(S)-(+)-3-Hydroxytetrahydrofuran CAS 86087-23-2
Introduction：Basic information about (S)-(+)-3-Hydroxytetrahydrofuran CAS 86087-23-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
(S)-(+)-3-Hydroxytetrahydrofuran Basic information
| Product Name: | (S)-(+)-3-Hydroxytetrahydrofuran |
| Synonyms: | (S)-TETRAHYDROFURAN-3-OL;(S)-(+)-TETRAHYDRO-3-FURANOL;(S)-(+)-3-HYDROXY TETAHYDRO FURAN;(S)-(-)-3-HYDROXY TETRAHYDRO FURAN;(3S)-oxolan-3-ol;(2S)-1,4-Epoxy-2-hydroxybutane, (3S)-Tetrahydrofuran-3-ol, (3S)-Oxolan-3-ol;Afatinib intermediate B;(S)-(+)-3-Hydroxytetrahydrofuran, ee: 95% |
| CAS: | 86087-23-2 |
| MF: | C4H8O2 |
| MW: | 88.11 |
| EINECS: | 425-090-2 |
| Product Categories: | Afatinib intermediate;Chiral Building Blocks;Chiral Reagents;Furans;Simple Alcohols (Chiral);Synthetic Organic Chemistry;Alcohols, Hydroxy Esters and Derivatives;Chiral Compounds;Starting Raw Materials & Intermediates;Small molecule;Tetrahydrofuran Series;bc0001;86087-23-2;john's;ADVANCED INT.;1 |
| Mol File: | 86087-23-2.mol |
(S)-(+)-3-Hydroxytetrahydrofuran Chemical Properties
| alpha | 18.5 º (c=2 MeOH) |
| Boiling point | 80 °C/15 mmHg (lit.) |
| density | 1.103 g/mL at 25 °C (lit.) |
| vapor pressure | 47Pa at 25℃ |
| refractive index | n |
| Fp | 175 °F |
| storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
| solubility | Chloroform, Methanol (Slightly) |
| form | Liquid |
| pka | 14.49±0.20(Predicted) |
| color | Clear colorless to pale yellow |
| Specific Gravity | 1.11 |
| Optical Rotation | [α]20/D +17.5°, c = 2.4 in methanol |
| Water Solubility | soluble |
| BRN | 4652609 |
| Stability: | Stable. Combustible. Incompatible with strong oxidizing agents. |
| InChI | 1S/C4H8O2/c5-4-1-2-6-3-4/h4-5H,1-3H2/t4-/m0/s1 |
| InChIKey | XDPCNPCKDGQBAN-BYPYZUCNSA-N |
| SMILES | O[C@H]1CCOC1 |
| LogP | -0.784 at 22℃ and pH6.8 |
| Surface tension | 72mN/m at 1g/L and 25℃ |
| CAS DataBase Reference | 86087-23-2(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-37/39 |
| RIDADR | NA 1993 / PGIII |
| WGK Germany | 3 |
| HS Code | 29321900 |
| Storage Class | 10 - Combustible liquids |
| Hazard Classifications | Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| Description | (S)-(+)-3-Hydroxytetrahydrofuran (3-OH THF) is a colorless liquid with a normal boiling point of 179 °C and boiling at 88-89 °C at 17 mmHg, with density (1.087 g/cm3 at 19 °C). 3-OH THF is a useful pharmaceutical intermediate. The chiral (absolute configuration S) version of this compound is an intermediate to launched retroviral drugs. |
| Chemical Properties | Colourless Liquid |
| Uses | (S)-(+)-3-Hydroxytetrahydrofuran is a useful reagent for the preparation of pyrazolo triazin ylamine derivatives as adenosine receptor antagonists. |
| Uses | (S)-(+)-3-Hydroxytetrahydrofuran is an intermediate to the AIDS drugs amprenavir and fosamprenavir. Additionally, it has been an intermediate to developmental drug substances, such as chemotherapy agents. |
| Application | (S)-(+)-3-Hydroxytetrahydrofuran is used as a synthetic intermediate for Empagliflozin, Afatinib and GS-9669. |
| Synthesis | (S)-(+)-3-Hydroxytetrahydrofuran was prepared from the reaction of (S)-1,2,4-butanetriol under hydrochloric acid modified montmorillonite catalyst. The steps were as follows：To the heatable reactor (with stirring device), 100g (S)-1,2,4-butanetriol, 200mL toluene, 15g hydrochloric acid modified montmorillonite catalyst prepared in were added successively. The reaction was stopped after 4 h at 110°C. After the reaction is finished, it is naturally cooled to room temperature, and the obtained material is filtered to recover the catalyst. After collecting the filtrate, the remaining solvent and by-product water in the filtrate are distilled off to obtain (S)-3-hydroxytetrahydrofuran crude product. Quantitative analysis was carried out by gas chromatography, and the yield was 96.8%. Finally, the (S)-3-hydroxytetrahydrofuran was obtained by rectification and purification. |
| References | [1] Journal of Organic Chemistry, 1983, vol. 48, # 16, p. 2767 - 2769 [2] Patent: WO2007/81065, 2007, A1. Location in patent: Page/Page column 5 [3] Patent: WO2007/81065, 2007, A1. Location in patent: Page/Page column 6; 7 [4] Patent: US5576343, 1996, A |
(S)-(+)-3-Hydroxytetrahydrofuran Preparation Products And Raw materials
| Raw materials | Ethanol-->Ethyl acetate-->Methanol-->Tetrahydrofuran-->Toluene-->Lithium Aluminum Hydride-->p-Toluenesulfonic acid-->L-Malic acid-->(S)-1,2,4-Butanetriol-->(S)-4-Chloro-1,3-butanediol |
| Preparation Products | (R)-(-)-3-Hydroxytetrahydrofuran-->(S)-3-P-MESYLOXYTETRAHYDROFURAN-->(2-Chloro-5-iodophenyl)[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methanone |
