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1191-99-7 - 2,3-Dihydrofuran, 98+% - B20575 - Alfa Aesar

B20575 2,3-Dihydrofuran, 98+%

Numéro de CAS
1191-99-7
Synonymes

Conditionnement Prix ($) Quantité Disponibilité
25g 26,10
100g 54,40
500g 221,00
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2,3-Dihydrofuran, 98+%

MDL
MFCD00003205
EINECS
214-747-7

Propriétés chimiques

Formule
C4H6O
Poids moleculaire
70.09
Point d'ébullition
54-55°
Point d'éclair
-24°(-11°F)
Densité
0.927
Indice de réfraction
1.4245
Solubilité
Soluble in water at 20°C, 20g/L and chloroform.

Applications

2,3-Dihydrofuran is a versatile reagent used in lanthanide-catalyzed Diels-Alder reactions with 2-pyrones and in Rh(II)-stabilized cycloadditions with vinylcarbenoids. It is applied for alkylation by active methylene compounds, catalyzed by trans-Dichlorobis(triphenyl­phosphine)­palladium(II). It is also used in the preparation of biologically active compounds such as antitumor agents.

Notes

Store away from oxidizing agents and air. Keep the container tightly closed and place it in a cool, dry and well ventilated condition. Protect from heat. Keep it refrigerated.

Références bibliographiques

Ulrike Kohlweyer, et al. Tetrahydrofuran degradation by a newly isolated culture of Pseudonocardia sp. strain K1.FEMS Microbiol. Lett.2000,186301-306.

Fumiyuki Ozawa, et al. Catalytic asymmetric arylation of 2,3-dihydrofuran with aryl triflates.J. Am. Chem. Soc.,1991,113(4), 1417-1419.

For lithiation at the 5-position, see: Tetrahedron Lett., 4187 (1977); Org. Synth. Coll., 9, 530 (1998). For alkylation by active methylene compounds, catalyzed by trans-Dichlorobis(triphenyl­phosphine)­palladium(II)­, 10491, see: J. Org. Chem., 47, 2812 (1982). For catalytic asymmetric arylation, see: J. Am. Chem. Soc., 113, 1417 (1991); Pure Appl. Chem., 64, 421 (1992).

Forms tetrahydrofuranyl esters (acyl hemiacetals) with carboxylic acids. These react with Grignard reagents to give good yields of ketones with minimal enolization or double addition (tertiary alcohol formation). The utility of other acyl hemiacetals as ketone precursors has also been studied: J. Org. Chem., 61, 6071 (1996):

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H225-H302-H319

Highly flammable liquid and vapour. Harmful if swallowed. Causes serious eye irritation.

Mentions de prudence: P210-P280a-P240-P303+P361+P353-P305+P351+P338-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves and eye/face protection. Ground/bond container and receiving equipment. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
103168
Classe de danger
3
Groupe d'emballage
II
Code tarifaire harmonisé
2932.19
TSCA
Yes

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Catalyseurs

Analytique et matériel de laboratoire