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Chemical Structure| 81-07-2
Chemical Structure| 81-07-2
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Product Details of [ 81-07-2 ]

CAS No. :81-07-2 MDL No. :MFCD00005866
Formula : C7H5NO3S Boiling Point : -
Linear Structure Formula :- InChI Key :CVHZOJJKTDOEJC-UHFFFAOYSA-N
M.W :183.18 Pubchem ID :5143
Synonyms :
Saccharin

Calculated chemistry of [ 81-07-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.72
TPSA : 71.62 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) : -6.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.74
Log Po/w (XLOGP3) : 0.91
Log Po/w (WLOGP) : 0.82
Log Po/w (MLOGP) : -0.02
Log Po/w (SILICOS-IT) : 0.56
Consensus Log Po/w : 0.6

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.92
Solubility : 2.21 mg/ml ; 0.012 mol/l
Class : Very soluble
Log S (Ali) : -2.0
Solubility : 1.83 mg/ml ; 0.01 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.54
Solubility : 0.534 mg/ml ; 0.00292 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.25

Safety of [ 81-07-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 81-07-2 ]

* 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 [ 81-07-2 ]
  • Downstream synthetic route of [ 81-07-2 ]

[ 81-07-2 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 81-07-2 ]
  • [ 936-16-3 ]
YieldReaction ConditionsOperation in experiment
97% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 15℃; for 3 h; Inert atmosphere Step 1. Saccharin (10.0 g, 54.6 mmol) was slowly added to solution of LiAlH4 (2.24 g, 59.0 mmol) in 300 mL of THF at 0°C. The reaction mixture was stirred for 3h at 15°C under an inert atmosphere. Upon completion, EtOAc (100 mL) was slowly added followed by addition of 10percent H2S04 (lOOmL). The organic layer was separated and washed with 100 mL of 5percent sodium carbonate solution, dried over anhydrous sodium sulfate, filtered, and concentrated to give 1 (4.4 g, 97percent).
87% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 15℃; for 16.5 h; tetrahydrofuran (2 mL) was added drop-wise to a 0 °C suspension of lithium aluminum hydride (45.6 mg, 1.20 mmol) in tetrahydrofuran (3 mL). After the reaction mixture had stirred for 30 minutes at 0 °C, it was gradually warmed to 15 °C and stirred at 15 °C for 16 hours. The white suspension was treated with saturated aqueous ammonium chloride solution, and then extracted with ethyl acetate (20 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to provide the product as a grey solid. Yield: 160 mg, 0.946 mmol, 87percent. 1H NMR (400 MHz, CDCI3) δ 7.81 (d, J=7.8 Hz, 1 H), 7.63 (dd, half of ABX pattern, J=7.5, 7.3 Hz, 1 H), 7.54 (dd, half of ABX pattern, J=7.5, 7.5 Hz, 1 H), 7.41 (d, J=7.8 Hz, 1 H), 4.95-4.80 (br s, 1 H), 4.55 (s, 2H).
81% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Preparation 16
2,3-Dihydrobenzo[d]isothiazole 1,1-dioxide
To a cold solution of lithium aluminum hydride (0.414 g) in anhydrous tetrahydrofuran (30 mL), kept at 0° C. with an external ice bath, was added sulfobenzimide (1 g, 5.5 mmol).
The reaction was allowed to warm to ambient temperature and stirred overnight.
The reaction was quenched with the addition of water and 2.5M aqueous sulfuric acid.
The mixture was filtered through Celite and washed with ethyl acetate.
The organic layer was washed with 1M aqueous sulfuric acid, dried (anhydrous magnesium sulfate), filtered, and concentrated to afford an off-white solid (0.75 g, 81percent).
1H NMR (CDCl3, 300 MHz) δ 7.81-7.78 (d, 1H, J=7.8 Hz), 7.64-7.59 (dt, 1H, J=1.2, 7.5 Hz), 7.52-7.49 (dt, 1H, J=0.75, 7.5 Hz), 7.41-7.37 (d, 1H, J=8.1 Hz), 4.8 (br s, 1H), 4.55-4.54 (d, 1H, J=3.6 Hz).
35.6% With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether for 48 h; Example 82
1,2-Benzisothiazoline-1,1-dioxide
To a solution of 1,2-benzisothiazoline-3-one-1,1-dioxide (25, 554 mg, 3.02 mmol) in THF (8.0 mL) was slowly added lithium aluminum hydride (1M in ether, 4.09 mL, 4.09 mmol).
The solution was stirred for 48 hrs, followed by the slow addition of drops of Na2SO4 10H2O at 0° C.
The reaction mixture was filtered through celite, and the filtrate was concentrated to dryness to afford the title compound (182 mg, 35.6percent).
1H NMR (300 MHz, CDCl3) δ 7.85 (d, J=7.65 Hz, 1H), 7.67 (d, J=7.49, 1.17 Hz, 1H), 7.58 (t, J=7.44 Hz, 1H), 7.44 (d, J=7.59 Hz, 1H), 4.74 (brs, 1H), 4.59 (s, 2H)
35.6% With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether for 0.8 h; Lithium aluminium hydride1 M in ether (4.09 mL) was addedslowly at 0 C to a solution of o-sulfobenzimide (7, 554 mg,3.02 mmol) in THF (8.0 mL), and stirred for 48 min. Subsequently,sodium sulfate hydrate was added to the solution and filteredthrough Celite. The organic layer was concentrated in reducedpressure to afford the title compound (182 mg, 35.6percent); 1H NMR(400 MHz, CDCl3) d 7.85 (d, J = 7.7, 1H), 7.67 (dt, J = 7.5, 1.2 Hz,1H), 7.58 (t, J = 7.4 Hz, 1H), 7.44 (d, J = 7.6 Hz, 1H), 4.74 (br, 1H),4.59 (s, 2H).

Reference: [1] Patent: WO2018/49324, 2018, A1, . Location in patent: Page/Page column 25
[2] Organic Letters, 2014, vol. 16, # 6, p. 1550 - 1553
[3] Patent: WO2017/21805, 2017, A1, . Location in patent: Page/Page column 174
[4] Patent: US2013/303524, 2013, A1, . Location in patent: Paragraph 0268-0269
[5] Journal of Medicinal Chemistry, 2016, vol. 59, # 19, p. 8868 - 8878
[6] Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5348 - 5355
[7] Tetrahedron, 1996, vol. 52, # 12, p. 4181 - 4198
[8] Journal of Medicinal Chemistry, 1983, vol. 26, # 2, p. 243 - 246
[9] Patent: US2015/329533, 2015, A1, . Location in patent: Paragraph 0294; 0295
[10] Bioorganic and Medicinal Chemistry, 2017,
[11] Mem. Coll. Sci. Kyoto Univ., 1932, vol. <A> 15, p. 151,153
  • 2
  • [ 7664-93-9 ]
  • [ 81-07-2 ]
  • [ 936-16-3 ]
Reference: [1] Mem. Coll. Sci. Kyoto Univ., 1932, vol. <A> 15, p. 151,152
  • 3
  • [ 81-07-2 ]
  • [ 27148-03-4 ]
Reference: [1] Pharmazie, 2005, vol. 60, # 10, p. 723 - 731
[2] Gazzetta Chimica Italiana, 1916, vol. 46 I, p. 234,236
[3] Gazzetta Chimica Italiana, 1915, vol. 45 I, p. 547
[4] Journal of Organic Chemistry, 1951, vol. 16, p. 1582,1585
[5] Journal of Chemical Crystallography, 1994, vol. 24, # 9, p. 581 - 586
[6] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2008, vol. 63, # 7, p. 877 - 879
[7] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2007, vol. 62, # 12, p. 1530 - 1534
[8] Inorganica Chimica Acta, 2018, vol. 479, p. 266 - 274
  • 4
  • [ 81-07-2 ]
  • [ 14070-51-0 ]
YieldReaction ConditionsOperation in experiment
84% With tert-butylhypochlorite In methanol at 20℃; for 0.0833333 h; Saccharin (6.0 g) was reacted in methanol (120 ml) at room temperature for 5 minutes with tert-butyl hypochlorite (5 ml) to give the compoundChloro-saccharin 1a (6.0 g, 84percent); Chloro-saccharin 1a (3.0 g) was reacted with trifluoromethylthio-silver (3.6 g) in acetonitrile (40 ml) at room temperature for 10 min to give Compound 1 (3.3 g, 86percent). Reagent 1 is a white solid at room temperature, soluble in organic solvents such as dichloromethane, chloroform, acetone and acetonitrile.
84% With tert-butylhypochlorite In methanol at 20℃; for 0.0833333 h; Saccharin (6.0 g of) in methanol (120ml) at room temperature and tert-butyl hypochlorite (5ml) for 5 minutes to give saccharin chloro compound 1a (6.0g, 84percent); chloro saccharin 1a (3.0g) and three difluoromethylthio-silver (3.6 g of) in acetonitrile (40ml) and reacted at room temperature for 10 minutes to give compound 1 (3.3g, 86percent).Reagent 1 at room temperature a white solid was soluble in methylene chloride, chloroform, acetone, and acetonitrile.N - trifluoromethylthio-saccharin (2 - ((Trifluoromethyl) Thio) of benzo [D] isothiazol-3 (2H) -one1,1-dioxide)
84% With tert-butylhypochlorite In methanol at 20℃; for 0.0833333 h; Saccharin (6.0 g of) in methanol (120ml) and tert-butyl hypochlorite (5ml) for 5 minutes to give saccharin chloro compound 1a (6.0g, 84percent) at room temperature; chloro saccharin 1a (3.0g) and three difluoromethylthio-silver (3.6 g of) the reaction at room temperature in acetonitrile (40ml) 10 minutes to give compound 1 (3.3g, 86percent).
84% With tert-butylhypochlorite In methanol at 20℃; for 0.0833333 h; Green chemistry Saccharin (6.0 g) was reacted with t-butyl hypochlorite (5 ml) in methanol (120 ml) for 5 minutes at room temperature to give the compound chlorosaccharide 1a (6.0 g, 84percent);The chloro saccharin 1a (3.0 g) was reacted with trifluoromethylthio silver (3.6 g) in acetonitrile (40 ml) at room temperature for 10 minutes to give compound II (3.3 g, 86percent).The compound II is a white solid at room temperature and is soluble in an organic solvent such as dichloromethane, chloroform, acetone or acetonitrile.

Reference: [1] Synlett, 2006, # 2, p. 194 - 200
[2] Angewandte Chemie, International Edition, 2014, vol. 53, # 35, p. 9316 - 9320,5[3] Angewandte Chemie, 2014, vol. 126, # 35, p. 9470 - 9474,5
[4] Patent: CN104945294, 2016, B, . Location in patent: Paragraph 0135; 0136; 0137; 0138
[5] Patent: CN104945298, 2016, B, . Location in patent: Paragraph 0187; 0188; 0189; 0190
[6] Patent: CN104945348, 2017, B, . Location in patent: Paragraph 0085-0087
[7] Patent: CN104945304, 2018, B, . Location in patent: Paragraph 0109; 0110; 0111
[8] Journal of Organic Chemistry, 2018, vol. 83, # 3, p. 1576 - 1583

[9] Synthesis, 2009, # 16, p. 2797 - 2801
[10] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1980, vol. 19, # 6, p. 576 - 578
  • 5
  • [ 81-07-2 ]
  • [ 108-95-2 ]
  • [ 143-74-8 ]
Reference: [1] Synthetic Communications, 2012, vol. 42, # 8, p. 1101 - 1107
[2] Journal of the American Chemical Society, 1928, vol. 50, p. 2017
  • 6
  • [ 64-17-5 ]
  • [ 81-07-2 ]
  • [ 59777-72-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 1, p. 210 - 219
[2] Chemische Berichte, 1887, vol. 20, p. 1603
[3] European Journal of Medicinal Chemistry, 2016, vol. 117, p. 167 - 178
  • 7
  • [ 81-07-2 ]
  • [ 59777-72-9 ]
Reference: [1] American Chemical Journal, 1889, vol. 11, p. 334
  • 8
  • [ 81-07-2 ]
  • [ 632-24-6 ]
Reference: [1] Chemische Berichte, 1888, vol. 21, p. 246
[2] Chemische Berichte, 1888, vol. 21, p. 246
[3] Zeitschrift fuer Elektrochemie und Angewandte Physikalische Chemie, 1928, vol. 34, p. 283
[4] American Chemical Journal, 1903, vol. 30, p. 363
  • 9
  • [ 81-07-2 ]
  • [ 71125-38-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 6, p. 980 - 989
  • 10
  • [ 616-47-7 ]
  • [ 81-07-2 ]
  • [ 482333-74-4 ]
Reference: [1] Patent: WO2004/35599, 2004, A1, . Location in patent: Page 9
[2] Organic and Biomolecular Chemistry, 2008, vol. 6, # 18, p. 3270 - 3275
  • 11
  • [ 81-07-2 ]
  • [ 2258-42-6 ]
  • [ 50978-45-5 ]
Reference: [1] Synlett, 2011, # 13, p. 1920 - 1922
[2] Chemical Communications, 2015, vol. 51, # 63, p. 12574 - 12577
  • 12
  • [ 81-07-2 ]
  • [ 2258-42-6 ]
  • [ 13361-42-7 ]
  • [ 50978-45-5 ]
Reference: [1] Chemical Communications, 2015, vol. 51, # 63, p. 12574 - 12577
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