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.)

Flash point:

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

CAS DataBase Reference

61550-02-5(CAS DataBase Reference)

Safety Information

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

MSDS

• Language:English Provider:SigmaAldrich

2-(TRIMETHYLSILYLOXY)FURAN Usage And Synthesis

Physical properties

bp 44–46 °C/17 mmHg; d 0.93 gmL?1.

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(61550-02-5)Related Product Information

• 4,5-Dihydro-3α,4α-bis(trimethylsilyloxy)furan-2(3H)-one
• 2-(TRIMETHYLSILYLOXY)FURAN