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[ CAS No. 53473-85-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 53473-85-1
Chemical Structure| 53473-85-1
Chemical Structure| 53473-85-1
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Product Details of [ 53473-85-1 ]

CAS No. :53473-85-1 MDL No. :MFCD01658890
Formula : C7H6N2S Boiling Point : -
Linear Structure Formula :- InChI Key :LPUJHVNRGNTQPL-UHFFFAOYSA-N
M.W : 150.20 Pubchem ID :198293
Synonyms :

Calculated chemistry of [ 53473-85-1 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.02
TPSA : 67.15 Ų

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) : -6.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.37
Log Po/w (XLOGP3) : 1.64
Log Po/w (WLOGP) : 1.89
Log Po/w (MLOGP) : 0.58
Log Po/w (SILICOS-IT) : 2.47
Consensus Log Po/w : 1.59

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.47
Solubility : 0.508 mg/ml ; 0.00338 mol/l
Class : Soluble
Log S (Ali) : -2.66
Solubility : 0.326 mg/ml ; 0.00217 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.59
Solubility : 0.384 mg/ml ; 0.00256 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.9

Safety of [ 53473-85-1 ]

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

Application In Synthesis of [ 53473-85-1 ]

* 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 [ 53473-85-1 ]
  • Downstream synthetic route of [ 53473-85-1 ]

[ 53473-85-1 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 60768-66-3 ]
  • [ 53473-85-1 ]
YieldReaction ConditionsOperation in experiment
85% With water; iron; acetic acid In ethyl acetate at 65℃; for 1 h; 5-Nitrobenzo[d]isothiazole (305 mg, 1.69 mmol), 5percent AcOH (aq.) (12 ml.) and EtOAc (12 ml.) at 65 °C was treated with iron powder (325 mesh, 473 mg) and stirred rapidly for 1 h. The mixture was cooled to ambient temperature, diluted with water and EtOAc and filtered through dicalite. The organic layer was separated and the aqueous layer extracted with further EtOAc. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound as a yellow solid (220 mg, 85 percent). Data for 5-aminobenzo[d]isothiazole : MS (ESI) m/z: 151 ([M+H]+).
85% With iron; acetic acid In water; ethyl acetate at 65℃; for 1 h; 5-Nitrobenzo[d]isothiazole (305 mg, 1.69 mmol), 5percent AcOH (aq.) (12 mL) and EtOAc (12 mL) at 65 C. was treated with iron powder (325 mesh, 473 mg) and stirred rapidly for 1 h. The mixture was cooled to ambient temperature, diluted with water and EtOAc and filtered through dicalite. The organic layer was separated and the aqueous layer extracted with further EtOAc. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound as a yellow solid (220 mg, 85percent).Data for 5-aminobenzo[d]isothiazole: MS (ESI) m/z: 151 ([M+H]+).
61.7% With iron In ethanolAcidic conditions; Reflux To a solution of crude Example 1 lb in EtOH (20 mL) was added with iron powder (986 mg, 17.6 mmol, 3.2 eq.) and HC1 (1 mL) in one batch, heated to reflux. TLC indicated the fully consumption of Example 1 lb. The mixture then firstly filtrated; the residue was extracted with EtOAc (50 mL * 2). The combined organic phase was washed with brine, dried over Na2S04, filtrated and concentrated under reduced pressure to give the crude product which was further purified by silica gel chromatography to give the pure product (Example 11c, 1.85 g, yield 61.7percent) as a yellow solid. LCMS [M+H]+=151.1
Reference: [1] Patent: WO2007/39563, 2007, A1, . Location in patent: Page/Page column 17
[2] Patent: US2007/112019, 2007, A1, . Location in patent: Page/Page column 9/1
[3] Patent: WO2017/218960, 2017, A1, . Location in patent: Paragraph 00425
  • 2
  • [ 27996-87-8 ]
  • [ 53473-85-1 ]
Reference: [1] Patent: WO2017/218960, 2017, A1,
  • 3
  • [ 66882-70-0 ]
  • [ 53473-85-1 ]
Reference: [1] Journal of the Chemical Society, 1959, p. 3061,3065
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