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Chemical Structure| 7089-68-1 Chemical Structure| 7089-68-1

Structure of 7089-68-1

Chemical Structure| 7089-68-1

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Product Details of [ 7089-68-1 ]

CAS No. :7089-68-1
Formula : C12H7ClN2
M.W : 214.65
SMILES Code : ClC1=CC=C2C=CC3=CC=CN=C3C2=N1
MDL No. :MFCD00185678
InChI Key :JHRMQHFRVPVGHL-UHFFFAOYSA-N
Pubchem ID :355193

Safety of [ 7089-68-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 7089-68-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 14
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 62.05
TPSA ?

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

25.78 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.98
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

2.74
Log Po/w (WLOGP)?

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

3.44
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.

2.4
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

3.58
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.83

Water Solubility

Log S (ESOL):?

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

-3.59
Solubility 0.0555 mg/ml ; 0.000258 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.

-2.94
Solubility 0.249 mg/ml ; 0.00116 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

-5.63
Solubility 0.000507 mg/ml ; 0.00000236 mol/l
Class?

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

Moderately 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

Yes
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.

-5.66 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

0.0
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

2.0 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)

1.77

Application In Synthesis of [ 7089-68-1 ]

* 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 [ 7089-68-1 ]

[ 7089-68-1 ] Synthesis Path-Downstream   1~55

  • 1
  • [ 7089-68-1 ]
  • [ 62-53-3 ]
  • N-phenyl-1,10-phenanthrolin-2-amine [ No CAS ]
  • 2
  • [ 7089-68-1 ]
  • [ 22426-16-0 ]
  • 3
  • [ 31535-89-4 ]
  • [ 7089-68-1 ]
YieldReaction ConditionsOperation in experiment
75% Reference Example 32-Chloro-1,10-phenanthroline (3) [0113] [Chem. 20] [0114] Under a stream of argon, to compound (2) (8 g; 38 mmol), phosphorus oxychloride (72 mL) and phosphorus pentachloride (9.8 g; 47.6 mmol) were added in an ice bath. The resulting reaction mixture was stirred and refluxed for 8 hours, and excess phosphorus oxychloride was removed under reduced pressure. To the resulting reaction concentrate, ice water and concentrated aqueous ammonia were added and the resulting mixture was made alkaline to precipitate crude crystals. The crude crystals were separated by filtration and washed with water, and then dried under reduced pressure to give 6.1 g (yield: 75percent) of the title compound (3). [0115] 1H NMR (DMSO-d6) d: 7.80-7.88 (m, 2 H), 8.07 (s, 2 H), 8.54 (d, J = 8.5 Hz, 1 H), 8.60 (d, J = 8.5 Hz, 1 H), 9.14 (d, J = 7 Hz, 1 H)
75% Production Example 32-Chloro-1,10-phenanthroline (3)[0149] [Chem. 26] [0150] Under a stream of argon, to compound (2) (8 g; 38 mmol), phosphorus oxychloride (72 mL) and phosphorus pentachloride (9.8 g; 47.6 mmol) were added in an ice bath. The resulting reaction mixture was stirred and refluxed for 8 hours, and excess phosphorus oxychloride was removed under reduced pressure. To the resulting reaction concentrate, ice water and concentrated aqueous ammonia were added and the resulting mixture was made alkaline to precipitate crude crystals. The crude crystals were separated by filtration and washed with water, and then dried under reduced pressure to give 6.1 g (yield: 75percent) of the title compound (3).[0151] 1H NMR (DMSO-d6)d: 7.80-7.88 (m, 2H), 8.07 (s, 2H), 8.54 (d, J=8.5 Hz, 1H), 8.60 (d, J=8.5 Hz, 1H), 9.14 (d, J=7 Hz, 1H)
  • 4
  • [ 504-29-0 ]
  • [ 7089-68-1 ]
  • [ 89702-49-8 ]
  • 5
  • [ 7089-68-1 ]
  • [ 65567-06-8 ]
  • [ 122768-45-0 ]
  • 6
  • [ 7089-68-1 ]
  • [ 124-41-4 ]
  • [ 22426-16-0 ]
  • 7
  • [ 7089-68-1 ]
  • [ 141-52-6 ]
  • [ 95631-63-3 ]
  • 8
  • [ 7089-68-1 ]
  • [ 84490-68-6 ]
  • [ 145514-98-3 ]
  • 9
  • [ 7089-68-1 ]
  • [ 60-34-4 ]
  • [ 74339-64-3 ]
  • 10
  • [ 7089-68-1 ]
  • [ 100-37-8 ]
  • 2-<2-(N,N-diethylamino)ethoxy>-1,10-phenanthroline [ No CAS ]
  • 12
  • [ 7089-68-1 ]
  • 2-hydrazino-1,10-phenanthroline hydrochloride [ No CAS ]
  • 13
  • [ 7089-68-1 ]
  • 2-(l-methylhydrazino)-1,10-phenanthroline monohydrochloride [ No CAS ]
  • 16
  • [ 7089-68-1 ]
  • [ 22426-18-2 ]
YieldReaction ConditionsOperation in experiment
94% With acetamide; potassium carbonate; at 200℃; for 5h; <strong>[7089-68-1]2-Chloro-1,10-phenanthroline</strong> (100 mg, 0.5 mmol) and potassiumcarbonate (451 mg, 3.3 mmol) and acetamide (688 mg,11.7 mmol) were stirred at 200 C for 5 h. The reaction mixturewas cooled to room temperature, and poured into water. The aqueouslayer was extracted with chloroform (40 mL) twice. The combinedorganic layers were washed with brine and dried overmagnesium sulfate. The crude product was purified by silica gelchromatography eluted with chloroform/methanol = 100:1 to give2 (85 mg, 94%) as white solids.
52.5% With acetamide; potassium carbonate; at 200℃; for 1h; <strong>[7089-68-1]2-chloro-1,10-phenanthroline</strong> (859 mg, 4 mmol), acetamide (4.73 g, 80 mmol), potassium carbonate (3.87 g, 28 mmol), and heated to 200 C, stirred for 1 hour, dropped to room temperature, add water (30 mL) to the reaction and extract with dichloromethane. The organic phase was collected, dried over anhydrous sodium sulfate and filtered. The organic phase was removed by concentration under reduced pressure. The residue was subjected to silica gel column chromatography to afford 2-amino-1,10-phenanthroline 409 mg (2.1 mmol, 52.5%).
  • 18
  • [ 7089-68-1 ]
  • [ 193816-65-8 ]
  • [ 163231-36-5 ]
  • 20
  • [ 7089-68-1 ]
  • [ 1100-88-5 ]
  • [ 163231-36-5 ]
  • 21
  • [ 7089-68-1 ]
  • [ 207461-11-8 ]
  • 22
  • [ 1003-29-8 ]
  • [ 7089-68-1 ]
  • [ 1779-49-3 ]
  • [ 207505-40-6 ]
  • 25
  • [ 7089-68-1 ]
  • [ 77544-92-4 ]
  • 26
  • [ 7089-68-1 ]
  • [ 498534-36-4 ]
  • [ 498534-32-0 ]
  • 27
  • [ 7089-68-1 ]
  • [ 498534-36-4 ]
  • [ 498534-34-2 ]
  • 28
  • [ 7089-68-1 ]
  • [ 23112-96-1 ]
  • [ 124318-70-3 ]
  • 29
  • [ 7089-68-1 ]
  • {2,6-dimethoxy-4-[(tetrahydro-2H-pyran-2-yloxy)methyl]phenyl}boronic acid [ No CAS ]
  • [ 500711-43-3 ]
  • 30
  • [ 7089-68-1 ]
  • [ 107-21-1 ]
  • [ 546125-23-9 ]
  • 31
  • [ 7089-68-1 ]
  • [ 504-63-2 ]
  • [ 546125-24-0 ]
  • 32
  • [ 7089-68-1 ]
  • [ 31535-91-8 ]
  • 33
  • [ 7089-68-1 ]
  • 2,2'-thiobis(1,10-phenanthroline) [ No CAS ]
  • 35
  • [ 7089-68-1 ]
  • [ 59087-17-1 ]
  • [3-({bis-[2-([1,10]phenanthrolin-2-yloxy)-ethyl]-amino}-methyl)-benzyl]-bis-[2-([1,10]phenanthrolin-2-yloxy)-ethyl]-amine [ No CAS ]
  • 36
  • [ 7089-68-1 ]
  • [ 20439-47-8 ]
  • RR-N,N'-bis(phenanthrolin-2-yl)-1,2-cyclohexanediamine [ No CAS ]
  • 37
  • [ 7089-68-1 ]
  • [ 1436-59-5 ]
  • cis-N,N'-bis(phenanthrolin-2-yl)-1,2-cyclohexanediamine [ No CAS ]
  • 38
  • [ 7089-68-1 ]
  • [ 21436-03-3 ]
  • SS-N,N'-bis(phenanthrolin-2-yl)-1,2-cyclohexanediamine [ No CAS ]
  • 39
  • [ 104-92-7 ]
  • [ 7089-68-1 ]
  • [ 865205-44-3 ]
  • 40
  • [ 7089-68-1 ]
  • [ 108-36-1 ]
  • [ 142942-21-0 ]
  • C37H23ClN4O [ No CAS ]
  • 41
  • [ 7089-68-1 ]
  • [ 107-15-3 ]
  • 1,2-bis(1,10-phenanthrolin-2-yl)ethylenediamine [ No CAS ]
  • 42
  • [ 7089-68-1 ]
  • [ 556082-02-1 ]
  • bis-[2-([1,10]phenanthrolin-2-ylamino)-ethyl]-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
  • 43
  • [ 7089-68-1 ]
  • [ 871951-71-2 ]
  • 44
  • [ 7089-68-1 ]
  • [ 56376-69-3 ]
  • 45
  • [ 1891-19-6 ]
  • [ 7089-68-1 ]
YieldReaction ConditionsOperation in experiment
57% With N,N-dimethyl-formamide; trichlorophosphate; In dichloromethane; at 0 - 25℃;Inert atmosphere; General procedure: The procedure is identical to general procedure I, except that reactions were conducted at 0.2 M concentration with N-oxide (1.00 equiv), POBr3 (3.00 equiv), DMF (1.50 equiv) at rt. 4.2 General procedure I for the bromination of azine N-oxides (0013) To a stirred solution of the appropriate azine N-oxides in anhydrous CH2Cl2 (0.1 M) at 0 C is added POBr3 (1.2 equiv) followed by dropwise addition of DMF (0.5 equiv) under argon. The resulting reaction mixture was warmed to 25 C and stirred for several hours until the reaction is complete as indicated by TLC. Saturated aqueous sodium carbonate solution is added to the reaction mixture slowly to adjust the pH to 7-8. The resulting mixture is separated and the aqueous phase is extracted with CH2Cl2 thoroughly. The organic phase is combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product, which is purified by flash column chromatography using PE/EA (100:1) as eluent.
48% With sodium chloride; trichlorophosphate; In N,N-dimethyl-formamide; at 100℃; for 6h; 1,10-phenanthroline-N-oxide (1.96 g, 10 mmol), NaCl (11.7 g, 0.2 mol) was added to DMF (40 mL). Slowly add POCl3 (30 mmol) to the solution. The reaction solution was heated at 100 C for 6 h and allowed to cool to room temperature. Ammonia water (50 mL) was added to the reaction mixture, and extracted with chloroform. The organic phase was collected, dried over anhydrous sodium sulfate and filtered. The organic phase was removed by concentration under reduced pressure. The residue was subjected to silica gel column chromatography to give 2-chloro-1,10-phenanthroline 1.03 g (4.8 mmol, 48.0%).
44% With sodium chloride; trichlorophosphate; In N,N-dimethyl-formamide; at 0 - 100℃; for 6h;Inert atmosphere; Schlenk technique; Sealed tube; To the mixture of 1,10-phenanthroline-N-oxide (196.1 mg, 1 mmol, 1.0 eq.),sodium chloride in anhydrous DMF, a neat POCl3 (3 mmol, 3.0 eq.) was added slowly after cooling to 0 C. Then, the mixture was heated to 100 C for 6 hours. After cooling to room temperature, water was added, and the mixture was quenched with saturated ammonium chloride (aqueous) and saturated with NaCl (20 mmol, 20.0 eq.), solids were filtered, and the solution was extracted with chloroform.The combined extracts were washed with brine, dried over MgSO4, and evaporated, and then purified by column chromatography using eluent EA/PE (3:2) to get the target product as a light yellow solid, (94.2 mg, 0.44 mmol, yield = 44%). The spectral data were in accordance with the literature [55]. 1H-NMR(400MHz, CDCl3) 9.12 (dd, J = 1.7, 4.1 Hz, 1H), 8.57 (d, J = 9.4 Hz, 1H), 8.53 (dd, J = 1.7, 8.0 Hz, 1H),8.07-8.03 (m, 2H), 7.84 (d, J = 8.4 Hz, 1H), 7.81 (dd, J = 4.3, 8.2 Hz, 1H); 13C-NMR (400MHz, CDCl3) 151.3, 150.7, 146.0, 145.0, 138.7, 136.0, 129.0, 127.2, 126.9, 125.7, 124.2, 123.4.
  • 46
  • [ 7089-68-1 ]
  • [ 1066-54-2 ]
  • C17H16N2Si [ No CAS ]
  • 47
  • [ 2637-34-5 ]
  • [ 7089-68-1 ]
  • 2-(2-pyridinylthio)-1,10-phenanthroline [ No CAS ]
  • 48
  • [ 7089-68-1 ]
  • [ 131242-36-9 ]
  • C16H10N4S [ No CAS ]
  • 49
  • [ 7089-68-1 ]
  • [ 84490-68-6 ]
  • 2,2'-thiobis-1,10-phenanthroline hydrochloride [ No CAS ]
  • 50
  • [ 7089-68-1 ]
  • [ 5188-07-8 ]
  • C13H10N2S [ No CAS ]
  • 51
  • [ 7089-68-1 ]
  • [ 1012323-22-6 ]
  • 52
  • [ 7089-68-1 ]
  • [ 911828-98-3 ]
  • 53
  • [ 66-71-7 ]
  • [ 7089-68-1 ]
YieldReaction ConditionsOperation in experiment
2-Chloro-1,10-Phenanthroline, (1) 2-Chloro-1,10-phenanthroline was prepared from 1,10-phenanthroline following the procedure of B. E. Halcrow, Wm. O. Kermack; Journal of the Chemical Society (1946), 155-7 and was isolated in satisfactory yield.
  • 54
  • [ 7089-68-1 ]
  • methyl 3-(1,10-phenanthrolin-2-ylcarbamoyl)-5-(2,5,8,11-tetraoxatridecan-13-yloxy)benzoate [ No CAS ]
  • 55
  • [ 7089-68-1 ]
  • 5-(2,5,8,11-tetraoxatridecan-13-yloxy)-N1,N3-di(1,10-phenanthrolin-2-yl)isophthalamide [ No CAS ]
 

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