| Identification | Back Directory | [Name]
TETRAHYDRO-3-FURANMETHANOL | [CAS]
15833-61-1 | [Synonyms]
3-Hydroxymethyl-THF
RARECHEM AL BD 0888
(3-Oxolanyl)Methanol
Tetrahydro-3-furanmethano
3-tetrahydrofuranmethanol
TETRAHYDRO-3-FURANMETHANOL
3-FuranMethanol,tetrahydro-
Tetrahydrofuran-3-ylmetha...
Tetrahydrofuranyl-3-methanol
Tetrahydro-3-furanylmethanol
(TETRAHYDROFURAN-3-YL)METHANOL
3-Hydroxymethyltetrahydrofuran
Tetrahydro-3-furanMethanol
3-(Hydroxymethyl)tetrahydrofuran (inhibited)
TETRAHYDRO-3-FURANMETHANOL ISO 9001：2015 REACH
Tetrahydro-3-furanMethanol contains 250 ppM BHT as inhibitor, 99% | [EINECS(EC#)]
629-195-6 | [Molecular Formula]
C5H10O2 | [MDL Number]
MFCD00075198 | [MOL File]
15833-61-1.mol | [Molecular Weight]
102.13 |
| Chemical Properties | Back Directory | [Boiling point ]
76-77 °C4 mm Hg(lit.)
| [density ]
1.061 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.456(lit.)
| [Fp ]
208 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
liquid | [pka]
14.81±0.10(Predicted) | [color ]
Colourless | [InChI]
1S/C5H10O2/c6-3-5-1-2-7-4-5/h5-6H,1-4H2 | [InChIKey]
PCPUMGYALMOCHF-UHFFFAOYSA-N | [SMILES]
OCC1CCOC1 |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/37/38 | [Safety Statements ]
26-37/39 | [WGK Germany ]
3
| [HS Code ]
29321900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless viscous liquid | [General Description]
Tetrahydro-3-furanmethanol was the main product formed during hydrolysis of 1,3-dioxolane compounds. | [Synthesis]
1) To a 500 mL four-necked reaction flask was added 152 g of diethyl malonate (0.95 mol) and 27.6 g of an isopropanol solution of 20% sodium isopropoxide (sodium isopropoxide content was 20%), and the reaction temperature was maintained at 25°C to 28°C. 46.5 g of 2-bromoethanol (0.372 mol) was started to be added dropwise, and then the temperature was raised to 50°C and the reaction was kept at a constant temperature for 1.5 h. After the reaction was completed, the solvent was removed by a rotary evaporator at less than 75°C and the reaction was completed. Upon completion of the reaction, the solvent was removed by rotary evaporator at less than 75°C to give diethyl 2-hydroxyethylmalonate, a colorless oily liquid with 97% purity (GC) and 94% yield.
2) To a 500 mL four-neck reaction flask was added 66.7 g of diethyl 2-hydroxyethyl malonate (0.317 mol) and 76.1 g of 20% sodium hydroxide solution, heated to 45°C, and reacted for 2 hours. After cooling to 25°C, 20% hydrochloric acid was added to adjust the pH to 6-7, then evaporated under reduced pressure at 80°C and filtered to obtain a colorless oily liquid 2-hydroxyethylmalonic acid 47.4 g (0.305 mol), purity 95% (GC), yield 96%.
3) To an autoclave was added 47.4 g of 2-hydroxyethylmalonic acid (0.305 mol), 50 g of water and 2.3 g of Cu/SiO2 catalyst. After purging the reaction vessel with nitrogen for 3-5 times, the reaction was carried out at 240°C for 4 hours. Upon completion of the reaction, the catalyst was removed by filtration to afford 36.2 g (0.280 mol) of 2-hydroxymethyl-1,4-butanediol as a colorless or light yellow oil with 96% purity (GC) and 95% yield.
4) To a 500 mL reaction flask equipped with a reflux condenser was added 36.2 g of 2-hydroxymethyl-1,4-butanediol (0.280 mol), 150 g of toluene and 1.6 g of methanesulfonic acid. After completion of the reaction, the solvent was removed by distillation under reduced pressure to afford 25.2 g (S)-tetrahydrofuran-3-methanol (0.192 mol) as a pale yellow oil with 95% purity (GC) and 86% yield. | [References]
[1] Patent: CN105254598, 2016, A. Location in patent: Paragraph 0007; 0022
[2] Patent: CN103709126, 2018, B. Location in patent: Paragraph 0029; 0035; 0036; 0044
[3] Patent: CN104193701, 2016, B. Location in patent: Paragraph 0023 |
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