3-Hydroxytetrahydrofuran

Product Name3-Hydroxytetrahydrofuran
CAS453-20-3
MFC4H8O2
MW88.11
EINECS207-219-2
MOL File453-20-3.mol

Chemical Properties

Melting point	25°C
Boiling point	181 °C (lit.)
Density	1.09 g/mL at 25 °C (lit.)
vapor pressure	760 mm Hg ( 181 °C)
refractive index	n20/D 1.45(lit.)
Flash point	178 °F
storage temp.	Sealed in dry,Room Temperature
pka	14.49±0.20(Predicted)
form	Liquid
color	Clear colorless to yellow
Specific Gravity	1.090
Water Solubility	500g/L(room temperature)
Stability	Stable. Incompatible with strong oxidizing agents, acid chlorides, acid anhydrides.
InChI	1S/C4H8O2/c5-4-1-2-6-3-4/h4-5H,1-3H2
InChIKey	XDPCNPCKDGQBAN-UHFFFAOYSA-N
SMILES	OC1CCOC1
LogP	-0.830 (est)
CAS DataBase Reference	453-20-3(CAS DataBase Reference)
NIST Chemistry Reference	Tetrahydrofuran, 3-hydroxy-(453-20-3)
EPA Substance Registry System	3-Furanol, tetrahydro- (453-20-3)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38-19
Safety Statements	26-36-37/39
WGK Germany	3
RTECS	LU3450050
TSCA	TSCA listed
HS Code	29321900
Storage Class	10 - Combustible liquids
Hazard Classifications	Eye Irrit. 2

MSDS

Provider	Language
3-Hydroxytetrahydrofuran	English
SigmaAldrich	English
ACROS	English

Usage And Synthesis

Chemical Properties

light yellow liquid

Uses

3-Hydroxytetrahydrofuran features two distinct hydrogen bonding sites. The compound serves as a theoretical model for nucleotide ring conformations and is used in spectroscopic studies, including Fourier transform microwave analysis of its water complex isotopomers[5][6]. For spectroscopic characterization, the material is incorporated into supersonic expansions after warming to 50 °C[5].

Synthesis

3068-00-6

453-20-3

The general procedure for the synthesis of 3-hydroxytetrahydrofuran from 1,2,4-butanetriol is as follows: 1,2,4-butanetriol is mixed with an equal volume of dioxane as a solvent in a batch reactor and a strongly acidic ion-exchange resin containing sulfonic acid groups (Amberlyst 15, in the H+ form) is added as a catalyst. The reaction was carried out at 100 °C for 20 h at atmospheric pressure. Upon completion of the reaction, the yield of 3-hydroxytetrahydrofuran was 96 mol%.

References

[1] Patent: WO2005/121111, 2005, A1. Location in patent: Page/Page column 33
[2] Patent: WO2007/81065, 2007, A1. Location in patent: Page/Page column 6
[3] Patent: WO2005/121111, 2005, A1. Location in patent: Page/Page column 31; 34
[4] Patent: WO2005/121111, 2005, A1. Location in patent: Page/Page column 33-34
[5] Lavrich, R. J., Torok, C. R., & Tubergen, M. J. (2001). A Microwave Spectroscopic Investigation of the Networked Structure of 3-Hydroxytetrahydrofuran-H₂O. The Journal of Physical Chemistry A, 105(36), 8317–8322. https://doi.org/10.1021/jp011437b
[6] Lavrich, R. J., Rhea, R. L., McCargar, J. W., Tubergen, M. J. (2000). Rotational Spectroscopy and Ring-Puckering Conformation of 3-Hydroxytetrahydrofuran. Journal of Molecular Spectroscopy, 199(1), 138–143. https://doi.org/10.1006/jmsp.1999.8002

3-Hydroxytetrahydrofuran

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