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Chemical Structure| 63089-50-9

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Product Details of [ 63089-50-9 ]

CAS No. :63089-50-9
Formula : C9H6N2
M.W : 142.16
SMILES Code : CC1=CC=C(C#N)C(=C1)C#N
MDL No. :MFCD02093739
InChI Key :MDXGRFMFORMPGT-UHFFFAOYSA-N
Pubchem ID :2733971

Safety of [ 63089-50-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302+H312+H332
Precautionary Statements:P280

Computational Chemistry of [ 63089-50-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.11
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 40.84
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.

1.64
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

1.72
Log Po/w (WLOGP)?

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

1.74
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.

1.08
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

2.24
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.68

Water Solubility

Log S (ESOL):?

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

-2.21
Solubility 0.879 mg/ml ; 0.00619 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.

-2.34
Solubility 0.657 mg/ml ; 0.00462 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

-2.93
Solubility 0.167 mg/ml ; 0.00117 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

Yes
Log Kp (skin permeation)?

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

-5.95 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)

1.41

Application In Synthesis of [ 63089-50-9 ]

* 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 [ 63089-50-9 ]

[ 63089-50-9 ] Synthesis Path-Downstream   1~35

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  • [ 1825-62-3 ]
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  • [ 107-46-0 ]
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  • 10
  • [ 920-68-3 ]
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  • [ 1943-88-0 ]
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  • [ 88830-20-0 ]
  • 11
  • [ 557-21-1 ]
  • Trifluoro-methanesulfonic acid 5-methyl-2-trifluoromethanesulfonyloxy-phenyl ester [ No CAS ]
  • [ 63089-50-9 ]
  • 14
  • diazotized 2-amino-4-methyl-benzonitrile [ No CAS ]
  • [ 63089-50-9 ]
  • 15
  • [ 504-29-0 ]
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  • [ 81560-22-7 ]
  • 16
  • [ 63089-50-9 ]
  • [ 33252-26-5 ]
  • C27H31N5 [ No CAS ]
  • 17
  • [ 452-86-8 ]
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  • 18
  • [ 26830-95-5 ]
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  • 19
  • [ 64113-86-6 ]
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  • [ 620-22-4 ]
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  • 21
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  • [ 910564-70-4 ]
  • 22
  • [ 63089-50-9 ]
  • [ 86665-25-0 ]
  • 23
  • [ 63089-50-9 ]
  • [ 12775-96-1 ]
  • CuMePc [ No CAS ]
  • 24
  • [ 3710-84-7 ]
  • [ 63089-50-9 ]
  • [ 1190-79-0 ]
  • [ 1015228-02-0 ]
  • [ 127511-07-3 ]
  • 25
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  • [ 1015228-02-0 ]
  • [ 127511-07-3 ]
  • 26
  • [ 3317-61-1 ]
  • [ 63089-50-9 ]
  • [ 40314-06-5 ]
  • 27
  • [ 63089-50-9 ]
  • 4-(bromomethyl)phthalonitrile [ No CAS ]
  • 4-(dibromomethyl)phthalonitrile [ No CAS ]
  • 4-(tribromomethyl)phthalonitrile [ No CAS ]
  • 28
  • [ 63089-50-9 ]
  • 4-(bromomethyl)phthalonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;Reflux; (1) Weigh 10 g (0.07 mol) of 4-methyl phthalonitrile and add it to a 1 L three-necked round bottom flask.A further 250 mL of a carbon tetrachloride solution was added to a three-neck round bottom flask.0.2g of BPO (dibenzoyl peroxide) is added in batches,13.8 g (0.077 mol) of NBS (N-bromosuccinimide in batches) was slowly warmed to the carbon tetrachloride reflux temperature,With the progress of the reaction system has a white solid,Reflux reaction 20-24 hours, suction filtration,The solvent was removed by spin-drying to give 10.78 g of a pale yellow solid product.Yield 70%.
  • 31
  • [ 78-67-1 ]
  • [ 63089-50-9 ]
  • 4-(dibromomethyl)phthalonitrile [ No CAS ]
  • 32
  • [ 63089-50-9 ]
  • C45H42N8OZn [ No CAS ]
  • 33
  • [ 63089-50-9 ]
  • 4-(dibromomethyl)phthalonitrile [ No CAS ]
  • 34
  • [ 63089-50-9 ]
  • 2(3),9(10),16(17),23(24)-tetrakis(methyl)phthalocyanine [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With butyl(2-hydroxyethyl)dimethylammonium acetate; at 100℃; for 2.5h;Inert atmosphere; Ionic liquid; General procedure: A mixture of phthalonitrile (4a-g, 200 mg) and functional ionic liquid 2c (1 equivalent) was stirred at 100C under a nitrogen atmosphere for the appropriate time (Table 4). The progress of the reaction was monitored by TLC and UV-Visible spectroscopic analysis. When reaction was completed, the mixture was cooled to room temperature, and distilled water (50 mL) was added to dissolve the functional ionic liquid. The blue-green solid mass was filtered and the aqueous filtrate was evaporated under reduced pressure to recover the ionic liquid pure enough for further use. The solid mass was further washed thoroughly with H2O-MeOH (1:1, 100 mL) to remove the impurities and phthalocyanines are obtained in pure form. All of the phthalocyanines are known compounds and their purities were confirmed by comparison with literature.
  • 35
  • [ 63089-50-9 ]
  • [ 6147-53-1 ]
  • [ 86665-25-0 ]
YieldReaction ConditionsOperation in experiment
82% With butyl(2-hydroxyethyl)dimethylammonium acetate; at 100℃; for 2h;Ionic liquid; Inert atmosphere; General procedure: A mixture of desired phthalonitrile (4a-i, 200mg) and corresponding metal salts (0.25 equivalents) were stirred at 100C with functional ionic liquid 2c (1 equivalent) for the appropriate time (Table 1, 2 and 3). The progress of the reaction was monitored by TLC and UV-Visible spectroscopic analysis. When reaction was completed, the mixture was cooled to room temperature, and distilled water (50 mL) was added to dissolve the functional ionic liquid. The blue-green solid mass was filtered and the aqueous filtrate was evaporated using reduced pressure to recover the pure ionic liquid for further use. The solid mass was further washed thoroughly with H2O-MeOH (1:1, 100 mL) to remove the colorless impurities and metallophthalocyanines are obtained in pure form. All of the phthalocyanines are known compounds and their purities were confirmed by UV-Visible spectroscopic analysis and further comparison with literature.
 

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Technical Information

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