1,3-diphenyl-2-benzofuran

• ChemBase ID: 146810
• Molecular Formular: C20H14O
• Molecular Mass: 270.32456
• Monoisotopic Mass: 270.10446507
• SMILES: c1ccc(cc1)c1c2ccccc2c(o1)c1ccccc1
• Canonical SMILES: c1ccc(cc1)c1oc(c2c1cccc2)c1ccccc1
• InChI: InChI=1S/C20H14O/c1-3-9-15(10-4-1)19-17-13-7-8-14-18(17)20(21-19)16-11-5-2-6-12-16/h1-14H
• InChIKey: ZKSVYBRJSMBDMV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-diphenyl-2-benzofuran
• IUPAC Traditional name: 1,3-diphenyl-2-benzofuran
• Synonyms: 1,3-Diphenyl-2-benzofuran; 2,5-Diphenyl-3,4-benzofuran; 1,3-Diphenylisobenzofuran; 1,3-Diphenylbenzo[c]furan; 1,3-Diphenylisobenzofuran; 1,3-联苯基异香豆酮; 2,5-二苯基-3,4-苯并呋喃; 1,3-二苯基异苯并呋喃; 1,3-联苯基异苯并呋喃

Database IDs

• CAS Number: 5471-63-6
• EC Number: 226-808-5
• MDL Number: MFCD00005931
• Beilstein Number: 199922
• PubChem SID: 162241002; 24866953; 24846701
• PubChem CID: 21649

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 5.237421
• LogD (pH = 7.4): 5.237421
• Log P: 5.237421
• Molar Refractivity: 85.049 cm^3
• Polarizability: 37.050076 Å^3
• Polar Surface Area: 13.14 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 128-130 °C(lit.); 130-132 °C; 133-136°C

Safety Information

• Storage Warning: Air & Light Sensitive
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥95.0% (HPLC); 97%
• Grade: purum
• Empirical Formula (Hill Notation): C20H14O

DETAILS

Sigma Aldrich - 105481

Packaging
1, 5 g in glass bottle

REFERENCES

• Reactive diene, particularly useful for trapping unstable alkenes and alkynes, e.g. benzyne from the action of Mg on 1-bromo-2-fluorobenzene in 85% yield: Liebigs Ann. Chem., 630, 10 (1960), or a highly-strained cyclopropene: J. Org. Chem., 57, 5959 (1992).
• Highly efficient agent for trapping singlet oxygen, as its endo-peroxide, and has been used as a standard for this purpose: J. Am. Chem. Soc., 93, 5774 (1971).
• Reaction temperatures with conventional dienophiles can be reduced in the presence of BF₃ etherate. For use in the addition to vinylphosphonic esters, see: J. Chem. Soc., Perkin 1, 99 (1988).
• For reviews of the chemistry of 1,3-diphenylisobenzofuran, see: Adv. Het. Chem., 26, 135 (1980); Tetrahedron, 44, 2093 (1988).