2,5-Diphenylfuran Property

Melting point:

86-90 °C

Boiling point:

345 °C

Density 

1.0588 (rough estimate)

refractive index 

1.5800 (estimate)

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Light yellow

BRN 

146933

CAS DataBase Reference

955-83-9(CAS DataBase Reference)

EPA Substance Registry System

Furan, 2,5-diphenyl- (955-83-9)

Safety

Risk Statements 

36/37/38

Safety Statements 

24/25

HS Code 

29321900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2,5-Diphenylfuran Chemical Properties,Usage,Production

Chemical Properties

yellow-beige powder and chunks

Preparation

2,5-Diphenylfuran Synthesis: Using the batch general procedure, commercially available trans,trans-1,4-diphenyl-1,3-butadiene (1) (412 mg, 2.00 mmol) and rose Bengal disodium salt (6 mg, 0.005 mmol) in 19:1 CH?Cl?/MeOH (60 mL) provided the intermediate endoperoxide, 3,6-diphenyl-3,6-dihydro-1,2-dioxine (3), as a colorless solid after column chromatography (308 mg, 1.30 mmol, 65%); R_f = 0.15 (9/1 hexanes/ethyl acetate).
1H NMR (CDCl?, 500 MHz): δ 7.77 (d, 4H, J = 8.0 Hz), 7.43 (t, 4H, J = 7.5 Hz), 7.29 (t, 2H, J = 7.5 Hz), 6.75 (s, 2H).
13C {1H} NMR (CDCl?, 126 MHz): δ 137.7, 128.8, 128.7, 128.5, 127.5, 80.3.
Using the general batch procedure and 3 (120 mg, 0.50 mmol), PPh? (144 mg, 0.55 mmol), and CBr? (182 mg, 0.55 mmol), 2,5-Diphenylfuran was obtained as a colorless solid after column chromatography (112 mg, 0.50 mmol, 99%); R_f = 0.40 (9/1 hexanes/ethyl acetate).
1H NMR (CDCl?, 500 MHz): δ 7.77 (d, 4H, J = 7.3 Hz), 7.43 (t, 4H, J = 7.5 Hz), 7.29 (t, 2H, J = 7.5 Hz), 6.76 (s, 2H).
13C {1H} NMR (CDCl?, 126 MHz): δ 153.4, 130.9, 128.8, 127.4, 123.8, 107.3.
IR (ν_max, cm?1): 2980, 1662, 1600, 1587, 1508, 1479, 1447, 1386.

Definition

ChEBI: 2,5-diphenylfuran is a diphenylfuran in the the phenyl groups are located at positions 2 and 5 on the furan ring.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 3475, 1989 DOI: 10.1021/jo00275a039

References

[1] HELENA F. GRANTHAM, MARC C. KIMBER* Transition-Metal-Free Continuous-Flow Synthesis of 2,5-Diaryl Furans: Access to Medicinal Building Blocks and Optoelectronic Materials[J]. The Journal of Organic Chemistry, 2023, 89 1: 484-497. DOI:10.1021/acs.joc.3c02237.
[2] EBERHARDT M K. Formation of cis-1,2-dibenzoylethylene from 2,5-diphenylfuran by Fenton’s reagent and by peroxydisulfate. Effect of oxygen[J]. The Journal of Organic Chemistry, 1993, 58 2: 497-498. DOI:10.1021/jo00054a038.
[3] HU SHENG-LI. Synthesis, Crystal Structure and Binding Properties of a New Fluorescent Molecular Clip Based on 2,5-diphenylfuran[J]. Journal of Chemical Research-s, 2013, 1 1: 210-212. DOI:10.3184/174751913X13626742215922.
[4] DR. LEONID V. ROMASHOV. Atom-economic Approach to the Synthesis of α-(Hetero)aryl-substituted Furan Derivatives from Biomass[J]. Chemistry - An Asian Journal, 2021, 17 1. DOI:10.1002/asia.202101227.