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Structure of m-Toluenesulfonyl chloride
CAS No.: 1899-93-0
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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.
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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. : | 1899-93-0 |
Formula : | C7H7ClO2S |
M.W : | 190.65 |
SMILES Code : | CC1=CC=CC(=C1)S(Cl)(=O)=O |
MDL No. : | MFCD00051747 |
InChI Key : | KFPMLWUKHQMEBU-UHFFFAOYSA-N |
Pubchem ID : | 2734595 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H314 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
Class: | 8 |
UN#: | 3265 |
Packing Group: | Ⅱ |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.14 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 44.49 |
TPSA ? Topological Polar Surface Area: Calculated from |
42.52 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.84 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.31 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.0 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.85 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.76 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.15 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.81 |
Solubility | 0.292 mg/ml ; 0.00153 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.84 |
Solubility | 0.275 mg/ml ; 0.00144 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.33 |
Solubility | 0.0896 mg/ml ; 0.00047 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 |
-5.82 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 |
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) |
1.76 |
* 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 |
---|---|---|
63% | EXAMPLE 30 N-(4-bromo-3-methyl-5-isoxazolyl)-3-toluenesulfonamide N-(4-bromo-3-methyl-5-isoxazolyl)-3-toluenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 3-toluenesulfonyl chloride according to the procedures described in Example 5. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 138-140 C., yield 63%. | |
63% | EXAMPLE 70 N-(4-bromo-3-methyl-5-isoxazolyl)-3-toluenesulfonamide N-(4-bromo-3-methyl.5-isoxazolyl)-3-toluenesulfonamide was prepared from <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> and 3-toluenesulfonyl chloride according to the procedures described in Example 45. The crude product was purified by recrystallization from ethyl acetate/hexanes to give a crystalline solid, m.p. 138-140 C., yield 63%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | m-Toluenesulfonyl chloride (0.076 ml, 0.53 mmol, 1.4 equiv.) and pyridine (0.103 ml, 1.27 mmol, 3.4 equiv.) were added to a stirred suspension of sodium cyanate (56 mg, 0.86 mmol, 2.3 equiv.) in dry acetonitrile (1 ml) and the mixture stirred at room temperature for 3 hours. 2-Amino-4,5-dimethylthiazole hydrochloride (34 mg, 0.28 mmol, 1.0 equiv.) was added and the reaction stirred for 1 hour. Water (2 ml) and acetic acid (3 drops) were added. The resulting precipitate was centrifuged for 10 minutes and the supernatant decanted. The solid washed with water (2 ml), the material centrifuged and supernatant decanted. The solid was dried under reduced pressure at 40 C. to give N-[(4,5-dimethyl-1,3-thiazol-2-yl)carbamoyl]-3-methylbenzenesulfonamide, 49 mg (55% yield). LC aUV215 nm; Rt 1.81: 93%, m/z (ES+): 326 (MH+), 651 (2 MH+); deltaH(400 MHz; d4-methanol) 7.54-7.98 (4H, m), 2.57 (3H, s), 2.31 (3H, s), 2.27 (3H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; | Example 138 3-(Toluene-3-sulfonylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure described for Example 121 using 3-methylbenzenesulfonyl chloride (1.91 g, 10 mmol), 3-amino-4-methoxy-N-phenyl-benzamide (2.43 g, 10 mmol), and pyridine (25 mL) to afford the product (3.587 g); m.p. 195-197 C. after trituration in hexanes/ethyl acetate (1:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | General procedure: To a stirred solution of compound 4 (0.50 g, 3 mmol) in 15 mLdichloromethane, pyridine (0.24 mL, 3 mmol) and correspondingbenzoyl chloride (3 mmol) were added at 0 C. The reaction mixturewas stirred for 30 min, after which it was washed with10 mL 4 N aqueous HCl solution and 10 mL saturated sodium chloridesolution. The organic layer was dried with anhydrous MgSO4and concentrated. The residue was dissolved in 20 mL dioxaneand then 15 mL of a 4 N aqueous HCl solution was added at roomtemperature. The reaction mixture was stirred at 50 C for 30 minafter which it was extracted with ethyl acetate (50 mL 3). Theextract was washed with saturated sodium chloride solution anddried with anhydrous MgSO4. After concentration, column chromatographyof the residue on silica gel (eluent PE/EA 7:1) generatedcompounds 5a-o. The spectral data are summarized in theSupplementary Information. |
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