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Chemical Structure| 217-59-4 Chemical Structure| 217-59-4
Chemical Structure| 217-59-4

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Triphenylene

CAS No.: 217-59-4

4.5 *For Research Use Only !

Cat. No.: A666345 Purity: 98%

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Product Details of [ 217-59-4 ]

CAS No. :217-59-4
Formula : C18H12
M.W : 228.29
SMILES Code : C12=CC=CC=C1C3=CC=CC=C3C4=CC=CC=C24
MDL No. :MFCD00001108
InChI Key :SLGBZMMZGDRARJ-UHFFFAOYSA-N
Pubchem ID :9170

Safety of [ 217-59-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H318-H410
Precautionary Statements:P273-P280-P305+P351+P338
Class:9
UN#:3077
Packing Group:

Calculated chemistry of [ 217-59-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 18
Num. arom. heavy atoms 18
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 78.96
TPSA ?

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

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.66
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

5.49
Log Po/w (WLOGP)?

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

5.15
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.

5.97
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

5.09
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

4.87

Water Solubility

Log S (ESOL):?

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

-5.45
Solubility 0.000802 mg/ml ; 0.00000351 mol/l
Class?

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

Moderately soluble
Log S (Ali)?

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

-5.25
Solubility 0.00129 mg/ml ; 0.00000565 mol/l
Class?

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

Moderately 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

-7.43
Solubility 0.00000846 mg/ml ; 0.0000000371 mol/l
Class?

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

Poorly soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

Low
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
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.

-3.79 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

1.0
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

2.0
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

1.0 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<2.0
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)

1.0

Application In Synthesis of [ 217-59-4 ]

* 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 [ 217-59-4 ]

[ 217-59-4 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 217-59-4 ]
  • [ 82632-80-2 ]
YieldReaction ConditionsOperation in experiment
95% With bromine; iron; In nitrobenzene; at 20 - 205℃; for 18.25h; To a solution of triphenylene (1, 1.07 g, 4.7 mmol) in nitrobenzene (40 mL) with iron powder (100 mg, 1.79 mmol) bromine (2.2 mL, 38.8 mmol) was slowly added over 15 minutes. The solution was then allowed to stand for 16 hours at room temperature. It was heated at 205 C for 2 hours. The mixture was cooled to room temperature and mixed with diethyl ether (150 mL) and filtered. The crude white solid was washed by diethyl ether (3x30 mL) and acetone (3x10 mL). After drying in vacuo for 12 hours, 3.13 g of 2,3,6,7, 10,11-hexabromotriphenylene (yield 95%) was collected. The product was used directly without characterization due to low solubility.
94.8% With bromine; iron; In nitrobenzene; at 20 - 210℃; for 3.33h;Inert atmosphere; Under nitrogen, bromine (9.0 mL, 349 mmol) was added dropwise to 9 (3.95 g, 17.3 mmol) and Fe (410 mg, 7.34 mmol) in nitrobenzene (200 mL) with stirring at rt for 20 min and furthermore at 210 C for 3 h. After cooling the reaction mixture to room temperature, Et2O was added and the precipitate was collected. The solid was washed thoroughly with Et2O, acetone, and CHCl3 to give white powder (11.5 g, 16.4 mmol, 94.8%). M.p. >300 C; 1HNMR (300 MHz, CDCl3): delta (ppm) = 8.72 (s, 6H, Ar-H); IR (KBr): numax(cm-1) = 1585, 1551, 1454, 1365, 1119, 873, 863.
84% With bromine; iron; at 170℃; for 10h;Inert atmosphere; 5.0 g of triphenylene, 0.49 g of iron powder and 10.1 ml of bromine were added to a reaction vessel purged with nitrogen and heated, followed by stirring at 170 C. for 10 hours. After cooling to room temperature, 100 ml of tetrahydrofuran was added and the mixture was further stirred for 0.5 hour. Filtration gave 2, 3, 6, 7, 10, 11-hexabromotriphenylene gray powder13.5 g (yield 84%) was obtained.
80% With bromine; iron; In nitrobenzene; Step a) [0222] Triphenylene (1 equivalent) is brominated with 8 equivalents of Br2 in the presence of catalytic amounts of iron in nitrobenzene to obtain 80% brominated triphenylene derivative.

  • 2
  • [ 217-59-4 ]
  • [ 7726-95-6 ]
  • [ 82632-80-2 ]
  • 3
  • [ 217-59-4 ]
  • [ 890042-13-4 ]
  • 4
  • [ 217-59-4 ]
  • [ 654664-63-8 ]
  • 5
  • [ 76-09-5 ]
  • [ 217-59-4 ]
  • [ 13517-10-7 ]
  • [ 890042-13-4 ]
  • 6
  • [ 217-59-4 ]
  • 2,3,6,7,10-pentabromotriphenylene [ No CAS ]
  • [ 82632-80-2 ]
 

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