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

B20575 2,3-Dihydrofuran, 98+%

CAS Number
1191-99-7
Synonyms

Size Price ($) Quantity Availability
25g 26.10
100g 54.40
500g 221.00
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2,3-Dihydrofuran, 98+%

MDL
MFCD00003205
EINECS
214-747-7

Chemical Properties

Formula
C4H6O
Formula Weight
70.09
Boiling Point
54-55°
Flash Point
-24°(-11°F)
Density
0.927
Refractive Index
1.4245
Solubility
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.

Literature References

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):

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H302-H319

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

Precautionary Statements: P210-P280-P240-P241-P233-P303+P361+P353-P305+P351+P338-P301+P312-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Keep container tightly closed. 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. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
103168
Hazard Class
3
Packing Group
II
Harmonized Tariff Code
2932.19
TSCA
Yes

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