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Chemical Structure| 134450-56-9 Chemical Structure| 134450-56-9

Structure of 134450-56-9

Chemical Structure| 134450-56-9

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Product Details of [ 134450-56-9 ]

CAS No. :134450-56-9
Formula : C8H2F2N2
M.W : 164.11
SMILES Code : N#CC1=CC(F)=C(F)C=C1C#N
MDL No. :MFCD00061281
InChI Key :KNDUBEZZKOOYMJ-UHFFFAOYSA-N
Pubchem ID :11960962

Safety of [ 134450-56-9 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301+H311+H331-H315-H319
Precautionary Statements:P261-P264-P270-P271-P280-P301+P310+P330-P302+P352+P312+P361+P364-P304+P340+P311-P305+P351+P338+P337+P313-P403+P233-P405-P501
Class:6.1
UN#:2811
Packing Group:

Computational Chemistry of [ 134450-56-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 35.79
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

47.58 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.3
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.56
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.55
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.62
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.62
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.93

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.21
Solubility 1.01 mg/ml ; 0.00616 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.17
Solubility 1.11 mg/ml ; 0.00677 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.12
Solubility 0.125 mg/ml ; 0.00076 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

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)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.19 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.75

Application In Synthesis of [ 134450-56-9 ]

* 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 [ 134450-56-9 ]

[ 134450-56-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 134450-56-9 ]
  • [ 18628-07-4 ]
  • 4,5-di(9H-[3,9'-bicarbazol]-9-yl)phthalonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% Sodium hydride (60% in oil, 0.16 g, 3.98 mmol) and 9H-3,9'-bicarbazole (0.85 g, 2.53 mmol) were stirred in 3 ml anhydrousDMF solvent under a nitrogen atmosphere. After 20 min, 4,5-difluorophthalonitrile (0.20 g, 1.21 mmol) in 5 ml DMF was addedthe mixture. The reaction mixture was stirred at room temperaturefor 1 h. The reaction mixture was quenched with distilled water.Organic layer of the mixture was extracted with dichloromethaneand distilled water. Then solvent of organic layer was evaporatedand purified by column chromatography (dichloromethane/nhexane).The yellow product final purified by sublimation. The lightyellow product was obtained in 50% yield (0.48 g).1H NMR (500 MHz, CDCl3): delta 8.36 (d, J = 2.5 Hz, 1H), 8.19-8.16(m, 1H), 8.16-8.09 (m, 5H), 7.94 (d, J = 3.5 Hz, 1H), 7.87 (d,J = 3.7 Hz, 3H), 7.80 (d, J = 2.5 Hz, 1H), 7.51 (d, J = 4.2 Hz, 1H),7.42-7.40 (m, 1H), 7.29-7.09 (m, 15H), 6.80-6.78 (m, 3H). 13C NMR(125 MHz, CDCl3): delta 141.65, 141.40, 140.06, 140.01, 139.81, 139.65,138.11, 138.01, 137.97, 137.40, 137.32, 134.58, 132.44, 132.39, 131.73,130.97, 130.73, 130.60, 127.11, 126.66, 126. 10, 125.83, 125.22, 125.01,124.63, 123.88, 123.14, 121.80, 121,71 120.68, 120.32, 119.77, 119.38,118.61, 117.46, 113.02, 112.95, 110.91, 110.67, 109.55, 109.44, 109.26,MS (API-) m/z: 789.8 [(M + H)-].
  • 2
  • [ 134450-56-9 ]
  • [ 56525-79-2 ]
  • 4,5-bis(3,6-diphenyl-9H-carbazol-9-yl)phthalonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% The syntheses of the three TADF emitters: 4,5-di(9H-carbazol-9-yl)phthalonitrile (2CzPN), 4,5-bis(3,6-di-tert-butyl-9H-carbazol-9-yl)phthalonitrile (2tBuCzPN), and 4,5-bis(3,6-diphenyl-9H-carbazol-9-yl)phthalonitrile (2PhCzPN),were easily achieved in a nitrogen atmosphere through aromaticnucleophilic substitution reactions by using carbazolylunits as nitrogen nucleophiles and the phthalonitrile unit asthe electrophile, as outlined in Scheme 1. The syntheses were performed according to the synthetic methods reported previously[7,41]. The reagents and all the solvents were used as received without any further purification. 9H-carbazole(2.04 g, 12.2 mmol), 3,6-di-tert-butyl-9H-carbazole (3.41 g,12.2 mmol), or <strong>[56525-79-2]3,6-di-phenyl-9H-carbazole</strong> (3.89 g,12.2 mmol) was dissolved in dry N,N-dimethylformamide(DMF) (20 mL) and then added dropwise to a stirred solution of potassium tert-butoxide (1.36 g, 12.2 mmol) in dry DMF(10 mL) under a nitrogen atmosphere at room temperature.After stirring at 40 °C for 30 min, 4,5-difluorophthalonitrile(1.0 g, 6.1 mmol) dissolved in dry DMF (10 mL) was added dropwise. The reaction mixture was stirred at 80 °C for 12 h.After it was cooled to room temperature, the reaction mixture was quenched with saturated potassium carbonate aqueous solution (100 mL), and the resulting precipitate was collectedby filtration. The residue was dried in a vacuum drying oven at 100 °C for 5 h, and then purified by the columnchromatography on the silica gel (petroleum ether:dichloromethane,5:1, v/v). The three compounds were furtherpurified by vacuum sublimation, yielding green or yellowish green powder. 2CzPN (1.95 g, 70percent), 1H NMR (400 MHz, DMSO-d6), delta (ppm): 7.05 (m, 8H), 7.27 (d, 4H), 7.88 (d,4H), 7.66 (t, 8H), 8.80 (s, 2H); HRMS (ESI) m/z: [M]+calculated for C32H18N4, 458.1526, found, 458.2921.2tBuCzPN (2.08 g, 50percent), 1H NMR (400 MHz, CDCl3), delta(ppm): 1.33 (s, 36H), 6.78 (d, 4H), 6.93?6.96 (m, 4H), 7.26(s, 4H), 7.63 (d, 4H), 8.26 (s, 2H); HRMS (ESI) m/z: [M]+calculated for C48H50N4, 682.4030, found, 682.5565.2PhCzPN (1.86 g, 40percent), 1H NMR (400 MHz, DMSO-d6), delta(ppm): 7.25?7.29 (m, 4H), 7.38 (t, 8H), 7.47 (s, 8H), 7.66 (t,8H), 8.42 (d, 4H), 8.89 (d, 2H); HRMS (ESI) m/z: [M+Na]+calculated for C56H34N4Na, 785.2676, found, 785.2676(Figure S1).
 

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