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CAS No. : | 3971-31-1 | MDL No. : | MFCD00134411 |
Formula : | C8H12O4 | Boiling Point : | - |
Linear Structure Formula : | C6H10(COOH)2 | InChI Key : | XBZSBBLNHFMTEB-UHFFFAOYSA-N |
M.W : | 172.18 | Pubchem ID : | 107205 |
Synonyms : |
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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 |
---|---|---|
With sulfuric acid; In methanol; | To a solution of 1,3-cyclohexanedicarboxylic acid (10 g, 58 mmol) in MeOH (50 mL) was added conc. H2SO4 (2 mL). Then the mixture was stirred at room temperature for 4 hrs. The mixture was concentrated under reduced pressure, and then partitioned between ethyl acetate and a saturated aqueous NaHCO3 solution. The organic phase was washed with brine, dried over Na2SO4, and evaporated to give dimethyl 1,3-cyclohexanedicarboxylate as a colorless oil (11.6 g, yield; quant.). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethyl acetate; | REFERENCE EXAMPLE 71 Dimethyl 1,3-cyclohexanedicarboxylate To a diazomethane-ether solution prepared accoding to Arndt's method (Arndt; Org. Synth. Collect Vol. II, 165) from 40.0 g of N-methylnitrosourea were added 11.0 g of 1,3-cyclohexanedicarboxylic acid, and the mixture was stirred at room temperature for 30 minutes. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was dissolved in ethyl acetate and washed with an aqueous sodium bicarbonate solution and an aqueous sodium chloride solution. After the residue was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 8.33 g of the desired compound as a pale yellow oil. NMR spectrum (CDCl3) delta ppm: 1.20-2.40(9.3H,m), 2.62-2.75(0.7H,m), 3.67(6H,m) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sulfuric acid; for 16h;Reflux; | A solution of cyclohexane-1,3-dicarboxylic acid (10.32 g, 60 mmol) in MeOH (130 mL) was added conc. H2504 (2.5 mL) and stirred at reflux for 16 hr. The mixture was concentrated and the residue was adjust pH to 7 with saturated aq. NaHCO3, extracted with of EA (200 mL*3), combined the organic layers and dried over Na2SO4, filtered and concentrated to give the desired compound as a colorless oil (12 g, 100%). ?H NMR (400 MHz, DMSO-d6) oe 3.61 (s, 6H), 2.69- 1.13 (m, 1OH). MS (ESI) m/e [M+1] 201.1 |
95% | With chloro-trimethyl-silane; at 18 - 25℃; for 96h;Inert atmosphere;Product distribution / selectivity; | Step 1 : Cyclohcxanc-l,3-dicarboxyIic acid dimethyl ester1 .3-Cyclohexanedicarboxylic acid (45.0 g, 261.4 mmol) was dissolved in methanol (250 mL). Chlorotrimethylsilane (10.00 mL, 78.79 mmol) was added and the reaction was stirred at room temperature for 4 days. The reaction was checked by LC-MS with the product mass [M+H]+ 201 seen. The mixture was concentrated under reduced pressure. The resulting residue was diluted with dichloromethane (200 mL). The organic layer was then washed with saturated NaHCOa, dried over sodium sulfate, filtered and concentrated under reduced pressure to give a slightly viscous, clear and colorless oil. The oil was redissolved in anhydrous THF and concentrated to yield 49.5 g (95%) of cyclohexane- l ,3-dicarboxylic acid dimethyl ester, which was used in the next step without further purification. |
94% | With sulfuric acid;Reflux; | Step 1: DimetTo a solution of cyclohexane-1,3-dicarboxylic acid (25 g, 0.145 mol) in eOH (250 ml,) was added concentraied H2SO (5 mL) and the reaction solution was retluxed overnight. After cooled to room temperature, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate (500 mL). The resulting solution was washed with Sat, NajCQj (2 300 mL) and brine (100 mL), dried: over MgS(? and concentrated under reduced pressure to give 27.4 g (94%) of the title compound, dimethyl cyclohexane- 1 -dicarboxv'late, as a light yellow oil. ES1-MS m z: 201 (WMi?. |
With sulfuric acid; at 70℃; for 16h; | To a solution of cyclohexane-1, 3-dicarboxylic acid (24.0 g, 139 mmol) in MeOH (300 mL) was added 5 mL con. H2SO4. The reaction mixture was stirred at 70 for 16hours. The mixture was cooled to room temperature, alkalized with 1N NaHCO3to pH7 and extracted with ethyl acetate (500 mL×2) . The combined organic layers were washed with brine (1000 mL×2) , dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (elute by petroleum ether/EtOAc100: 1-20: 1) to give dimethyl cyclohexane-1, 3-dicarboxylate.1H NMR (400MHz, CDCl3-d) delta: 3.67-3.46 (m, 6H), 2.60 (q, J5.8 Hz, 1H) , 2.34-2.09 (m, 1H) , 1.94-1.78 (m, 2H) , 1.75-1.58 (m, 2H) , 1.49-1.43 (m, 1H) , 1.35-1.14 (m, 2H) , 0.85-0.66 (m, 1H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,3-dimethyl-2-imidazolidinone; ammonia; tin(II) oxide; at 210 - 280℃; for 9h; | A four-neck flask equipped with a stirrer, a gas inlet tube, a thermometer, a gas purge line, and a condenser was charged with 15.1 g of 1,3-cyclohexanedicarboxylic acid obtained in the same manner as in Example 2, 17.4 g of <strong>[62638-06-6]dimethyl 1,3-cyclohexanedicarboxylate</strong>, 5.0 g of N,N?-dimethylimidazolidinone (boiling point 226 C.), and 0.40 g of tin (II) oxide, and the mixture was heated to 210 C. while stirring at 250 rpm. [0189] Thereafter, ammonia gas was introduced at a rate of 72 mL/min (1.1 mol equivalent/1,3-cyclohexanedicarboxylic acid +<strong>[62638-06-6]dimethyl 1,3-cyclohexanedicarboxylate</strong>/hr). The temperature inside the reactor was kept at 210 C. for 1 hour, and then thereafter, increased to 280 C.: while the temperature was kept constant, reaction was performed. After 8 hours, the reaction was terminated, and the reaction product was cooled to 90 C. When the reaction was terminated, almost no white solid was observed in the gas purge line and the condenser. [0190] Then, 31.6 g of 1-butanol was added thereto and the mixture was stirred to produce a reaction mixture. The reaction mixture was filtered by hot filtration to remove the catalyst. The filtrate was analyzed by gas chromatography, and it was found that the conversion of 1,3-cyclohexanedicarboxylic acid was 100%, the conversion of dimethyl 1,4-cyclohexanedicarboxylate was 99%, the yield of 1,3-dicyanocyclohexane was 86%, and the trans isomer/cis isomer ratio was 47/53. [0191] Then, the solvent was distilled off from the filtrate obtained as described above and the filtrate was dried, thereby producing a yellow solid. The yellow solid was analyzed by gas chromatography, and it was found that solid was 1,3-dicyanocyclohexane having a purity of 96.1%. [0192] A metal (tin) content of the solid was 10 ppm or less, which was 9.61 (10×0.961) ppm or less relative to 1,3-dicyanocyclohexane (including trans isomer and cis isomer). |
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