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B20575 2,3-Dihydrofuran, 98+%

CAS Number
1191-99-7
Synonyms

Stock No. Size Price ($) Quantity Availability
B20575-14 25g 28.00
B20575-22 100g 58.00
B20575-36 500g 234.00
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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
Storage & Sensitivity
Keep Cold.
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-P233-P240-P241-P242-P243-P264b-P270-P280-P301+P312-P303+P361+P353-P305+P351+P338-P330-P372-P374-P380-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. 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. Rinse mouth. Explosion risk in case of fire. Fight fire with normal precautions from a reasonable distance. Evacuate area. Dispose of contents/ container to an approved waste disposal plant

Other References

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

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