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[ CAS No. 209917-48-6 ] {[proInfo.proName]}

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Chemical Structure| 209917-48-6
Chemical Structure| 209917-48-6
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Product Details of [ 209917-48-6 ]

CAS No. :209917-48-6 MDL No. :MFCD03002128
Formula : C10H16N2O2S Boiling Point : -
Linear Structure Formula :- InChI Key :XEJAJZSTMLRDKH-UHFFFAOYSA-N
M.W : 228.31 Pubchem ID :832627
Synonyms :

Calculated chemistry of [ 209917-48-6 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 61.2
TPSA : 80.57 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.4
Log Po/w (XLOGP3) : 1.19
Log Po/w (WLOGP) : 2.43
Log Po/w (MLOGP) : 1.0
Log Po/w (SILICOS-IT) : 0.35
Consensus Log Po/w : 1.28

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.1
Solubility : 1.8 mg/ml ; 0.00788 mol/l
Class : Soluble
Log S (Ali) : -2.48
Solubility : 0.759 mg/ml ; 0.00333 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.23
Solubility : 0.134 mg/ml ; 0.000585 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.07

Safety of [ 209917-48-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P272-P280-P302+P352-P305+P351+P338-P321-P332+P313-P333+P313-P337+P313-P362-P363-P501 UN#:N/A
Hazard Statements:H315-H317-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 209917-48-6 ]

* 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 [ 209917-48-6 ]

[ 209917-48-6 ] Synthesis Path-Downstream   1~30

  • 1
  • [ 54178-87-9 ]
  • [ 209917-48-6 ]
  • 4-Amino-1-hydroxy-naphthalene-2-carboxylic acid {4-[2,4-bis-(2,2-dimethyl-propyl)-phenoxy]-butyl}-amide [ No CAS ]
  • 4-[4-Acetylamino-8-(4-tert-butylsulfamoyl-phenylazo)-5-hydroxy-naphthalene-1-sulfonylamino]-1-hydroxy-naphthalene-2-carboxylic acid {4-[2,4-bis-(2,2-dimethyl-propyl)-phenoxy]-butyl}-amide [ No CAS ]
  • 2
  • [ 294885-56-6 ]
  • [ 209917-48-6 ]
YieldReaction ConditionsOperation in experiment
89% b) Title compound A solution of 4-acetylamino-N-tert-butylbenzenesulfonamide (8.0 g, 29.6 mmol), KOH (8.30 g, 148 mmol), H2O (6 mL) and MeOH (24 mL) is heated at 100C for 2 h. H2O (24 mL) is added and the mixture is heated for two more hours. It is allowed to cool, H2O is added and it is brought to pH 8 with 1N HCl. It is then extracted with EtOAc, dried over Na2SO4 and the solvent is removed, to give 6.0 g of the product as a white solid (yield: 89%).
87% With hydrogenchloride; water; In methanol; for 1h;Reflux; General procedure: 10 mL of concentrated HCl were added to a suspension of 25 mmol N-substituted 4-acetylaminobenzenesulfonyl amide in 40 mL of MeOH and the reaction mixture was refluxed for 1 h in a flaskequipped with a reflux condenser. After the end of the reaction, the reaction mixture was poured into150 mL of 10% NaHCO3 in H2O. The precipitate was separated, washed with 200 mL H2O and driedin vacuum under KOH.
78.85% With sodium hydroxide; water; Example 32-N- (1, 1-DIMETHYLETHYL)-4-AMINOBENZENESULFONAMIDE [108] N- (1, 1-DIMETHYLETHYL)-4- (ACETYLAMINO) BENZENESULFONAMIDE (Example 11) is deprotected by saponification in 20 % NaOH (5 mL), followed by neutralization with 10 % HCL. The precipitate that is formed is collected by filtration and recrystallized from methanol/diethyl ether. [109] 78.85% yield; white solid. m. p. 129-131 C. 1H NMR (CDCl3) : 8 1.20 (s, 9H); 4.08 (bs, 2H); 4.44 (bs, 1H); 6.64-6. 68 (d, 2H, J=8); 7.63-7. 67 (d, 2H, J=8).
  • 3
  • [ 351-54-2 ]
  • [ 209917-48-6 ]
  • N-(3-fluoro-4-methoxybenzylidene)-4-(tert-butylaminosulfonyl)aniline [ No CAS ]
  • 4
  • [ 209917-48-6 ]
  • [ 915006-43-8 ]
YieldReaction ConditionsOperation in experiment
53% With N-Bromosuccinimide; In dichloromethane; at 20℃; for 0.5h; Example 48; 5-Cyano-lH-imidazole-2-carboxylic acid (2-cyclohex-l-enyl-4-sulfamoyl-phenyl)-amide trifluoroacetic acid salt; a) 4-Amino-N-tert-butyl-3-cyclohex-l-enyl-benzenesulfonamide; To a solution of <strong>[209917-48-6]4-amino-N-tert-butyl-benzenesulfonamide</strong> (J. Med. Chem. (2003), 46(16), 3463-3475, 228 mg, 1.00 mmol) in DCM (10 mL), NBS (178 mg, 1.00 mmol) was added. The resulting mixture was stirred at RT for 30 min and washed with satd NaHCO3 (10 mL) and 10% aq Na2S2O3 (10 mL). The organic layer was separated, dried and concentrated to obtain 4-amino-3-bromo-N-tert-butyl-benzenesulfonamide (163 mg, 53 %).
  • 5
  • [ 209917-48-6 ]
  • [ 265114-23-6 ]
  • 6
  • [ 209917-48-6 ]
  • [ 499777-84-3 ]
  • 7
  • [ 209917-48-6 ]
  • [ 499777-85-4 ]
  • 8
  • [ 121-60-8 ]
  • (+-)-3-<3-amino-4-hydroxy-phenyl>-3-<4-hydroxy-phenyl>-phthalide [ No CAS ]
  • [ 209917-48-6 ]
  • 9
  • [ 121-60-8 ]
  • 1.5-diamino-naphthalene hydrochloride [ No CAS ]
  • [ 209917-48-6 ]
  • 10
  • [ 351-54-2 ]
  • [ 209917-48-6 ]
  • N-tert-butyl-4-[(3-fluoro-4-methoxybenzylidene)amino]benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% In toluene; for 24h;Heating / reflux; EXAMPLE 2 N-tert-Butyl-4-[(3-fluoro-4-methoxybenzylidene)amino]benzenesulfonamide A mixture of <strong>[209917-48-6]4-amino-N-tert-butylbenzenesulfonamide</strong> (52.3 g, 0.23 mol, obtained in example 1), 3-fluoro-4-methoxybenzaldehyde (35.3 g, 0.23 mol) and toluene (2.5 L) is heated at reflux in a Dean-Stark for 24 h.. The solvent is removed, yielding 83.5 g of the title compound (yield: quantitative). Mp: 129-131 C; 1H-NMR (300 MHz, CDCl3) delta (TMS): 1.23 (s, 9 H), 3.98 (s, 3 H), 4.65 (s, 1 H), 7.04 (t, J = 8.1 Hz, 1 H), 7.21 (d, J = 6.7 Hz, 2 H), 7.58 (m, 1 H), 7.73 (dd, JH-F = 11.8 Hz, J = 2 Hz, 1 H), 7.90 (d, J = 6.7 Hz, 2 H), 8.33 (s, 1 H).
  • 11
  • [ 49690-09-7 ]
  • [ 209917-48-6 ]
YieldReaction ConditionsOperation in experiment
98% With hydrogen;palladium 10% on activated carbon; In ethanol; for 48.0h; b) Title compound A solution of <strong>[49690-09-7]N-tert-butyl-4-nitrobenzenesulfonamide</strong> (10.0 g, 39 mmol) in EtOH (100 mL) is stirred for 48 h under a H2 atmosphere in the presence of 10% Pd/C (1.50 g). The resulting mixture is filtered and concentrated to give the desired product as a slightly-coloured solid (8.7 g, yield: 98%). Mp: 127 C; 1H-NMR (300 MHz, CDCl3 + CD3OD) delta (TMS): 1.19 (s, 9 H), 3.74 (s, CD3OD + 1 H), 6.93 (d, J = 9 Hz, 2 H), 7.66 (d, J = 9 Hz, 2 H).
90% With palladium 10% on activated carbon; hydrazine hydrate; In ethanol; for 4.5h;Inert atmosphere; Reflux; General procedure: Method b: To a solution of nitroarene (1.0 equiv.) in EtOH or MeOH (deoxygenated with bubbled Argon) was added Pd/C (10%) and hydrazine monohydrate 65% (3.0 equiv.) under Argon. The solution was stirred and heated at reflux for the indicated time. The reaction mixture was filtered over Celite, and the filtrate concentrated under reduced pressure.
90% With palladium on activated charcoal; hydrazine hydrate; In ethanol; for 4.5h;Inert atmosphere; Reflux; This was prepared from SG1-174 (10.64 g), hydrazine monohydrate 65% (5.92 mL), Pd/C (1.00 g), and EtOH (80 mL) using the general method b (reaction time, 4.5 h) to provide the title compound as a light tangerine solid (8.50 g, 90%). Mp: 122-123 C. NMR (400 MHz, DMSO-ifc) delta: 7.40 (d, / = 8.7 Hz, 2H), 6.98 (s, 1H, disappeared on D20 shake), 6.56 (d, / = 8.7 Hz, 2H), 5.83 (s, 2H, disappeared on D20 shake), 1.03 (s, 9H). HPLC-MS (ESI+): m/z 479.3 [100%, (2M+Na)+], 229.2 [25%, (M+H)+], 173.2 [60%, (M-tBu+H)+]. Method b: To a solution of nitroarene (1.0 equiv.) in EtOH or MeOH (deoxygenated with bubbled Argon) was added Pd/C (10%) and hydrazine monohydrate 65% (3.0 equiv.) under Argon. The solution was stirred and heated at reflux for the indicated time. The reaction mixture was filtered over Celite, and the filtrate concentrated under reduced pressure.
With hydrogen;palladium over charcoal; In methanol; under 2068.65 Torr; Step 2:; <strong>[49690-09-7]N-tert-butyl-4-nitrobenzenesulfonamide</strong> (500 mg, 1.936 mmol) from step 1 was dissolved in methanol (30 ml). Pd-C was added under nitrogen. The flask was pressurized with hydrogen gas to 40 PSI and shaken on a Parr apparatus overnight. Pd-C was filtered away, evaporated solvent to dryness. The residue was used directly in the next step without further purification. LC-MS, MS m/z 229 (M++H).

  • 12
  • [ 54-47-7 ]
  • [ 209917-48-6 ]
  • [ 608523-50-8 ]
YieldReaction ConditionsOperation in experiment
82% Step B. Preparation of 6-[4-(tert-Butylsulfamoyl)phenylazo]-pyridoxal-5-phosphate The title material was prepared from <strong>[209917-48-6]4-amino-N-tert-butyl-benzenesulfonamide</strong> (step A) and pyridoxal-5-phosphate as described in general procedure D, method A. The final productproduct was obtained in 82% yield. 1H NMR (D2O): delta 1.00 (s, 9H), 2.33 (s, 3H), 5.63 (s, 2H), 7.72 (d, J=7.0, 2H), 7.99 (d, J=8.1, 2H), 10.32 (s, 1H). 31P NMR (D2O): delta 7.04 (s).
  • 13
  • [ 209917-48-6 ]
  • [ 815-17-8 ]
  • [ 1028253-29-3 ]
YieldReaction ConditionsOperation in experiment
Step 3; To a mixture of <strong>[209917-48-6]4-amino-N-tert-butylbenzenesulfonamide</strong> (180 mg, 0.788 mmol, from step 2) and 3,3-dimethyl-2-oxobutanoic acid (308 mg, 2.4 mmol) in a 100 ml RBF at RT was added tetraisopropoxytitanium (2 ml,) via a pipet. The color of the mixture soon changed into a characteristic canary color. The solution was warmed to 75 C. for about 15 minutes and the color remained the same. The solution was diluted with absolute ethanol (8 ml) at RT, followed by the addition of 1.5× of sodium cyanotrihydroborate (245 mg, 3.90 mmol), and the remaining half after the bubbling and sizzling was over. The color of the solution became lighter. The solution was mixed with 4 mL of water, forming a suspension, and the white PPT was removed by centrifuge. The organic was extracted into ethyl acetate, and the organic phase was dried over Na2SO4, filtered, and evaporated to dryness. A yellow oil was obtained and was used directly in the next step without further purification. LC-MS, MS m/z 343 (M++H).
  • 14
  • [ 209917-48-6 ]
  • C17H17N5O3S [ No CAS ]
  • 15
  • [ 209917-48-6 ]
  • [ 915006-42-7 ]
  • 17
  • [ 209917-48-6 ]
  • 4-cyano-1H-imidazole-2-carboxylic acid [2-(4,4-dimethyl-cyclohex-1-enyl)-4-sulfamoyl-phenyl]-amide [ No CAS ]
  • 18
  • [ 209917-48-6 ]
  • 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(2-methyl-propane-2-sulfonylamino)-phenyl]-amide [ No CAS ]
  • 20
  • 2-chloro-5,11-dimethyl-5H-benzo[e]pyrido[3,2-b][1,4]diazepin-6(11H)-one [ No CAS ]
  • [ 209917-48-6 ]
  • N-(tert-butyl)-4-((5,11-dimethyl-6-oxo-6,11-dihydro-5H-benzo[e]pyrido[3,2-b][1,4]diazepin-2-yl)amino)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; XPhos; In tert-butyl alcohol; at 100℃; for 23h; N-(tert-butyl)-4-((5,ll-dimethyl-6-oxo-6,ll-dihydro-5H-benzo[e]pyrido[3,2- b ] [ 1 ,4] diazepin-2-yl)amino)benzenesulf onamide 2-Chloro-5,l l-dimethyl-5H-benzo[e]pyrido[3,2-b][l,4]diazepin-6(l lH)-one (17.2 mg, 0.0628 mmol, 1 eq), 4-amino-N-(/ert-butyl)benzenesulfonamide (17.2 mg, 0.0754 mmol, 1.2 eq), Pd2dba3 (2.9 mg, 0.00314 mmol, 5 mol%), XPhos (4.5 mg, 0.00942 mmol, 15 mol%) and potassium carbonate (34.7 mg, 0.251 mmol, 4 eq) were dissolved in tBuOH (0.63 mL, 0.1M) and heated to 100 C for 23 hours. The mixture was filtered through CELITE, washed with DCM/MeOH and concentrated under reduced pressure. Purification by column chromatography (ISCO, 12 g column, 0-10%MeOH/DCM, 15 minute gradient) gave the desired product as a yellow solid (24.79 mg, 0.0532 mmol, 84%). 1H NMR (400 MHz, Chloroform-J) delta 7.85 - 7.77 (m, 3H), 7.57 (d, J = 8.8 Hz, 2H), 7.38 (t, J = 8.5 Hz, 2H), 7.09 (dd, J = 7.8, 2.1 Hz, 2H), 6.72 (s, 1H), 6.58 (d, J = 8.5 Hz, 1H), 4.44 (s, 1H), 3.48 (s, 3H), 3.38 (s, 3H), 1.25 (s, 9H). 13C NMR (100 MHz, cdcl3) delta 168.67, 155.72, 151.67, 149.25, 144.22, 134.99, 132.95, 132.20, 131.97, 128.49, 126.92, 123.89, 123.13, 117.15, 116.82, 105.58, 54.52, 37.66, 36.11, 30.20. LCMS 466.47 (M+H).
  • 21
  • [ 5750-76-5 ]
  • [ 209917-48-6 ]
  • 2,5-dichloro-N4-(4-[N-(1,1-dimethylethyl)sulfamoyl]phenyl)pyrimidin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% In methanol; water; at 45℃; for 96h; General procedure: Procedure A: A mixture of substituted 2,4-dichloropyrimidine (1.0 equiv.) and substituted aniline (1.15 equiv.) in MeOH/water (1 : 1.5, 0.2 M) was stirred at 45 C. The reaction time is indicated below. Upon cooling to ambient temperature, the desired product precipitated and was filtered, washed with MeOH/water (1 : 1.5, 20 mL), and dried.
58% In methanol; water; at 45℃; for 96h; A mixture of substituted 2,4-dichloropyrimidine (1.0 equiv.) and substituted aniline (1.15 equiv.) in MeOH/water (1 : 1.5, 0.2 M) was stirred at 45 C. The reaction time is indicated below. Upon cooling to ambient temperature, the desired product precipitated and was filtered, washed with MeOH/water (1 : 1.5, 20 mL), and dried. 2,5-Dichloro-/Y4-(4-[/Y-(l,l-dimethylethyl)sulfamoyl]phenyl)pyrimidin-4-amine (SG1-182): This was prepared from 2,4,5-trichloropyrimidine (0.500 g) and SG1-177 (0.715 g) using procedure A (stirred for 4 d). The crude solid was purified via flash chromatography (S1O2) eluting with hexanes/EtOAc (0: 10 to 4:6 v/v) to provide the title compound as a tangerine-colored solid (0.590 g, 58%). Mp: 180-181 C. NMR (400 MHz, DMSO-ifc): delta 9.73 (s, IH, disappeared on D20 shake), 8.46 (s, IH), 7.80 (s, 4H), 7.48 (s, IH, disappeared on D20 shake), 1.09 (s, 9H). HPLC-MS (ESI+): m/z 773.1 [10%, (MCl35Cl37+M35Cl35Cl+Na)+], 379.1 [10%, (MC137C137+H)+], 377.1 [70%, (MC135C137+H)+], 375.1 [100%, (M35C135C1+H)+].
  • 22
  • [ 209917-48-6 ]
  • [ 1028253-30-6 ]
  • 23
  • [ 209917-48-6 ]
  • [ 1028253-28-2 ]
  • 24
  • [ 209917-48-6 ]
  • [ 1028253-27-1 ]
  • 25
  • [ 98-74-8 ]
  • [ 209917-48-6 ]
  • 26
  • [ 121-60-8 ]
  • [ 209917-48-6 ]
  • 27
  • [ 103-84-4 ]
  • [ 209917-48-6 ]
  • 28
  • [ 209917-48-6 ]
  • [ 103678-36-0 ]
  • (S)-N-(1-((4-(N-(tert-butyl)sulfamoyl)phenyl)amino)-1-oxo-3-phenylpropan-2-yl)cyclohexanecarboxamide [ No CAS ]
  • 29
  • [ 24939-24-0 ]
  • [ 209917-48-6 ]
  • 30
  • [ 105776-76-9 ]
  • [ 209917-48-6 ]
  • (S)-N-(4-(N-tert-butylsulfamoyl)phenyl)-2-(1-oxoisoindolin-2-yl)-3-phenylpropanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
5.6% With 1-methyl-1H-imidazole; N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate In acetonitrile at 20℃; 41 Preparation of (S)-N-(4-(N-tert-butylsulfamoyl)phenyl)-2-(1-oxoisoindolin-2-yl)- 3-phenylpropanamide, I-69 A mixture of 300 mg (S)-2-(1-oxoisoindolin-2-yl)-3-phenylpropanoic acid (1.1 mmol, 1.00 equiv), 251 mg 4-amino-N-tert-butylbenzenesulfonamide (1.1 mmol, 1.00 equiv), 339 mg N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate (1.21 mmol, 1.10 equiv) and 316 mg 1-methyl-1H-imidazole (3.85 mmol, 3.50 equiv) in 5 mL acetonitrile was stirred at room temperature overnight. To the mixture was added 20 mL ethyl acetate and the solution washed with 3 x 20 mL volumes of water. The organic phase was concentrated and the compound was purified by reversed phase preparative HPLC on a Gilson GX-281. A concentrated solution of crude product dissolved in DMSO was injected in 800 uL volumes onto a 10 um C18 reversed phase X-Bridge 19 mm diameter x 250 mm length column eluting with a gradient of 50-95% acetonitrile in water with 10 mmol/liter ammonium carbonate. Peaks were detected by UV absorbance at 214 nm and 254 nm and fractions collected by 1.5 mV threshold trigger on the 214 nm channel. Fractions containing product were combined, concentrated and lyophilized to afford 30 mg (S)-N-(4-(N-tert-butylsulfamoyl)phenyl)-2-(1-oxoisoindolin-2-yl)-3-phenylpropanamide (I-69) as a white solid (5.6 % yield). MS (ESI+) m/z 492 [M+H]+ ; 1H NMR (400 MHz, d6-DMSO) d 10.71 (s, 1H), 7.75 (s, 4H), 7.64 (d, J = 7.5 Hz, 1H), 7.58 (t, J = 5.9 Hz, 2H), 7.52 - 7.19 (m, 6H), 7.15 (t, J = 7.3 Hz, 1H), 5.40 (dd, J = 10.4, 5.5 Hz, 1H), 4.80 (d, J = 17.7 Hz, 1H), 4.57 (d, J = 17.7 Hz, 1H), 3.39 (dt, J = 14.0, 7.0 Hz, 1H), 3.24 (dd, J = 14.5, 10.5 Hz, 1H), 1.07 (s, 9H).
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