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CAS No. : | 58759-63-0 | MDL No. : | MFCD11111675 |
Formula : | C7H4N2O2S2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NFZDOFMXGCPMCX-UHFFFAOYSA-N |
M.W : | 212.25 | Pubchem ID : | 4995376 |
Synonyms : |
|
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 : | 0.0 |
Molar Refractivity : | 55.69 |
TPSA : | 125.75 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.0 cm/s |
Log Po/w (iLOGP) : | 1.33 |
Log Po/w (XLOGP3) : | 2.25 |
Log Po/w (WLOGP) : | 2.49 |
Log Po/w (MLOGP) : | 0.59 |
Log Po/w (SILICOS-IT) : | 1.23 |
Consensus Log Po/w : | 1.58 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.02 |
Solubility : | 0.203 mg/ml ; 0.000956 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.53 |
Solubility : | 0.00631 mg/ml ; 0.0000297 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -2.47 |
Solubility : | 0.723 mg/ml ; 0.0034 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 3.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.37 |
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With sulfuryl dichloride In dichloromethane at 20℃; for 1 h; Cooling with ice | General procedure: GP3-1: A solution of 2-halo substituted aniline (1.0 eq), potassium ethyl xanthate (1.2 eq or 2.2 eq,typically 2.2 eq) in 10 volume of anhydrous DMF was heated at 100 0Cor 120 0C for 4 hours under nitrogen. TLC monitored the progress ofreaction. After completion, the reaction mixture was cooled to room temperature,diluted with water (10 volume) and neutralized by 1 M HCl solution to pH 5. Theformed precipitate was collected by filtration, rinsed with water, firstlydried by rotavapor, and then dried by oil pump to afford 2-mercaptobenzothiazole.GP3-2: 2-mercaptobenzothiazole in 10 volume ofanhydrous DCM, was added by sulfuryl chloride (SO2Cl2, 1volume) under ice-cooled condition. The mixture was stirred at rt for 1 hour,which was monitored by TLC. After consumption of starting material, the mixturewas diluted by 30 volume of ether, following quenching carefully by addingwater. Stirring was kept for 1 hour to make sure the SO2Cl2was totally consumed and product was released. Organic layer was collected,neutralized by saturated NaHCO3, dried over Na2SO4and purified by silica gel chromatograph to give the pure product, which wasfinally characterized by LC-MS and NMR. |
2.02 g | at 0 - 20℃; for 2 h; | Solid 5-nitrobenzo[d]thiazole-2-thiol (4.0 g, 18.8 mmol) was placed in a round bottom flask and cooled to 0°C while S02CI2(9.1 mL, 1 13 mmol) was slowly added at 0°C. Upon complete additions, the yellow suspension was stirred at 0°C for 5 min, then at rt for 2 h. The mixture was poured onto ice/water (200 mL) and stirred for 1 h. The precipitate that formed was collected, washed with water and dried under high vacuum. The material was slurried in EA (25 mL), vigorously stirred for 15 min and filtered. The filtrate was concentrated and dried. The obtained solid absorbed to silica gel and purified by CC eluting with heptane:EA 4:1 to give the title compound (2.02 g) as a solid; LC-MS: tR= 0.84 min; [M+H]+= 214.51 ;1H NMR (400 MHz, CDCI3) δ: 8.84 (d, J = 2.2 Hz, 1 H), 8.35 (dd, J, = 2.2 Hz, J2= 8.9 Hz, 1 H), 7.98 (d, J = 8.9 Hz, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | at 110℃; | 5-Mtro-2-mercapto benzothiazole (12): A mixture of 2-fluoro-5-nitro aniline (11,1.00 g, 6.40 mmol) and potassium O-ethyl dithiocarbonate (1.53 g, 9.60 mmol) inDMF (15 mL) was heated overnight at 110-110 0C under N2. After cooling, the reaction mixture was diluted with water and acidified with IN HCl. The precipitate was collected by filtration, washed with water, and dried under vacuum to yield compound 12 (1.27 g, 94percent). |
3.99 g | at 100℃; for 5 h; | To a solution of 2-fluoro-5-nitroaniline (3.12 g, 20 mmol) in DMF (15 mL) potassium ethyl xanthogenate (3.93 g, 24 mmol) was added. The mixture was stirred at 100°C for 5 h before it was cooled to rt, diluted with water (25 mL) and 1 M aq. HCI (35 mL). The precipitate that formed was collected, washed with water (15 mL) and dried to give the title compound (or tautomer) (3.99 g) as a beige solid; LC-MS: tR= 0.76 min; [M+H]+= not detectable;1H NMR (400 MHz, D6-DMSO) δ: 14.17 (s, 1 H), 8.15 (dd, J, = 2.2 Hz, J2= 8.8 Hz, 1 H), 7.99 (d, J = 9.0 Hz), 7.97 (d, J = 2.3 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66.3% | at 10℃; for 4 h; Inert atmosphere | 5-nitro-2-fluoroaniline (200 mg, 1.28 mmol)And sodium ethyl xanthate (250 mg, 1.73 mmol)Was dissolved in dry DMF (10 mL)Solution, nitrogen protection to warm up to 100 reaction 4h.After completion of the reaction, the temperature was lowered to room temperature,Slowly add water (10 mL) and 1 M / L hydrochloric acid solution (10 mL)Precipitation of solid, continue stirring 30min,Suction filtration, solid water washing,The filter cake was then dissolved with ethyl acetate,Dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a tan solid product which was used directly in the next step.(180 mg, 66.3percent); |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | at 100℃; for 4 h; Inert atmosphere | General procedure: GP3-1: A solution of 2-halo substituted aniline (1.0 eq), potassium ethyl xanthate (1.2 eq or 2.2 eq,typically 2.2 eq) in 10 volume of anhydrous DMF was heated at 100 0Cor 120 0C for 4 hours under nitrogen. TLC monitored the progress ofreaction. After completion, the reaction mixture was cooled to room temperature,diluted with water (10 volume) and neutralized by 1 M HCl solution to pH 5. Theformed precipitate was collected by filtration, rinsed with water, firstlydried by rotavapor, and then dried by oil pump to afford 2-mercaptobenzothiazole.GP3-2: 2-mercaptobenzothiazole in 10 volume ofanhydrous DCM, was added by sulfuryl chloride (SO2Cl2, 1volume) under ice-cooled condition. The mixture was stirred at rt for 1 hour,which was monitored by TLC. After consumption of starting material, the mixturewas diluted by 30 volume of ether, following quenching carefully by addingwater. Stirring was kept for 1 hour to make sure the SO2Cl2was totally consumed and product was released. Organic layer was collected,neutralized by saturated NaHCO3, dried over Na2SO4and purified by silica gel chromatograph to give the pure product, which wasfinally characterized by LC-MS and NMR. |
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