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CAS No. : | 111-77-3 | MDL No. : | MFCD00002871 |
Formula : | C5H12O3 | Boiling Point : | 194°C at 760 mmHg |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 120.15 g/mol | Pubchem ID : | 8134 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P201-P202-P210-P280-P308+P313-P370+P378-P403+P235-P405-P501 | UN#: | N/A |
Hazard Statements: | H227-H361 | Packing Group: | N/A |
GHS Pictogram: |
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Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.12 g | Stage #1: With sodium hydride In tetrahydrofuran; mineral oil for 1 h; Inert atmosphere; Cooling with ice Stage #2: at 20℃; for 1 h; Inert atmosphere; Cooling with ice |
Sodium hydride (60percent dispersion) (21.0 g) and THF (200 ml) were added to a reaction container equipped with a stirrer and a thermometer in a nitrogen atmosphere, and the mixture was stirred under ice cooling, and a THF (100 ml) solution of the compound (S-14) (20.0 g) was slowly added dropwise thereto. After stirring for 1 hour after the dropwise addition, 1-chloroethanol (23.3 g) was added dropwise thereto under ice cooling, the temperature was gradually raised to room temperature and stirring was carried out for 1 hour. After stopping the reaction by adding water (200 ml), the organic layer was collected, the aqueous layer was extracted with THF (100 ml) four times, the resulting THF was mixed with the organic layer obtained above and washed with 5percent aqueous sodium hydroxide solution (400 ml) and subsequently with saturated saline (400 ml), dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was distilled under reduced pressure to obtain a compound (5-15) (31.2 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5 h; Inert atmosphere Stage #2: at 20℃; for 12 h; Inert atmosphere Stage #3: With sulfuric acid; water In tetrahydrofuran for 3 h; Inert atmosphere; Reflux |
(Using the synthesis of M-PEG 7 as an example). Under the atmosphere of N2, to a suspension of NaH (1.0 g, 60percent dispersed in mineral oil, 25.0 mmol) in THF (60 mL) at 0 was added a solution of M-PEG 5 (2.0 g, 16.6 mmol) in THF (20 mL). After the addition, the stirring mixture was warmed to rt and stirred for 30 min. Then, a solution of macrocyclic sulfate 8 (5.1 g, 20.0 mmol) in THF (20 mL) was added. The resulting mixture was stirred for 12 h at rt, and concentrated under vacuum. The resulting residue was dissolved in water (50 mL), and washed with CH2Cl2. The aqueous layer was concentrated and then dissolved in THF (100 mL). Then, water (0.6 mL, 33.3 mmol) and H2SO4 (0.4 mL, 8.4 mmol) were added to the reaction mixture and the resulting mixture was refluxed for 3 h. The reaction was neutralized with saturated NaHCO3 solution, extracted with CH2Cl2. The organic layers were dried over anhydrous Na2SO4, concentrated under vacuum, and purified by flash chromatography on silica gel (CH2Cl2/MeOH = 20/1) to give M-OEG 7 as clear oil (4.3 g, 88percent yield). 1H NMR (400 MHz, CDCl3) δ 3.73-3.70 (m, 2H), 3.70-3.63 (m, 18H), 3.62-3.59 (m, 2H), 3.57-3.55 (m, 2H), 3.39 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | Stage #1: With phthalimide; triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 20℃; Stage #2: With hydrazine hydrate In ethanolReflux |
Diethylene glycol monomethyl ether (3.9 mL, 33.3 mmol) and diethyl azodicarboxylate (2.2 mol/L toluenesolution) (15.5 mL, 34.1 mmol) were added to a solution of phthalimide (4.90 g, 34.2 mmol) and triphenylphosphine(9.00 g, 34.2 mmol) in tetrahydrofuran (180 mL) at room temperature, and stirred overnight. To the resulting solution,ethanol (60 mL) was further added, stirred at room temperature for 30 minutes, and then the solvent was distilled awayunder a reduced pressure. Ethyl acetate (50 mL) and hexane (50 mL) were added to the residue, and insolubles werefiltered off. After the filtrate was concentrated under a reduced pressure, ethanol (120 mL) and hydrazine monohydrate(2.4 mL, 68.6 mmol) were added, and stirred under heat reflux overnight. After this solution was cooled to room temperature,concentrated hydrochloric acid (15 mL) was added, and stirred under heat reflux for 1 hour. After this solutionwas cooled to room temperature, insolubles were filtered off, and the filtrate was concentrated under a reduced pressure.Water was added to the residue, which was washed with diethyl ether. The aqueous layer was adjusted to pH = 13 witha 3N sodium hydroxide aqueous solution, and extraction was carried out with dichloromethane. The organic layer wasdried with anhydrous sodium sulfate, the solvent was distilled away under a reduced pressure to obtain the title compound(1.74 g, 44percent) as a pale yellow oily matter.1H NMR (400 MHz, CDCl3) δ 3.64-3.61 (2H, m), 3.57-3.55 (2H, m), 3.51 (2H, t, J = 5.2 Hz), 3.39 (3H, s), 2.89-2.87 (2H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | Stage #1: With sodium In tetrahydrofuran at 0 - 20℃; for 24 h; Inert atmosphere Stage #2: for 5 h; |
PREPARATION EXAMPLE 4 Synthesis of 3-[2-(2-methoxyethoxy)ethoxy]propanoic acid To a 500 mL four neck flask purged with argon, 110 mL (0.93 mol) of 2-(2-methoxyethoxy)ethanol and 50 mL of dehydrated THF were added. After cooling to 0° C., 1.4 g (0.06 mol) of sodium metal was added thereto. After confirming no gas generation from the resulting reaction solution, a solution in which 44 mL (0.31 mol) of tertiary butyl acrylate is diluted in 50 mL of THF was slowly added dropwise thereto. Once the dropwise addition is completed, the reaction solution was heated from 0° C. to room temperature and then stirred for 24 hours at room temperature. The resulting reaction solution was dried under reduced pressure for removing THF by distillation. Then, 100 mL (0.3 mol) of 3 mol/L aqueous solution of sodium hydroxide was added and stirred for 5 hours. After adjustment to have pH=2 by adding 10percent aqueous solution of sulfuric acid to the obtained reaction solution, extraction was performed three times by using methylene chloride. The obtained organic layer was dried over anhydrous magnesium sulfate and dried under reduced pressure. The obtained crude 3-[2-(2-methoxyethoxy)ethoxy]propanoic acid was distilled twice under reduced pressure at 140° C., 0.1 kPa to obtain 14 g of 3-[2-(2-methoxymethyl)ethoxy]propanoic acid (yield: 24percent). 1H-NMR analysis data of the obtained 3-[2-(2-methoxyethoxy)ethoxy]propanoic acid is given below. 1H-NMR(DMSO-d6) δ(ppm)=2.67(q,2H), 2.51(q,2H), 2.07(s,3H) |
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