| Identification | More | [Name]
2,5-DIPHENYLFURAN | [CAS]
955-83-9 | [Synonyms]
2,5-DIPHENYLFURAN
TIMTEC-BB SBB008172
2,5-diphenyl-fura
PPF
2,5-Diphenylfurane
2,5-Diphenylfuran,98% | [EINECS(EC#)]
213-474-0 | [Molecular Formula]
C16H12O | [MDL Number]
MFCD00037353 | [Molecular Weight]
220.27 | [MOL File]
955-83-9.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow-beige powder and chunks | [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 | [InChI]
InChI=1S/C16H12O/c1-3-7-13(8-4-1)15-11-12-16(17-15)14-9-5-2-6-10-14/h1-12H | [InChIKey]
VUPDHIIPAKIKAB-UHFFFAOYSA-N | [SMILES]
O1C(C2=CC=CC=C2)=CC=C1C1=CC=CC=C1 | [CAS DataBase Reference]
955-83-9(CAS DataBase Reference) | [EPA Substance Registry System]
Furan, 2,5-diphenyl- (955-83-9) |
| Questions And Answer | Back Directory | [Uses]
2,5-Diphenylfuran has good reactivity and multiple reaction sites, and is often used to synthesize complex organic compounds in laboratory research and development. |
| Hazard Information | Back Directory | [Chemical Properties]
yellow-beige powder and chunks | [Definition]
ChEBI: A diphenylfuran in the the phenyl groups are located at positions 2 and 5 on the furan ring. | [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. | [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. |
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