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Chemical Structure| 15084-51-2 Chemical Structure| 15084-51-2
Chemical Structure| 15084-51-2

4-tert-Butylbenzenesulfonyl chloride

CAS No.: 15084-51-2

4.5 *For Research Use Only !

Cat. No.: A392201 Purity: 98%

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Product Details of [ 15084-51-2 ]

CAS No. :15084-51-2
Formula : C10H13ClO2S
M.W : 232.73
SMILES Code : O=S(C1=CC=C(C(C)(C)C)C=C1)(Cl)=O
MDL No. :MFCD00007449
InChI Key :YEZADZMMVHWFIY-UHFFFAOYSA-N
Pubchem ID :139882

Safety of [ 15084-51-2 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3261
Packing Group:

Calculated chemistry of [ 15084-51-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 6
Fraction Csp3 0.4
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 58.8
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

42.52 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.43
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

3.62
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

3.99
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.76
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.47
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.05

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.75
Solubility 0.0415 mg/ml ; 0.000178 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-4.2
Solubility 0.0147 mg/ml ; 0.000063 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-4.16
Solubility 0.0162 mg/ml ; 0.0000698 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble

Pharmacokinetics

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)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

Yes
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.15 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<2.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.68

Application In Synthesis of [ 15084-51-2 ]

* 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.

  • Downstream synthetic route of [ 15084-51-2 ]

[ 15084-51-2 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 15084-51-2 ]
  • [ 2133-34-8 ]
  • [ 201466-06-0 ]
  • 2
  • [ 15084-51-2 ]
  • [ 33084-49-0 ]
  • 4-tert-butyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% In tetrahydrofuran; methanol; water; mineral oil; EXAMPLE 39 4-tert-Butyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide A solution of <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (354 mg, 2.0 mmol) in dry THF (1 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 188 mg, 4.4 mmol) in dry THF (1 ml) at 0-5 C. After stirring at 0-5 C. for 10 min., the reaction was warmed to room temperature for 10 min. to complete the reaction. The reaction mixture was re-cooled to 0 C. and 4-tert-butylbenzenesulfonyl chloride (512 mg, 2.2 mmol) was added slowly. Stirring was continued for 20 min. at 0-5 C. Excess sodium hydride was decomposed by addition of methanol (0.4 ml) followed by water (0.5 ml). The mixture was acidified with hydrochloric acid and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to give a crude product, which was purified by recrystallization from ethyl acetate/hexanes to give a white solid in 21% yield, m.p. 170 C. (dec.).
21% In tetrahydrofuran; methanol; water; mineral oil; EXAMPLE 5 4-tert-Butyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide A solution of <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (354 mg, 2.0 mmol) in dry THF (1 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 188 mg, 4.4 mmol)in dry THF (1 ml) at 0-5 C. After stirring at 0-5 C. for 10 min., the reaction was warmed to room temperature for 10 min. to complete the reaction. The reaction mixture was re-cooled to 0 C. and 4-tert-butylbenzenesulfonyl chloride (512 mg, 2.2 mmol) was added slowly. Stirring was continued for 20 min. at 0-5 C. Excess sodium hydride was decomposed by addition of methanol (0.4 ml) followed by water (0.5 ml). The mixture was acidified with hydrochloric acid and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to give a crude product, which was purified by recrystallization from ethyl acetate/hexanes to give a white solid in 21% yield, m.p. 170 C. (dec.).
21% In tetrahydrofuran; methanol; water; mineral oil; EXAMPLE 39 4-tert-Butyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide A solution of <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (354 mg, 2.0 mmol) in dry THF (1 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 188 mg, 4.4 mmol) in dry THF (1 ml) at 0-5 C. After stirring at 0-5 C. for 10 min., the reaction was warmed to room temperature for 10 min. to complete the reaction. The reaction mixture was re-cooled to 0 C. and 4-tert-butylbenzenesulfonyl chloride (512 mg, 2.2 mmol) was added slowly. Stirring was continued for 20 min. at 0-5 C. Excess sodium hydride was decomposed by addition of methanol (0.4 ml) followed by water (0.5 ml). The mixture was acidified with hydrochloric acid and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to give a crude product, which was purified by recrystallization from ethyl acetate/hexanes to give a white solid in 21% yield, m.p. 170 C. (dec.).
21% In tetrahydrofuran; methanol; water; mineral oil; EXAMPLE 45 4-tert-Butyl-N-(4-bromo-3-methyl-5-isoxazolyl)benzenesulfonamide A solution of <strong>[33084-49-0]5-amino-4-bromo-3-methylisoxazole</strong> (354 mg, 2.0 mmol) in dry THF (1 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 188 mg, 4.4 mmol) in dry THF (1 ml) at 0-5 C. After stirring at 0-5 C. for 10 min., the reaction was warmed to room temperature for 10 min. to complete the reaction. The reaction mixture was re-cooled to 0 C. and 4-tert-butylbenzenesulfonyl chloride (512 mg, 2.2 mmol) was added slowly. Stirring was continued for 20 min. at 0-5 C. Excess sodium hydride was decomposed by addition of methanol (0.4 ml) followed by water (0.5 ml). The mixture was acidified with hydrochloric acid and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to give a crude product, which was purified by recrystallization from ethyl acetate/hexanes to give a white solid in 21% yield, m.p. 170 C. (dec.).

  • 3
  • [ 15084-51-2 ]
  • [ 24629-25-2 ]
  • [ 1032477-05-6 ]
  • 4
  • [ 15084-51-2 ]
  • [ 111628-39-8 ]
  • [ 695221-93-3 ]
YieldReaction ConditionsOperation in experiment
77% With triethylamine; In dichloromethane; at 0 - 20℃; for 6h; General procedure: 2-(Piperazin-1-yl)benzazolyl derivatives 8a-d (1 equivalent) and triethylamine (1.5 equivalents) were dissolved in 25 ml dry CH2Cl2 and cooled to 0C in an ice salt bath. Then the required phenylsulfonyl chloride (1.1 equivalents) dissolved in 20 ml dry CH2Cl2 was added dropwise. After the addition, the reaction mixture was stirred at 0C for a further 1h and then allowed to warm to room temperature and the course of the reaction followed by TLC. After completion, the mixture was diluted with additional 50 ml of CH2Cl2 and extracted with 10% NaHCO3 solution (3 x 50 ml). The organic phase was washed with dist. H2O, sat. NaCl solution, dried over anhyd. Na2SO4, filtered and evaporated to dryness. The product was recrystallised from the appropriate solvent, the precipitate formed was filtered under suction and dried at 60C under high vacuum.
  • 5
  • [ 15084-51-2 ]
  • [ 36936-23-9 ]
  • 4-(tert-butyl)-N-(5-chloro-6-methylpyridin-2-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With pyridine; In chloroform; at 0 - 100℃; for 12.0h; To a stirred solution of compound LXVIII (3 g, 21.12 mmol) in chloroform (60 ml) was addedpyridine (15 ml) at 0C followed by addition of 4-tert-butylbenzenesulfonyl chloride (XI, 5.89g, 25.34 mmol). The reaction mixture was heated at 100C for 12 h, cooled to room temperature and concentrated under reduced pressure. The crude material was diluted with a saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with brine solution, dried over anhydrous Na2SO4 and evaporated under reducedpressure to afford 4-(tert-butyl)-N-(5 -chloro-6-methylpyridin-2-yl)benzenesulfonamide(LXIX; 6 g, 84% yield). ?H NMR (400 MHz, DMSO-d6) oe 11.11 (bs, 1H), 7.86-7.84 (d, J8.4 Hz, 2H), 7.72-7.70 (d, J 8.8 Hz, 1H), 7.60-7.58 (d, J 8.4 Hz, 2H), 6.94-6.93 (d, J= 7.6Hz, 1H), 2.36 (s, 3H), 1.27 (s, 9H). MS (M+1): 339.2.
  • 6
  • [ 15084-51-2 ]
  • [ 1080-12-2 ]
  • (E)-2-methoxy-4-(3-oxobut-1-enyl)phenyl 4-tert-butylbenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With triethylamine; In methanol; at 20℃; General procedure: Solutions of selected methyl ketones (2 mmol) in methanol(6 mL) were stirred and corresponding sulfonylchlorides (2.4 mmol) were added. Then, triethylamine(0.6 mL) was added dropwise. The mixtures were stirredovernight at room temperature. After completion of thereactions, mixtures were poured into iced water withstirring. In some cases (for our compounds 7f, 7g, 8e, 8f,8g, and 9g; see below), the formed precipitate was filteredand washed with cold diethyl ether. In other cases, whenno precipitate formed, the organic layer was extractedwith dichloromethane (3 × 50 mL), dried over anhydrousNa2SO4 and evaporated under vacuum. The residue waspurified by short column chromatography on silica gel,using dichloromethane as eluent. The oil obtained usuallycrystallized; if not, the oily residue was dissolved indiethyl ether from which products crystallized on standingin a deepfreeze. Crude products were washed with coldether, and 21 pure, mostly white crystals were obtained, asfollows:
  • 7
  • [ 15084-51-2 ]
  • [ 38226-86-7 ]
  • 5-hydroxy-2-(4-methoxyphenyl)-8,8-dimethyl-4-oxo-9,10-dihydro-4H,8H-pyrano[2,3-f]chromen-3-yl 4-(tert-butyl)benzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72.9% With triethylamine; In dichloromethane; at 25℃; for 4h; General procedure: To a mechanically stirred suspension of suspension of 1 (0.21 g, 0.53 mmol) in 30 ml CH2Cl2 were added triethylamine (0.5 ml) and aromatic sulfonyl chloride (0.53 mmol) at 25 C for 4 h. The reaction process was detected by TLC method. Then, antagonized by dilute sodium hydroxide, extracted, and washed with ether and water, evaporated under vacuum. Finally, the mixture was recrys-tallizated from ethyl acetate , providing a total product yield of 65.4%-88.6 %.
  • 8
  • [ 15084-51-2 ]
  • [ 19008-43-6 ]
  • benzyl 4-((4-(tert-butyl)phenyl)sulfonamido)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% at 20℃; for 24h;Cooling with ice; Inert atmosphere; General procedure: The acid or sulfonyl chloride (1.0-1.1 equiv.) was added in one go to an ice-cooled solution of the appropriate amine or amine hydrochloride (1.0-1.1 equiv.) and diisopropylethylamine, triethylamine or pyridine (2.0-3.0 equiv.) in CH2Cl2 or chloroform (0.1-0.2M) and stirred at RT. After 24h, the reaction was quenched with 1M HCl. The layers were separated, and the aqueous layer was extracted with CH2Cl2. The organic layer was dried (MgSO4), filtered and concentrated in vacuo, and column chromatography isolated the target compound.
 

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Technical Information

Categories

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