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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+ |
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Structure of 4299-07-4
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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. : | 4299-07-4 |
Formula : | C11H13NOS |
M.W : | 207.29 |
SMILES Code : | O=C1N(CCCC)SC2=C1C=CC=C2 |
MDL No. : | MFCD09751282 |
InChI Key : | LUYIHWDYPAZCNN-UHFFFAOYSA-N |
Pubchem ID : | 9837171 |
GHS Pictogram: |
![]() ![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H314-H317-H410 |
Precautionary Statements: | P501-P261-P273-P272-P264-P280-P391-P362+P364-P303+P361+P353-P333+P313-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310-P405 |
Class: | 8 |
UN#: | 1760 |
Packing Group: | Ⅱ |
Num. heavy atoms | 14 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.36 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 61.77 |
TPSA ? Topological Polar Surface Area: Calculated from |
50.24 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.72 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.71 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.86 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.55 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.66 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.9 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.11 |
Solubility | 0.161 mg/ml ; 0.000776 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.42 |
Solubility | 0.0791 mg/ml ; 0.000382 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.66 |
Solubility | 0.0455 mg/ml ; 0.000219 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) |
Yes |
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 |
-5.64 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) |
2.63 |
* 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 |
---|---|---|
95% | With potassium bromide In N,N-dimethyl-formamide at 110℃; for 12 h; | General procedure: A mixture of 2-mercapto-N-substituted benzamide (1, 0.20 mmol), KBr (1.18 mg, 0.01 mmol) and DMF (2.0 mL) was stirred at 110 °C in the sealed tube for 12 h under air condition. The mixture was then cooled to room temperature, diluted with water, extracted with ethyl acetate, dried over sodium sulfate and concentrated. The crude products were purified by column chromatography on silica gel to give the corresponding products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | Stage #1: With sodium methylate In methanol at 0℃; for 1 h; Stage #2: for 6 h; |
151 g of 99percent 1,2'-benzisothiazolin-3-one(1 mol) was added to 257 g of methanol, and 193 g of a 28percent solution of sodium methoxide in methanol (sodium methanol) was added dropwise, followed by stirring and stirring for 1 hour to 0 0C. 160 g of n-butyl methanesulfonate Mol, the reaction was carried out for 6 hours, the solvent was distilled off under reduced pressure, 300 g of toluene was added, washed twice with water, and toluene was recovered under reduced pressure to give 2-butyl-1,2-benzisothiazoline -3-carboxylate (HPLC> 98percent) in a yield of 98percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | Stage #1: With sodium ethanolate In ethanol at 25℃; for 0.5 h; Stage #2: for 5 h; |
75.5 g of 99percent 1,2'-benzisothiazolin-3-one(0.5 mol) was added to 110 g of ethanol, 200 g of a 17percent solution of sodium ethoxide in ethanol (0.5 ml of sodium ethoxide) was added dropwise, followed by stirring and stirring for 0.5 hour to 25 0C. n-butyl sulfonate (0.5 mol) After the dropwise addition, the reaction was carried out for 5 hours. The solvent was distilled off under reduced pressure, 150 g of toluene was added, washed twice with water, and toluene was recovered under reduced pressure to give 2-butyl-1,2-benzisothiazoline-3-one 97 g (HPLC> 98percent) in a yield of 94percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Stage #1: With sodium methylate In methanol at 25℃; for 1 h; Stage #2: for 4 h; |
151 g of 99percent 1,2'-benzisothiazolin-3-one(1 mol) was added to 257 g of methanol, 193 g of a 28percent solution of sodium methoxide in methanol (sodium methanol) was added dropwise, followed by stirring and stirring for 1 hour to 25 0C, 133 g of tri-n-butyl phosphate After the dropwise addition, the reaction was carried out for 4 hours. The solvent was distilled off under reduced pressure, and 300 g of toluene was added, washed twice with water, and toluene was recovered under reduced pressure to give 2-butyl-1,2-benzisothiazolin-3 -one 201 g (HPLC> 98percent) in a yield of 95percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With ammonia In toluene at 50℃; for 3 h; | General procedure: 1,3-Benzoxathiin-4-one 1-oxide (2, 1.0 mmol) and the appropriate amine or aniline (3 mmol) were stirred in toluene (10 mL) at 50-100 °C until 2 was consumed (2-8 h). After the solvent was removed by evaporation, the products were purified by silica gel chromatography with an appropriate eluent. In the case of 3m, a 1,4-dioxane solution of ammonia (0.5 M) was used. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | at 50℃; for 3 h; | General procedure: 1,3-Benzoxathiin-4-one 1-oxide (2, 1.0 mmol) and the appropriate amine or aniline (3 mmol) were stirred in toluene (10 mL) at 50-100 °C until 2 was consumed (2-8 h). After the solvent was removed by evaporation, the products were purified by silica gel chromatography with an appropriate eluent. In the case of 3m, a 1,4-dioxane solution of ammonia (0.5 M) was used. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | at 50℃; for 5 h; | The lithium salt of 1,2-benzisothiazolin-3-one prepared in Example 2 (150 g, 0.95 mol) and DMF (450 ml) were mixedTogether,N-butyl chloride was added dropwise at room temperature(96.7 g, 1.05 mol),Drop finished,The temperature was raised to 50 ° C for 5 hours,Reaction is completed,Down to room temperature,The reaction solution was poured into 2.2 L of water,Ethyl acetate extract product,The organic phase was recovered under reduced pressure to give a mixture of 2-Butyl-1,2-benzisothiazolin-3-one and 3-butoxy-1,2-benzisothiazoline,Yield 93percent. Main productionProportion of product and by - product: 79: 21.The resulting mixture was dissolved in ethyl acetate (450 ml)Down to 0 ° C,A solution of concentrated sulfuric acid (34.2 g, 0.35 mol)The mixture was stirred for 3 hours, filtered and dried to give 155.5 g of a white solid.Relative to the main product yield of 87percent.The resulting solid was added to 10percent sodium hydroxide solution (466 ml)Then add toluene 200ml * 3 extraction, organic phase recoverySolvent to give pale yellow oil 121 g 2-Butyl-1,2-benzisothiazolin-3-one,Yield 96.5percent. The purity of the product 2-butyl-1,2-benzisothiazolin-3-one is greater than 98percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.5% | at 50℃; for 5 h; | The lithium salt of 1,2-benzisothiazolin-3-one prepared in Example 2 (150 g, 0.95 mol) and DMF (450 ml) were mixedTogether,N-butyl chloride was added dropwise at room temperature(96.7 g, 1.05 mol),Drop finished,The temperature was raised to 50 ° C for 5 hours,Reaction is completed,Down to room temperature,The reaction solution was poured into 2.2 L of water,Ethyl acetate extract product,The organic phase was recovered under reduced pressure to give a mixture of 2-Butyl-1,2-benzisothiazolin-3-one and 3-butoxy-1,2-benzisothiazoline,Yield 93percent. Main productionProportion of product and by - product: 79: 21.The resulting mixture was dissolved in ethyl acetate (450 ml)Down to 0 ° C,A solution of concentrated sulfuric acid (34.2 g, 0.35 mol)The mixture was stirred for 3 hours, filtered and dried to give 155.5 g of a white solid.Relative to the main product yield of 87percent.The resulting solid was added to 10percent sodium hydroxide solution (466 ml)Then add toluene 200ml * 3 extraction, organic phase recoverySolvent to give pale yellow oil 121 g 2-Butyl-1,2-benzisothiazolin-3-one,Yield 96.5percent. The purity of the product 2-butyl-1,2-benzisothiazolin-3-one is greater than 98percent. |
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