Structure of 10601-80-6
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CAS No. : | 10601-80-6 |
Formula : | C9H18O4 |
M.W : | 190.24 |
SMILES Code : | C(OC(=O)CC(OCC)OCC)C |
MDL No. : | MFCD00009865 |
InChI Key : | SIALOQYKFQEKOG-UHFFFAOYSA-N |
Pubchem ID : | 66389 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335-H227 |
Precautionary Statements: | P210-P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P370+P378-P362+P364-P403+P233-P501 |
Num. heavy atoms | 13 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.89 |
Num. rotatable bonds | 8 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 48.83 |
TPSA ? Topological Polar Surface Area: Calculated from |
44.76 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.89 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.02 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.34 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.95 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.41 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.52 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.13 |
Solubility | 14.0 mg/ml ; 0.0734 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.55 |
Solubility | 5.37 mg/ml ; 0.0282 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.88 |
Solubility | 2.5 mg/ml ; 0.0131 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.74 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<2.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.41 |
* 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 |
---|---|---|
60% | With tin(II) chloride dihdyrate In ethanol at 20 - 90℃; | Step 1: ethyl 6-bromoquinoline-3-carboxylate To a solution of 5-bromo-2-nitrobenzaldehyde (2 g, 9 mmol) in ethanol (46 mL) was added tin(II) chloride dihydrate (7.95 g, 35.2 mmol) and 3,3-diethoxypropionic acid ethyl ester (4.2 mL, 22 mmol). The reaction was heated to 90° C. for 16 hours. The reaction was then allowed to cool to room temperature and stir overnight. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate. The mixture was poured into saturated aqueous sodium bicarbonate. The resulting emulsion was filtered through Celite, rinsing with ethyl acetate. The layers were separated and the aqueous was extracted with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulfate, filtered, and concentrated. Purification by flash column chromatography (0-50percent ethyl acetate/heptanes) gave the title compound (1.41 g, 60percent) as a solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | at 190 - 200℃; for 2h; | 40 g of powder Zetaeta were washed with dilute hydrochloric acid once, H20 washed 3 times, washed once in methanol, acetone and once with 20 Mm Hg and 100 degrees Celsius for 10 minutes after drying, remove the nitrogen 25 g was added to 100 ml three Zetaeta Round-bottomed flask containing a catalytic amount of iodine was added 6 ml of anhydrous benzene was heated and stirred at reflux, was added over 45 minutes containing 8.35 grams, 0.05 mole of ethyl bromoacetate and 8.89 g XI, 0 06 mol triethylorthoformate XII. After the dropwise addition, the treated again take Zetaeta 6.25 g flour added to the system, after the reaction was refluxed for 6 hours, the reaction solution was transferred to a 100 ml ice-water and 50 g, excess acetic acid was added, the ether layer was separated, with washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under 1.5 mm Hg vacuum distillation, 79-81 ° C was collected as a colorless oil distillate 3, 3-ethoxy-propionate esters XIII2 8 g, yield 29.4percent; collected above to give the 2.8 g 3, 3-ethoxypropionate XIII at 190-200 degrees Celsius was heated under reflux for 2 hours with a delicate smell ., colorless liquid of ethyl acrylate, 3- XIV2 2 g, yield 100percent;. the 2.2 g, 152 mmol of ethyl acrylate, 3- XIV added to 7.5 ml of water and 7.5 ml two six ring oxygen mixed solvent, -10 degrees centigrade to cool large, slowly added 2.97 g after 16.72 mmol of NBS, the reaction 1 hour at room temperature, then 1.15 g, 15.2 mmol) was added thiourea after 1 hour at 80 ° C, ice-cooling, after addition of an excess of ammonia brown solid appeared, suction filtered to give a solid, after washing with water and drying give 1.4 g 2-aminothiazol-5-carboxylate XV of sitting Jie, The yield was 53.8percent |
62.1 g | With potassium hydrogensulfate; at 100℃; for 5h;Inert atmosphere; Green chemistry; | In a three-necked flask, 91 g (0.5 mol) of trichloroacetyl chloride was added, and 54 g (0.75 mol) of vinyl ether was slowly added dropwise, and the mixture was dropped for about 1.5 hours. The temperature was controlled at 30 ° C for 5 hours, and then steamed under 40 ° C. The low-boiling by-product is obtained; after steaming, 66 g (0.65 mol) of triethylamine and 100 g of ethanol are added, and the reaction is kept at 35 ° C for 5 h, filtered, and the cake is recovered. The filtrate is evaporated under reduced pressure at 50 ° C or less; Add 6.8 g (0.05 mol) of potassium hydrogen sulfate, raise the temperature to 100 ° C, pass nitrogen gas, the flow rate of nitrogen is 300 mL / min, keep the reaction for 5 h, the reaction is finished, and distilled under reduced pressure to obtain 62.1 g of ethyl 3-ethoxyacrylate. The rate was 86.1percent, and the purity by gas phase normalization was 98.8percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium hydride; In diethyl ether; at 0 - 20℃; for 15h; | 12.6 g of sodium hydride (purity: 60percent, 525.0 mmoles) was washed with diethyl ether by decantation several times and then made into a solution in 500 ml of diethyl ether. Thereto were added, in a nitrogen current at 0 to 10°C, 194 g (2.6 moles) of ethyl formate and 50 g (262.0 mmoles) of ethyl 3,3-diethoxy-propionate. The resulting mixture was stirred at room temperature for 15 hours to give rise to a reaction. After confirmation of the completion of the reaction, the reaction mixture was poured into water, followed by washing with diethyl ether. The resulting aqueous layer was allowed to have a pH of 1 with hydrochloric acid, followed by extraction with dichloromethane. The resulting organic layer was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein, to obtain 37.6 g (yield: 100percent) of crude (ethoxycarbonyl)malondialdehyde as a dark red oily substance. 1H-NMR [CDCl3/TMS, delta (ppm)]: 9.09 (2H,s), 5.26 (1H,s), 4.27 (2H,q), 1.28 (3H,t) |
100% | With sodium hydride; In diethyl ether; at 0 - 20℃; for 15h; | REFERENCE EXAMPLE 28 Production of (ethoxycarbonyl)malondialdehyde; 12.6 g of sodium hydride (purity: 60percent, 525.0 mmoles) was washed with diethyl ether by decantation several times and then made into a solution in 500 ml of diethyl ether. Thereto were added, in a nitrogen current at 0 to 10° C., 194 g (2.6 moles) of ethyl formate and 50 g (262.0 mmoles) of ethyl 3,3-diethoxy-propionate. The resulting mixture was stirred at room temperature for 15 hours to give rise to a reaction. After confirmation of the completion of the reaction, the reaction mixture was poured into water, followed by washing with diethyl ether. The resulting aqueous layer was allowed to have a pH of 1 with hydrochloric acid, followed by extraction with dichloromethane. The resulting organic layer was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein, to obtain 37.6 g (yield: 100percent) of crude (ethoxycarbonyl)malondialdehyde as a dark red oily substance. 1H-NMR [CDCl3/TMS, delta (ppm)]: 9.09 (2H,s), 5.26 (1H,s), 4.27 (2H,q), 1.28 (3H,t) |
99.7% | With sodium hydride; In tetrahydrofuran; at 0 - 20℃; | [00442] To a stirred suspension of sodium hydride (60percent, 1.68 g, 42.1 mmol) in THF (20 mL) was added ethyl formate (8.5 mL, 105.7 mmol). The solution was cooled to 0 °C and a solution of ethyl 3,3-diethoxypropanoate (4 g, 21.0 mmol) in THF (10 mL) was added dropwise over 30 mins and the reaction mixture stirred at r.t. overnight. 2M aq HCl (30 mL) was added under whilst cooling with ice and the reaction stirred at r.t. for 30 mins. The reaction mixture was extracted with diethyl ether (2 x 50 mL) and the combined organic extracts were dried over MgS04 and concentrated in vacuo to afford the title compound (3.02 g, 99.7percent) as an amber liquid. [00443] 1H NMR (250 MHz, Chloroform-d) delta 9.13 (s, 2H), 4.29 (q, J = 7.1 Hz, 2H), 1.37 - 1.28 (m, 3H). |
74.2% | With sodium hydride; In diethyl ether; hexane; at 20℃; for 15h;Cooling with ice; | Weighed out sodium hydride (2.46 g, 61.5 mmol) in a dry 100-mL pear flask. Washed with hexanes then with diethyl ether. Suspended in ether (100 mL), cooled in ice bath then ethyl formate (24.84 ml, 308 mmol) was added then ethyl 3,3-diethoxypropanoate (5.98 ml, 30.8 mmol). The resulting mixture was stirred at room temperature for 15 hours to give rise to a reaction. After confirmation of the completion of the reaction, the reaction mixture was poured into water, followed by washing with diethyl ether. The resulting aqueous layer was allowed to have a pH of 1 with hydrochloric acid, followed by extraction with dichloromethane. The resulting organic layer was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate, filtered and concentrated to give ethyl 2-formyl-3-oxopropanoate (3.29 g, 22.83 mmol, 74.2 percent yield) as a golden syrup |
70% | EXAMPLE 1Preparation of Ethyl-2-formyl-3-oxopropionate[0059] A three- or four-neck round bottom flask equipped with magnetic stir bar, thermocouple, digital thermometer, gas inlet and outlet and addition funnel was flushed <n="19"/>with argon. Ethyl 3,3-diethoxypropionate (64.5 g) in tetrahydrofuran were charged to the addition funnel. Sodium hydride (21.2 g of a 60percent dispersion) was charged to the reaction flask followed by tetrahydrofuran. The contents of the flask were cooled to 0- 5°C in an ice-bath, and ethyl formate (257 g) was added. The mixture was cooled to 0- 50C and the contents of the addition funnel added drop wise, maintaining an internal temperature of less than 5°C. The ice-bath was removed and the contents allowed to warm to ambient temperature. Consumption of ethyl 3,3-diethoxypropionate was monitored by TLC analysis. The reaction was quenched by addition of ice-water (10.6 vol), and extracted three times with methyl t-butyl ether (5.4 vol each), and the organic layers discarded. The aqueous phase was acidified with cone, hydrochloric acid to a pH of 1 to 1.5. The acidified aqueous layer was extracted three times with dichloromethane and the combined organic layers dried over sodium sulfate. The solvent was removed under reduced pressure, and the residue distilled under vacuum, to provide ethyl 2-formyl-3-oxopropionate, 27.92 g, 70percent yield. | |
70% | With sodium hydride; In tetrahydrofuran; at 0 - 20℃; | [0066] A three- or four-neck round bottom flask equipped with magnetic stir bar, thermocouple, digital thermometer, gas inlet and outlet and addition funnel was flushed with argon. Ethyl 3,3- diethoxypropionate (64.5 g) in tetrahydrofuran were charged to the addition funnel. Sodium hydride (21.2 g of a 60percent dispersion) was charged to the reaction flask followed by tetrahydrofuran. The contents of the flask were cooled to 0-50C in an ice-bath, and ethyl formate (257 g) was added. The mixture was cooled to 0-50C and the contents of the addition funnel added dropwise, maintaining an internal temperature of less than 5°C. The ice-bath was removed and the contents allowed to warm to ambient temperature. Consumption of ethyl 3,3- diethoxypropionate was monitored by TLC analysis. The reaction was quenched by addition of ice-water (10.6 vol), and extracted three times with methyl t-butyl ether (5.4 vol each), and the organic layers discarded. The aqueous phase was acidified with cone, hydrochloric acid to a pH of 1 to 1.5. The acidified aqueous layer was extracted three times with dichloromethane and the combined organic layers dried over sodium sulfate. The solvent was removed under reduced pressure, and the residue distilled under vacuum, to provide ethyl 2-formyl-3 -oxopropionate, 27.92 g, 70percent yield. |
59% | With sodium hydride; In tetrahydrofuran; at 0 - 30℃; for 24h; | 4) In a 500 ml four-necked flask equipped with magnetic stirring, 160 ml of tetrahydrofuran and9.84g NaH, mass fraction of NaH in tetrahydrofuran solution is 60percent, the solution is cooled in an ice bath to 0 °C to 5 °C, and then 119g of ethyl formate is added to slowly increase the temperature, when the temperature stabilizes to 0 °C At 5 °C, 80 ml of a tetrahydrofuran solution containing D was continuously added dropwise into a 500 ml four-necked flask, wherein the mass fraction of D was 5percent. After the dropwise addition, the water bath was removed and heated to room temperature. At this time, a large amount of hydrogen was evolved. It will first rise to 30 °C and then gradually decrease to 25 °C. After 24 hours of reaction, the reaction solution was poured into ice water and quenched. 5) The resulting product is first extracted with 500 ml of tert-butyl methyl ether three times to remove the organic phase, and then with concentrated hydrochloric acid to adjust the pH of the aqueous phase to 1~1.5; then extract the aqueous phase with 300 ml of dichloromethane, twice The combined organic phases were combined; the combined organic phases were then dried over anhydrous sodium sulfate and evaporated to give a brown-red liquid which was evaporated in vacuo. GC yield was 99.3percent. The yield was 85.9percent. Finally, the 9 mm Hg diaphragm was distilled under reduced pressure. The colorless transparent liquid E, ethyl 2-formyl-3-oxopropanoate, was obtained in a yield of 59percent. |
Step 1: 2-Formyl-3-oxo-propionic acid ethyl ester Ethyl 3,3-diethoxypropionate (100 g, 525.7 mmol) was dissolved in THF (360 ml) at room temp. Ethyl formate (175.1 ml, 2.1 mol) was added at room temp. The solution was cooled in an ice-bath to 0° C. and tBuOK (1M solution in THF, 1,156 ml, 1.156 mol) was added via an addition funnel slowly over 30 min, maintaining internal temperature below 5° C. The color changed instantly from colorless to dark orange. The reaction mixture was allowed to warm up to room temp. and stirred for 2 h. The reaction was allowed to stir at room temp. for 18 h. The reaction mixture was concentrated in vacuo and 1 L of solvent was removed. The remaining brownish solution with white solid in it was cooled in an ice-bath and hydrochloric acid (6N, 200 ml) was added to adjust pH=3, maintaining internal temperature below 20° C. The resulting bright yellow suspension was then warmed up to room temp. and stirred for 1 h. Additional 700 ml solvent was removed in vacuo at room temp. Water (400 ml) was added to dissolve all the white solid and ethyl acetate (500 ml) was added and the mixture transferred to a separatory funnel. The aqueous was extracted once with ethyl acetate (200 ml). The combined organic extracts was washed once with brine (100 ml). After drying over MgSO4 and concentrating in vacuo, 2-formyl-3-oxo-propionic acid ethyl ester (75.85 g) was obtained as yellow oil. | ||
With sodium hydride; In tetrahydrofuran; at 0 - 20℃; for 24h; | Sodium hydride (2.00 g, 50.6 mmol, 60percent) was added to a solution of ethyl formate (10.13 g, 168.7 mmol) in tetrahydrofuran while maintaining the internal temperature below 0 °C. Then, ethyl 3,3-diethoxy propionate (5.00 g, 33.75 mmol) was added dropwise to the reaction mixture and stirred for 24 h at ambient temperature. After confirming that the reaction was complete by using TLC analysis, the reaction was quenched with 20 mL water and the tetrahydrofuran was removed under reduced pressure. The mixture was extracted with ethyl acetate and then brine. The organic phase was dried over Na2SO4 overnight and the solvent was removed in vacuo to give the title compound 14. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With tin(II) chloride dihdyrate; In ethanol; at 20 - 90℃; | Step 1: ethyl 6-bromoquinoline-3-carboxylate To a solution of 5-bromo-2-nitrobenzaldehyde (2 g, 9 mmol) in ethanol (46 mL) was added tin(II) chloride dihydrate (7.95 g, 35.2 mmol) and 3,3-diethoxypropionic acid ethyl ester (4.2 mL, 22 mmol). The reaction was heated to 90 C. for 16 hours. The reaction was then allowed to cool to room temperature and stir overnight. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate. The mixture was poured into saturated aqueous sodium bicarbonate. The resulting emulsion was filtered through Celite, rinsing with ethyl acetate. The layers were separated and the aqueous was extracted with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulfate, filtered, and concentrated. Purification by flash column chromatography (0-50% ethyl acetate/heptanes) gave the title compound (1.41 g, 60%) as a solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With [methyl-3-(butyl-4-sulfonate) imidazolium]CuPW12O40; oxygen; at 159.84℃; under 6000.6 Torr; for 5h; | General procedure: In a typical process, 0.25 g lignin, 0.9 mmol POM-IL catalyst and 20 mL 100% ethanol werecharged into a 100 mL stainless autoclave (Andorra MED1220, Premex Co. Ltd.). After airpurging with pure oxygen five times and pressurizing to 0.8 MPa, the reactor was heated to thedesignated temperature and maintained for the desired time. Once the latter elapsed, the autoclavewas cooled rapidly to room temperature in an ice water bath. The reaction mixture was removedand the reactor was washed with anhydrous ethanol (3 5.0 mL). The IL catalyst was precipitatedat room temperature and used for the next run after drying (extra fresh catalyst was added tooffset transfer losses). The liquid mixture was then diluted by ethanol to 50 mL for qualitative andquantitative analysis, while dimethyl phthalate was used as the internal standard. When aqueoussolutions of ethanol were used, the spent mixture was rotary evaporated under reduced pressurefor solvent recovery. The concentrated liquor was esterified with 10 mL anhydrous ethanol at 373K for 2 h and then diluted to 50 mL with ethanol. Volatile products were qualitatively andquantitatively analyzed via gas chromatography-mass spectrometry (GC-MS) and gaschromatography-flame ionization detection (GC-FID). Residual lignin can be obtained throughsimple precipitation processes. Organosolv lignin was recovered as follows: 60 mL deionized water was added into 20 mL of the above reaction mixture causing precipitation. The mixture wasthen separated using centrifugation and was dried until a constant weight was obtained. For therecovery of dealkaline lignin the mixture obtained after reaction was acidified to pH=2 with 1.0mol L-1 HCl solution and the same procedure described for organosolv lignin was conducted.In the atmosphere investigation, a mixture of nitrogen and oxygen with various molar ratioswas used, while depolymerization of lignin was conducted at 433 K for 5.0 h in the single stageexperiments. For a typical two-stage process, the lignin was first depolymerized employing theaforementioned conditions. When the mixture was cooled to room temperature, an extra 0.8 MPanitrogen or oxygen was purged into the reactor and the reaction was heated to 433 K for 1.0 or 2.0h. The product separation and analysis procedure remained unchanged to that describedpreviously. In comparative and control experiments, a series of model compounds (monolignolsand potential intermediate products) were tested under the same procedures as that for lignin (i.e.,0.25 g model compound, 0.9 mmol POM-IL catalyst and 20 mL 100% ethanol solvent). Triplicateexperiments were conducted and the data shown in this study is the average. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With polyphosphoric acid; at 85℃; for 23.0h;Sealed tube; | A mixture of 6-chIoro-3-amino-4,5-dimethylpyridazine (550 mg), ethyl 3,3-dietboxypropiQnate (1.02 mL), and poyphosphoric acid (5 mL) was added to a sealed tube. The mixture was stirred at 85 C for 5 hours then cooled to room temperature where additional ethyl 3,3-diethoxypropionate (1.02 L) was added to the reaction mixture. The vial was sealed and the mixture heated to 85 C for 18 hours. The reaction mixture was then slowly added to a stirred solution of 150 L of saturated aqueous NaHCCb and 100 mL of DCM. After complete addition, the mixture was allowed to stir for 20 minutes, the organic layer was separated, and the aqueous layer was further extracted with chioroform/PA (4:1) (x3). The organic layers were pooled, dried over MgSG4, filtered, and concentrated. The crude product was purified using Teledyne ISCO Combi- Flash system (liquid loading with DCM, 40G column, 0 - 70% EtGAc/Hex, 35 min run) to give the title compound as a solid (366 mg, 50% yield). XH MMR (400 MHz, CDC ) d 8.22-8.20 (d, J = 6.5 Hz, 1H), 6.64 - 6.62 (d, J = 6.5 Hz, 1H), 2.62 (d, J = 0.6 Hz, 3H), 2.51 (d, J = 0.6 Hz, 3H). ES-MS [M+l]+: 210 |
50% | With polyphosphoric acid; at 85℃; for 23.0h;Sealed tube; | A mixture of 6-chIoro-3-amino-4,5-dimethylpyridazine (550 mg), ethyl 3,3-dietboxypropiQnate (1.02 mL), and poyphosphoric acid (5 mL) was added to a sealed tube. The mixture was stirred at 85 C for 5 hours then cooled to room temperature where additional ethyl 3,3-diethoxypropionate (1.02 L) was added to the reaction mixture. The vial was sealed and the mixture heated to 85 C for 18 hours. The reaction mixture was then slowly added to a stirred solution of 150 L of saturated aqueous NaHCCb and 100 mL of DCM. After complete addition, the mixture was allowed to stir for 20 minutes, the organic layer was separated, and the aqueous layer was further extracted with chioroform/PA (4:1) (x3). The organic layers were pooled, dried over MgSG4, filtered, and concentrated. The crude product was purified using Teledyne ISCO Combi- Flash system (liquid loading with DCM, 40G column, 0 - 70% EtGAc/Hex, 35 min run) to give the title compound as a solid (366 mg, 50% yield). XH MMR (400 MHz, CDC ) d 8.22-8.20 (d, J = 6.5 Hz, 1H), 6.64 - 6.62 (d, J = 6.5 Hz, 1H), 2.62 (d, J = 0.6 Hz, 3H), 2.51 (d, J = 0.6 Hz, 3H). ES-MS [M+l]+: 210 |
50% | With polyphosphoric acid; at 85℃; for 23.0h;Sealed tube; | A mixture of 6-chIoro-3-amino-4,5-dimethylpyridazine (550 mg), ethyl 3,3-dietboxypropiQnate (1.02 mL), and poyphosphoric acid (5 mL) was added to a sealed tube. The mixture was stirred at 85 C for 5 hours then cooled to room temperature where additional ethyl 3,3-diethoxypropionate (1.02 L) was added to the reaction mixture. The vial was sealed and the mixture heated to 85 C for 18 hours. The reaction mixture was then slowly added to a stirred solution of 150 L of saturated aqueous NaHCCb and 100 mL of DCM. After complete addition, the mixture was allowed to stir for 20 minutes, the organic layer was separated, and the aqueous layer was further extracted with chioroform/PA (4:1) (x3). The organic layers were pooled, dried over MgSG4, filtered, and concentrated. The crude product was purified using Teledyne ISCO Combi- Flash system (liquid loading with DCM, 40G column, 0 - 70% EtGAc/Hex, 35 min run) to give the title compound as a solid (366 mg, 50% yield). XH MMR (400 MHz, CDC ) d 8.22-8.20 (d, J = 6.5 Hz, 1H), 6.64 - 6.62 (d, J = 6.5 Hz, 1H), 2.62 (d, J = 0.6 Hz, 3H), 2.51 (d, J = 0.6 Hz, 3H). ES-MS [M+l]+: 210 |
Tags: 10601-80-6 synthesis path| 10601-80-6 SDS| 10601-80-6 COA| 10601-80-6 purity| 10601-80-6 application| 10601-80-6 NMR| 10601-80-6 COA| 10601-80-6 structure
A127066 [7424-91-1]
Methyl 3,3-dimethoxypropanoate
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Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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