[ CAS No. 1788-08-5 ] {[proInfo.proName]}

Name: 1788-08-5|4-Ethynylbenzenesulfonamide|98%
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Quality Control of [ 1788-08-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1788-08-5 ]

Product Details of [ 1788-08-5 ]

CAS No. :	1788-08-5	MDL No. :	MFCD11040256
Formula :	C₈H₇NO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OQPUCENNUFNCQO-UHFFFAOYSA-N
M.W :	181.21	Pubchem ID :	44457221
Synonyms :

Calculated chemistry of [ 1788-08-5 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	45.37
TPSA :	68.54 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.91 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.35
Log Po/w (XLOGP3) :	0.7
Log Po/w (WLOGP) :	1.48
Log Po/w (MLOGP) :	0.88
Log Po/w (SILICOS-IT) :	0.56
Consensus Log Po/w :	0.99

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.71
Solubility :	3.55 mg/ml ; 0.0196 mol/l
Class :	Very soluble
Log S (Ali) :	-1.72
Solubility :	3.48 mg/ml ; 0.0192 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.04
Solubility :	1.63 mg/ml ; 0.00902 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.0

Safety of [ 1788-08-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1788-08-5 ]

* 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.

Upstream synthesis route of [ 1788-08-5 ]
Downstream synthetic route of [ 1788-08-5 ]

[ 1788-08-5 ] Synthesis Path-Upstream 1~5

1
[ 775331-26-5 ]
[ 1788-08-5 ]

Yield	Reaction Conditions	Operation in experiment
62%	With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃;	[0477] To a solution OF 4- [ (TRIMETHYLSILYL) ETHYNYL] BENZENESULFONAMIDE prepared as in Step 1 (1.69 g, 3.13 mmole) in anhydrous THF under A N2 atmosphere was added TBAF (10 mL-1.0 M in THF, 10 mmole) and the resulting mixture was stirred at room temperature. When silica TLC (1: 1 hexanes: EtOAc) indicated the reaction was complete, 10percent HC1 and EtOAc were added. The EtOAc layer was separated, washed twice with H20, aqueous NH4C1, dried over NA2S04 and concentrated IN VACUO to give 0. 748 g (62percent yield) of the product: ESHRMS M/Z 199.0506 (M+NH4, CGH7NO2SNH4, Calc'd 199. 0541).
1.5 g	With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2 h;	The crude intermediate 1 was treated with TBAF in THF (20 mL. 20 mmol) and stirred for 2 hours at r.t. then quenched by water and extracted with EtOAc (50 mL x 2). The combine organic layer was dried over anhydrous Na2SO4 concentrated to give crude intermediate 2 which was purified by column chromatography to give pure intermediate 2 (1.5 g, 84percent) as yellow solid.
1.5 g	With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2 h;	The crude intermediate 1 was treated with TBAF in THF (20 mL, 20 mmol) and stirred for 2 h at r.t., then quenched by water and extracted with EtOAc (50 mL×2). The combine organic layer was dried over anhydrous Na₂SO₄, concentrated to give crude intermediate 2, which was purified by column chromatography to give pure intermediate 2 (1.5 g, 84percent) as yellow solid. ¹H NMR (300 MHz, DMSO-d6) δ7.82 (d, 2H), 7.68 (d, 2H), 7.46 (s, 2H), 4.45 (s,

Reference： [1] MedChemComm, 2018, vol. 9, # 3, p. 534 - 544
[2] Patent: WO2004/87686, 2004, A2, . Location in patent: Page 229
[3] Patent: WO2004/87687, 2004, A1, . Location in patent: Page 229
[4] Organic and biomolecular chemistry, 2003, vol. 1, # 3, p. 498 - 506
[5] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 4, p. 1948 - 1956
[6] Journal of Medicinal Chemistry, 2008, vol. 51, # 6, p. 1945 - 1953
[7] Patent: WO2014/82286, 2014, A1, . Location in patent: Paragraph 73
[8] Patent: US2015/51242, 2015, A1, . Location in patent: Paragraph 0121

2
[ 701-34-8 ]
[ 1788-08-5 ]

Reference： [1] Organic and biomolecular chemistry, 2003, vol. 1, # 3, p. 498 - 506
[2] Patent: WO2014/82286, 2014, A1,
[3] MedChemComm, 2018, vol. 9, # 3, p. 534 - 544

3
[ 701-34-8 ]
[ 1066-54-2 ]
[ 1788-08-5 ]

Reference： [1] Patent: WO2006/71184, 2006, A1, . Location in patent: Page/Page column 15

4
[ 1056474-58-8 ]
[ 1788-08-5 ]

Reference： [1] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2009, vol. 64, # 3, p. 292 - 296

5
[ 138-36-3 ]
[ 1788-08-5 ]

Reference： [1] Patent: US2015/51242, 2015, A1,

[ 1788-08-5 ] Synthesis Path-Downstream 1~88

1
[ 624-90-8 ]
[ 1788-08-5 ]
4-(1-methyl-1H-1,2,3-triazol-4-yl)benzenesulfonamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 116 - 120

2
2-azido-N-benzyl-3-methyl-butyramide [ No CAS ]
[ 1788-08-5 ]
N-benzyl-3-methyl-2-[4-(4-sulfamoyl-phenyl)-[1,2,3]triazol-1-yl]-butyramide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 116 - 120
[2]Angewandte Chemie - International Edition,2006,vol. 45,p. 5276 - 5281

3
2-azido-N-cyclopentyl-3-methyl-butyramide [ No CAS ]
[ 1788-08-5 ]
N-cyclopentyl-3-methyl-2-[4-(4-sulfamoyl-phenyl)-[1,2,3]triazol-1-yl]-butyramide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 116 - 120
[2]Angewandte Chemie - International Edition,2006,vol. 45,p. 5276 - 5281

4
2-azido-3-methyl-N-pyridin-2-ylmethyl-butyramide [ No CAS ]
[ 1788-08-5 ]
DHK₁₇₈ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 116 - 120
[2]Angewandte Chemie - International Edition,2006,vol. 45,p. 5276 - 5281

5
2-azido-N-cyclohexyl-3-methyl-butyramide [ No CAS ]
[ 1788-08-5 ]
DHK₁₇₉ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 116 - 120
[2]Angewandte Chemie - International Edition,2006,vol. 45,p. 5276 - 5281

6
7-(2-azidoethoxy)-2H-chromen-2-one [ No CAS ]
[ 1788-08-5 ]
DHK₆₃ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 116 - 120
[2]Angewandte Chemie - International Edition,2006,vol. 45,p. 5276 - 5281

7
azido-acetic acid N'-benzooxazol-2-yl-N'-methyl-hydrazide [ No CAS ]
[ 1788-08-5 ]
4-[1-(N'-benzooxazol-2-yl-N'-methyl-hydrazinocarbonylmethyl)-1H-[1,2,3]triazol-4-yl]-benzenesulfonamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 116 - 120

8
(S)-1-(3-Aza-bicyclo[3.2.2]non-3-yl)-2-azido-3-methyl-butan-1-one [ No CAS ]
[ 1788-08-5 ]
4-{1-[1-(3-aza-bicyclo[3.2.2]nonane-3-carbonyl)-2-methyl-propyl]-1H-[1,2,3]triazol-4-yl}-benzenesulfonamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 116 - 120

9
2-azido-3-phenyl-N-(2-thiophen-3-yl-ethyl)-propionamide [ No CAS ]
[ 1788-08-5 ]
3-phenyl-2-[4-(4-sulfamoyl-phenyl)-[1,2,3]triazol-1-yl]-N-(2-thiophen-3-yl-ethyl)-propionamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 116 - 120
[2]Angewandte Chemie - International Edition,2006,vol. 45,p. 5276 - 5281

10
2-azido-3-phenyl-propionic acid N'-benzyl-hydrazide [ No CAS ]
[ 1788-08-5 ]
4-{1-[1-(N'-benzyl-hydrazinocarbonyl)-2-phenyl-ethyl]-1H-[1,2,3]triazol-4-yl}-benzenesulfonamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 116 - 120

11
(R)-2-(2-Azido-acetylamino)-3-benzylsulfanyl-propionic acid methyl ester [ No CAS ]
[ 1788-08-5 ]
DHK₄ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 116 - 120
[2]Angewandte Chemie - International Edition,2006,vol. 45,p. 5276 - 5281

12
2-azido-N-cyclohexyl-3-phenyl-propionamide [ No CAS ]
[ 1788-08-5 ]
DHK₂-12 [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 116 - 120
[2]Angewandte Chemie - International Edition,2006,vol. 45,p. 5276 - 5281

13
(S)-2-Azido-1-(octahydro-quinolin-1-yl)-3-phenyl-propan-1-one [ No CAS ]
[ 1788-08-5 ]
4-{1-[1-benzyl-2-(octahydro-quinolin-1-yl)-2-oxo-ethyl]-1H-[1,2,3]triazol-4-yl}-benzenesulfonamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 116 - 120

14
C₂₃H₂₁N₃O [ No CAS ]
[ 1788-08-5 ]
4-{1-[(1S,2R)-1,2-Diphenyl-2-((E)-3-phenyl-allyloxy)-ethyl]-1H-[1,2,3]triazol-4-yl}-benzenesulfonamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 116 - 120

15
[ 1788-08-5 ]
[ 40224-47-3 ]
(S)-3-methyl-2-(4-(4-sulfamoylphenyl)-1H-1,2,3-triazol-1-yl)butanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With copper(II) sulfate; sodium L-ascorbate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine; In aq. phosphate buffer; water; tert-butyl alcohol; at 20.0℃; for 12.0h;	(S)-3-methyl-2-(4-(4-sulfamoylphenyl)- 1H-1 ,2,3-triazol- 1-yl)butanoic acid - 27 Ethynyl benzene sulfonamide (54 mg, 0.3 mmol), azido valine 20 (42 mg, 0.3 mmol) and tris-(benzyltriazolylmethyl)amine (TBTA, 0.3 mg, cat.) were dissolved in a mixture of tBuOH (3.7 mL), a 0.04 M CuSO4 solution in PBS pH 7.4 (2.0 mL) and a 0.1 M sodium ascorbate solution in PBS pH 7.4 (1.7 mL) and stirred for 12 h at room temperature. Allsolvents had previously been de-gassed and flushed with Ar. The reaction was poured onto25 mL H20 acidified to pH 2.0 and the mixture extracted with EtOAc (4 x 20 mL), the pooled organic phases washed with brine and dried over Mg504. The solvent was removed under vacuum and the residue purified over silica (20% MeOH in DCM with 0.1% Et3N) to yield the product as a white solid (70 mg, 72%).1H-NMR (400 MHz, DMSO-d6) [ppm] = 8.86 (s, 1H), 8.10 (d, J = 8.5 Hz, 2H), 7.90 (d, J = 8.5 Hz, 2H), 7.39 (s, 1H), 5.24 (d, J = 8.0 Hz, 1H), 2.64-2.55 (m, 1H), 1.00 (d, J = 6.7 Hz, 3H), 0.88 (d, J = 6.7 Hz); 13C-NMR (100 MHz, DMSO-d6) [ppm] = 169.6, 145.0,143.2, 133.7, 126.3, 125.4, 122.6, 68.3, 30.4, 19.0, 18.3; HRMS: (mlz) [M + H] calcd. for C13H15N4Na2O4S, 369.0604; found 369.0609.

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 4231 - 4235
Angew. Chem.,2014,vol. 126,p. 4315 - 4320,6
[2]Patent: WO2015/114171,2015,A1 .Location in patent: Page/Page column 54
[3]Angewandte Chemie - International Edition,2005,vol. 44,p. 116 - 120

16
[ 1788-08-5 ]
(E)-1-(4-Azido-piperidin-1-yl)-3-phenyl-propenone [ No CAS ]
4-{1-[1-(3-phenyl-acryloyl)-piperidin-4-yl]-1H-[1,2,3]triazol-4-yl}-benzenesulfonamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 116 - 120

17
4-azido-6-methoxy-quinoline [ No CAS ]
[ 1788-08-5 ]
4-[1-(6-methoxy-quinolin-4-yl)-1H-[1,2,3]triazol-4-yl]-benzenesulfonamide [ No CAS ]