3,3-Diethoxy-1-Propanol

Name: 3,3-Diethoxy-1-Propanol
SKU: ACM16777870-1
Rating: 5 (1 reviews)

CAS

16777-87-0

Catalog Number

ACM16777870-1

Category

Main Products

Molecular Weight

148.20

Molecular Formula

C7H16O3

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Specification

Synonyms

3,3-Diethoxypropan-1-Ol

IUPAC Name

3,3-diethoxypropan-1-ol

Canonical SMILES

CCOC(CCO)OCC

InChI Key

ASERXEZXVIJBRO-UHFFFAOYSA-N

Boiling Point

90-93 °C (lit.)

Flash Point

196°F

Density

0.941g/mL at 25°C(lit.)

Appearance

Colourless liquid

Exact Mass

148.11000

H-Bond Acceptor

H-Bond Donor

WGK Germany

3,3-Diethoxy-1-Propanol for the Versatile Synthesis of Terminal Functionalized Thermosensitive Poly(2-Isopropyl-2-Oxazoline)

Park, Joon-Sik, et al. Macromolecules, 2004, 37(18), 6786-6792.

Several terminal functionalized poly(2-isopropyl-2-oxazoline) (PiPrOx) were synthesized by cationic ring-opening polymerization of 2-isopropyl-2-oxazoline. Among them, isotelechelic PiPrOx (acetal-PiPrOx-OH) with α-acetal and ω-hydroxyl groups was prepared by cationic ring-opening polymerization of 2-isopropyl-2-oxazoline initiated by 3,3-diethoxy-1-propyl toluenesulfonate. 3,3-Diethoxy-1-propanol is the key raw material for the synthesis of 3,3-diethoxy-1-propyl toluenesulfonate.
Synthesis of 3,3-Diethoxy-1-propyl Tosylate
· A chloroform solution of p-toluenesulfonyl chloride (9.61 g, 50.4 mmol, 1.5-fold excess relative to OH) was introduced into a stirred mixture of 3,3-diethoxy-1-propanol (4.98 g, 33.60 mmol) and triethylamine (23.5 mL, 168 mmol, 5-fold excess relative to OH) in anhydrous chloroform (150 mL) that was maintained at 0 °C under an argon atmosphere.
· The reaction mixture was heated to room temperature after the addition and stirred for 24 hours. The filtrate resulted from filtering the mixture which was then concentrated through reduced pressure. Column chromatography on silica gel was used to separate the residue by eluting with chloroform. The target product fractions underwent drying with anhydrous sodium sulfate followed by filtration and concentration until dry. The final product remained stored at -20 °C while being protected by an argon atmosphere.

Application of 3,3-Diethoxy-1-Propanol in the Synthesis of Glycoconjugated Graft Copolymers Suitable for Targeted Drug Delivery

Freichels, Helene, et al. Bioconjugate Chemistry, 2012, 23(9), 1740-1752.

Researchers presented a synthetic method for glycoconjugated graft copolymers aimed at targeted drug delivery which utilizes α-acetal and ω-alkyne poly(ethylene oxide) as multifunctional building blocks. Among the synthesis, α-acetal-ω-hydroxy poly(ethylene oxide) (α-acetal-ω-hydroxy PEO) can be obtained using 3,3-diethoxy-1-propanol as a raw material.
Synthesis procedure of α-acetal-ω-hydroxy PEO
· Under argon protection in a flame-dried flask 1.2 mL of 3,3-diethoxy-1-propanol (1.13 g; 7.6 mmol) dissolved in 200 mL of anhydrous THF underwent titration with potassium naphthalenide which was in a 0.72 M THF solution.
· After stirring the mixture vigorously for 15 minutes at room temperature it was moved to a 500 mL Parr reactor before adding 15 g of ethylene oxide (340 mmol). After polymerization at 30 °C for 19 hours, added 2-propanol to the mixture before precipitating the polymer with excessive diethyl ether and vacuum-drying it at 30 °C.
· Size-exclusion chromatography determined that the number-average molecular weight of the synthesized α-acetal-ω-hydroxy PEO reached 2000 g/mol. Adjustments to the reactant amounts allowed the creation of polymers with varying molecular weights.
· The 1H NMR (CDCl3, 400 MHz) spectrum showed the following peak assignments (δ in ppm): The nuclear magnetic resonance (NMR) spectrum indicated signals at 1.17 ppm (t, 6H for CH3-CH2-O), 1.88 ppm (q, 2H for CH-CH2-CH2), 3.4 ppm (q, 4H for CH3-CH2-O), 3.46 ppm (t, 2H for CH2-CH2-OH), 3.6 ppm (s, 4H for O-CH2-CH2-O from DPEO), and 4.6 ppm (t, 1H for CH-CH2) while the recovery rate reached 90%.

What is the molecular formula of 3,3-Diethoxy-1-Propanol?

The molecular formula of 3,3-Diethoxy-1-Propanol is C7H16O3.

What are the synonyms for 3,3-Diethoxy-1-Propanol?

The synonyms for 3,3-Diethoxy-1-Propanol are 3,3-diethoxypropan-1-ol, 1-Propanol, 3,3-diethoxy-, and 3,3-diethoxypropanol.

What is the molecular weight of 3,3-Diethoxy-1-Propanol?

The molecular weight of 3,3-Diethoxy-1-Propanol is 148.20 g/mol.

What is the IUPAC name of 3,3-Diethoxy-1-Propanol?

The IUPAC name of 3,3-Diethoxy-1-Propanol is 3,3-diethoxypropan-1-ol.

What is the InChI of 3,3-Diethoxy-1-Propanol?

The InChI of 3,3-Diethoxy-1-Propanol is InChI=1S/C7H16O3/c1-3-9-7(5-6-8)10-4-2/h7-8H,3-6H2,1-2H3.

What is the InChIKey of 3,3-Diethoxy-1-Propanol?

The InChIKey of 3,3-Diethoxy-1-Propanol is ASERXEZXVIJBRO-UHFFFAOYSA-N.