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335274

Sigma-Aldrich

2,2-Dimethyl-3(2H)-furanone

96%

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Empirical Formula (Hill Notation):
C6H8O2
CAS Number:
Molecular Weight:
112.13
MDL number:
PubChem Substance ID:

assay

96%

form

liquid

refractive index

n20/D 1.455 (lit.)

bp

46-47 °C/18 mmHg (lit.)

density

1.027 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC1(C)OC=CC1=O

InChI

1S/C6H8O2/c1-6(2)5(7)3-4-8-6/h3-4H,1-2H3

InChI key

HVNICCSXGONRCB-UHFFFAOYSA-N

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This Item
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2,2-Dimethyl-3(2H)-furanone 96%

335274

2,2-Dimethyl-3(2H)-furanone

2,2-Dimethyl-1,3-dioxolan-4-one 96%

541389

2,2-Dimethyl-1,3-dioxolan-4-one

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

-

form

liquid

form

-

form

solid

form

-

refractive index

n20/D 1.455 (lit.)

refractive index

n20/D 1.541 (lit.)

refractive index

-

refractive index

n20/D 1.415 (lit.)

density

1.027 g/mL at 25 °C (lit.)

density

1.101 g/mL at 25 °C (lit.)

density

-

density

0.989 g/mL at 25 °C (lit.)

bp

46-47 °C/18 mmHg (lit.)

bp

-

bp

-

bp

41 °C (lit.)

General description

2,2-Dimethyl-3(2H)-furanone is an β-oxo enol ether. Conjugate addition of 2,2-dimethyl-3(2H)-furanone to organocuprates has been reported. Photoannelation of alkenes to 2,2-dimethyl-3(2H)-furanone yields cyclohexenone.

Application

2,2-Dimethyl-3(2H)-furanone was used in the synthesis of epoxides via epoxidation. It was also used in the preparation of racemic methyl nonactate.

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Dimethyldioxirane epoxidation of ?-oxo enol ethers.
Adam W and Hadjiarapoglou L.
Chemische Berichte, 123(10), 2077-2079 (1990)
Conjugated Addition to 2, 2-Dimethyl-3 (2h)-furanone: Support for the Baldwin Rules for Ring Closure.
Smith AB and Jerris PJ.
Synthetic Communications, 8(7), 421-426 (1978)
Cyclohexenones by the photoannelation of alkenes with 2, 2-dimethyl-3 (2H)-furanone.
Baldwin SW and Wilkinson JM.
Tetrahedron Letters, 20(29), 2657-2660 (1979)
Stereoselective synthesis of (.+-.) methyl nonactate.
Baldwin SW and McIver JM.
The Journal of Organic Chemistry, 52(2), 320-322 (1987)

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