2,3-dihydrofuran

• ChemBase ID: 85864
• Molecular Formular: C4H6O
• Molecular Mass: 70.08984
• Monoisotopic Mass: 70.04186481
• SMILES: O1C=CCC1
• Canonical SMILES: C1CC=CO1
• InChI: InChI=1S/C4H6O/c1-2-4-5-3-1/h1,3H,2,4H2
• InChIKey: JKTCBAGSMQIFNL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-dihydrofuran
• IUPAC Traditional name: 2,3-dihydrofuran
• Synonyms: 2,3-DHF; 2,3-Dihydrofuran; 2,3-Dihydrofuran; 4,5-Dihydrofuran; NSC 85221; 2,3-二氢呋喃

Database IDs

• CAS Number: 1191-99-7
• EC Number: 214-747-7
• MDL Number: MFCD00003205
• Beilstein Number: 103168
• PubChem SID: 162072980; 24863187; 24851953
• PubChem CID: 70934
• CHEBI ID: 51662
• Chemspider ID: 64096
• Wikipedia Title: 2,3-Dihydrofuran

CALCULATED PROPERTIES

• LogD (pH = 7.4): 0.542326
• Log P: 0.542326
• Molar Refractivity: 20.6466 cm^3
• Polarizability: 7.817887 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.542326

PROPERTIES

Physical Property

• Boiling Point: 54°C; 54.6°C (source); 54-55 °C(lit.); 54-55°C; 54-55°C
• Flash Point: -20 °C; -24.4°C; -24°C(-11°F); -4 °F
• Density: 0,927 g/mL; 0.927; 0.927 g/ml; 0.927 g/mL at 25 °C(lit.)
• Refractive Index: 1.4245; n20/D 1.423; n20/D 1.423(lit.)
• Vapor Pressure: 14.46 psi ( 55 °C); 3.67 psi ( 20 °C)

Safety Information

• Storage Condition: 2-8°C
• Storage Warning: Irritant
• European Hazard Symbols: Flammable (F); X
• UN Number: 1993; UN3271
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Australian Hazchem: 3YE
• Risk Statements: 11-19; 11-19-22-36; R:11
• Safety Statements: 16-33; 9-16-26-33-36; S:9-16-29
• EU Classification: F1
• EU Hazard Identification Number: 3B
• Emergency Response Guidebook(ERG) Number: 128
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H225; H225-H301-H319
• GHS Precautionary statements: P210; P210-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1993 3/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99%; ≥99.0% (GC); 97%; 98+%; 99%
• Grade: purum
• Contains: ~0.5% potassium carbonate as stabilizer
• Empirical Formula (Hill Notation): C4H6O

DETAILS

MP Biomedicals - 05221761

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02157728

1 ml = approx. 0.93 g

Toronto Research Chemicals - D446410

2,3-Dihydrofuran is a dehydration product of tetrahydrofuran (THF). 2,3-Dihydrofuran is also used in the preparation of niologically active compounds such as antitumor agents.

Sigma Aldrich - 37298

Other Notes
α-Lithiation/alkylation en route to γ-keto acids1

Sigma Aldrich - 200018

Packaging
1 L in glass bottle
100 mL in glass bottle
Application
Versatile reagent used in lanthanide-catalyzed Diels-Alder reactions with 2-pyrones1,2 and in Rh(II)-stabilized cycloadditions with vinylcarbenoids.3

Sigma Aldrich - 482080

Legal Information
Manufactured by Eastman Chemical Company. Distributed by Aldrich Chemical Company.

REFERENCES

• Kohlweyer, U. et al.: FEMS Microbiol. Lett., 186, 301 (2000)
• Li, J. et al.: Lett. Drug Design Disc., 9, 379 (2000)
• 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):