| Identification | Back Directory | [Name]
4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE | [CAS]
5754-34-7 | [Synonyms]
2-(2,2-Dimethyl-1,3-dioxolan-4-yl)
2,2-dimethyl-1,3-dioxolane-4-ethanol
1,3-Dioxolane-4-ethanol, 2,2-diMethyl-
4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIO&
4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE
4-(2-Hydroxyethyl)-2,2-diMethyl-1,3-dioxolaMe
(RAC)-2-(2,2-DIMETHYL[1,3]DIOXOLANE-4YL)ETHANOL
4-(2-Hydroxyethyl)-2,2-diMethyl-1,3-dioxolane 98% | [Molecular Formula]
C7H14O3 | [MDL Number]
MFCD03701622 | [MOL File]
5754-34-7.mol | [Molecular Weight]
146.18 |
| Chemical Properties | Back Directory | [Boiling point ]
199-200 °C(lit.)
| [density ]
1.031 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.4400(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
Inert atmosphere,2-8°C | [pka]
14.80±0.10(Predicted) | [Appearance]
Colorless to light yellow Liquid | [InChI]
InChI=1S/C7H14O3/c1-7(2)9-5-6(10-7)3-4-8/h6,8H,3-5H2,1-2H3 | [InChIKey]
YYEZYENJAMOWHW-UHFFFAOYSA-N | [SMILES]
O1CC(CCO)OC1(C)C |
| Hazard Information | Back Directory | [Uses]
2-(2,2-Dimethyl-1,3-dioxolan-4-yl)ethanol is used in preparation of cationic lipids and stealth lipids for treating a variety of disorders. | [Synthesis]
GENERAL STEPS: A mixture of 1,2,4-butanetriol (15 g, 141 mmol), acetone (100 mL, 1362 mmol), and p-toluenesulfonic acid monohydrate (700 mg, 3.68 mmol) was stirred for 16 hours at room temperature. Upon completion of the reaction, triethylamine (2 mL, 14.3 mmol) was added to the reaction mixture to neutralize the acidic catalyst and the mixture was subsequently concentrated. The resulting residue was purified by silica gel column chromatography (silica gel, eluting solvent: heptane/ethyl acetate = 1/0 → 1/1-1/3 gradient) to afford 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (16.55 g, yield: 80.3%) as a colorless oil. 1H-NMR (400 MHz, CDCl3) δ ppm: 1.37 (3H, s), 1.43 (3H, s), 1.79-1.86 (2H, m), 2.18-2.24 (1H, br), 3.60 (1H, dd, J = 7.8 Hz), 3.76-3.86 (2H, m), 4.10 (1H, dd, J = 6.8 Hz), 4.23-4.32 (1H, m). | [References]
[1] Nucleosides, Nucleotides and Nucleic Acids, 2005, vol. 24, # 10-12, p. 1543 - 1568
[2] European Journal of Organic Chemistry, 2015, vol. 2015, # 27, p. 6075 - 6083
[3] Journal of Organic Chemistry, 1996, vol. 61, # 3, p. 831 - 837
[4] Tetrahedron Letters, 1999, vol. 40, # 2, p. 209 - 212
[5] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 9, p. 1247 - 1250 |
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