3-Methyl-3-oxetanemethanol Chemical Properties

Boiling point:

80 °C/40 mmHg (lit.)

Density 

1.024 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.446(lit.)

Flash point:

210 °F

storage temp. 

2-8°C

solubility 

Soluble in chloroform, methanol.

form 

Liquid

pka

14.58±0.10(Predicted)

Specific Gravity

1.024

color 

Clear colorless to pale yellow

BRN 

102773

InChI

InChI=1S/C5H10O2/c1-5(2-6)3-7-4-5/h6H,2-4H2,1H3

InChIKey

NLQMSBJFLQPLIJ-UHFFFAOYSA-N

SMILES

O1CC(C)(CO)C1

CAS DataBase Reference

3143-02-0(CAS DataBase Reference)

NIST Chemistry Reference

3-Methyl-3-oxetanemethanol(3143-02-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

43

Safety Statements 

23-24/25-36/37

WGK Germany 

3

HS Code 

29329990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Methyl-3-oxetanemethanol Usage And Synthesis

Chemical Properties

Clear colorless to pale yellow liquid

Uses

3-Methyl-3-oxetanemethanol has been used in the preparation of star-shaped copolymer consisting of a hyperbranched poly(3-methyl-3-oxetanemethanol) core and polytetrahydrofuran arms, pyridyl disulfide-functionalized cyclic carbonate monomer, required for the synthesis of of functional poly(ε-caprolactone) containing pendant pyridyl disulphide groups and δ-lactams. It is used to synthesize octahydroindole alkaloids and γ-butenolides.

Definition

ChEBI: (3-Methyl-3-oxetanyl)methanol is a 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-ol.

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 5571, 1983 DOI: 10.1016/S0040-4039(00)94143-1

Synthesis

In a three-necked flask equipped with a stirrer, a reflux condenser and a thermometer, 215 mL of diethyl carbonate, 180 g of trimethylolpropane, and an appropriate amount of KOH were added.The mixture was heated with stirring to 115° C. and kept at reflux for 1 hr. The by-product alcohol was collected via a reflux distillation unit. Continued heating of the reaction mixture and subsequent distillation to collect the 205-210 °C fractions afforded the target product 3-hydroxymethyl-3-methoxybutane (2) in a total amount of 128.2 g in 83.7% yield. The structure of the product was confirmed by 1HNMR (Figure 2).

Purification Methods

Purify the oxetane by fractionation through a glass column [Pattison J Am Chem Soc 79 3455 1957, Corey et al. J Am Chem Soc 106 2736 1984]. [Beilstein 17 III/IV 1128.]

Structure and conformation

Sun et al. found that the microsolvation effects influence the conformation of the 3-methyl-3-oxetanemethanol geometry. The hydrogen-bond arrangements in the hydrate complexes, governed by the water-water and water-solute interactions, exhibit characteristic configurations with an increasing number of water molecules and resemble the main isomers of the corresponding pure water clusters. In the jet expansion, two conformations are adopted by the 3-Methyl-3-oxetanemethanol (MOM) monomer, namely gauche- and cis-O4C1C6O7. As the cis conformer provides a better interaction space, most observed MOM-water clusters are formed with the cis conformation, even though the gauche conformer is energetically favored. Starting with the MOM monohydrate and dihydrate, 1D H-bonded chains are formed between the two oxygen atoms of MOM. The interplay between the MOM conformation and the water chain is observed. For the MOM trihydrate and tetrahydrate, 2D H-bonded rings are more favored than the 1D chain, restricted by the space between the two MOM oxygen atoms[1].

References

[1] Dr. Wenhao Sun, Prof. Dr. Melanie Schnell. “Microhydrated 3-Methyl-3-oxetanemethanol: Evolution of the Hydrogen-Bonding Network from Chains to Cubes.” Angewandte Chemie 134 49 (2022).

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