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CAS No. : | 108354-78-5 | MDL No. : | MFCD00130099 |
Formula : | C10H13NO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DKYYKIHEIOOWRB-UHFFFAOYSA-N |
M.W : | 211.28 | Pubchem ID : | 2756552 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 57.43 |
TPSA : | 80.56 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) : | -5.54 cm/s |
Log Po/w (iLOGP) : | 2.33 |
Log Po/w (XLOGP3) : | 2.89 |
Log Po/w (WLOGP) : | 2.0 |
Log Po/w (MLOGP) : | 1.59 |
Log Po/w (SILICOS-IT) : | 3.09 |
Consensus Log Po/w : | 2.38 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.1 |
Solubility : | 0.167 mg/ml ; 0.000789 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.24 |
Solubility : | 0.0121 mg/ml ; 0.0000573 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -2.5 |
Solubility : | 0.668 mg/ml ; 0.00316 mol/l |
Class : | Soluble |
PAINS : | 1.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.83 |
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: |
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* 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 |
---|---|---|
82% | With morpholine; sulfur In ethanol for 3 h; Reflux | Synthesis of compounds 1, 2a-i and 3a-i Compound 1 was prepared through standard Gewald reaction. 14 4.4 g (0.05 mol) of morpholine was added dropwise into a stirred solution of cyclohexanone (4.91 g, 0.05 mol), methyl cyanoacetate (4.95 g, 0.05 mol) and sulfur (1.92 g, 0.06 mol) in 35 mL ethanol. On completion, the mixture was refluxed for further 3 h. After cooling to room temperature, the precipitate was separated by filtration and recrystallized from ethanol to give 1 as pale yellow powders (8.6 g, 82percent yield), mp 128.2-129.4 °C (lit. 15 128-130 °C), MS (GC-MS): m/z, 211 [M+H]+, 179, 151, 125, 91, 77, 65, 53. |
70% | With sulfur; triethylamine In ethanol at 20℃; Inert atmosphere | To EtOH (37.5 mL) in an open flask was added S8 (4.68 g, 150 mmol, 1.0 eq.),cyclohexanone (23.3 mL, 225 mmol, 1.5 eq.), methyl cyanoacetate (13.3. mL, 150 mmol,1.0 eq.), and Et3N (10.4 mL, 75 mmol, 0.5 eq.), and the reaction was stirred at rt overnight.The flask was cooled to 0 °C with no stirring for 5 h followed by collection of theprecipitate by filtration. The solid was washed with ice cold EtOH then dried at rt overnight to yield 6a asan off-white solid (22.1 g, 105 mmol, 70percent) |
20% | Stage #1: With diethylamine In ethanol for 0.166667 h; Reflux Stage #2: With sulfur In ethanol for 3 h; Reflux |
EXAMPLE 11; The reaction scheme for the synthesis of azo dye 11 is shown below. In a Gewald reaction, diethylamine (8 ml) was added to a solution of equimolar quantities of cyclohexanone (9.80 g, 0.10 mol) and methyl cyanoacetate (9.90 g, 0.10 mol) in ethanol, and the mixture was refluxed for 10 minutes. Then sulfur (3.53 g, 0.11 mol) was added, and the solution was refluxed for a further 3 hours. The pale yellow precipitate that formed was filtered and washed with cooled ethanol to give 11a as a pale yellow powder (4.22 g, 20percent yield), m.p. 132-133° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With sulfur; diethylamine In ethanol at 45 - 50℃; for 1 h; | Intermediate 1. To a suspension of sulfur (11.5 g, 359 mmol) and ethyl 2- cyanoacetate (38.7 g, 342 mmol) in 50 mL of ethanol was added cyclohexan-l-one (33.6 g, 342 mmol) drop-wise at room temperature, followed by addition of diethyl amine (DEA) (25.0 g, 342 mmol), making sure the temperature was maintained below 50 °C. The resulting mixture was stirred at 45 °C for 1 h, before being cooled to 0 °C and filtered. The collected material was washed with cold ethanol and dried under vacuum to give Intermediate 1 as yellow solid (57.8 g, yield: 75percent). |