4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE Chemical Properties

Boiling point:

199-200 °C(lit.)

Density 

1.031 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.4400(lit.)

Flash point:

>230 °F

storage temp. 

under inert gas (nitrogen or Argon) at 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

Safety Information

RIDADR 

NA 1993 / PGIII

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

4-(2-HYDROXYETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE Usage And Synthesis

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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