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CAS No. : | 4282-29-5 | MDL No. : | MFCD00067079 |
Formula : | C6H4O4S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZWWLLYJRPKYTDF-UHFFFAOYSA-N |
M.W : | 172.16 | Pubchem ID : | 255853 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 38.24 |
TPSA : | 102.84 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.88 cm/s |
Log Po/w (iLOGP) : | 0.42 |
Log Po/w (XLOGP3) : | 0.66 |
Log Po/w (WLOGP) : | 1.14 |
Log Po/w (MLOGP) : | 0.16 |
Log Po/w (SILICOS-IT) : | 1.31 |
Consensus Log Po/w : | 0.74 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.53 |
Solubility : | 5.11 mg/ml ; 0.0297 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.4 |
Solubility : | 0.692 mg/ml ; 0.00402 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -0.41 |
Solubility : | 67.1 mg/ml ; 0.39 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.15 |
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: |
* 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 |
---|---|---|
88% | Stage #1: With potassium hydroxide In ethylene glycol Stage #2: With hydrogenchloride; water In ethylene glycol |
Thiophene-3,4-dicarbonitrile (13.4 g, 100 mmol) and KOH (56.1 g, 1 mol) were dissolved in ethylene glycol (167 ml), and heated under stirring overnight. The solution was cooled and put into distilled water, and washed with diethyl ether. The aqueous layer was oxidized with saturated hydrochloric acid, and organic materials were extracted with ethyl acetate. The organic layer was dried over MgSO and the4, solvent was evaporated Then, recrystallization was performed in distilled water to obtain thiophene-3,4-dicarboxylic acid (15.2 g, 88percent). |
88% | With potassium hydroxide In water; ethylene glycol | 2) Synthesis of thiophene-3,4-dicarboxylic acid Thiophene-3,4-dicarbonitrile (13.4 g, 100 mmol) and KOH (56.1 g, 1 mol) were dissolved in ethylene glycol (167 ml), and heated under stirring overnight. The solution was cooled and put into distilled water, and washed with diethyl ether. The aqueous layer was oxidized with saturated hydrochloric acid, and organic materials were extracted with ethyl acetate. The organic layer was dried over MgSO4 and the solvent was evaporated Then, recrystallization was performed in distilled water to obtain thiophene-3,4-dicarboxylic acid (15.2 g, 88percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With sodium hydroxide In water at 80℃; | Dimethyl thiophene-3,4-dicarboxylate was in round-bottom flask. To this 1M solution of NaOH was added and the mixture was stirred at 80 oC for overnight. The solution was the acidified with HCl to pH=3 and extracted with ethyl acetate, dried over sodium sulfate and concentrated to obtain the yellow solid compound. Yield 80percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.6% | at 20℃; for 12 h; | 3,4-dicarboxylic acid thiophene (5 g, 29.04 mmol) and 40 mL of glacial acetic acid were sequentially added to a 100 mL single-mouth bottle.Stir at room temperature, add liquid bromine (8.9 mL, 174.24 mol) to a 25 mL constant pressure dropping funnel.Slowly drip into the reaction flask and react for 12 h. After the reaction is over,The reaction solution was poured into 500 mL of a saturated sodium hydrogensulfate solution and stirred until a beige solid precipitated.Filter under reduced pressure and dry to give a beige solid (8.2 g, 85.6percent). |
60% | With bromine In acetic acid at 20℃; for 12 h; | A 500 mL one neck round bottom flask was charged with thiophene-3,4-dicarboxylic acid (29 g, 0.17 mol) and glacial acetic acid (280 mL). Bromine (52 mL, 1.0 mol) was added dropwise to the reaction flask and the mixture was stirred for 12 hours at RT. An aqueous solution of sodium bisulfate was added until the reddish color disappeared. The mixture was basified and filtered. The filtrate was acidified to give a gray solid which was filtered, washed with cold water, and dried to give the product. The crude product was recrystalized twice from water (60percent).Spectral data: 1H NMR (300 MHz, CDC13): 13.6 (br s, 2H).13C NMR (300 MHz, DMSO): δ 162.5, 135.0, 118. |
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