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[ CAS No. 22952-24-5 ] {[proInfo.proName]}

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Chemical Structure| 22952-24-5
Chemical Structure| 22952-24-5
Structure of 22952-24-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 22952-24-5 ]

CAS No. :22952-24-5 MDL No. :MFCD00110677
Formula : C7H4N2O5S Boiling Point : -
Linear Structure Formula :- InChI Key :HZZFBUZSKAVIOV-UHFFFAOYSA-N
M.W : 228.18 Pubchem ID :100187
Synonyms :

Calculated chemistry of [ 22952-24-5 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 53.54
TPSA : 117.44 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) : -7.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.2
Log Po/w (XLOGP3) : 0.74
Log Po/w (WLOGP) : 0.73
Log Po/w (MLOGP) : -1.39
Log Po/w (SILICOS-IT) : -1.58
Consensus Log Po/w : -0.26

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.95
Solubility : 2.55 mg/ml ; 0.0112 mol/l
Class : Very soluble
Log S (Ali) : -2.79
Solubility : 0.374 mg/ml ; 0.00164 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.92
Solubility : 2.72 mg/ml ; 0.0119 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.44

Safety of [ 22952-24-5 ]

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 [ 22952-24-5 ]

* 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 [ 22952-24-5 ]
  • Downstream synthetic route of [ 22952-24-5 ]

[ 22952-24-5 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 6269-91-6 ]
  • [ 22952-24-5 ]
YieldReaction ConditionsOperation in experiment
72% With chromium(VI) oxide; sulfuric acid In water at 20℃; for 24 h; To solution chromium trioxide (20.4 g, 0.204 mol) in water (150 mL) was added concentrated sulfuric acid (190 mL) dropwise in the ice bath. 2-Methyl-5-nitrobenzenesulfonamide (10 g, 46.3 mmol) was added and the mixture was stirred at room temperature for 24 h. The mixture was filtered and the residue washed with water, dissolved in sodium bicarbonate solution and filtered under vacuum. The filtrate was acidified with concentrated HCl. After the precipitated product was filtered and washed with abundant cold water, it was dried in the vacuum-oven at 40 °C. The product was obtained a white powder in 72percent yield. Mp 205.6-205.8 °C, (lit.36 205-207 °C); IR: 3103, 1720, 1608, 1541, 1354, 1340, 1184, 1128 cm-1; 1H NMR (DMSO-d6, 300 MHz) δ/ppm: 8.02 (1H, d, J = 8.5 Hz), 8.56 (1H, d, J = 8.2 Hz), 8.71 (1H, s), 10.2 (1H, br, NH); 13C NMR (DMSO-d6, 75 MHz) δ/ppm: 117.2, 126.4, 129.8, 135.2, 143.0, 151.7, 162.2.
71.4% With potassium permanganate; N-benzyl-N,N,N-triethylammonium chloride In water at 95℃; for 8 h; 2-Methyl-5-nitrobenzene sulfonamide (3, 26.1 g, 0.10 mol), benzyl triethyl ammonium chloride (TEBA) (1.2 g, 5.2 mmol) and water (250 mL) were mixed together and heated to 95 °C. The potassium permanganate (15.7 g, 0.1 mmol) was added in batches and then added water (50 mL) finally. The reaction mixture was heated to 95 °C for 8 h. The reaction residue was filtered and washed with hot water (80 mL) twice, the solution was acidified with concentrated hydrochloric acid to pH 2. A white solid was filtered off and recrystallized from ethyl alcohol to give 6-nitrosaccharin (4, 16.3 g, 71.4 percent yield), m.p.: 205.5-206.9 °C (lit. [11,12]m.p.: 212-214 °C). 1H NMR (DMSO-d6, 300 MHz) δ, ppm:7.93 (1H, d, J = 8.4 Hz), 8.41 (1H, dd, J = 1.6, 2.1 Hz), 8.47(1H, s), 10.6 (1H, br, NH).
68% With chromium(VI) oxide; sulfuric acid In water at 20℃; for 42 h; Step C: 6-Nitro-l,l-dioxo-l,2-dihydro-llambda*6*-benzo[i/|isothiazol-3-oneTo a solution of Cr03 (20.8 g, 208 mmol) in water (150 mL) was slowly added concentrated sulfuric acid (190 mL). To the resulting mixture was added 2-methyl-5-nitrobenzenesulfonamide (10.0 g, 46.3 mmol) and the mixture was stirred at rt for about 42 h. The mixture was filtered and the filter cake was washed with water (100 mL). The solid was dissolved in 10percent aqueous NaHCC>3, filtered and the filtrate acidified with 2 N HC1 (pH = 1). The precipitate was collected by filtration and washed with water (2 x 50 mL) to provide 6-nitro-l,l-dioxo-l,2-dihydro- llambda*6*-benzo[i/]isothiazol-3-one (7.2 g, 68percent). .H NMR (DMSO- ) δ: 8.42-8.53 (m, 2H), 8.00 (s, 1H), 3.70 (br s, 1H).
55% With chromium(VI) oxide; sulfuric acid In water at 20℃; for 24 h; 5.1.1
6-Nitrobenzo[d]isothiazol-3(2H)-one 1,1-dioxide (4)
To a solution of chromium trioxide (9.0 g, 900 mmol) in water (67 ml), concentrated sulfuric acid (83.5 ml) was added gradually.
The mixture was added 2-methyl-5-nitrobenzenesulfonamide 3 (4.32 g, 20 mmol) and then stirred at room temperature for 24 h.
Crude product was obtained by filtration and then washed with water.
The filter cake was stirred in 10percent sodium bicarbonate solution and the insoluble residue was removed by filtration.
The filtrate was acidified with 5percent hydrochloric acid solution to generate the purified product with 55percent yield, mp: 203-205 °C. 1H NMR (DMSO-d6) δ 7.91 (d, J = 8.4 Hz, 1H), 8.47 (dd, J = 7.8 Hz, 1.8 Hz, 1H), 8.54 (s, 1H). MS (ESI) m/z: 227.1 [M-H]-.

Reference: [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 9, p. 2811 - 2821
[2] Asian Journal of Chemistry, 2017, vol. 29, # 7, p. 1622 - 1624
[3] Patent: WO2012/48222, 2012, A1, . Location in patent: Page/Page column 98
[4] Tetrahedron, 2006, vol. 62, # 33, p. 7902 - 7910
[5] Bulletin of the Chemical Society of Japan, 1982, vol. 55, # 12, p. 3824 - 3827
[6] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 5, p. 1529 - 1538
[7] Chemical Communications, 2011, vol. 47, # 29, p. 8301 - 8303
[8] Journal of Medicinal Chemistry, 2014, vol. 57, # 8, p. 3522 - 3531
[9] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 19, p. 676
[10] Patent: WO2008/24634, 2008, A1, . Location in patent: Page/Page column 167
[11] Journal of Enzyme Inhibition and Medicinal Chemistry, 2014, vol. 29, # 1, p. 118 - 123
[12] Journal of Agricultural and Food Chemistry, 2017, vol. 65, # 35, p. 7661 - 7668
  • 2
  • [ 309735-34-0 ]
  • [ 22952-24-5 ]
Reference: [1] Synthesis, 2001, # 11, p. 1659 - 1664
  • 3
  • [ 515884-30-7 ]
  • [ 22952-24-5 ]
Reference: [1] Russian Chemical Bulletin, 2002, vol. 51, # 8, p. 1549 - 1555
  • 4
  • [ 121-02-8 ]
  • [ 22952-24-5 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1982, vol. 55, # 12, p. 3824 - 3827
[2] Patent: WO2012/48222, 2012, A1,
[3] Journal of Enzyme Inhibition and Medicinal Chemistry, 2014, vol. 29, # 1, p. 118 - 123
[4] Journal of Agricultural and Food Chemistry, 2017, vol. 65, # 35, p. 7661 - 7668
  • 5
  • [ 99-99-0 ]
  • [ 22952-24-5 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 29, p. 8301 - 8303
[2] Patent: WO2012/48222, 2012, A1,
[3] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 9, p. 2811 - 2821
[4] Journal of Enzyme Inhibition and Medicinal Chemistry, 2014, vol. 29, # 1, p. 118 - 123
[5] Journal of Medicinal Chemistry, 2014, vol. 57, # 8, p. 3522 - 3531
[6] Asian Journal of Chemistry, 2017, vol. 29, # 7, p. 1622 - 1624
  • 6
  • [ 89795-77-7 ]
  • [ 22952-24-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 14, p. 4181 - 4185
  • 7
  • [ 4337-51-3 ]
  • [ 22952-24-5 ]
Reference: [1] Il Farmaco; edizione scientifica, 1964, vol. 19, p. 254 - 268
  • 8
  • [ 13296-87-2 ]
  • [ 22952-24-5 ]
Reference: [1] Russian Chemical Bulletin, 2002, vol. 51, # 8, p. 1549 - 1555
  • 9
  • [ 99-55-8 ]
  • [ 22952-24-5 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2017, vol. 65, # 35, p. 7661 - 7668
  • 10
  • [ 3558-19-8 ]
  • [ 22952-24-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 18, p. 2467 - 2472
  • 11
  • [ 63480-10-4 ]
  • [ 22952-24-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 18, p. 2467 - 2472
  • 12
  • [ 22952-24-5 ]
  • [ 2297-06-5 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2017, vol. 65, # 35, p. 7661 - 7668
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