1-AMINO-3,3-DIETHOXYPROPANE

Chemical Properties

CLEAR COLOURLESS TO YELLOW LIQUID

Uses

1-Amino-3,3-diethoxypropane has been used:

• with alginate in the preparation of hydrogel
• in the generation of polyethylene glycol (PEG) polyethylenimine (PEI) polyplexes conjugate for transfection studies in hepatocellular carcinoma cell cultures
• as a component of pH-sensitive PEG derivative for lipopolyplexes formation

General Description

1-Amino-3,3-diethoxypropane is an effective modulator of alginate and chitosan based hydrogels and effectively used for the delivery of bone marrow stromal cells (BMSCs) for regeneration of cartilage.

Synthesis

107833-73-8

41365-75-7

The general procedure for the synthesis of 1-amino-3,3-diethoxypropane from the compound (CAS:107833-73-8) was as follows: 10% Pd/C catalyst (15 mg) was added to a solution of compound 5 (17.7 g, 0.1 mol) in methanol (20 mL), and the reaction was stirred for 12 hr at room temperature and 10 atmospheres of hydrogen atmosphere. After completion of the reaction, the filtrate was filtered through diatomaceous earth and concentrated under reduced pressure to afford compound 6 (14.4 g, 98% yield) as a colorless oil. The product was characterized by 1H NMR (400 MHz, CDCl3): δ = 1.14 (t, 6H, J = 6.8 Hz), 1.29 (br s, 2H), 1.71 (q, 2H, J = 6.4 Hz), 2.73 (t, 2H, J = 6.4 Hz), 3.45 (q, 2H, J = 7.2 Hz), 3.60 (q, 2H, J = 7.2 Hz), 4.53 (t, 1H, J=5.2 Hz). IR (pure sample): 3385,2953,2831,1621,1389 cm-1; mass spectrum (EI): m/z: 147 [M+].

References

[1] Tetrahedron Asymmetry, 2013, vol. 24, # 4, p. 207 - 211