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CAS No. : | 95453-58-0 | MDL No. : | MFCD01568717 |
Formula : | C4H2ClNOS | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PKCBQQXHFIDIIG-UHFFFAOYSA-N |
M.W : | 147.58 | Pubchem ID : | 1479765 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 32.51 |
TPSA : | 58.2 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.99 cm/s |
Log Po/w (iLOGP) : | 1.25 |
Log Po/w (XLOGP3) : | 1.71 |
Log Po/w (WLOGP) : | 1.61 |
Log Po/w (MLOGP) : | -0.29 |
Log Po/w (SILICOS-IT) : | 2.96 |
Consensus Log Po/w : | 1.45 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.23 |
Solubility : | 0.871 mg/ml ; 0.0059 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.55 |
Solubility : | 0.418 mg/ml ; 0.00283 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.84 |
Solubility : | 2.14 mg/ml ; 0.0145 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.35 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H317-H319 | 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 |
---|---|---|
73% | Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h; Stage #2: at -78℃; for 1 h; |
To a stirred solution of 2-chlorothiazole E-1 (80 g) in anhydrous THF (1000 ml.) was added n- BuLi (320 ml_, 0.8 mol) drop wise at -78 °C for one hour. Ethyl formate (74 g) was added dropwise to the solution at -78 °C, and stirred for one additional hour. Saturated NH4CI was added to the reaction mixture and stirred for 30 min, then diluted with ethyl acetate. The aqueous phase was extracted with ethyl acetate. The organic phase was washed and dried, then concentrated to give the crude product, which was purified by re-crystallized with hexane/ethyl acetate to give 2-chlorothiazole-5-carbaldehyde E-2 (72 g yield: 73 percent,); 1 H NMR (400 MHz, CDCI3): δ ppm 9.96 (s., 1 H), 8.21 (s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With n-butyllithium In tetrahydrofuran; hexane; ethyl acetate; N,N-dimethyl-formamide; Petroleum ether | Example 53 Preparation of 2-chlorothiazole-5-carboxaldehyde (Prepared by the Literature Procedure: I. Sawhney and J. R. H. Wilson. J. Chem. Soc. Perkin Trans I, 1990, 329-331) To a solution of 2-chlorothiazole (see Example 51, 500 mg, 4.2 mmol) in distilled tetrahydrofuran (7 mL) at -78° C. was added n-butyllithium (2.5M solution in hexane, 4.5 mmol, 1.78 mL) slowly dropwise. After stirring 10 min at -78° C., N,N-dimethylformamide (5.4 mmol, 0.42 mL) was added and the reaction was warmed slowly to room temperature over 2 h. The reaction mixture was then poured slowly onto 2N hydrochloric acid solution (10 mL), stirred 5 min and then was made basic with 50percent ammonium hydroxide solution. The water layer was extracted with dichloromethane (2*50 mL) and the combined organic layers were washed with brine (25 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was flash chromatographed (silica gel, 20percent ethyl acetate in petroleum ether) to yield 2-chlorothiazole-5-carboxaldehyde (387 mg, 62percent yield) as a yellow solid. |
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