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[ CAS No. 72452-47-2 ] {[proInfo.proName]}

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Chemical Structure| 72452-47-2
Chemical Structure| 72452-47-2
Structure of 72452-47-2 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 72452-47-2 ]

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Product Details of [ 72452-47-2 ]

CAS No. :72452-47-2 MDL No. :MFCD00187723
Formula : C22H10N4O2 Boiling Point : -
Linear Structure Formula :- InChI Key :SSIIVKRGBWPLNS-UHFFFAOYSA-N
M.W : 362.34 Pubchem ID :988678
Synonyms :

Calculated chemistry of [ 72452-47-2 ]

Physicochemical Properties

Num. heavy atoms : 28
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.0
Num. rotatable bonds : 4
Num. H-bond acceptors : 6.0
Num. H-bond donors : 0.0
Molar Refractivity : 98.33
TPSA : 113.62 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.73
Log Po/w (XLOGP3) : 3.85
Log Po/w (WLOGP) : 4.76
Log Po/w (MLOGP) : 1.48
Log Po/w (SILICOS-IT) : 4.24
Consensus Log Po/w : 3.41

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.72
Solubility : 0.00685 mg/ml ; 0.0000189 mol/l
Class : Moderately soluble
Log S (Ali) : -5.93
Solubility : 0.000423 mg/ml ; 0.00000117 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.21
Solubility : 0.0000224 mg/ml ; 0.0000000618 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.49

Safety of [ 72452-47-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 72452-47-2 ]

* 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.

  • Downstream synthetic route of [ 72452-47-2 ]

[ 72452-47-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 31643-49-9 ]
  • [ 108-46-3 ]
  • [ 72452-47-2 ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: recorcinol With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 0.5h; Stage #2: 4-Nitrophthalonitrile In N,N-dimethyl-formamide for 8h; Inert atmosphere;
90.3% With potassium carbonate In (methylsulfinyl)methane at 20℃; for 48h; Inert atmosphere; 1 Comparative Example 1Preparation of RPN monomer and its characterization. Resorcinol diphthalonitrile (i.e., bis(3 ,4-dicyanophenyl) ether of resorcinol) was derived from the nucleophilic substitution reaction of 4-nitrophthalonitrile and resorcinol. To a three necked 500 mL reaction flask was added 18 g (0.104 mol) of 4-nitrophthalonitnle, 5.72 g (0.52 mol) of resorcinol, 28.74 g (0.208 mol) of anhydrous K2C03 and 180 g of dry DMSO), then stirredfor 48 hours at room temperature under a nitrogen atmosphere. The reaction solution was poured into 600 mL of stirring deionized water, leaving undissolved salts behind in the reaction flask. The precipitated product was collected on a Buchner funnel by suction filtration. The precipitate was added to 200 mL of methanol and stirred for 30 minutes to remove impurities. The solid product was collected a second time on a Buchner funnel by suction filtration and washed with 200 mL ofmethanol. The product was collected and dried in a convection oven at 120°C. The product, 17 g (90.3%), had a melt temperature of 185°C. The product was identified as the desired compound by infrared and NMR analysis.RPN characterizing data: DSC Tm= 185°C. FTIR(ATR; cm’): 2231 (-CN), 1244 (C-OC). ‘H NMR (500JVIF-Tz, CDC13 with 0.05% v/v TMS; , ppm): 7.79 (d, J=8.68 Hz, 2H), 7.57 (t,J=8.24 Hz, 1H), 7.37 (d, J=2.52 Hz, 2H), 7.33 (q, Jab8.68 Hz, Jbc=2.54, 2H), 7.03 (q, Jab8.25 Hz, Jbc=2.30, 2H), 6.86 (t, J=2.27 Hz, 1H), ‘3C NMR (500MHz, CDC13 with 0.05% v/v TMS; , ppm):160.68, 155.46, 135.66, 132.35, 122.05, 122.01, 117.86, 117.71, 115.15, 114.78, 112.88, 109.83.
87% With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 5h; 2 Synthesis of compound (PN 2) 16.5 g of the compound of the following formula E and 100 ml of dimethyl formamide were added to 3 neck round bottom flasK), and the mixture was stirred at room temperature for dissolution. In Production Example 1,51.9 g of the nitropthalonitrile of the formula C used was added, and 50 g of DMFAnd the mixture was stirred and dissolved. Subsequently, 62.6 g of potassium carbonate and 50 g of DMFAfter the addition, the temperature was elevated to 85 while stirring. After reacting for about 5 hours, it was cooled to room temperature.The cooled reaction solution was poured into 0.2N hydrochloric acid aqueous solution to neutralize and precipitate. After filtration, it was washed with water. The filtered reaction was then dried in a vacuum oven at 100 for one day. After removing water and residual solvent, a compound (PN2) of the following formula (D) was obtained in a yield of 87% by weight. The NMR analysis results for the compound of formula (D)
85% With potassium carbonate sesquihydrate In lithium hydroxide monohydrate; N,N-dimethyl-formamide at 85℃; 2.4.1. 4,4’-[benzene-1,3-diylbis(oxy)]dibenzene-1,2-dicarbonitrile (1) In a three-necked flask equipped with a magnetic stirrer, reflux condenser and thermometer 10.00 g (0.058 mol) of 4-nitrophthalonitrile, 3.2 g (0.029 mol) of resorcinol, 40 mL of DMF were added. Then, 10 g (0.072 mol) of K2CO3 1.5H2O preliminarily dissolved in 13.3 mL of deionized water and added to the reacting solution. The reaction was carried out for 1.5 h at the temperature of 85 °C. The precipitate formed was filtered off, washed with isopropyl alcohol and water. The final product was dried under vacuum. Yield: 85%, m.p. 185 °C (DSC). 1H NMR (250 MHz, DMSO-d6, δ, ppm): 8.13 (d, J = 8.8 Hz, 2H, H1), 7.92 (d, J = 2.6 Hz, 2H, H2), 7.60 (m, 1H, H6), 7.55 (dd, J = 8.8, 2.9 Hz, 2H, H3), 7.13 (m, 3H, H4, H5). FT-IR (ν, cm-1): 3079 (CAr-H), 2231 (CN), 1586 (CAr-CAr), 1249 (CAr-O-CAr).
84.1% With potassium carbonate In (methylsulfinyl)methane at 20℃; for 24h;
82% With potassium carbonate In (methylsulfinyl)methane at 70℃; for 8h; 3.4.1. Synthesis of 4,4’-[1,3-Phenylenebis(oxy)]diphthalonitrile Resorcinol (0.09 g, 0.86 mmol), potassium carbonate (0.12 g, 0.86 mmol) and 50 mLof dry DMSO were mixed in a two-necked flask and stirred at 70 C for 1 h. Then 4-nitrophthalonitrile (1, 0.30 g, 1.70 mmol) and potassium carbonate (0.18 g, 1.30 mmol) wereadded to the reaction mixture, after which stirring was continued for additional 7 h at aconstant temperature. After a lapse of time, the reaction mixture was cooled and pouredinto 150 mL of a 0.1 mol/L aqueous solution of HCl and left until a precipitate formed.The precipitate was filtered off and sequentially washed with distilled water (2 30 mL),0.1 mol/L HCl solution (2 30 mL) and distilled water (2 30 mL) to neutral pH, andthen recrystallized from ethanol. The output was a beige fluffy powder, soluble in acetone,ethanol, chloroform, DMF. Yield: 0.26 g (82%). FT-IR: nmax, cm1 3088, 2917, 2850 (Car-H);2243 (CN); 1586, 1474, 1389 (Car=Car); 1256 (Ar-O-Ar). 1H-NMR (500 MHz, CDCl3):δ, ppm 7.76 (dd, 2 H, J = 8.6); 7.55 (t, 1 H, J = 8.3); 7.32 (d, 2 H, 4J = 2.5); 7.29 (dd, 2 H,4J = 2.5, 3J = 8.3); 6.99 (dd, 2 H, 3J = 8.3, 4J = 2.2); 6.82 (m, 1 H, 4J = 2.2). 13C-NMR (100 MHz,acetone-d6): δ, ppm 160.66, 155.52, 135.65, 132.35, 122.03, 117.91, 117.66, 115.10, 114.74,112.85, 109.91. MS (MALDI-TOF): m/z 362.11 [M]+, calcd. 363.08
70% With potassium carbonate In (methylsulfinyl)methane at 20 - 70℃; for 430h; Inert atmosphere; Synthesis of 4, 4′-(1, 3-phenylenebis (oxy)) diphthalonitrile (3) Compound 2 (1.272 g) was dissolved in dry DMSO (10 mL) andcompound 1 (4.00 g, 28.90 mmol) was added under inert atmosphere.Finely ground anhydrous potassium carbonate (8.00 g) was added tothis reaction mixture and stirred for 10 h at 70 °C. After stirring at roomtemperature for 7 days, the reaction was monitored by thin layerchromatography (TLC) as it proceeded under Ar. Finally, the reactionmixture was poured onto ice and crystalized from ethanol to form alight yellow precipitate. The pure product was dried using P2O5 under avacuum for 15 days. The yield was 2.80 g or 70%. The following FT-IR(ATR) signals were observed (υmax/cm-1): 3120/3093/3074 (Ar-CH), 2235 (C^N), 1587/1593 (C]C), 1310/1285/1247 (CeOeC). 1H NMR(DMSO-d6), δ (ppm): 8.14 (2H, d, Ar-H), 7.93 (2H, d, Ar-H), 7.61 (H, t,Ar-H), 7.56 (H, d, Ar-H), 7.57 (H, d, Ar-H) 7.15 (2H, s, Ar-H), 7.14 (H,s, Ar-H). Anal. calcd. for C22H10N4O2 C, 72.92; H, 2.78; N, 15.46, foundC, 72.65; H, 2.29; and N, 15.75%. LC-MS, m/z anal. calcd. 362.34,found [M]+: 362.09, and [M + H2O]+: 380.12.
68.7% With potassium carbonate In (methylsulfinyl)methane at 40℃; for 12h; Inert atmosphere; 2.3. Synthesis of phthalonitrile compound (CN) To a 500 mL three-neck rounde-bottom flask was added resorcinol (16.52 g, 0.15 mol), 4-nitrophthalonitrile (51.94 g, 0.30 mol) and 180 mL DMSO. During the course of the reaction, the K2CO3 (62.19 g, 0.45 mol) was added in three portions at an interval of 20 min. Then the resulting mixture was heated at 40 °C for 12 h under nitrogen. After cooling, the product mixture was poured into water. The light yellow filtrate was collected by suction filtration and washed with large amount of water until the filtrate was neutral. The crude product (42.0 g) was purified by rinsing with CH2Cl2 in Buchner funnel and suction flask, and the filtrate was then dried by evaporation under a vacuum at 80 °C for 5 h to remove CH2Cl2. The yellow-white powder was obtained in 68.7 wt% yield (28.9 g), m. p. peak at 183 °C (sharp) (DSC) at a heat rate of 10 °C/min. FTIR (KBr), 2232 (C≡N), 1284 (Ar-O-Ar), 1248 (Ar-O-Ar). 1H NMR (400 MHz, DMSO-d6): 8.14-8.11 (d, 2H; Ar H), 7.92 (s, 2H; Ar H), 7.63-7.53 (m, 3H; Ar H), 7.15-7.12 (m, 3H; Ar H).
65% Stage #1: 4-Nitrophthalonitrile; recorcinol In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Synthesis of 4,4-[1,3-phenylenebis(oxy)]diphthalonitrile (2). 4-Nitrophthalonitrile (1.00 g, 5.78 mmol), resorcinol (0.32 g,2.89 mmol), and DMF (100 mL) were placed in a three-necked flask equipped with a magnetic stirrer, a thermometer, and a refl uxcondenser. After the substances were completely dissolved, thereaction mixture was stirred for 1 h at 20 °C. Then potassium carbonate (1.00 g, 7.26 mmol) was introduced by equal portions.The mixture was stirred for 48 h at ~20 °C, after which it waspoured into 300 mL of a 0.1 M solution of NaOH and filtered off . The obtained pale yellow precipitate was washed with water,a 10% solution of alkali, and water again to the neutral pH, andwashed from the fi lter with DMF. Then DMF was distilled offin vacuo. The subsequent purifi cation was performed by recrystallizationfrom ethanol (65% yield). 1 NMR (CDCl3), δ: 7.76(dd, 2 H, H(12,18), J = 8.6 Hz); 7.55 (t, AX2 pattern, 1 H, H(6),J = 8.3 Hz); 7.32 (d, 2 H, H(7,13), 4J = 2.5 Hz); 7.29 (dd, 2 H,H(9,17), 4J = 2.5 Hz, 3J = 8.3 Hz); 6.99 (dd, 2 H, H(3,5), 3J == 8.3 Hz, 4J = 2.2 Hz); 6.82 (m, AX2 pattern, 1 H, 4J = 2.2 Hz).13 NMR (acetone-d6), δ: 160.66 ((8,16)); 155.52 ((2,4));135.65 ((12,18)); 132.35 ((6)); 122.03 ((7,9,13,17); 117.91((20,22); 117.66 ((19,21)); 115.10 ((10,14)); 114.74 ((3,5));112.85 ((1)); 109.91 ((11,15)). MS MALDI-TOF, found:362.11 [M]+. C22H10N4O2. Calculated: M = 362.08.
65% With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 48h; 4.3.1. Synthesis of 4,4’-[1,3-phenylenebis(oxy)]diphthalonitrile (2) 4-Nitrophthalonitrile (1.00 g, 5.77 mmol) and resorcinol (0.32 g,2.88 mmol) were dissolved in 100 ml of dry DMF. After stirring for 1 h atroom temperature, finely ground anhydrous potassium carbonate(0.99 g, 2.5 mmol) was added to the described solution. The reactionmixture was stirred at 25 C for 48 h and then it was poured into 300 mlof 0.1 M NaOH aqueous solution. The resulting precipitate were filteredoff and washed with deionized water (2 30 ml), 0.1 M aqueous solutionof NaOH (2 30 ml) and finally with deionized water (2 30 ml)until neutral pH. Obtaining coarse crude crystals were recrystallizedform ethanol to remove any residual of reagents. The pure product wasobtained as light yellow powder and it was soluble in chloroform,ethanol, and acetone. Yield 0.68 g (65%) mp 190 C. FT-IR: max, cm 13088, 2917, 2850 (Car - H); 2243 (C- - -N); 1586, 1474, 1389 (Car Car);1256 (Ar-O-Ar). 1H NMR (500 MHz, CDCl3): , ppm 7.76 (dd, 2 H,J 8.6); 7.55 (t, 1 , J 8.3); 7.32 (d, 2 , 4J 2.5); 7.29 (dd, 2 ,4J 2.5, 3J 8.3); 6.99 (dd, 2 , 3J 8.3, 4J 2.2)); 6.82 (m, 1 ,4J 2.2). 13C NMR (100 MHz, Acetone-d6): , ppm 160.66, 155.52,135.65, 132.35, 122.03, 117.91, 117.66, 115.10, 114.74, 112.85,109.91. MS (MALDI-TOF): m/z 362.11 [M], calcd. 363.08.
With potassium carbonate In (methylsulfinyl)methane

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