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CAS No. : | 4282-31-9 | MDL No. : | MFCD00016896 |
Formula : | C6H4O4S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 172.16 g/mol | Pubchem ID : | 20273 |
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) : | -6.41 cm/s |
Log Po/w (iLOGP) : | 0.66 |
Log Po/w (XLOGP3) : | 1.32 |
Log Po/w (WLOGP) : | 1.14 |
Log Po/w (MLOGP) : | 0.16 |
Log Po/w (SILICOS-IT) : | 1.31 |
Consensus Log Po/w : | 0.92 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.94 |
Solubility : | 1.96 mg/ml ; 0.0114 mol/l |
Class : | Very soluble |
Log S (Ali) : | -3.08 |
Solubility : | 0.143 mg/ml ; 0.000831 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 : | 2.2 |
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 |
---|---|---|
28% | With sodium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; | Thiophene-2,5-dicarboxylic acid (1.72 g, 10 mmol) and sodium carbonate (3.18 g, 30 mmol) suspended in dimethylformamide (25 mL) were stirred with methyl iodide (623 uL) at room temperature overnight. The sodium salt of the desired product was extracted with water, and 12 M hydrochloric acid was added to the combined aqueous layer. The desired product was extracted with ethyl acetate, and the combined organic layer was washed with saturated aqueous ammonium chloride, dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to give 0.49 g of the desired product as a colorless solid (yield 28percent). XH-NMR (ppm in CDC13)d 3.93 (s, 3H), 7.77 (d, J = 4.2 Hz, 1H), 7.83 (d, J = 4.2 Hz, 1H).LC/MS(ESI) 186(M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.9% | With thionyl chloride; at 0 - 20℃; for 3h;Heating / reflux; | 2,5-Thiophenedicarboxylic acid (5 g, 29 mmol), which is compound 22 and commercial, was dissolved in methanol (300 ml) and thionyl chloride (SOC12) was slowly added dropwise thereto at 0C. The reaction vessel was warmed up to room temperature, followed by reflux for 3hours. After confirming the disappearance of the starting material using TLC, methanol was removed under reduced pressure. The residue was dissolved in 200 ml of chloroform and the solution was slowly added to 300ml of chloroform saturated with NH3. The formed white solid was filtered and then recrystallized in methanol to obtain the desirable compound 23 (5.75 g, 99.9%). HNMR (300MHZ, CDC13) 7. 71 (s, 2H), 3.89 (s, 6H). 13C NMR (300MHZ, CDC13) 161.96, 133. 99, 130. 84,51. 96. |
99% | With thionyl chloride;Reflux; | Example 1; Lambda^lJ-Benzodioxol-5-ylmethyl)-3-[5,6-bis(methyloxy)-2-pyridinyll-2,4-dioxo-l,2,3,4- tetrahydrothieno[3,2-</|pyrimidine-6-carboxamide Ia) Dimethyl 2,5-thiophenedicarboxylateTo a stirred solution of thiophene-2,5-dicarboxylic acid (25g, 145 mmol) in 500 mLCH3OH, was added SOCl2 (42.4 mL, 581 mmol ) dropwise over a period of 2h (the reaction generated some heat and the starting.material was gradually dissolved), then the mixture was refluxed in the reflux work station for 19h. The reaction was monitored by TLC and LC-MS. After the reaction was completed (19h), the reaction mixture was concentrated. The crude diester product was obtained as white powder (28.7g, 99%). LC-MS showed 100% of purity (rt=0.92min, MH+ = 201). IH NMR confirmed the structure [400 MHz, DMSO-<i6, delta ppm 3.88 (s, 6 H) 7.82 (s, 2 H)]. The crude product was used for next step without further purification. |
99% | With thionyl chloride;Reflux; | Ia) Dimethyl 2,5-thiophenedicarboxylate; To a stirred solution of thiophene-2,5-dicarboxylic acid (25g, 145 mmol) in 500 mL CH3OH, was added SOCl2 (42.4 mL, 581 mmol ) dropwise over a period of 2h (the reaction generated some heat and the s.m. was gradually dissolved), then the mixture was refluxed in the reflux work station for 19h. The reaction was monitored by TLC and LC-MS. After the reaction was completed (19h), the reaction mixture was concentrated. The crude diester product was obtained as white powder (28.7g, 99%). LC-MS showed 100% of purity (rt=0.92min, MH+ = 201). IH NMR confirmed the structure [400 MHz, DMSO-^6, delta ppm 3.88 (s, 6 H) 7.82 (s, 2 H)]. The crude product was used for next step without further purification. |
96.6% | sulfuric acid; for 48h;Heating / reflux; | Dimethyl thiophene-2,5-dicarboxylate To a stirred suspension of thiophene- 2,5-dicarboxylic acid (6.886g, 40mmol) in 40 ml_ of dry methanol was added 1 mL of sulfuric acid, and the reaction was refluxed for 48 hours. After cooled to room temperature, the reaction mixture was put in refrigerator overnight. The solid was collected by suction filtration, washed with methanol, and dried under vacuum. 7.737g (96.6 %) of product was obtained as a white solid, mp 146.0 - 148.0 C [lit. EPO <DP n="25"/>mp: 148-149 0C (Nippon Kagaku Kaishi 1987, (7), 1424-9), 142-146 0C (Khimiya Geterotsiklicheskikh Soedinenii 1986, (6), 826-36)]. |
91% | sulfuric acid; In 1,2-dichloro-ethane; for 40h;Heating / reflux; | (1). 3,5-Thiophenedicarboxylic acid (21.2 g, 123 mmol) was dissolved in methanol (70 mL, anhydrous) and dichloroethane (70 mL, anhydrous). c.H2SO4 (10.6 mL) was added and the reaction mixture was heated at reflux for 40 h. Solvent was removed in vacuo and the solid was suspended in EtOAc, washed with saturated NaHCO3 (2×200 nL) and brine and dried over MgSO4. Solvent was removed in vacuo to yield 1 as a white powder (22.4 g, 91%). |
88% | In thionyl chloride; for 18h;Reflux; Inert atmosphere; | To a solution of 2,5-Thiophenedicarboxylic acid (2.50 g, 14.5 mmol) in dry MeOH (50 mL) was added thionyl chloride (4.43 mL, 61.0 mmol) over 10 min and the resulting solution heated at reflux for 18 h under a nitrogen atmosphere. The solution was cooled and the resulting precipitate was filtered, washed with MeOH (3x 10 mL) and air dried to afford dimethyl thiophene-2,5-dicarboxylate as an off-white solid (2.52 g, 88%). Experimental data as per literature. ADDIN EN.CITE Khusnutdinov2008802808017Khusnutdinov, R. I.Shchadneva, N. A.Baiguzina, A. R.Mukminov, R. R. Mayakova, Yu. Yu.Smirnov, A. A.Dzhemilev, U. M. Synthesis of 2-thiophenecarboxylic and 2,5-thiophenedicarboxylic acid esters via the reaction of thiophenes with the CCl4-ROH reagent in the presence of vanadium, iron, and molybdenum catalystsPetroleum ChemistryPetroleum ChemistryPet. Chem.471-47848620082 1H NMR (500 MHz, CDCl3) delta3.93 (s, 6H), 7.74 (s, 2H). 13C NMR (125 MHz, CDCl3) delta 55.2, 135.7, 141.5, 164.7. |
86% | sulfuric acid;Heating / reflux; | A mixture of concentrated sulfuric acid (150 [P. L)] and of 2, 5-thiophenedicarboxylic acid (1.0 g, 5.81 mmol) in of methanol (15 [MI)] were heated to reflux under nitrogen over night. The reaction mixture was cooled to room temperature and a white crystalline solid was filtered and [DRIED (MGS04)] to give [THIOPHENE-2, 5-DICARBOXYLIC] acid dimethyl ester [(0.] 995 g, 4.97 mmol, 86% [YIELD).'H] NMR [(CD30D) 8H] 7.73 (s, 2H), 3.87 (s, [6H).] |
81.7% | sulfuric acid;Heating / reflux; | <strong>[4282-31-9]Thiophene-2,5-dicarboxylic acid</strong> (4 g, 23.3 mmol) was dissolved in methanol (300ml). Catalytic amount of sulfuric acid was slowly added therein. The reaction mixture was refluxed to give 3.8 g (yield: 81. 7%, white solid) of thiophene-2,5-dicarboxylic acid dimethylester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; In tetrahydrofuran; for 4h;Inert atmosphere; Reflux; | The solution of thiophene-2,5-dicarboxylic acid (1.0g, 6.0mmol) and 2.0mL of thionyl chloride (0.016mol) was gently refluxed in dry THF for 4h under nitrogen atmosphere. The excess of thionyl chloride was removed under reduced vacuum. The compound prepared was then used directly for the following step. The solution of 4-(octyloxy)benzohydrazide (3.2g, 0.012mol) dissolved in 60mL of THF was dropwise added 0.14mL of triethylamine (1.0mmol) at ice bath. The solution was stirred at rt for 24h. The solution was extracted twice with 100mL of CH2Cl2/H2O. The organic layers were combined and concentrated to give white solids. The products, isolated as white solids were obtained after recrystallization from THF/MeOH. Yield 83%, 1H NMR (300MHz, CDCl3): delta 0.86 (t, 6H, -CH3, J=6.3Hz), 1.27-1.42 (m, 20H, -CH2), 1.70-1.75 (m, 4H, -CH2), 4.04 (t, 4H, -OCH2, J=6Hz), 7.04 (d, 4H, Ar-H, J=8.4Hz), 7.87 (d, 4H, Ar-H, J=9Hz), 7.90 (s, 2H, thiophene-H), 10.4 (s, 2H, N-H), 10.7 (s, 2H, N-H). 13C NMR (75MHz, CDCl3): delta 13.99, 22.11, 25.49, 28.58, 28.68, 28.74, 31.26, 67.77, 106.52, 114.23, 124.26, 129.41, 141.34, 160.33, 161.63, 165.41. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With sodium carbonate; In DMF (N,N-dimethyl-formamide); at 20℃; | Thiophene-2,5-dicarboxylic acid (1.72 g, 10 mmol) and sodium carbonate (3.18 g, 30 mmol) suspended in dimethylformamide (25 mL) were stirred with methyl iodide (623 uL) at room temperature overnight. The sodium salt of the desired product was extracted with water, and 12 M hydrochloric acid was added to the combined aqueous layer. The desired product was extracted with ethyl acetate, and the combined organic layer was washed with saturated aqueous ammonium chloride, dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to give 0.49 g of the desired product as a colorless solid (yield 28%). XH-NMR (ppm in CDC13)d 3.93 (s, 3H), 7.77 (d, J = 4.2 Hz, 1H), 7.83 (d, J = 4.2 Hz, 1H).LC/MS(ESI) 186(M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5.5% | A solution of amino compound (XV) (5.8 mmoles) and 2,5- thiophenedicarboxylic acid (5.8 mmoles) in PPA (10 ml) was stirred under N2 atmosphere at 150 C for 2h. Cooled the reaction mass to RT, poured into cold water, neutralized with ammonia solution to pH~ 10-1 1, then extracted with ethyl acetate, washed with brine followed by water, dried the organic layer over anhydrous Na2SO4 and distilled to give the crude product, which was then purified by using silica gel 60-120 mesh column chromatography and DCM: methanol 100-5 % as mobile phase to get the pure compound (XX). Table 11: preparation of thiophene benzimidazole dimer (XX). | |
With boric acid; In 1-methyl-pyrrolidin-2-one; toluene; at 20 - 185℃; for 13h; | 200 g of N-methylpyrrolidone are charged to a reaction vessel and 52 g of 98% thiophene-2,5-dicarboxylic acid, followed by 72 g of 99% 2-aminophenol, 10 g of boric acid and 30 g of toluene are added with stirring. The apparatus, equipped with a Dean and Stark water trap, is evacuated and the vacuum released with nitrogen. The light yellow suspension is heated to 185[deg.] C. and stirred at this temperature for 12 hours, during which time 23-25 ml of water and approximately 25 g of toluene are distilled off through the water trap. The reaction mixture is cooled to 20[deg.] C. and stirring continued for 1 hour at this temperature. The yellow suspension is filtered, washed with 100 g of N-methylpyrrolidone to give 300 g of a brown solution which may be used as solvent for a further charge and then with three 80 g portions of water. The resulting press-cake is dried under a vacuum of 50 mbar at 100[deg.] C. to yield 75 g of the compound of formula (104) as a yellow solid, characterized by a UV absorption maximum [lambda]max at 372 nm with an extinction coefficient [epsilon] of 52000 and by the following <1>H-NMR data in D6-DMSO: [0045] 8.10, 2H, s; 7.82, 4H, m and 7.50, 4H, m. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetone; at 20℃; for 21h; | Preparation 2; Isopropyl 5-chloromethylthiophene-2-carboxylate Step 1. Preparation of the bis-isopropyl ester DBU (31.3 mL, 209 mmol) and 2-iodopropane (20.9 mL, 209 mmol) were added to a solution of thiophene-2,5-dicarboxylic acid (6.0 g, 34.9 mmol) in acetone (60 mL) at rt under nitrogen. After 21 h at rt, the reaction was quenched with saturated aqueous NaHCO3 (300 mL) and extracted with EtOAc (3 x 150 mL). The combined extracts were washed with brine (200 mL), dried (Na2SO4), filtered and concentrated in vacuo to afford 7.59g (85%) of the diester. |
85% | With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetone; at 20℃; for 21h; | Preparation 2; Isopropyl 5-chloromethylthiophene-2-carboxylateStep 1. Preparation of the Bis-Isopropyl EsterDBU (31.3 mL, 209 mmol) and 2-iodopropane (20.9 mL, 209 mmol) were added to a solution of thiophene-2,5-dicarboxylic acid (6.0 g, 34.9 mmol) in acetone (60 mL) at rt under nitrogen. After 21 h at rt, the reaction was quenched with saturated aqueous NaHCO3 (300 mL) and extracted with EtOAc (3×150 mL). The combined extracts were washed with brine (200 mL), dried (Na2SO4), filtered and concentrated in vacuo to afford 7.59 g (85%) of the diester. |
85% | With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetone; at 20℃; for 21h;Inert atmosphere; | DBU (31.3 mL, 209 mmol) and 2-iodopropane (20.9 mL, 209 mmol) were added to a solution of thiophene-2,5-dicarboxylic acid (6.0 g, 34.9 mmol) in acetone (60 mL) at rt under nitrogen. After 21 h at rt, the reaction was quenched with saturated aqueous NaHCO3 (300 mL) and extracted with EtOAc (3*150 mL). The combined extracts were washed with brine (200 mL), dried (Na2SO4), filtered and concentrated in vacuo to afford 7.59 g (85%) of the diester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In N,N-dimethyl acetamide; at 90℃; for 116.667h;Heating; | A mixture comprising Zn(NO3)2·6H2O (0.149g, 0.50mmol) and H2tdc (0.086g, 0.50mmol) in a mixed solvent of 8mL DMA (or NMP) and 2mL pyridine was heated at 90C for 7000min. Colorless crystals were obtained (0.118g, 75%). IR (cm-1): 3440, 1607 (s), 1573, 1528, 1384 (vs), 1218 (w), 770, 501(w). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With diphenylphosphoranyl azide; triethylamine; for 24h;Reflux; | Add 5.16 g (30 mmol) of thiophene-2,5-dicarboxylic acid to the reaction flask.8.25 g (30 mmol) of diphenylphosphoryl azide, 6.06 g (60 mmol) of triethylamine and 140 mL of tert-butanol,The reaction was heated to reflux for 24 hours, the reaction mixture was allowed to cool to room temperature, and the excess tert-butanol was removed by rotary evaporation.Crude 5-(N-tert-butoxycarbonyl)-aminothiophene-2-carboxylic acid (Compound 2) was obtained,A suitable amount of ethyl acetate was added thereto to dissolve, and successively washed with 5% sodium bicarbonate (10 mL×3), 5% citric acid (10 mL×3), saturated sodium chloride solution (10 mL×3), and dried over anhydrous sodium sulfate. . Filter, wash, remove solvent,Purification by column chromatography (ethyl acetate:petroleum ether=1:1, v/v) gave 5.90 g of a white solid, yield 81% |
With diphenyl phosphoryl azide; triethylamine; for 5h;Heating / reflux; | EXAMPLE 52A solution of thiophene-2,5-dicarboxylic acid (2.73 g, 15.84 mmol), diphenylphosphoryl azide (3.41 mL g, 15.84 mmol) and triethylamine (4.4 mL, 31.68 mmol) in tert-butanol (80 mL) was heated at refluxing 5h. The reaction mixture was cooled to room temperature and then concentrated to afford the crude title compound. HPLC-MS tR =1.52 Min (UV 254nm)- Mass calculated for M+ 243.0, observed LC/MS m/z 244.1 (M+H). | |
With diphenylphosphoranyl azide; triethylamine; at 82℃; for 5h; | a) 5-Carbokappay-2-t°/t-butoxycarbonylaminothiophene; 1.45 mL (10.4 mmol) of TEA, and 1.11 ml_ (5.2 mmol) of diphenylphosphory. azide were added to a solution of thiophene-2,5-dicarboxylic acid (895 mg, 5.2 mmol) in terf-butanoi (30 mL). The reaction mixture was stirred at 82 0C for 5 h. The solvent was then evaporated to dryness. The desired compound was obtained and used in next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | A solution of glycine benzimidazole dihydrochloride (5.0 g, 22.7 mmol) and 2,5-thiophenedicarboxylic acid (1.95 g, 11.4 mmol) in 20 ml pyridine was stirred for 5 min till a white precipitate was obtained. Then, triphenyl phosphite (TPP) (6.38 ml, 22.7 mmol) was added to the reaction mixture at a temperature of 50 C and the temperature was slowly raised to 80-85 C. Within half an hour, the precipitate redissolved and the clear solution was stirred for 30 h. The resulting orange brown solution was allowed to cool and washed with saturated NaHCO3 solution in a separating funnel, till no effervescence could be seen. Then, it was washed with water 2-3 times. Upon further washing with acetone, a white solid precipitated. This was dried and washed with boiling methanol. This recrystallized white product was filtered, washed with cold water, dried in air and was analyzed for the composition C22H18N6O2S·2H2O. Yield: 72%, M.P.:284-285 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sulfuric acid;Reflux; | In ethanol (10 mL), 2,5-thiophenedicarboxylic acid (861 mg, 5 mmol) was suspended, and concentrated sulfuric acid (1.6 mL, 30 mmol) was added to the suspension. The mixture was heated under reflux overnight. After the completion of the reaction was confirmed by HPLC, the reaction mixture was allowed to cool down to a room temperature, and ethanol was distilled off under a reduced pressure. Then, water and ethyl acetate were added to the residue, and the extraction with ethyl acetate was performed 3 times. The organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate, and solvent was distilled off. Thus the title compound (1.14 g, 100%) was obtained as a crystal. 1H-NMR (CDCl3, delta): 1.39 (6H,t,J=7.3 Hz), 4.38 (4H,q,J=7.3 Hz), 7.73 (2H,s) |
67% | With graphene oxide; at 100℃; for 24h; | General procedure: A mixture of acid (0.2 mmol), alcohol (0.6 mmol) and GO (50 wt%, calculated with the mass of acid) in ethyl alcohol or DCE (1 mL) was placed in a test tube equipped with a magnetic stirring bar. The mixture was stirred at 100 C for 24 h. After the reaction was finished, filtered the GO, solvent was removed, and the residue was separated by column chromatography to give the pure sample. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In ethanol; water; at 100℃; for 83.3333h;Heating; | General procedure: A mixture comprising a Mn(NO3)2 50% aqueous solution (0.30g, 1.7mmol) and H2tdc (0.086g, 0.50mmol) in a mixed solvent of 8mL DMA and 2mL ethanol was heated at 100C for 5000min. Pale yellow crystals were obtained (0.128g, 82%). Elemental analysis, Anal. (Calc.) for C10H11MnNO5S: C, 38.39 (38.47); H, 3.58 (3.55); N, 4.51 (4.49)%. IR (cm-1): 3371, 1624, 1551 (vs), 1508 (s), 1452 (w), 1372 (vs), 1126 (w), 1044, 779 (s), 681 (w), 540 (w), 496 (w). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In ethanol; water; at 100℃; for 83.3333h;Heating; | Same procedure for 2 was applied with NMP in place of DMA. Pale yellow crystals were obtained (0.134g, 83%). Elemental analysis, Anal. (Calc.) for C11H11MnNO5S: C, 40.66 (40.75); H, 3.44 (3.42); N, 4.33 (4.32)%. IR (cm-1): 3429, 1618 (s), 1583 (s), 1527 (s), 1383 (s), 1367 (vs), 1312, 1050 (w), 772 (s), 676 (w), 476(w). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In ethanol; water; at 100℃; for 83.3333h;Heating; | Same procedure for 2 was applied with DMSO in place of ethanol. Pale yellow crystals were obtained (0.099g, 65%). Elemental analysis, Anal. (Calc.) for C8H8MnO5S2: C, 31.63 (31.69); H, 2.65 (2.66)%. IR (cm-1): 3446, 1575 (s), 1528 (s), 1373 (vs), 1315, 996, 940, 793, 772 (w), 677 (w), 475. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | In N,N-dimethyl acetamide; at 20℃; for 730.5h; | A mixture comprising Cu(NO3)2·2H2O (0.121g, 0.50mmol) and H2tdc (0.086g, 0.50mmol) in a mixed solvent of 8mL DMA (or NMP) and 2mL aqueous ammonia was left to stand at room temperature for 1month. Blue crystals were obtained (0.073g, 55%). Elemental analysis, Anal. (Calc.) for C8H6CuN2O4S: C, 33.16 (33.03); H, 2.09 (2.10); N, 9.67 (9.71)%. IR (cm-1): 3355, 2989 (w), 1634, 1586 (s), 1552, 1523, 1384 (s), 1361 (vs), 823 (w), 767, 476 (w). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With sodium hydroxide; In water; at 160℃; for 96h;High pressure; | General procedure: A mixture of Zn(NO3)2·6H2O (0.297 g, 1 mmol),H2bpdc (0.242 g, 1mmol), bip (0.211 g, 1mmol), NaOH (0.08 g, 2mmol), and deionizedwater (18 mL) was sealed in a 25mL Teflon-lined stainless steel vessel and heated at 160 C for 96 h. After cooling to room temperature, colorless block crystals were obtained andwashed with alcohol several times (Yield: 32% based on Zn). Elemental Anal. Calcd (%)for C25H21ZnN5O6: C, 54.31; H, 3.83; N, 12.67. Found: C, 54.34; H, 3.81; N, 12.68. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With sodium hydroxide; at 130℃; for 72h; | A mixture of Cd(NO3)2·4H2O (61.7mg, 0.2mmol), H2TDC (34.4mg, 0.2mmol) and bix (27.6mg, 0.2mmol) was dissolved in 50ml distilled water. The solution pH value was adjusted to 8.0 with 0.5M NaOH solution. The resulting mixture was sealed in a 100ml Teflon-lined stainless steel vessel and heated at 130C for 3days in an oven and then slowly cooled to room temperature. Colorless blockshaped crystals were obtained in 72% yield (based on Cd). Elemental Anal. (%): calcd. for [Cd(bix)(TDC)]n: C 44.58, H 3.37, N 10.40; found: C 44.47, H 3.45, N 10.32. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29.8% | With sodium hydroxide; In water; N,N-dimethyl-formamide; at 160℃; for 72h;Autoclave; | A mixtureof CoSO4 7H2O (0.20mmol,0.056g),HL(0.10mmol,0.034g), H2tdc (0.20mmol,0.021g) and NaOH (0.50mmol,0.02g) in H2O (14ml) and DMF ( 2 drops )was sealed in a 25ml Teflon-lined stainlesssteel container,which was heated to 160 1C for 72h and then cooled down to room temperature at a rate of 5 C h. Purple crystals of 4 were collected and washed with distilled water and dried in air to give the product: 29.8% yield (based on HL). Anal.Calc.for C44H32Co2N4O12S (%):C,55.11;H,3.34;N,5.85. Found C,55.12;H,3.36;N,5.81.IR (KBr pellet,cm1): 3432,2976,1630,1595,1556,1466,1371,1167,1090,1061,900,808,786,and719. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | General procedure: A solution of NHMe(OMe) (0.360 g, 6.0 mmol) and benzoic acid (0.244 g, 2.0 mmol) was stirred in dry toluene (10 mL) at 0 C for 10 min. A solution of PCl3 (0.137 g, 1.0 mmol) in dry toluene (2 mL) was then added dropwise to the mixture. The mixture was warmed to r.t. slowly and then stirred at 60 C for 0.5 h. When the reaction was complete (TLC monitoring), the mixture was cooled to r.t. The mixture was then quenched with sat. NaHCO3 soln (20 mL) and extracted with EtOAc (3 × 10 mL). The combined organic layers were dried (anhyd MgSO4). The solvent was removed in vacuo.The product was purified by column chromatography (silica gel, petroleum ether-EtOAc, 3:2) to give pure 3a as a colorless oil; yield: 320 mg (97%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With sodium hydroxide; In water; at 120℃; for 2h;Sealed tube; High pressure; | Cu(NO3)2·2.5H2O (86 mg, 0.47 mmol), 2,5-thiophenedicarboxylic acid (64 mg, 0.37 mmol) and 4-ppbp (156 mg, 0.37 mmol) and 0.5 mL of a 1.0 M NaOH solution were placed into 10 mL distilled H2O in a Teflon-lined acid digestion bomb. The bomb was sealed and heated in an oven at 120 C for 2d, and then cooled slowly to 25 C. Blue crystals of 1 (165 mg, 50% yield based on Cu) were isolated after washing with distilled water and acetone, and drying in air. Anal. Calc. for C31H36CuN4O9S 1: C, 52.87; H, 5.15; N, 7.96. Found: C, 53.67; H, 6.07; N, 8.05%. IR (cm-1): 2927(w), 2850(w), 1663(m), 1631(m), 1565(w), 1527(w), 1475(w), 1415(w), 1379(w), 1349(w), 1264(m), 1230(w), 1114(w), 1097(w), 1067(w), 1038(w), 1018(w), 925(w), 853(w), 810(w), 754(s), 707(w), 696(w). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With sodium hydroxide; In water; at 120℃; for 2h;Sealed tube; High pressure; | Co(NO3)26H2O (108 mg, 0.37 mmol), 2,5-thiophenedicarboxylicacid (64 mg, 0.37 mmol) and 4-ppbp (156 mg, 0.37 mmol)and 1.5 mL of a 1.0 M NaOH solution were placed into 10 mL distilledH2O in a Teflon-lined acid digestion bomb. The bomb wassealed and heated in an oven at 120 C for 2d, and then cooledslowly to 25 C. Purple crystals of 2 (50 mg, 20% yield based onCo) were isolated after washing with distilled water and acetone,and drying in air. Anal. Calc. for C62H70Co2N8O14S2 2: C, 55.85; H,5.29; N, 8.40. Found: C, 57.19; H, 6.21; N, 8.51%. IR (cm1): 3383(w), 3001(w), 2918(w), 2857(w), 1698(w), 1626(s), 1613(s), 1602(m), 1551(w), 1527(m), 1499(w), 1462(w), 1439(m), 1413(m),1403(m), 1354(s), 1315(m), 1282(m), 1255(w), 1221(w), 1142(w), 1119(w), 1092(w), 1046(w), 1065(w), 1019(w), 999(w), 965(w), 941(w), 881(w), 842(m), 821(w), 765(s), 732(w), 707(w),684(w). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With sodium hydroxide; In water; at 120℃; for 2h;Sealed tube; High pressure; | Ni(NO3)26H2O (108 mg, 0.37 mmol), 2,5-thiophenedicarboxylicacid (64 mg, 0.37 mmol) and 4-ppbp (156 mg, 0.37 mmol) and1.0 mL of a 1.0 M NaOH solution were placed into 10 mL distilledH2O in a Teflon-lined acid digestion bomb. The bomb was sealedand heated in an oven at 120 C for 2d, and then cooled slowly to25 C. Green-blue crystals of 3 (135 mg, 34% yield based on4-ppbp) were isolated after washing with distilled water and acetone,and drying in air. Anal. Calc. for C56H68N8NiO9S 3: C, 61.82; H,6.30; N, 10.30. Found: C, 59.44; H, 6.02; N, 9.64%. IR (cm1): 3409(w), 2927(w), 2854(w), 1635(m), 1612(m), 1553(w), 1523(w),1501(w), 1440(m), 1413(w), 1357(s), 1282(m), 1246(w), 1224(w), 1162(w), 1146(w), 1119(w), 1063(w), 1017(w), 968(w), 943(w), 899(w), 843(s), 807(w), 774(s), 739(w), 704(m), 675(w). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Ca. 28% | General procedure: A mixture of CuCl2*2H2O (0.034 g, 0.2 mmol), 2,5-H2tdc(0.026 g, 0.15 mmol), L (0.030 g, 0.1 mmol), and H2O (12 mL) was stirred 30 min at room temperature, after which the pH was adjusted to 4.8 with 0.1 mol L-1 NaOH. Then the mixture was placed in a 25-mL of Teflon-lined stainless steel vessel, heated to 120C and maintained at this temperature for 4 days, then cooled to room temperature. Blue block crystals 3 were picked out by hand from the mixture of many blue crystals and a few small purple crystals with ~46% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Ca. 46% | A mixture of CuCl2*2H2O (0.034 g, 0.2 mmol), 2,5-H2tdc(0.026 g, 0.15 mmol), L (0.030 g, 0.1 mmol), and H2O (12 mL) was stirred 30 min at room temperature, after which the pH was adjusted to 4.8 with 0.1 mol L-1 NaOH. Then the mixture was placed in a 25-mL of Teflon-lined stainless steel vessel, heated to 120C and maintained at this temperature for 4 days, then cooled to room temperature. Blue block crystals 3 were picked out by hand from the mixture of many blue crystals and a few small purple crystals with ~46% yield. Anal. calc. for C20H18CuN4O7S (521.98): C 45.98, H 3.45, N 10.73. Found: C 45.96, H 3.48, N 10.78%. upsilonmax (KBr)/cm-1 3267 (w),2365 (w), 1704 (s), 1704 (s), 1610 (s), 1555 (s), 1489 (s), 1408 (s),1333 (s), 1278 (m), 1193 (m), 1164 (s), 930 (m), 809 (w), 747 (w),693 (m), 653 (m), 559 (w). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In water; at 150℃; for 72h;Autoclave; High pressure; | General procedure: To a suspension of thiophene-2,5-dicarboxylic acid (H2TDA)(0.034 g, 0.20 mmol) in 6 mL of N,N0-diethylformamide (DEF), 4 mLof an aqueous solution of Nd(NO3)36H2O (0.088 g, 0.20 mmol) wasadded. After 15 min of stirring, the resulting solution was transferredto a 25 mL Teflon-lined stainless steel vessel. The reactionmixture was heated at 150 C for 72 h under autogenous pressureand then cooled to room temperature in 24 h. Light-purple prismaticcrystals were obtained (yield 72% based on Nd). Anal. Calcd.(%) for C28H30N2O15S3Nd2 (1041.20): C, 33.00; H, 2.97; N, 2.75.Found (%): C, 32.75; H, 2.99; N, 2.55. FT-IR (KBr pellets, cm1):3583(s), 3502(m), 3091(s), 2980(s), 2939(w), 2588(w), 1651(m),1608(w), 1519(w), 1450(w), 1373(s), 1128(s), 1037(s), 945(w),850(s), 775(s), 653(s), 466(s), 351(s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | In water; at 150℃; for 72h;Autoclave; High pressure; | General procedure: This MOF was synthesized by a procedure analogous to that of 1except Y(NO3)36H2O was used instead of Nd(NO3)36H2O and thereaction mixture was heated at 150 C for 72 h in Teflon-linedstainless steel. Colorless prismatic crystals were obtained(yield 63% based on Y). Anal. Calcd. (%) for C56H58N4O56S6Y4(1781.64): C, 30.15; H, 2.62; N, 2.51. Found. (%): C, 30.00; H, 2.78; N,2.78. FT-IR (KBr pellets, cm1): 3647(m), 3666(w), 3089(s), 2980(s),2939(w), 2592(m), 1629(w), 1591(w), 1525(s), 1465(w), 1382(br),1265(m), 1213(m), 1126(m), 1033(m), 947(m), 775(s), 661(m),472(s), 351(s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27.2% | at 160℃; for 72h;High pressure; Autoclave; | General procedure: A mixture of CdCl2·2.5H2O (24.0mg, 0.10mmol), Hcpt (18.3mg, 0.05mmol), H2tpd (12.1mg, 0.05mmol), H2O (10mL) was sealed in a 23-mL Teflon-lined stainless steel Parr acid digestion bomb, heated at 160C for 72h, and then allowed to cool to room temperature for 60h. Brown rod-shaped crystals of 1 were isolated on a filter and washed with deionized water and ethanol, and dried in air. Yield 27.2% (15.8mg, 0.0136mmol, based on CdII). Elem. Anal. (%) Calcd. for Cd2C50H37N6O11.5S: C, 51.65; H, 3.21; N, 7.23. Found: C, 51.11; H, 3.09; N, 7.32. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 160℃; for 72h;High pressure; Autoclave; | General procedure: Compound 2 was synthesized under similar reaction conditions using the same molar ratios of reactants, except that MnCl2·4H2O (21.7mg, 0.10mmol) was used instead of CdCl2·2.5H2O. Red rod-shaped crystals of 2 were isolated on a filter and washed with deionized water and ethanol, and dried in air. Elem. Anal. (%) Calcd. for Mn2C50H35.5N6O10.75S: C, 58.06; H, 3.46; N, 8.13. Found: C, 58.10; H, 3.43; N, 8.22. |
Tags: 4282-31-9 synthesis path| 4282-31-9 SDS| 4282-31-9 COA| 4282-31-9 purity| 4282-31-9 application| 4282-31-9 NMR| 4282-31-9 COA| 4282-31-9 structure
[ 50340-79-9 ]
5-(Methoxycarbonyl)thiophene-2-carboxylic acid
Similarity: 0.89
[ 23806-24-8 ]
3-Methylthiophene-2-carboxylic acid
Similarity: 0.86
[ 1723-27-9 ]
Thieno[3,2-b]thiophene-2-carboxylic acid
Similarity: 0.84
[ 32431-72-4 ]
4-Fluorothiophene-2-carboxylic acid
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[ 89639-74-7 ]
3,4-Dimethylthiophene-2-carboxylic acid
Similarity: 0.82
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