 0.000822 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.64 |
Solubility : | 0.587 mg/ml ; 0.00231 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.52 |
Solubility : | 0.076 mg/ml ; 0.000299 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.08 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302+H312+H332-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 |
---|---|---|
87% | 2. Synthesis of 4-iodophthalonitrile 4-Aminophthalonitrile (5 g, 35 mmol) was dissolved in a mixture of ethanol (120 mL) and 10% HCl (120 mL). The reaction was kept at C with an ice bath, then NaNO2 (3.89 g, 56 mmol) dissolved in water (50 mL) was added slowly into the solution. The reaction was stirred for 30 mins, then KI (9.93 g, 60 mmol) dissolved in water (50 mL) was added slowly. After warming to room temperature, the reaction was stirred overnight. The precipitation was collected by filtration and washed with water to give 4-iodophthalonitrile (7.8 g, 87% yield) as a dark yellow solid. | |
70% | With sulfuric acid; sodium iodide; sodium nitrite; In water; at -10 - 20℃; | Sulfuric acid (H 2 SO 4, 12 mL) and water (6 mL) were mixed, 4-aminophthalonitrile (Compound 1: 2.5 g, 17.48 mmol) was added thereto, and the mixture was stirred and cooled to -10 C.Sodium nitrite (NaNO 2: 1.206 g, 17.487 mmol) dissolved in water was added dropwise to this reaction mixture while stirring while maintaining the temperature of the reaction mixture at -10 to 0 C.After completion of the dropwise addition, the reaction mixture was rapidly filtered using a suction filter, and the filtrate was separated.Sodium iodide (7.9 g, 47 mmol) was dissolved in 20 ml of water, and the filtrate prepared previously was added dropwise to the cooled solution, and the mixture was kept at 0 C. and stirring was continued.When the temperature of the mixed solution changed to black was raised to room temperature while stirring, a black precipitate appeared, and this solid matter was separated by filtration.This solid was dissolved in dichloromethane (CH 2 Cl 2: 50 mL), washed twice with cold water (50 ml), washed with 50 ml of 10% sodium bicarbonate (NaHCO 3) solution, once with 50 ml of cold water once again, with saturated sodium sulfite (Na 2 S 2 O 3) Once with 50 ml and finally three times with 50 ml of water.After washing, the solution was dried with magnesium sulfate (MgSO 4), and the solvent was distilled off until the total amount became about 10 ml.Purification by chromatography using a silica gel column gave a white solid of the objective 4-iodo phthalonitrile (Compound 2) in 70% yield. |
59% | 4-aminophthalonitrile (a) (3.0 g, 20.96 mmol)Was dissolved in 42 ml of 2M sulfuric acid (H2SO4)Lower the temperature to 0 .Then, sodium nitrite (NaNO2) (1.93 g, 3.94 mmol) was dissolved in 55 mL of water,The reactorWhile maintaining the temperature at 0 C,The mixture was slowly dropped over 30 minutes and then stirred for 30 minutes.The mixture was decompressed and 210 ml of water and potassium iodide (KI) were added to the reduced pressure mixed solution,(3.72 g, 22.42 mmol) is slowly added dropwise.The mixture is slowly stirred at room temperature and stirred, and the precipitated mixture is reduced in pressure to obtain a solid precipitate. The solid precipitate thus obtained was dissolved in dichloromethane (CH2Cl2), washed with 5% sodium bicarbonate (NaHCO3), dried with anhydrous Na2SO4, filtered, and concentrated. The mixture was purified by flash column chromatography on SiO2The compound (g) was separated by flash column chromatography (MC) to obtain 2.9 g (59% yield) of the compound (g). |
51% | 4-amino-phthalonitrile wasplaced in a three-necked round bottom flask. 50 g of crushed iceand 80 mL of hydrochloric acid (37%) were added. Then a solutionof sodium nitrite (3 mg, 43 mmol) in water (30 mL) was slowlyadded to the reaction mixture at 5 C over 30 min. The reactionmixture was stirred at 5 C for 1 h. The precipitate formed was filtratedand washed with water (50 mL). The filtrate was addeddropwise on a potassium iodide solution (7 mg, 42 mmol) in 30mL of water at 5 C over a period of 1 h. The reaction mixturewas warmed to room temperature during 14 h. An orange powderwas filtrated on Buechner, and dissolved in toluene (affording anorange filtrate). The organic phase was washed with saturatedbicarbonate sodium solution, saturated sodium thionite solution,brine, then dried over magnesium sulphate. After concentrationunder reduced pressure, the resulting solid was subjected to columnchromatography (silica gel, eluent = dichloromethane:toluene, 50: 50 vol). Yield = 51%.1H NMR (300 MHz, d-DMSO, 300 K): d (ppm) = 7.85 (d, 3J = 7.8Hz, 1H); 8.31 (dd, 3J = 7.8, 1.6 Hz, 1H); 8.58 (d, 3J = 1.6 Hz, 1H). 13CNMR {1H} (75 MHz, CDCl3, 300 K): d (ppm) = 99.78; 113.95;115.05; 115.22; 117.16; 134.12; 142.18; 142.59. ESI-MS: m/z =276.81 [M+Na]+; 252.83 [MH]; (calcd for C8H3IN2: 253.93 (exactmass); 254.03 (FW)). | |
With sulfuric acid; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; | EXAMPLE I Synthesis of 4-Iodophthalonitrile 4-Aminophthalonitrile (40 g, 0.28 mol) was slowly added to 80 ml of concentrated sulfuric acid and the mixture was stirred with cooling (below 25 C.) until dissolution was complete. After cooling below 15 C., ice water (175 ml) was slowly added to precipitate the amine bisulfate. | |
51 g (72%) | With potassium iodide; sulfuric acid; urea; sodium nitrite; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water; | EXAMPLE I Synthesis of 4-Iodophthalonitrile. 4-Aminophthalonitrile (40 g, 0.28 mol) was slowly added to 80 ml of concentrated sulfuric acid and the mixture was stirred with cooling (below 25 C.) until dissolution was complete. After cooling below 15 C., ice water (175 ml) was slowly added to precipitate the amine bisulfate. A solution of sodium nitrite (20 g, 0.29 mol) in 40 ml of water was then added at such a rate as to maintain the temperature at 0-10 C. After stirring the solution for an additional 15 minutes, a few crystals of urea were added to decompose any excess sodium nitrite. The homogeneous solution was then poured into a breaker containing potassium iodide (75 g, 0.45 mol) dissolved in 150 ml of water. After the evolution of nitrogen had ceased and a negative test with alkaline p-methoxyphenol indicated that the reaction was complete, the brown precipitate was collected by suction filtration and washed with 10% sodium bisulfite, with saturated sodium bicarbonate and finally with water. Recrystallization from ethanol-water afforded 51 g (72%) of the desired product, m.p. 141-142 C. |