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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
Accessible (Haz class 3, 4, 5 or 8), Domestic | USD 100+ |
Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
Structure of 13920-91-7
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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.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 13920-91-7 |
Formula : | C8H11NS |
M.W : | 153.24 |
SMILES Code : | NC1=CC=CC=C1SCC |
MDL No. : | MFCD08691983 |
InChI Key : | OXFMPJRLJLBBRQ-UHFFFAOYSA-N |
Pubchem ID : | 10149009 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H301-H311-H315-H319-H331-H335 |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P310-P302+P352-P304+P340-P305+P351+P338-P311-P330-P361-P363-P403+P233-P405-P501 |
Class: | 6.1 |
UN#: | 2810 |
Packing Group: | Ⅲ |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.25 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 47.37 |
TPSA ? Topological Polar Surface Area: Calculated from |
51.32 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.96 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.57 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.39 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.41 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.99 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.06 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.09 |
Solubility | 1.24 mg/ml ; 0.00811 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.26 |
Solubility | 0.846 mg/ml ; 0.00552 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.92 |
Solubility | 0.183 mg/ml ; 0.00119 mol/l |
Class? Solubility class: Log S scale |
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 |
Yes |
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) |
Yes |
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) |
No |
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 |
-6.12 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
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 |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.63 |
* 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 |
---|---|---|
93% | A 35% hydrochloric acid (30 mL) and water (30 mL) mixed solution of 2-ethylsulfanylaniline (17.8 g, 115.8 mmol) was cooled to -5 C., and an aqueous sodium nitrite (9.6 g, 139.0 mmol) solution (35 mL) was added dropwise. After the completion of dropwise addition, the resulting solution was stirred at -5 C. for 30 minutes and subsequently, an aqueous sodium azide (11.3 g, 173.7 mmol) solution (40 mL) was added dropwise. The resulting solution was stirred at -5 C. for 60 minutes and at room temperature for 4 hours. The reaction solution was extracted by adding ethyl acetate, and the organic layer was washed with saturated brine, dried over sodium sulfate, filtered to remove the white precipitate, and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane=1:20) to afford the title compound (19.3 g, yield: 93%) as a yellow oily product. 1HNMR Spectrum (CDCl3) sigma: 7.30 (1H, dd, J1=7.8 Hz, J2=1.4 Hz), 7.24-7.22 (1H, m), 7.14 (1H, dd, J1=7.8 Hz, J2=0.9 Hz), 7.10 (1H, td, J1=7.6 Hz, J2=1.4 Hz), 2.94 (2H, q, J=7.3 Hz), 1.32 (3H, t, J=7.3 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With sodium methylate; In methanol; for 6h;Reflux; | To a methanol (25 mL) solution of 2-aminothiophenol (15.0 g, 119.8 mmol), a 28% sodium methoxide-methanol solution (27.7 g, 143.8 mmol) was added, and a methanol (15 mL) solution of iodoethane (18.7 g, 119.8 mmol) was added dropwise under heating at reflux. After the completion of dropwise addition, the solution was heated at reflux for 6 hours and allowed to cool to room temperature, and the solvent was then distilled off. Water was added to the obtained reaction solution, and the resulting solution was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, filtered to remove the white precipitate, and concentrated under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane=1:20) to afford the title compound (yielded 17.8 g, yield: 97%) as an orange-tan oily product. 1HNMR Spectrum (CDCl3) sigma: 7.37 (1H, dd, J1=7.6 Hz, J2=1.6 Hz), 7.11 (1H, td, J1=7.7 Hz, J2=1.8 Hz), 6.73 (1H, dd, J1=8.0 Hz, J2=1.1 Hz), 6.69 (1H, td, J1=7.6 Hz, J2=1.4 Hz), 4.34 (2H, br), 2.76 (2H, q, J=7.3 Hz), 1.23 (3H, t, J=7.3 Hz). |
2-Aminothiophenol (5.0 g, 40 mmol, Lancaster Synthesis Inc., Windham, N.H.) was stirred in dry ethanol (100 mL) and cooled in an ice bath. Potassium t-butoxide (4.5 g, 40 mmol) was added portionwise over 15 minutes and the mixture was stirred for an additional 45 minutes. Ethyl iodide (3.3 mL, 41 mmol) was added dropwise over 15 minutes and the mixture was allowed to warm to room temperature and stirred for 45 minutes. The mixture was filtered and the filtrate evaporated to dryness in vacuo. The resulting residue was treated with dichloromethane (100 mL) and filtered and the resulting filtrate was evaporated to dryness in vacuo to give 2-(ethylthio)aniline (5.2 g). |
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