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Chemical Structure| 6813-38-3 Chemical Structure| 6813-38-3

Structure of 6813-38-3

Chemical Structure| 6813-38-3

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Product Citations

Product Citations

Goodwin, Matthew J ; Deetz, Alexander M ; Griffin, Paul J ; Meyer, Gerald J ;

Abstract: The preassociation of reactants in a photoinitiated redox reaction through the use of noncovalent interactions can have a significant impact on excited state reactivity. As these noncovalent interactions render some stabilization to the associated species, they impact the kinetics and thermodynamics of photoinitiated electron transfer. Reported herein is a novel iridium(III) photocatalyst, equipped with an anion-sensitive, amide-substituted bipyridine ligand, and its reactivity with the halides (X = I, Brsup>−, Clsup>−) in acetonitrile and dichloromethane. A noteworthy periodic trend was observed, where the size and electron affinity dramatically altered the observed photoredox behavior. The binding affinity for the halides increased with decreasing ionic radius (Keq ~103 to >106 ) in a polar medium but association was stoichiometric for each halide in a nonpolar medium. Evidence for the static quenching of and is presented while dynamic quenching was observed with all halides. These results highlight how the photophysics of halide adducts and the thermodynamics of intra-ionic photo-oxidation are impacted as a consequence of preassociation of a quencher through hydrogen bonding.

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Product Details of [ 6813-38-3 ]

CAS No. :6813-38-3
Formula : C12H8N2O4
M.W : 244.20
SMILES Code : O=C(C1=CC(C2=NC=CC(C(O)=O)=C2)=NC=C1)O
MDL No. :MFCD00015430
InChI Key :FXPLCAKVOYHAJA-UHFFFAOYSA-N
Pubchem ID :688094

Safety of [ 6813-38-3 ]

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

Computational Chemistry of [ 6813-38-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 18
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 3
Num. H-bond acceptors 6.0
Num. H-bond donors 2.0
Molar Refractivity 61.39
TPSA ?

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

100.38 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.08
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

0.53
Log Po/w (WLOGP)?

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

1.54
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.

-0.99
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

1.22
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.68

Water Solubility

Log S (ESOL):?

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

-1.98
Solubility 2.54 mg/ml ; 0.0104 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-2.21
Solubility 1.51 mg/ml ; 0.00618 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

-2.92
Solubility 0.292 mg/ml ; 0.00119 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

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

No
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.

-7.41 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.

0.56

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)

2.22

Application In Synthesis of [ 6813-38-3 ]

* 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 [ 6813-38-3 ]

[ 6813-38-3 ] Synthesis Path-Downstream   1~5

  • 3
  • [ 52462-29-0 ]
  • [ 6813-38-3 ]
  • [ 1189458-67-0 ]
  • [ 1147550-11-5 ]
  • [RuII(4,4'-dicarboxy-2,2'-bipyridyl)(4,4'-dithiocyanate-2,2'-bipyridyl)dithiocyanate] [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% A mixture of [Ru(p-cymene)Cl2]2 (102.7 mg, 0.16 mmol) and H2-dcbpy (81.3 mg, 0.33 mmol) were heated under N2 in dry DMF (20 ml) at 60 C overnight. 4,4'-F2-bpy (63.7 mg, 0.33 mmol) was added and the temperature increased to 140 C for 2 h. Excess NH4NCS (1.0073 g, 13.23 mol, 40 times excess) was then added and heating continued at 140 C for 3 h. After allowing to cool, the solvent was then removed using reduced pressure and the resulting black solid stirred in water overnight to remove any unreacted NH4NCS. Upon filtering the crude product was formed as a darkred/brown solid. Purification was achieved by dissolving the crude product in NaOH solution (0.1 M, in methanol) and performing Sephadex column chromatography using methanol as the eluent. This produced the pure product 1 (69.8 mg, 0.10 mmol, 60% yield)as a dark red solid. 1H NMR (600 MHz, CD3OD) delta (ppm): 9.54 (d,J = 5.7 Hz, 1H), 8.93 (s, 1H), 8.85 (d, J = 6.7 Hz, 1H), 8.78 (s, 1H),8.15 (dd, J = 5.6 Hz, 1.6 Hz, 1H), 7.76 (d, J = 6.0 Hz), 7.53 (dd,J = 5.9 Hz, 1.6 Hz, 1H), 7.52 (s, 1H), 7.40 (s, 1H), 7.01 (dd,J = 6.60 Hz, 2.47 Hz, 1H), 6.85 (d, J = 6.9 Hz, 1H), 6.32 (dd,J = 6.7 Hz, 2.6 Hz, 1H). ESI-MS: m/z 730 [M-H]-. Anal. Calc.: C,44.10; H, 2.18; N, 12.91. Found: C, 44.08; H, 2.13; N, 12.80%.
  • 4
  • ruthenium(III) chloride trihydrate [ No CAS ]
  • [ 6813-38-3 ]
  • ammonium thiocyanate [ No CAS ]
  • [ 142646-58-0 ]
  • [ 502693-09-6 ]
YieldReaction ConditionsOperation in experiment
61% 0.851 g of ruthenium (III) chloride hydrate and 40 ml ofN-methylpyrrolidone were added to the first reactor and (4,4'-dinonyl-2,2'bipyridine)was added thereto while stirring and the mixture was stirred for 0.5 hour. In the second reactor, ligand 2(2,2'-bipyridine-4,4'-dicarboxylicacid) and 60 ml of N-methylpyrrolidone were placed and maintained at 140 to 150 C. The mixed solution of the first reactor was added to the secondreactor, stirring was continued for 1.5 hours while maintaining the temperatureat 140 to 150 C, and ammonium thiocyanate 5.16 g was added and stirred for 1hour and then the reactor was cooled. The reaction mixture was poured into distilled water toprecipitate a solid. The solid was dissolved in 40 ml of methanol and NaOH wereused to maintain the pH of 10 to 11. After purification by column usingSephadex resin, the solution was adjusted to pH 4.8 with nitric acid to give togive the desired compound as a solid.
  • 5
  • [ 52462-29-0 ]
  • [ 6813-38-3 ]
  • ammonium thiocyanate [ No CAS ]
  • [ 142646-58-0 ]
  • [ 502693-09-6 ]
YieldReaction ConditionsOperation in experiment
28% General procedure: 0.851 g of ruthenium (III) chloride hydrate and 40 ml of N-methylpyrrolidone were added to the first reactor(4,4'-dinonyl-2,2'bipyridine) was added thereto while stirring and the mixture was stirred for 0.5 hour. In the second reactor, ligand 2(2,2'-bipyridine-4,4'-dicarboxylic acid) and 60 ml of N-methylpyrrolidone were placed and maintained at 140 to 150 C. The mixed solution of the first reactor was added to the second reactor,Stirring was continued for 1.5 hours while maintaining the temperature at 140 to 150 C, and ammonium thiocyanate5.16 g was added and stirred for 1 hour and then the reactor was cooled. The reaction mixture was poured into distilled water to precipitate a solid. The solid was dissolved in methanol40 ml and NaOH were used to maintain the pH of 10 to 11, After purification by column using Sephadex resin,the solution was adjusted to pH 4.8 with nitric acid to give a solid to give the desired compound. Instead of ruthenium (III) chloride hydrate, [RuCl2 (p-cymene)] 2 Except that the complex compound was used, a heteroleptic ruthenium complex dye was synthesized in the same manner.
 

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