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[ CAS No. 28620-12-4 ] {[proInfo.proName]}

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Chemical Structure| 28620-12-4
Chemical Structure| 28620-12-4
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Product Details of [ 28620-12-4 ]

CAS No. :28620-12-4 MDL No. :MFCD00239350
Formula : C7H4N2O3S Boiling Point : -
Linear Structure Formula :- InChI Key :QITPMSSAFSZYOP-UHFFFAOYSA-N
M.W : 196.18 Pubchem ID :641571
Synonyms :

Calculated chemistry of [ 28620-12-4 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.27
TPSA : 106.92 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.95
Log Po/w (XLOGP3) : 1.59
Log Po/w (WLOGP) : 1.5
Log Po/w (MLOGP) : 0.22
Log Po/w (SILICOS-IT) : 1.1
Consensus Log Po/w : 1.07

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.5
Solubility : 0.614 mg/ml ; 0.00313 mol/l
Class : Soluble
Log S (Ali) : -3.45
Solubility : 0.0702 mg/ml ; 0.000358 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.26
Solubility : 1.07 mg/ml ; 0.00547 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.41

Safety of [ 28620-12-4 ]

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 [ 28620-12-4 ]

* 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 [ 28620-12-4 ]
  • Downstream synthetic route of [ 28620-12-4 ]

[ 28620-12-4 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 28620-12-4 ]
  • [ 533-30-2 ]
Reference: [1] Yakugaku Zasshi, 1942, vol. 62, p. 47,51; dtsch. Ref. S. 19, 22[2] Chem.Abstr., 1951, p. 609
  • 2
  • [ 28620-12-4 ]
  • [ 56354-98-4 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 24, p. 6518 - 6521
  • 3
  • [ 934-34-9 ]
  • [ 28620-12-4 ]
YieldReaction ConditionsOperation in experiment
90% at 20℃; for 3 h; To 70percent HNO3 (20 mL) was added 3H-benzothiazol-2-one (10 g, 66 mmol) and the mixture stirred at 20 °C for 3 h. The precipitate was filtered and washed with water. The product was recrystallised in absolute ethanol. Yield 90percent; mp 228–229 °C; 1H NMR (300 MHz, DMSO-d6) δ: 7.28 (d, J=8.9Hz, 1H, H4), 8.18 (dd, J=8.9Hz, J=2.4Hz, 1H, H5), 8.65 (d, J=2.5Hz, 1H, H7), 12.54 (br s, 1H, NH). 13C NMR (75 MHz, DMSO-d6) δ: 111.9 (CH), 119.6 (CH), 123.2 (CH), 125.0 (Caro), 142.5 (Caro), 142.9 (Caro), 171.0 (CO). LCMS (ESI): calc for [M−H+]: 195.0; found: 195.0.
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 92, p. 807 - 817
[2] Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 1503 - 1509
[3] Monatshefte fur Chemie, 2011, vol. 142, # 1, p. 67 - 80
[4] Chemistry of Heterocyclic Compounds, 1990, vol. 25, # 11, p. 1294 - 1296
[5] Patent: US2003/40533, 2003, A1,
  • 4
  • [ 934-34-9 ]
  • [ 28620-12-4 ]
YieldReaction ConditionsOperation in experiment
87% at 0℃; for 0.5 h; To a solution of 2hydroxybenzothiazole (1.0 g, 6.5inmol) in concentrated sulfuric acid (26 mL) at 0 °C was added dropwise fuming nitric acid, 90percent ACS reagent grade (042 mL. 6.5 mmoi). The mixture was stirred at 0 °C for 30 mm, and then the mixture was poured into ice (83 mL). A saturated aqueous solution of NaHCO3 was added until pH7 and the mixture was extracted with DCM. The organic layer was separated, dried (Mg504), filtered, and concentrated in vaeuo to afford the title compound (1.11 g, 87percent). MS (ES1): mass caicd. for C7H4N2035 196.0, mz found 197.0 [M+H]’. ‘H NMR (300 MHz, DMSOd6) d 12.56 (s, 1H), 8.65 (d, J= 2.2 Hz, 1H), 8.18 (dd, J= 88, 2.3 Hz, iH, 7.28 (d, J 8.8 Hz. IH).
Reference: [1] Patent: WO2016/176460, 2016, A1, . Location in patent: Page/Page column 99
  • 5
  • [ 4845-58-3 ]
  • [ 28620-12-4 ]
Reference: [1] Patent: US2108712, 1934, ,
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 22, p. 324
[3] Journal of Organic Chemistry, 1958, vol. 23, p. 1768,1771
[4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 22, p. 324
  • 6
  • [ 1131-75-5 ]
  • [ 28620-12-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2358 - 2361
  • 7
  • [ 6285-57-0 ]
  • [ 28620-12-4 ]
Reference: [1] Yakugaku Zasshi, 1942, vol. 62, p. 47,51; dtsch. Ref. S. 19, 22[2] Chem.Abstr., 1951, p. 609
[3] Yakugaku Zasshi, 1942, vol. 62, p. 47,51; dtsch. Ref. S. 19, 22[4] Chem.Abstr., 1951, p. 609
[5] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 5, p. 1069 - 1076
  • 8
  • [ 3621-99-6 ]
  • [ 28620-12-4 ]
Reference: [1] Journal of the Chemical Society, 1949, p. 3311,3314
[2] Chemical and Pharmaceutical Bulletin, 1976, vol. 24, # 5, p. 1050 - 1058
  • 9
  • [ 21554-41-6 ]
  • [ 28620-12-4 ]
Reference: [1] Journal of the Chemical Society, 1949, p. 3311,3314
[2] Chemical and Pharmaceutical Bulletin, 1976, vol. 24, # 5, p. 1050 - 1058
  • 10
  • [ 934-34-9 ]
  • [ 625-58-1 ]
  • [ 28620-12-4 ]
Reference: [1] Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1944, vol. 5, p. 11,14, 16, 18
[2] Journal of the Chemical Society, 1935, p. 1755,1760
  • 11
  • [ 941-57-1 ]
  • [ 28620-12-4 ]
Reference: [1] Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1944, vol. 5, p. 11,14, 16, 18
  • 12
  • [ 63321-86-8 ]
  • [ 7664-93-9 ]
  • [ 7697-37-2 ]
  • [ 28620-12-4 ]
  • [ 4308-10-5 ]
Reference: [1] Yakugaku Zasshi, 1952, vol. 72, p. 269[2] Chem.Abstr., 1953, p. 2177
[3] Yakugaku Zasshi, 1952, vol. 72, p. 1266[4] Chem.Abstr., 1953, p. 12357
  • 13
  • [ 28620-12-4 ]
  • [ 2407-11-6 ]
Reference: [1] Yakugaku Zasshi, 1942, vol. 62, p. 47,51; dtsch. Ref. S. 19, 22[2] Chem.Abstr., 1951, p. 609
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