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N-tert-Butyl-2-thiophenesulfonamide

N-tert-Butyl-2-thiophenesulfonamide

N-tert-Butyl-2-thiophenesulfonamide

CAS No.: 100342-30-1

Category Products

Cat.NO.:A118049 Purity:98%

Product Details of [ 100342-30-1 ]

CAS No. :	100342-30-1
Formula :	C₈H₁₃NO₂S₂
M.W :	219.32
SMILES Code :	C(C)(C)(C)N[S](=O)(=O)C1=CC=CS1
MDL No. :	MFCD02047252
InChI Key :	CLKMBGGZGFULOO-UHFFFAOYSA-N
Pubchem ID :	765814

Safety of [ 100342-30-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 100342-30-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	5
Fraction Csp3	0.5
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	54.67
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	82.79 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.69
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.09
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.91
Log P_o/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.	0.62
Log P_o/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	1.7
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.6

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.97
Solubility	2.33 mg/ml ; 0.0106 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.42
Solubility	0.832 mg/ml ; 0.00379 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-2.86
Solubility	0.302 mg/ml ; 0.00138 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	No
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	No
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	No
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.	-6.86 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<1.0
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)	2.84

Application In Synthesis of [ 100342-30-1 ]

* 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 [ 100342-30-1 ]

[ 100342-30-1 ] Synthesis Path-Downstream 1~24

1
[ 500-22-1 ]
[ 100342-30-1 ]
[ 134286-91-2 ]
[ 134286-92-3 ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 4260 – 4263.
[2]Journal of Organic Chemistry,1991,vol. 56,p. 4260 – 4263.

2
[ 630-18-2 ]
[ 100342-30-1 ]
5-(2,2-Dimethyl-propionyl)-thiophene-2-sulfonic acid tert-butylamide [ No CAS ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 4260 – 4263.

3
[ 132289-57-7 ]
[ 100342-30-1 ]
[ 132289-58-8 ]
[ 132305-13-6 ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 4260 – 4263.
[2]Tetrahedron Letters,1990,vol. 31,p. 6269 – 6272.
[3]Tetrahedron Letters,1990,vol. 31,p. 6269 – 6272.

4
[ 100342-30-1 ]
[ 104863-67-4 ]
5-(2,2,2-Trifluoro-acetyl)-thiophene-2-sulfonic acid tert-butylamide [ No CAS ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 4260 – 4263.

5
[ 100342-30-1 ]
[ 134286-96-7 ]
[ 134286-94-5 ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 4260 – 4263.

6
[ 100342-30-1 ]
[ 134286-85-4 ]
[ 68848-05-5 ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 4260 – 4263.

7
[ 100342-30-1 ]
[ 814-49-3 ]
(5-tert-Butylsulfamoyl-thiophen-2-yl)-phosphonic acid diethyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 4260 – 4263.

8
[ 100342-30-1 ]
[ 874-90-8 ]
5-(4-Methoxy-benzoyl)-thiophene-2-sulfonic acid tert-butylamide [ No CAS ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 4260 – 4263.

9
[ 100342-30-1 ]
[ 6339-87-3 ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 4523 – 4525.
[2]Synthetic Communications,2005,vol. 35,p. 417 – 425.

10
[ 100342-30-1 ]
[ 126-30-7 ]
5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-thiophene-2-sulfonic acid <i>tert</i>-butylamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2305 – 2312.

11
[ 542-69-8 ]
[ 100342-30-1 ]
[ 146013-27-6 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In ethyl acetate;	EXAMPLE 1 5-butyl-<strong>[100342-30-1]2-(N-t-butylaminosulfonyl)thiophene</strong> To a solution of <strong>[100342-30-1]2-(N-t-butylaminosulfonyl)thiophene</strong> (2.01 g, 9.18 mmol) in anhydrous THF (17 mL) cooled to -78 C. under N2 was added 2.5 M n-BuLi (10 mL, 2.7 equiv). After stirring at -78 C. for 30 min the bath temperature was raised to -40 C. and the mixture was stirred for an additional 2 hrs. To this mixure was added n-butyliodide (2.0 mL, 2 equiv) and the reaction was allowed to warm to room temperature. After stirring overnight the darkened reaction mixture was quenched with NH4 Cl soln and extracted with EtOAc. The organic was washed with brine and dried over anhydrous MgSO4 and concentrated in vacuo. The titled compound was purified by flash chromatography eluding with hex/EtOAc (15:1 to 7:1). Rf=0.32 (6:1 Hex/EtOAc).

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 7160 – 7168.
[2]Patent: US5444067,1995,A .

12
[ 100342-30-1 ]
[ 107-08-4 ]
N-tert-butyl-5-propylthiophene-2-sulfonamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 7160 – 7168.

13
[ 100342-30-1 ]
[ 874-98-6 ]
N-tert-butyl-5-(3-methoxy-benzyl)-thiophene-2-sulfonamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 7160 – 7168.

14
[ 16629-19-9 ]
[ 75-64-9 ]
[ 100342-30-1 ]

Yield	Reaction Conditions	Operation in experiment
5.62 g (94%)	In tetrahydrofuran;	Step A: N-(1,1-Dimethylethyl)-2-thiophenesulfonamide To a solution of t-butylamine (8.35 g, 0.114 mol) in dry tetrahydrofuran (THF) (20 mL) cooled to 0 C. was added dropwise 2-thiophenesulfonyl chloride (5.0 g, 27.4 mmol). After the addition was completed, the reaction mixture was warmed to ambient temperature and stirred overnight. The mixture was extracted with ethyl acetate (3*80 mL) and the combined extracts were washed with water, dried over molecular sieves and concentrated. The residue was chromatographed on (silica, eluding with 25% ethyl acetate-hexane) to yield 5.62 g (94%) of solid: mp 80-82 C.
5.62 g (94%)	In tetrahydrofuran;	Step A: N-(1,1-Dimethylethyl)-2-thiophenesulfonamide To a solution of t-butylamine (8.35 g, 0.114 mol) in dry tetrahydrofuran (THF) (20 mL) cooled to 0 C. was added dropwise 2-thiophenesulfonyl chloride (5.0 g, 27.4 mmol). After the addition was completed, the reaction mixture was warmed to ambient temperature and stirred overnight. The mixture was extracted with ethyl acetate (3*80 mL) and the combined extracts were washed with water, dried over molecular sieves and concentrated. The residue was chromatographed on silica, eluding with 25% ethyl acetate-hexane, to yield 5.62 g (94%) of solid: mp 80-82 C.
	In chloroform; at 0 – 20℃; for 1.16667h;Heating / reflux;	Thiophene-2-sulfonyl chloride (15 g, 0.082 mol) was dissolved in CHC13 (200 mL) under N2 atmosphere and then cooled to 0C. tert-Butylamine (25.9 mL, 0.246 mol) dissolved in CHC13 (50 mL) was then added dropwise to the reaction mixture. The reaction mixture was stirred for 1 h at room temperature and then at reflux for 10 min. Toluene (700 mL) was added and the organic phase was washed with water (3 x 50 mL), dried, and concentrated in vacuo. The sub-title product was used without further purification in the next step. IH NMR B (CDC13) : 7.60 (1H, dd, J= 1.3, 3.8 Hz), 7.53 (1H, dd, J= 1.3, 5.0 Hz), 7.02 (1H, dd, J = 5. 0,3. 8 Hz), 5.13 (1H, m), 1.24 (9H, m) 13C NMR B (CDC13) : 145.0, 131.7, 131.2, 127.0, 55.1, 29.9

	In chloroform; at 0℃; for 1.16667h;Heating / reflux;	Thiophene-2-sulfonyl chloride (15 g, 0.082 mol) was dissolved in CHC13 (200 mL) under N2 atmosphere and then cooled to 0C. TERT-BUTYLAMINE (25.9 mL, 0.246 mol) dissolved in CHC13 (50 ML) was then added dropwise to the reaction mixture. The reaction mixture was stirred for 1 hour at room temperature and then at reflux for 10 min. Toluene (700 mL) was added and the organic phase was washed with water (3 x 50 mL), dried, and concentrated in vacuo. The sub-title product was used without further purification in the next step. 1H NMR No.(CDCL3) : 7.60 (1H, dd, J= 1.3, 3.8 Hz), 7.53 (1H, dd, J= 1.3, 5.0 Hz), 7.02 (1H, dd, J = 5.0, 3.8 Hz), 5. 13- (1 H, m), 1.24 (9H, m) 13C NMR 6 (CDC13) : 145.0, 131.7, 131.2, 127.0, 55.1, 29.9
	In chloroform; at 20℃; for 1.16667h;Heating / reflux;	Thiophene-2-sulfonyl chloride (15 g, 0.082 mol) was dissolved in CHC13 (200 mL) under N2 atmosphere and then cooled to 0C. tert-Butylamine (25.9 mL, 0.246 mol) dissolved in CHC13 (50 ML) was then added dropwise to the reaction mixture. The reaction mixture was stirred for 1 h at room temperature and then at reflux for 10 min. Toluene (700 mL) was added and the organic phase was wa Details Products CAS 57-22-7 Read more Products CAS 53-18-9 Read more Products CAS 51-23-0 Read more Reviews There are no reviews yet. Be the first to review “N-tert-Butyl-2-thiophenesulfonamide” Cancel reply Your email address will not be published. Required fields are marked * Your rating * Your review * Name * Email * Save my name, email, and website in this browser for the next time I comment. Previous 1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidin-2-one Next Benzofuran-5-carbaldehyde Easy CDMO Easy CDMO is China TOP100 CDMO company. We believe: Easy CDMO, Medicinal Chemical is Big. More than 100 scientists are serving you. Quick Links About Us Products Blog Contacts Support Links Privacy Policy Term And Condition Locations Office address: Chenxun Technology Building, No. 633, Jinzhong Road, Changning District, Shanghai info@easycdmo.com +8602161734564 © Copyright Easy CDMO 2025. All Rights Reserved.