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Structure of 108847-76-3

Chemical Structure| 108847-76-3

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Asif, Nehal ;

Abstract: This study investigates the development and application of organocatalysts for the reduction of CO2 under mild and sustainable conditions. A key focus is the synthesis of an organo-boronic acid–amine catalyst system (derived from thianthren-1-ylboronic acid and diethanolamine) and its subsequent evaluation in reactions with labeled CO2. Through NMR analyses, including time-resolved monitoring of isotopically labeled substrates, the formation of formyl intermediates and downstream products such as formate and methoxy species was confirmed, demonstrating active CO2 transformation. Multiple catalyst variants (NA1 series) were screened to assess activity and selectivity, with experimental conditions optimized in terms of temperature, solvent selection, and the use of boron-based reductants (HBpin). Complementary electrochemical approaches using amine co-substrates (isopropylamine, diisopropylamine, and methylpiperazine) were also explored, broadening the scope of potential pathways for carbon capture and conversion. Together, these results highlight the versatility, cost-effectiveness, and reduced environmental impact of organocatalyst-mediated processes compared to conventional metal-based routes. The research thus provides a foundational framework for further optimizing organocatalytic CO2 reduction and underscores the promise of these catalysts for sustainable chemical transformations.

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Product Details of [ 108847-76-3 ]

CAS No. :108847-76-3
Formula : C12H9BO2S2
M.W : 260.14
SMILES Code : OB(O)C1=C2SC3=CC=CC=C3SC2=CC=C1
MDL No. :MFCD00093039
InChI Key :FZEWPLIHPXGNTB-UHFFFAOYSA-N
Pubchem ID :2734382

Safety of [ 108847-76-3 ]

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

Computational Chemistry of [ 108847-76-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 17
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 70.96
TPSA ?

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

91.06 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.0
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

3.04
Log Po/w (WLOGP)?

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

1.98
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.

2.56
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

1.44
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.8

Water Solubility

Log S (ESOL):?

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

-3.82
Solubility 0.039 mg/ml ; 0.00015 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.

-4.62
Solubility 0.00627 mg/ml ; 0.0000241 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

-4.02
Solubility 0.0247 mg/ml ; 0.0000948 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

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

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

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

Yes
Log Kp (skin permeation)?

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

-5.73 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

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<0.0
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)

2.98

Application In Synthesis of [ 108847-76-3 ]

* 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 [ 108847-76-3 ]

[ 108847-76-3 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 1920-66-7 ]
  • [ 108847-76-3 ]
  • 4-amino-5-nitro-2-(1-thianthrene)pyrimidine [ No CAS ]
  • 2
  • [ 108847-76-3 ]
  • [ 57381-62-1 ]
  • C20H13ClO2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 70℃; for 8h;Inert atmosphere; Thianthrene-1-boronic acid 20g (76.88mmol), <strong>[57381-62-1]methyl-2-bromo-4-chlorobenzoate</strong>21.1 g (84.57mmol) and tetrakis triphenylphosphinepalladium 0.89g (0.769mmol) were placed in a flask, and under a nitrogen atmosphere, it was dissolved in tetrahydrofuran 257 ml, and then an aqueous solution 128ml of dissolved potassium carbonate 17g (115.3mmol) was added, and stirred at reflux at 70 ° Cfor 8 h. After completion of the reaction, it was extracted with ethyl acetate,the extract was dried over magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The product was purified by silica gelcolumn chromatography using n-hexane / ethyl acetate (9: 1 volume ratio) toobtain intermediate M-28 of the desired compound 27.2 g (92percent yield).
  • 3
  • [ 108847-76-3 ]
  • [ 57103-20-5 ]
  • C42H25NS4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; for 15h;Inert atmosphere; Reflux; Under nitrogen atmosphere, 3,6-dibromo-9-phenyl-9H- carbazole 4.0g (10mmol) ,thianthren-1-ylboronic acid 6.5g (25mmol) was dissolved in toluene 50ml and Pd(PPh3) 4 0.5g (0.5mmol), 2M K2CO3 30ml (60mmol) was added and refluxed for 15 hours. After the reaction is complete, the temperature of the reaction was cooled to room temperature, toluene 300ml H2O and 300ml of water was added and the organic layer was extracted, concentrated and filtered under reduced pressure, then it was dried over anhydrous MgSO4, and separated by column chromatography using Hex: MC = 3:1 to give the compound 31 5.04g (75percent).
  • 4
  • [ 108847-76-3 ]
  • [ 2050-48-8 ]
  • 4-bromo-4‘-thianthrene-1-yl-diphenylsulfone [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With bis-triphenylphosphine-palladium(II) chloride; potassium hydroxide; In tetrahydrofuran; water; at 80℃; for 3h;Inert atmosphere; general procedure for Suzuki cross-coupling reaction. Adried 100 mL flask was charged with 1-thianthrenyl boronic acid (1.0equiv.), bromoaryl derivative (1.0 equiv.), bis(triphenylphosphine)palladium(II) dichloride (Pd(PPh3)2Cl2, 0.05 equiv.), and powderedpotassium hydroxide (5 equiv.). The reaction vessel was vacuumed andfiled with argon. Degassed tetrahydrofuran (THF) and degassed waterwere added, and the reaction mixture was stirred at 80 C for 3 h. Thecrude product was extracted into DCM, and the organic phase waswashed with water and dried over Na2SO4. The solvent was removedand the residue was purified by column chromatography using hexane/ethyl acetate (6/1) as eluent. The target product was crystallized fromthe eluent.4-Bromo-4?-thianthrene-1-yl-benzophenone (Br-BP-TA) was preparedby method A from 1-thianthrenyl boronic acid (0.38 g, 1.47 mmol),4,4?-dibromobenzophenone (0.50 g, 1.47 mmol), Pd(PPh3)2Cl2 (0.05 g,0.07 mmol), KOH (0.41 g, 7.35 mmol), 10 mL of THF and 2 mL of waterwere used. The yield of white crystals (fw=474 g/mol,mp=138-139 C) was 76%.1H NMR (400 MHz, CDCl3), delta (ppm): 7.82 (d, J=8.2 Hz, 2H, Ar),7.69 (d, J=8.5 Hz, 2H, Ar), 7.60 (d, J=8.5 Hz 2H, Ar), 7.42-7.50 (m,4H, Ar), 7.30 (dd, J=7.5, 1.4 Hz, 1H, Ar), 7.10-7.26 (m, 4H, Ar).13C NMR (100 MHz, CDCl3), delta (ppm): 195.23, 144.59, 141.29,136.35, 136.32, 136.21, 136.07, 135.51, 134.90, 131.72, 131.59,129.92, 129.62, 129.07, 128.89, 128.84, 128.62, 127.97, 127.70,127.61, 127.28.IR numax in cm-1: (CH Ar) 3087, 3068, 3051; (C=O) 1647; (C=CAr) 1480; (CH Ar) 929, 857; (CS) 746; (CBr) 634.MS (APCI+, 20V), m/z (%): 475 ([M+H]+, 100)Elemental analysis. Calcd. for C25H15BrOS2 (%): C 63.16, H 3.18, Br16.81, O 3.37, S 13.49. Found (%): C 63.17, H 3.23, O 3.44.
  • 5
  • [ 108847-76-3 ]
  • [ 2050-48-8 ]
  • 4-bromo-4‘-thianthrene-1-yl-diphenylsulfone [ No CAS ]
  • C36H22O2S5 [ No CAS ]
 

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