Structure of TCPO
CAS No.: 1165-91-9
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Synonyms: Bis(2,4,6-trichlorophenyl) oxalate
4.5
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| CAS No. : | 1165-91-9 |
| Formula : | C14H4Cl6O4 |
| M.W : | 448.90 |
| SMILES Code : | O=C(OC1=C(Cl)C=C(Cl)C=C1Cl)C(OC2=C(Cl)C=C(Cl)C=C2Cl)=O |
| Synonyms : |
Bis(2,4,6-trichlorophenyl) oxalate
|
| English Name : | Bis(2,4,6-trichlorophenyl) oxalate |
| MDL No. : | MFCD00043061 |
| InChI Key : | GEVPIWPYWJZSPR-UHFFFAOYSA-N |
| Pubchem ID : | 160567 |
| Num. heavy atoms | 24 |
| Num. arom. heavy atoms | 12 |
| Fraction Csp3 | 0.0 |
| Num. rotatable bonds | 5 |
| Num. H-bond acceptors | 4.0 |
| Num. H-bond donors | 0.0 |
| Molar Refractivity | 94.21 |
| TPSA ? Topological Polar Surface Area: Calculated from |
52.6 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.77 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
7.28 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
6.12 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
5.74 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
6.24 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
5.83 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-7.25 |
| Solubility | 0.0000253 mg/ml ; 0.0000000563 mol/l |
| Class? Solubility class: Log S scale |
Poorly soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-8.21 |
| Solubility | 0.00000277 mg/ml ; 0.0000000062 mol/l |
| Class? Solubility class: Log S scale |
Poorly soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-7.87 |
| Solubility | 0.00000613 mg/ml ; 0.0000000136 mol/l |
| Class? Solubility class: Log S scale |
Poorly soluble |
| 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) |
No |
| CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
| CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
| CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
Yes |
| CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
| CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
| Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-3.87 cm/s |
| Lipinski? Lipinski (Pfizer) filter: implemented from |
1.0 |
| Ghose? Ghose filter: implemented from |
None |
| Veber? Veber (GSK) filter: implemented from |
0.0 |
| Egan? Egan (Pharmacia) filter: implemented from |
1.0 |
| Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
| Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
| PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
| Brenk? Structural Alert: implemented from |
2.0 alert: heavy_metal |
| Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<2.0 |
| Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.41 |
* 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.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In acetonitrile at 5.8 - 44.7℃; stoped-flow technique; kinetics and mechanism of the nucleophilic substitution reaction; activation energy; spectral study; effect of imidazole concentraton on rate constant; effect of triethylamine; | ||
| With 9,10-diphenylanthracene; dihydrogen peroxide In ethyl acetate at 25℃; | ||
| In ethyl acetate at 25℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 50% | With pyridine In diethyl ether at 0℃; for 1h; | |
| With triethylamine | ||
| With triethylamine In benzene | 4.1. General General procedure: Melting points were determined using a hot stage microscope apparatus and were uncorrected. 1H and 13C NMR spectra were recorded on an FT-NMR spectrometer at 400 MHz and 100 MHz, respectively. The chemical shifts (δ) of the 1H and 13C NMR spectra are reported in parts per million downfield from TMS as an internal standard or from the residual solvent peak. Coupling constants (J) are reported in hertz. Fluorescence quantum yields were estimated using 9,10-diphenylanthracene (ΦF=0.91 in benzene) as a standard. Chemiluminescence quantum yields (ΦCL) were measured by a photon-counting method using a Hamamatsu Photonics R464 photomultiplier connected to a photon-counting unit (C3866) and a photon-counting board M8784 according to a previously reported procedure.2l Luminol chemiluminescence was used as a standard in DMSO for the calibration of the photomultiplier tube. Compound (1) was prepared by an established method according to the literature. TCPO and 4-CPO were prepared by reacting oxalyl chloride and the corresponding phenols in the presence of triethylamine in benzene and were used after recrystallization. |
| With triethylamine | ||
| With triethylamine | ||
| With triethylamine In benzene |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dihydrogen peroxide In acetone chemiluminescence reaction; max reaction rate; pH 9.0; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dihydrogen peroxide In acetone chemiluminescence reaction; max reaction rate; pH 9.0; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dihydrogen peroxide In acetone chemiluminescence reaction; max reaction rate; pH 9.0; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dihydrogen peroxide In acetone chemiluminescence reaction; max reaction rate; pH 9.0; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dihydrogen peroxide In acetone chemiluminescence reaction; max reaction rate; effect pH and reagent concentration; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dihydrogen peroxide In acetone chemiluminescence reaction; max reaction rate; pH 9.0; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dihydrogen peroxide In acetone chemiluminescence reaction; max reaction rate; pH 9.0; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Rk. mit H2O2: Chemilumineszenz; | ||
| Rk. m. polycycl. Aromaten (H2O2): Messung der Chemilumineszenz; | ||
| With oxygen In ethyl acetate; isopropyl alcohol Irradiation; chemoluminescence, various catalysts; |
| With 1H-imidazole; 9,10-diphenylanthracene; dihydrogen peroxide In water; acetonitrile at 25℃; effect of the reagents concentrations on the rise and fall of chemiluminescence rate constants; | ||
| With 9,10-diphenylanthracene; imidazole buffer In ethyl acetate at 24.9℃; Irradiation; var: light intensity, conc. of imidazole, oxalate ester and chemiluminophore, timing of catalyst addition; | ||
| With 9,10-diphenylanthracene; dihydrogen peroxide; triethylamine In ethyl acetate | ||
| With PERYLENE; dihydrogen peroxide In <i>tert</i>-butyl alcohol for 0.0566667h; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Oxalylchlorid, 2,4,6-Trichlor-phenol (Triethylamin, Dioethylether); | ||
| 1, 2,4,6-Trichlorphenol; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With 1H-imidazole; 3-aminofluoranthene; dihydrogen peroxide In water; acetonitrile at 22℃; | ||
| With gold nanoparticles In water; ethyl acetate; acetone | ||
| With 2,6-dimethylpyridine; dihydrogen peroxide; fluorescein In water at 25℃; | A typical essay was made at (25.0±0.5) oC adding the solvent (either 1,2-dimethoxyethane, DME, or water), H2O2, and Lut to an appropriate quartz cuvette. For emission experiments 2,5-diphenyloxazol (PPO, 10mmol L-1, in DME) or fluorescein (FLU, 0.1mmol L-1, in water) were used as well. After starting the measurement, the reaction was initiated by adding bis(2,4,6-trichlorophenyl) oxalate (TCPO, 0.1mmol L-1). The borate buffer (20mmol L-1), used in experiments where the constant pH was maintained, was prepared from a 0.1mol L-1 H3BO3 solution and a 0.1mol L-1 Na2B4O7·10H2O; for each [Lut], the pH of the final solution was adjusted to 8.2 by addition of the appropriate amount of H3BO3 solution (0.1mol L-1). |
| With dihydrogen peroxide In 1,2-dimethoxyethane |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With PERYLENE; dihydrogen peroxide In water; acetonitrile |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dihydrogen peroxide; sodium salicylate In ethyl acetate at 20℃; |