Structure of 1709-71-3
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CAS No. : | 1709-71-3 |
Formula : | C10H14O5 |
M.W : | 214.22 |
SMILES Code : | CC(C(OCC(O)COC(C=C)=O)=O)=C |
MDL No. : | MFCD00274303 |
InChI Key : | ZODNDDPVCIAZIQ-UHFFFAOYSA-N |
Pubchem ID : | 5062351 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H317-H319 |
Precautionary Statements: | P280-P305+P351+P338 |
* 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 |
---|---|---|
2,6-di-tert-butyl-4-methyl-phenol; triethylamine; at 80℃; for 48h;Product distribution / selectivity; | 13.27 g of glycidyl methacrylate, 0.02 g of 2,6-ditert.-butyl-4-methylphenol, 6.78 g of acrylic acid and 0.10 g of one of the catalysts set forth in Table 1 were reacted each time at 80 C. in a glass vessel with a small opening and with magnetic stirring. The acid value was determined after 24 and 48 hours. If it was greater than 4 mg KOH/g after 48 hours, the batch was discarded without further analysis. The catalysts in comparison examples C2 to C6 exhibit, for a given weight, much lower activity, and those in C7 and C8 a lower activity, than the catalyst in example 9 according to the invention. The reaction product was at least equal to the comparison products according to the acid value, hydroxyl value and purity (GPC analysis). | |
2,6-di-tert-butyl-4-methyl-phenol; triphenylphosphine; at 80℃; for 48h;Product distribution / selectivity; | 13.27 g of glycidyl methacrylate, 0.02 g of 2,6-ditert.-butyl-4-methylphenol, 6.78 g of acrylic acid and 0.10 g of one of the catalysts set forth in Table 1 were reacted each time at 80 C. in a glass vessel with a small opening and with magnetic stirring. The acid value was determined after 24 and 48 hours. If it was greater than 4 mg KOH/g after 48 hours, the batch was discarded without further analysis. The catalysts in comparison examples C2 to C6 exhibit, for a given weight, much lower activity, and those in C7 and C8 a lower activity, than the catalyst in example 9 according to the invention. The reaction product was at least equal to the comparison products according to the acid value, hydroxyl value and purity (GPC analysis). | |
1,4-diaza-bicyclo[2.2.2]octane; 2,6-di-tert-butyl-4-methyl-phenol; at 80℃; for 48h;Product distribution / selectivity; | 13.27 g of glycidyl methacrylate, 0.02 g of 2,6-ditert.-butyl-4-methylphenol, 6.78 g of acrylic acid and 0.10 g of one of the catalysts set forth in Table 1 were reacted each time at 80 C. in a glass vessel with a small opening and with magnetic stirring. The acid value was determined after 24 and 48 hours. If it was greater than 4 mg KOH/g after 48 hours, the batch was discarded without further analysis. The catalysts in comparison examples C2 to C6 exhibit, for a given weight, much lower activity, and those in C7 and C8 a lower activity, than the catalyst in example 9 according to the invention. The reaction product was at least equal to the comparison products according to the acid value, hydroxyl value and purity (GPC analysis). |
2,6-di-tert-butyl-4-methyl-phenol; N-benzyl-N,N,N-triethylammonium chloride; at 80℃; for 48h;Product distribution / selectivity; | 13.27 g of glycidyl methacrylate, 0.02 g of 2,6-ditert.-butyl-4-methylphenol, 6.78 g of acrylic acid and 0.10 g of one of the catalysts set forth in Table 1 were reacted each time at 80 C. in a glass vessel with a small opening and with magnetic stirring. The acid value was determined after 24 and 48 hours. If it was greater than 4 mg KOH/g after 48 hours, the batch was discarded without further analysis. The catalysts in comparison examples C2 to C6 exhibit, for a given weight, much lower activity, and those in C7 and C8 a lower activity, than the catalyst in example 9 according to the invention. The reaction product was at least equal to the comparison products according to the acid value, hydroxyl value and purity (GPC analysis). | |
2,6-di-tert-butyl-4-methyl-phenol; dibutyltin dilaurate; at 80℃; for 48h;Product distribution / selectivity; | 13.27 g of glycidyl methacrylate, 0.02 g of 2,6-ditert.-butyl-4-methylphenol, 6.78 g of acrylic acid and 0.10 g of one of the catalysts set forth in Table 1 were reacted each time at 80 C. in a glass vessel with a small opening and with magnetic stirring. The acid value was determined after 24 and 48 hours. If it was greater than 4 mg KOH/g after 48 hours, the batch was discarded without further analysis. The catalysts in comparison examples C2 to C6 exhibit, for a given weight, much lower activity, and those in C7 and C8 a lower activity, than the catalyst in example 9 according to the invention. The reaction product was at least equal to the comparison products according to the acid value, hydroxyl value and purity (GPC analysis). | |
2,2'-thiobis-ethanol; 2,6-di-tert-butyl-4-methyl-phenol; at 80℃; for 48h;Product distribution / selectivity; | 13.27 g of glycidyl methacrylate, 0.02 g of 2,6-ditert.-butyl-4-methylphenol, 6.78 g of acrylic acid and 0.10 g of one of the catalysts set forth in Table 1 were reacted each time at 80 C. in a glass vessel with a small opening and with magnetic stirring. The acid value was determined after 24 and 48 hours. If it was greater than 4 mg KOH/g after 48 hours, the batch was discarded without further analysis. The catalysts in comparison examples C2 to C6 exhibit, for a given weight, much lower activity, and those in C7 and C8 a lower activity, than the catalyst in example 9 according to the invention. The reaction product was at least equal to the comparison products according to the acid value, hydroxyl value and purity (GPC analysis). | |
stannous octoate; 2,6-di-tert-butyl-4-methyl-phenol; at 80℃; for 24h;Product distribution / selectivity; | 13.27 g of glycidyl methacrylate, 0.02 g of 2,6-ditert.-butyl-4-methylphenol, 6.78 g of acrylic acid and 0.10 g of one of the catalysts set forth in Table 1 were reacted each time at 80 C. in a glass vessel with a small opening and with magnetic stirring. The acid value was determined after 24 and 48 hours. If it was greater than 4 mg KOH/g after 48 hours, the batch was discarded without further analysis. The catalysts in comparison examples C2 to C6 exhibit, for a given weight, much lower activity, and those in C7 and C8 a lower activity, than the catalyst in example 9 according to the invention. The reaction product was at least equal to the comparison products according to the acid value, hydroxyl value and purity (GPC analysis). | |
tris(dimethylamino)borane; 2,6-di-tert-butyl-4-methyl-phenol; at 80℃; for 48h;Product distribution / selectivity; | 13.27 g of glycidyl methacrylate, 0.02 g of 2,6-ditert.-butyl-4-methylphenol, 6.78 g of acrylic acid and 0.10 g of one of the catalysts set forth in Table 1 were reacted each time at 80 C. in a glass vessel with a small opening and with magnetic stirring. The acid value was determined after 24 and 48 hours. If it was greater than 4 mg KOH/g after 48 hours, the batch was discarded without further analysis. The catalysts in comparison examples C2 to C6 exhibit, for a given weight, much lower activity, and those in C7 and C8 a lower activity, than the catalyst in example 9 according to the invention. The reaction product was at least equal to the comparison products according to the acid value, hydroxyl value and purity (GPC analysis). | |
With 10H-phenothiazine; triphenylphosphine; at 80 - 110℃; | Example 2Synthesis of 3-acryloyloxy-2-hydroxypropyl methacrylate (GAMA); The apparatus from Example 1 is used. All of the chemicals used are available commercially, from Sigma Aldrich, for example.Reservoir 1 is charged with a GMA solution whose composition is as follows:Glycidyl methacrylate (GMA): 98.2% by weightTriphenylphosphine (TPP): 1.5% by weightPhenothiazine: 0.004% by weightDi-tert-butylmethylphenol (inhibitor KB) 0.22% by weightReservoir 2 is charged with acrylic acid.The reaction apparatus is heated to 80 C. empty. Reactant is metered in from reservoir 1 with a mass flow rate of 3.07 kg/h; from reservoir 2, reactant is metered in with a mass flow rate of 1.56 kg/h.The reactors are each thermally conditioned with a mass flow rate of 500 kg of thermostat oil (silicone oil) per hour (WK1, WK2).After the start of the metered feeds, the plant is slowly flooded. When the reactors of the first heating circuit (WK1) have been filled, the temperature in this circuit is slowly raised, in a number of steps, to a jacket temperature of 110 C. The same procedure at the same rate is carried out with the reactors of the second thermal conditioning circuit (WK2) when they are filled, the jacket temperature set here being 110 C. After a further 3 residence times, the product (GAMA) is obtained.Result: residual monomer content: 0.5% by weight acrylic acid, 0.48% by weight GMA | |
With tetramethlyammonium chloride; at 90℃; for 4h; | (1) Weigh 64 g of glycidyl methacrylate, Adding tetramethylammonium chloride 3.0g, Hydroxyanisole 0.1g, In a three-necked flask, Stirring to 90 C, Using a constant pressure dropping funnel, 37.8 g of acrylic acid was added dropwise to the reaction system. After the addition is completed, The acid value was tested after 4 hours of reaction. When the acid value is less than 10 mg KOH / g, the reaction is stopped. | |
With tetramethlyammonium chloride; at 90℃; for 4h; | A method for preparing a methacrylate monomer for a dental restorative material, comprising the following steps: (1) Weigh 64 g of glycidyl methacrylate, and add 3.0 g of tetramethylammonium chloride and 0.1 g of hydroxyanisole in a three-necked flask.The temperature was raised to 90 C, and 37.8 g of acrylic acid was added dropwise to the reaction system by a constant pressure dropping funnel. After the completion of the dropwise addition, the acid value was measured after the reaction was continued for 4 hours, and when the acid value was less than 10 mg KOH/g, the reaction was stopped |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With dmap; 2,6-di-tert-butyl-4-methyl-phenol; triethylamine; In acetone; at 20℃; for 1.5h; | Synthesis of photoinitiator INI-1 30 g (0.15 mol) 2-hydroxy-3-methacryloyloxypropyl acrylate, 1.83 g (15 mmol) 4-dimethylamino-pyridine and 1.5 g BHT were dissolved in 200 mL acetone. 20.9 mL (0.15 mol) triethyl amine was added at room temperature. 34.6 g (0.23 mol) methacrylic anhydride was added drop wise over 30 minutes and the reaction was allowed to continue at room temperature for one hour. The solvent was removed under reduced pressure and 2,3-di-methacryloyloxypropyl acrylate was purified by preparative column chromatography on Prochrom LC 80 column, using Kromasil Si 60A 10 mm as silica and a gradient elution from methylene chloride to methylene chloride/methanol 95/5 at a flow rate of 150 mL per minute. 21.3 g (50%) of 2,3-di-methacryloyloxypropyl acrylate was isolated. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Preparation of Compound I: 2-methylacrylic acid 2-hydroxy-3-[3-(2-methylaziridin-1-yl)propionyloxy]propyl ester To a 250 mL round bottomed flask were added <strong>[1709-71-3]3-(acryloyloxy)-2-hydroxypropyl methacrylate</strong> (32.1 g, 0.15 mol, available from Aldrich) and 2-methylaziridine (10.8 g, about 0.17 mol, 90% pure, available from Aldrich) to cause a slight exotherm. The reaction mixture was allowed to stand at room temperature overnight. Excess 2-methylaziridine was removed at reduced pressure to leave the desired product (40.4 g) as a colorless liquid. NMR and IR spectral analyses confirmed the structure of the product. | ||
at 20℃; | Preparation of Compound I: 2-methylacrylic acid 2-hvdroxy-3-r3-(2-methylaziridin-l- yDpropionyloxylpropyl esterTo a 250 mL round bottomed flask were added <strong>[1709-71-3]3-(acryloyloxy)-2-hydroxypropyl methacrylate</strong> (32.1 g, 0.15 mol, available from Aldrich) and 2-methylaziridine (10.8 g, about 0.17 mol, 90% pure, available from Aldrich) to cause a slight exotherm. The reaction mixture was allowed to stand at room temperature overnight. Excess 2- methylaziridine was removed at reduced pressure to leave the desired product (40.4 g) as a colorless liquid. NMR and IR spectral analyses confirmed the structure of the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; at 35℃; for 6h; | Example 5 [0034] IEM-based monoimidazole-monomethacrylate Resins (FIG. 11) was prepared via a two-step process as described in the following: to a 500 ml 3-nech round flask, 237 grams of <strong>[1709-71-3]AMAHP</strong> and 146.2 grams of 2-isocynate ethoxylmethacrylate (IEM), and 0.53 gam of DBTOL were charged at 35 C. Keep reaction for 6 hrs. 339 grams liquid resin was collected. Then 185.1 grams of the precursor resin and 800 ml of methylene dichloride were charged into a 1000 ml three neck round flask at room temperature. Then slowly it was added of 55.5 grams of imidazole crystalline powder. Keep reaction for overnight. The resulting solution was extracted several times by using aqueous solution of potassium carbonate. Then it was dried over night with magnesium sulphate prior to remove the solvent via Rotovapor at 35-40 C. under vacuum. 214 grams of liquid resin was collected |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 3 [0032] HEMA-based Monoimidazole-dimethacrylate Resins (FIG. 9) was also prepared via a two-step process as described in the following: to a 1000 ml 3-nech round flask, 81.8 g of CDI, 450 ml of methylene dichloride and 107.5 g of <strong>[1709-71-3]AMAHP</strong> were charged and soon the system turns clear at room temperature. After 6 hrs reaction at RT, 66.5 g of HEMA, 40.0 g of potassium carbonate and 4.0 g of terabutylamoniumbromide were added. Keep the reaction proceeding at room temperature for additional 10-12 hrs prior to 200 ml of water was added to stop the reaction. The resulting solution was extraction several times with DI water to remove all of imidazole and catalysts. Then it was dried over magnesium sulfate overnight at RT prior to it was filtrated. Solvent was removed via Rotovapor at 35-40 C. under vacuum. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In dichloromethane; at 20℃; | Example 4 [0033] <strong>[1709-71-3]AMAHP</strong>-based monoimidazole-monomethacrylate Resins (FIG. 10) was also prepared via a one-step process as described in the following: to a 1000 ml 3-nech round flask, 102 grams of imidazole, 700 ml of methylene dichloride and 161 grams of <strong>[1709-71-3]AMAHP</strong> were charged and soon the system turns clear at room temperature. After reaction over night at RT, the resulting solution was extracted several times by using aqueous solution of potassium carbonate. Then it was dried over night with magnesium sulphate prior to remove the solvent via Rotovapor at 35-40 C. under vacuum. Liquid resin was collected. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; at 20℃; for 6h; | Example 2 [0031] TCDC-based bisimidazole-dimethacrylate Resins (FIG. 8) was prepared via a two-step process as described in the following: to a 1000 ml 3-nech round flask, 74.45 g of CDI, 400 ml of methylene dichloride and 98.36 g of <strong>[1709-71-3]AMAHP</strong> were charged and soon the system turns clear at room temperature. After 6 hrs reaction at RT, a bisimidazole precursor was formed as shown in FIG. 7, then 45.0 g of 4,8-bis(hydroxymethyl)-tricyclo[5,2,1,02.5](TCDC) and 40.0 g of potassium carbonate and 3.8 g of terabutylamoniumbromide were added. Keep the reaction proceeding at room temperature for additional 10-12 hrs prior to 250 ml of DI water was added to stop the reaction. The resulting solution was extraction several times with water to remove all of imidazole and catalysts. Then it was dried over magnesium sulfate overnight at RT prior to it was filtrated. Solvent was removed via Rotovapor at 35-40 C. under vacuum. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With tetrabutylammomium bromide; potassium carbonate; In dichloromethane; at 20℃; | Example 1 [0030] Isosorbide-based bisimidazoledimethacrylate Resin (FIG. 6) was prepared via a two-step process as described in the following: to a 1000 ml 3-nech round flask, 98.88 g of 1,1-carbonydiimidazole (CDI), 550 g of methylene dichloride and 43.9 g of isosorbide were charged and soon the system turns clear at room temperature. Then the crystal was developed as resulted of imidazole formation. After 2 hrs reaction at RT, 131.1 g of <strong>[1709-71-3]3-(acryloyloxy)-2-hydroxypropyl methacrylate</strong> (<strong>[1709-71-3]AMAHP</strong>), 40.0 g of potassium carbonate and 4.0 g of terabutylamoniumbromide were added. Keep the reaction proceeding at room temperature for additional 10-12 hrs prior to 200 ml of water was added to stop the reaction. The resulting solution was extraction several times with water to remove all of imidazole and catalysts. Then it was dried over magnesium sulfate overnight at RT prior to it was filtrated. Solvent was removed via Rotovapor at 35-40 C. under vacuum. 240 g of liquid resin was collected with yield of 89%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With triethylamine; In dichloromethane; at 0 - 20℃; for 16h;Schlenk technique; Inert atmosphere; | To a solution of <strong>[1709-71-3]3-(acryloyloxy)-2-hydroxypropyl methacrylate</strong> (3g; AHM, 3.94 g, 8.98 mmol) and Et3N (2.6 mL, 1.9 g,18.9 mmol) in anhydrous CH2Cl2 (20 mL) was slowly added a solution of pyridine-2,6-dicarbonyl dichloride (1.83 g, 8.98 mmol) in anhydrous CH2Cl2 (20 mL) at 0 C. The slightly turbid mixture was stirred at r.t. for 16 h, filtered through Celite, and concentrated in vacuo under addition of MEHQ as polymerization inhibitor. The crude product was purified by flash chromatography (hexanes-EtOAc, 3:1 ? 2:1) to yield 8g (3.56 g, 6.36 mmol, 71%) as a clear colorless oil; Rf = 0.21 (hexanes-EtOAc, 2:1). FT-IR (ATR): 2931 (w), 2184 (w), 1962 (w), 1720 (s), 1293 (m),1236 (m), 1162 cm-1 (s). 1H NMR (300 MHz, CDCl3): delta = 1.93 (s, 6 H, CH3), 4.41-4.69 (m,8 H, OCH2), 5.59-5.62 (m, 2 H, cis-3?-H), 5.65-5.73 (m, 2 H,OCH), 5.85-5.91 (m, 2 H, cis-3??-H), 6.08-6.21 (m, 4 H, trans-3?-H,2??-H), 6.40-6.49 (m, 2 H, trans-3??-H), 7.99-8.04 (m, 1 H, 4-H),8.23-8.26 (m, 2 H, 3-H, 5-H). 13C NMR (75 MHz, CDCl3): delta = 18.2 (CH3), 62.4 (OCH2), 71.0(OCH), 126.6 (C-3?), 127.6 (C-2??), 128.2 (C-3, C-5), 131.9 (C-3??),135.6 (C-2?), 138.3 (C-4), 148.1 (C-2, C-6), 163.3 (Ar-C=O), 165.6(C-1??), 166.7 (C-1?). MS (ESI): m/z = 582.2 [M + Na]+, 560.2 [M + H]+, 197.1 [C10H13O4(AHM - OH)]+.HRMS (ESI): m/z calcd for C27H29NO12: 582.1582; found: 582.1586 [M + Na]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With pyridine; In dichloromethane; at 0 - 20℃;Schlenk technique; Inert atmosphere; | General procedure: To a solution of <strong>[1709-71-3]3-(acryloyloxy)-2-hydroxypropyl methacrylate</strong> (3g; AHM, 3.94 g, 8.98 mmol) and Et3N (2.6 mL, 1.9 g,18.9 mmol) in anhydrous CH2Cl2 (20 mL) was slowly added a solution of pyridine-2,6-dicarbonyl dichloride (1.83 g, 8.98 mmol) in anhydrous CH2Cl2 (20 mL) at 0 C. The slightly turbid mixture was stirred at r.t. for 16 h, filtered through Celite, and concentrated in vacuo under addition of MEHQ as polymerization inhibitor. The crude product was purified by flash chromatography (hexanes-EtOAc, 3:1 ? 2:1) to yield 8g (3.56 g, 6.36 mmol, 71%) as a clear colorless oil; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With pyridine; In dichloromethane; at 0 - 20℃; for 2h;Schlenk technique; Inert atmosphere; | General procedure: To a solution of <strong>[1709-71-3]3-(acryloyloxy)-2-hydroxypropyl methacrylate</strong> (3g; AHM, 3.94 g, 8.98 mmol) and Et3N (2.6 mL, 1.9 g,18.9 mmol) in anhydrous CH2Cl2 (20 mL) was slowly added a solution of pyridine-2,6-dicarbonyl dichloride (1.83 g, 8.98 mmol) in anhydrous CH2Cl2 (20 mL) at 0 C. The slightly turbid mixture was stirred at r.t. for 16 h, filtered through Celite, and concentrated in vacuo under addition of MEHQ as polymerization inhibitor. The crude product was purified by flash chromatography (hexanes-EtOAc, 3:1 ? 2:1) to yield 8g (3.56 g, 6.36 mmol, 71%) as a clear colorless oil; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 0 - 20℃; for 26h; | The compound 2b 2g (8.187mmol), 2e 2.055g (9.006mmol), ethyl carbodiimide hydrochloride (EDC-HCl) 1.736g (9.006mmol), dimethylaminopyridine (DMAP ) 0.2 g of (1.637mmol), placed in a 0 ~ 4 C. in tetrahydrofuran (THF) 40 ml, after stirring for 2 hours and then stirred at room temperature for 24 hours. The reaction was added to water 150 ml, and extracted with methyl chloride (MC) 600ml. The water extracted organic layer was removed by passing through a magnesium sulfate, the solvent was removed in vacuo, and purified by column (hexane / ethyl acetate = 6/1), the compound represented by Formula 1-4 It was obtained 3.102g (6.825mmol). Yield (83%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 0 - 20℃; for 26h; | The compound obtained in 1b2g (9.249mmol), 1e3.963g (18.4986mmol), ethylcarbodiimide hydrochloride (EDC-HCl) 1.7736g (9.246mmol), dimethylaminopyridine (DMAP) 0 .227g the (1.859mmol), placed in a 0 ~ 4 C. in tetrahydrofuran (THF) 40 ml, after stirring for 2 hours and then stirred at room temperature for 24 hours. The reaction was added to water 150 ml, and extracted with methyl chloride (MC) 600ml. The water extracted organic layer was removed by passing through a magnesium sulfide, the solvent was removed in vacuo, and purified by column (hexane / ethyl acetate 6/1), the compound represented by Formula 1-2 to obtain a 2.67g (6.474mmol). Yield (70%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31.32 g | With triethylamine; In acetic acid methyl ester; for 1h; | In a separate reaction vessel, 15.32 g (71.52 mmol) of 1- (acryloyl oxy) -3- (methacryloyl oxy) -2-propanol, 7.95 g (78.71 mmol) of triethylamine and 40 ml of methyl acetate were mixed , and the previously prepared acid chloride was added dropwise thereto. After completion of the dropwise addition, the mixture was further stirred for 1 hour. The reaction solution was poured into a separating funnel and washed with 2M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated saline in this order. After washing, anhydrous magnesium sulfate was added and the solution was dried. After drying, anhydrous magnesium sulfate was filtered off and the solvent was removed to obtain 31.32 g of acrylimide 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8.56 g | With pyridine; In acetic acid methyl ester; for 1h; | In a separate reaction vessel, 3.86 g (18.02 mmol) of 1-(acryloyloxy) -3-(methacryloyloxy)-2-propanol, 1.64 g (20.73 mmol) of pyridine and 20 ml of methyl acetate were mixed, To this was added dropwise the acid chloride previously prepared. After completion of the dropwise addition, the mixture was further stirred for 1 hour. The reaction solution was poured into a separating funnel and washed with 2M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated saline in this order. After washing, anhydrous magnesium sulfate was added and the solution was dried. After drying, anhydrous magnesium sulfate was filtered off and the solvent was removed to obtain 8.56 g of acrylic imide 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9.08 g | With pyridine; In acetic acid methyl ester; for 1h; | In a separate reaction vessel, 3.96 g (18.49 mmol) of 1-(acryloyloxy) -3-(methacryloyloxy)-2-propanol, 1.83 g (23.14 mmol) of pyridine and 20 ml of methyl acetate were mixed ,and the previously prepared acid chloride was added dropwise thereto. After completion of the dropwise addition, the mixture was further stirred for 1 hour. The reaction solution was poured into a separating funnel and washed with 2 M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated saline in this order. After washing, anhydrous magnesium sulfate was added and the solution was dried. After drying, anhydrous magnesium sulfate was filtered off and the solvent was removed to obtain 9.08 g of acrylic imide 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7.24 g | With pyridine; In acetic acid methyl ester; for 1h; | In a separate reaction vessel, 3.02 g (14.10 mmol) of 1- (acryloyloxy) -3- (methacryloyloxy) -2-propanol, 1.66 g (20.99 mmol) of pyridine and 20 ml of methyl acetate were mixed and the previously prepared acid chloride was added dropwise thereto. After completion of the dropwise addition, the mixture was further stirred for 1 hour. After completion of the dropwise addition, the mixture was further stirred for 1 hour. The reaction solution was poured into a separating funnel and washed with 2 M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated saline in this order. After washing, anhydrous magnesium sulfate was added and the solution was dried. After drying, anhydrous magnesium sulfate was filtered off, and the solvent was removed to obtain 7.24 g of acrylic imide 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7.43 g | In acetic acid methyl ester; for 1h; | In a separate reaction vessel, 2.82 g (13.16 mmol) of 1- (acryloyloxy) -3- (methacryloyloxy) -2-propanol, 1.80 g (22.76 mmol) of pyridine and 20 ml of methyl acetate were mixed , and the previously prepared acid chloride was added dropwise thereto. After completion of the dropwise addition, the mixture was further stirred for 1 hour. After completion of the dropwise addition, the mixture was further stirred for 1 hour. The reaction solution was poured into a separating funnel, 2 M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine in this order. After washing, anhydrous magnesium sulfate was added and the solution was dried. After drying, anhydrous magnesium sulfate was filtered off and the solvent was removed to obtain 7.43 g of acrylic imide 5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8.93 g | With triethylamine; In acetic acid methyl ester; for 1h; | In a separate reaction vessel, 3.86 g (18.02 mmol) of <strong>[1709-71-3]1-(acryloyloxy)-3-(methacryloyloxy)-2-propanol</strong>, 1.75 g (22.12 mmol) of triethylamine and 20 ml of methyl acetate were mixed, to this was added dropwise the acid chloride previously prepared. After completion of the dropwise addition, the mixture was further stirred for 1 hour. The reaction solution was poured into a separating funnel and washed with 2 M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated saline in this order. After washing, anhydrous magnesium sulfate was added and the solution was dried. After drying, anhydrous magnesium sulfate was separated by filtration, and the solvent was removed, whereby 8.93 g of acrylic imide 6 was obtained. |
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