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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 1101120-80-2
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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.
4.5
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CAS No. : | 1101120-80-2 |
Formula : | C7H3ClFNO2S |
M.W : | 219.62 |
SMILES Code : | O=S(C1=CC(C#N)=CC=C1F)(Cl)=O |
MDL No. : | MFCD18394026 |
InChI Key : | XLPGJVFDGAPUIH-UHFFFAOYSA-N |
Pubchem ID : | 55280060 |
GHS Pictogram: |
![]() |
Signal Word: | Danger |
Hazard Statements: | H314 |
Precautionary Statements: | P260-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310 |
Class: | 8 |
UN#: | 3261 |
Packing Group: | Ⅲ |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 44.2 |
TPSA ? Topological Polar Surface Area: Calculated from |
66.31 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.4 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.76 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.13 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.31 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.74 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.87 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.59 |
Solubility | 0.57 mg/ml ; 0.00259 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.77 |
Solubility | 0.373 mg/ml ; 0.0017 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.31 |
Solubility | 0.107 mg/ml ; 0.000489 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 |
-6.39 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 |
0.0 |
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 |
0.0 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) |
2.24 |
* 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 |
---|---|---|
71% | A solution of NaNO2 (380 mg, 5.51 mmol) in water (2 mL) was added to a suspension of <strong>[859855-53-1]3-amino-4-fluorobenzonitrile</strong> (500 mg, 3.67 mmol) in concentrated HCl (5 mL) at 0 °C over 5 mins., and the solution stirred for a further 30 mins. Meanwhile, AcOH (5 mL) was saturated with SO2, then CuCl2.2H2O (188 mg, 1.10 mmol) was added and SO2 bubbled through for a further 5 mins. The AcOH mixture was cooled to 5 C, then the diazonium solution added over 5 mins. The resulting mixture was stirred for a further 1h at 0 C then 1h at room temperature. The solution was diluted with water and extracted twice with CH2Cl2. The combined organic extracts were washed twice with water, dried (Na2SO4) and the solvent removed in vacuo. Chromatography (hexanes: EtOAc 19:1 to 9:1) gave the title compound as a yellow oil (569 mg, 71percent). 1H NMR delta (400 MHz, CDCl3) 8.31 (dd, J 6.2, 2.1 Hz, 1H), 8.04 (ddd, J 8.7, 4.3, 2.1 Hz, 1H), 7.51 (t, J 8.7 Hz, 1H). LCMS (APCI-) 200 (M-Cl+O, 100percent). | |
3-Amino-4-fluorobenzonitrile (2) (2 g, 0.015 mol) in acidic medium (28 mL HCl 6 N) reacted with sodium nitrite (1.4 g in2 mL of water). The resulting solution of diazonium salt was mixed with a solution of sulphur dioxide in acetic acid in the presence of CuCl2 (0.8 g in 2 mL of water) to generate 3-chlorosulfonyl-4-fluorobenzonitrile (3) according to the Meerwein variation of Sandmeyer reaction. Compound 3 was pouredinto a solution of ammonium hydroxide and gently heated,resulting in the synthesis of intermediate 4-fluoro-3-sulfamoylbenzonitrile (4) (Yield: 40e65percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium hydroxide; | 3-Amino-4-fluorobenzonitrile (2) (2 g, 0.015 mol) in acidic medium (28 mL HCl 6 N) reacted with sodium nitrite (1.4 g in2 mL of water). The resulting solution of diazonium salt was mixed with a solution of sulphur dioxide in acetic acid in the presence of CuCl2 (0.8 g in 2 mL of water) to generate <strong>[1101120-80-2]3-chlorosulfonyl-4-fluorobenzonitrile</strong> (3) according to the Meerwein variation of Sandmeyer reaction. Compound 3 was pouredinto a solution of ammonium hydroxide and gently heated,resulting in the synthesis of intermediate 4-fluoro-3-sulfamoylbenzonitrile (4) (Yield: 40e65percent). | |
With ammonia; In tetrahydrofuran; methanol; for 0.5h;Cooling with ice; | A solution of ammonia (7 M in MeOH, 4.5 mL, 31.5 mmol) is cooled in iced water and solution of <strong>[1101120-80-2]5-cyano-2-fluorobenzenesulfonyl chloride</strong> (SM 8.1, 0.99 g, 4.51 mmol) in THF (20 mL) is added drop wise. The reaction mixture is stirred for 30 minutes, after which time LC-MS analysis shows the reaction to be complete. The reaction mixture is concentrated under vacuum, water (40 ml) added and then extracted with DCM (100 ml then 2 x 50 mL). The organic phases are passed through a phase separator, combined and concentrated to dryness under vacuum to give 5-cyano-2-fluoro-benzenesulfonamide (i-7.1) as a white solid that is used without further purification. |
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