[ CAS No. 5339-69-5 ] {[proInfo.proName]}

Name: 5339-69-5|N-Isopropylbenzenesulfonamide|98%
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SKU: A169028
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Quality Control of [ 5339-69-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 5339-69-5 ]

SDS Specification

Alternatived Products of [ 5339-69-5 ]

Product Details of [ 5339-69-5 ]

CAS No. :	5339-69-5	MDL No. :	MFCD00591077
Formula :	C₉H₁₃NO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QKIWHADSHFVRFN-UHFFFAOYSA-N
M.W :	199.27	Pubchem ID :	220600
Synonyms :

Calculated chemistry of [ 5339-69-5 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	51.95
TPSA :	54.55 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) :	-6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.81
Log Po/w (XLOGP3) :	1.69
Log Po/w (WLOGP) :	2.45
Log Po/w (MLOGP) :	1.28
Log Po/w (SILICOS-IT) :	0.84
Consensus Log Po/w :	1.62

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.28
Solubility :	1.04 mg/ml ; 0.0052 mol/l
Class :	Soluble
Log S (Ali) :	-2.45
Solubility :	0.706 mg/ml ; 0.00354 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.2
Solubility :	0.125 mg/ml ; 0.000628 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.95

Safety of [ 5339-69-5 ]

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

Application In Synthesis of [ 5339-69-5 ]

* 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 [ 5339-69-5 ]
Downstream synthetic route of [ 5339-69-5 ]

[ 5339-69-5 ] Synthesis Path-Upstream 1~5

1
[ 98-10-2 ]
[ 67-63-0 ]
[ 5339-69-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With trifluoromethylsulfonic anhydride In 1,4-dioxane at 120℃; for 48 h;	General procedure: To a mixture of sulfonamide (2 mmol) and alcohol (10 mmol) in 1,4-dioxane (3 mL) was added Tf₂O (2 mmol). The mixture was then sealed and stirred at 120 °C until the reaction was completed as judged by TLC. After quenching with satd. aq. NaHCO₃, the reaction mixture was extracted three times with EtOAc, dried over Na₂SO₄ and concentrated in vacuo. The residue was purified by flash chromatography with PE and EtOAc (3: 1) as the eluent to give the pure product.

Reference： [1] Bulletin of the Chemical Society of Japan, 2015, vol. 88, # 4, p. 610 - 612

2
[ 98-10-2 ]
[ 108-20-3 ]
[ 5339-69-5 ]

Yield	Reaction Conditions	Operation in experiment
69%	With trifluorormethanesulfonic acid In toluene at 120℃; for 35 h;	General procedure: To a mixture of tolsulfonamide (0.5mmol) and THF (2mmol) in toluene (1mL), was added TfOH (40molpercent). The resulting mixture was than sealed and stirred for 18h at 120°C. After quenching with satdaqNaHCO₃, the reaction mixture was extracted three times with EtOAc, dried over Na₂SO₄, and concentrated in vacuo. The residue was purified by flash chromatography with PE and EtOAc (3:1) as the eluent to give the pure product.

Reference： [1] Tetrahedron, 2014, vol. 70, # 2, p. 434 - 438

3
[ 75-31-0 ]
[ 98-09-9 ]
[ 5339-69-5 ]

Reference： [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1899, vol. 31, p. 648,650[2] Chem. Zentralbl., 1899, vol. 70, # II, p. 868
[3] Journal of the American Chemical Society, 1971, vol. 93, # 11, p. 2692 - 2699
[4] Tetrahedron Letters, 2015, vol. 56, # 1, p. 66 - 68
[5] Synlett, 2015, vol. 26, # 5, p. 635 - 638

4
[ 349098-30-2 ]
[ 5339-69-5 ]

Reference： [1] Organic Letters, 2014, vol. 16, # 14, p. 3812 - 3815

5
[ 98-10-2 ]
[ 75-26-3 ]
[ 23705-46-6 ]
[ 5339-69-5 ]

Reference： [1] Synthesis, 1981, # 12, p. 1005 - 1008

[ 5339-69-5 ] Synthesis Path-Downstream 1~35

1
[ 5339-69-5 ]
[ 59263-13-7 ]

Reference： [1]Zhurnal Russkago Fiziko-Khimicheskago Obshchestva,1899,vol. 31,p. 648,650
Chemisches Zentralblatt,1899,vol. 70,p. 868

2
[ 75-31-0 ]
[ 98-09-9 ]
[ 5339-69-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 20℃; for 0.5h;	General procedure: To a solution of aryl sulphonamide (10 mmol) in CH2Cl2 (50 mL) was added isopropylamine (10 mmol) and triethylamine (20 mmol). The resulting solution was stirred for 30 mins at room temperature, and was then quesnched with water (20 mL). The mixture was extracted with CH2Cl2 (2 x 10 mL), dried over sodium sulphate and filtered to give the crude sulfonamide. IF required, the sulphonamide was further purified by recrystalisation from EtOH / water.
	With triethylamine; In dichloromethane; at 0℃;Sealed tube;	General procedure: Primary amine (1.2 equiv) and Et3N (2 equiv) were added to a dried flask, thenbenzenesulfonyl chloride (1 equiv) in dichloromethane was injected into it. The mixture wasstirred at 0C until TLC showed that benzenesulfonyl chloride was totally consumed. Waterwas added to the reaction mixture and extracted with dichloromethane. The combined organiclayers were dried over Na2SO4, concentrated under reduced pressure. Without furtherpurification, the residue was used for the next step. Methacryloyl chloride (2 equiv) indichloromethane was added to the mixture of the above residue, triethylamine (2 equiv) andDMAP (0.1 equiv) in dichloromethane. The mixture was stirred overnight at roomtemperature. Then the reaction mixture was washed with saturated aqueous Na2CO3 (5 mL)and extracted with dichloromethane. The combined organic layers were dried over Na2SO4,filtered, and concentrated in vacuo. The residue was purified by column chromatography(petroleum ether : ethyl acetate =12:1) on silica gel to afford the corresponding product 2 in atotal yield of 62~74%.

Reference： [1]Zhurnal Russkago Fiziko-Khimicheskago Obshchestva,1899,vol. 31,p. 648,650
Chemisches Zentralblatt,1899,vol. 70,p. 868
[2]Journal of the American Chemical Society,1971,vol. 93,p. 2692 - 2699
[3]Tetrahedron Letters,2015,vol. 56,p. 66 - 68
[4]Synlett,2015,vol. 26,p. 635 - 638

3
[ 5339-69-5 ]
[ 74-88-4 ]
[ 4747-21-1 ]

Reference： [1]Chemische Berichte,1928,vol. 61,p. 1428

4
[ 5339-69-5 ]
[ 74-88-4 ]
[ 91252-31-2 ]

Reference： [1]Chemische Berichte,1928,vol. 61,p. 1428

5
[ 5339-69-5 ]
[ 609-65-4 ]
[ 66896-78-4 ]

Reference： [1]Patent: DE2744137,1978,
Chem.Abstr.,1978,vol. 89

6
[ 5339-69-5 ]
[ 18080-84-7 ]
[ 1678-25-7 ]
C₆H₅HgN(SO₂C₆H₅)CH(CH₃)2 [ No CAS ]

Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1983,vol. 32,p. 468 - 474
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1983,p. 522 - 528
[2]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1983,vol. 32,p. 468 - 474
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1983,p. 522 - 528

7
[ 5339-69-5 ]
[ 54128-89-1 ]
[ 312-63-0 ]
C₆H₅HgN(SO₂C₆H₅)CH(CH₃)2 [ No CAS ]

Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1983,vol. 32,p. 468 - 474
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1983,p. 522 - 528

9
[ 98-10-2 ]
[ 75-26-3 ]
[ 23705-46-6 ]
[ 5339-69-5 ]

Reference： [1]Synthesis,1981,p. 1005 - 1008

10
[ 37692-14-1 ]
[ 5339-69-5 ]
[ 33489-84-8 ]