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| | 2-(Trimethylsilyloxy)furan Basic information |
| | 2-(Trimethylsilyloxy)furan Chemical Properties |
| Boiling point | 34-35 °C/9 mmHg (lit.) | | density | 0.929 g/mL at 25 °C (lit.) | | refractive index | n20/D 1.436(lit.) | | Fp | 76 °F | | storage temp. | -20°C | | solubility | sol most organic solvents, e.g. CH2Cl2, Et2O, benzene,
THF, MeCN. | | form | clear liquid | | color | Colorless to Light orange to Yellow | | Specific Gravity | 0.950 | | Hydrolytic Sensitivity | 7: reacts slowly with moisture/water | | BRN | 1423066 | | InChI | 1S/C7H12O2Si/c1-10(2,3)9-7-5-4-6-8-7/h4-6H,1-3H3 | | InChIKey | ILBCDLOQMRDXLN-UHFFFAOYSA-N | | SMILES | C[Si](C)(C)Oc1ccco1 | | CAS DataBase Reference | 61550-02-5(CAS DataBase Reference) |
| Hazard Codes | F,Xi | | Risk Statements | 11-36/37/38 | | Safety Statements | 26 | | RIDADR | UN 1993 3/PG 2 | | WGK Germany | 3 | | F | 10-21 | | TSCA | No | | HS Code | 2932.19.5100 | | HazardClass | 3.2 | | PackingGroup | III | | Storage Class | 3 - Flammable liquids | | Hazard Classifications | Eye Irrit. 2
Flam. Liq. 2
Skin Irrit. 2
STOT SE 3 |
| | 2-(Trimethylsilyloxy)furan Usage And Synthesis |
| Physical properties | bp 44–46 °C/17 mmHg; d 0.93 gmL1. | | Uses | 2-Trimethylsilyloxyfuran provides 5-substituted 2(5H)-furanones by alkylation, aldolization,
3 and conjugate addition; transforms quinones into furo-[3,2-b]benzofurans; useful for the four-carbon elongation of sugars. It is used in Synthetic Applications, Carbon–Heteroatom Bond Formation, Alkylation, Aldol-Type Reactions, Conjugate Addition, and Diels–Alder Reaction. | | Uses | 2-(Trimethylsilyloxy)furan is a useful reagent for the preparation of natural and synthetic furanones with anticancer activity. | | Preparation | Accessible by silylation of 2(5H)-furanone, which is obtained at very low cost by oxidation of furfural. | | Purification Methods | Fractionally distil it using a short path column. 1H NMR in CCl4 has : 4.90 (dd, J 1.3Hz, 3H), 6.00 (t, J 3Hz, 4H) and 6.60 (m, 5H). [Yoshii et al. Heterocycles 4 1663 1976.] 4-Trimethylsilyloxy-3-penten-2-one (cis) (acetylacetone enol trimethylsilyl ether) [13257-81-3] M 172.3, b 66-68o/4mm, 61-63o/5mm, d 4 0.917, n D 1.452. Fractionally distil it and store it in glass ampoules which are sealed under N2. It hydrolyses readily in contact with moisture giving, as likely impurities, hexamethyldisiloxane and 2,4-pentanedione. [West J Am Chem Soc 80 3246 1958, Beilstein 4 IV 4003.] |
| | 2-(Trimethylsilyloxy)furan Preparation Products And Raw materials |
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