1,3-dihydro-2-benzofuran

• ChemBase ID: 82197
• Molecular Formular: C8H8O
• Molecular Mass: 120.14852
• Monoisotopic Mass: 120.05751488
• SMILES: O1Cc2ccccc2C1
• Canonical SMILES: O1Cc2c(C1)cccc2
• InChI: InChI=1S/C8H8O/c1-2-4-8-6-9-5-7(8)3-1/h1-4H,5-6H2
• InChIKey: SFLGSKRGOWRGBR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-dihydro-2-benzofuran
• IUPAC Traditional name: phthalan
• Synonyms: 1,3-Dihydrobenzo[c]furan; 1,3-Dihydroisobenzofuran; 1,3-Dihydro-2-benzofuran; o-Xylylene oxide; Phthalan; Phthalane; 1,3-Dihydroisobenzofuran; 二氢异苯并呋喃; 1,3-二氢异苯并呋喃

Database IDs

• CAS Number: 496-14-0
• EC Number: 207-815-2
• MDL Number: MFCD00005932
• Beilstein Number: 111932
• PubChem SID: 24850604; 162069316
• PubChem CID: 10327
• Wikipedia Title: Phthalane

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.6002499
• LogD (pH = 7.4): 1.6002499
• Log P: 1.6002499
• Molar Refractivity: 36.1797 cm^3
• Polarizability: 13.970074 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 192 °C(lit.); 192°C
• Flash Point: 145.4 °F; 63 °C; 63°C(145°F)
• Density: 1.094; 1.098 g/mL at 25 °C(lit.)
• Refractive Index: 1.5460; n20/D 1.546(lit.)

Safety Information

• Storage Warning: Irritant
• German water hazard class: 3
• TSCA Listed: 否
• GHS Hazard statements: H227
• GHS Precautionary statements: P210-P280-P370+P378A-P403+P235-P501A
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: 95+%; 97%; 98%
• Empirical Formula (Hill Notation): C8H8O

DETAILS

Sigma Aldrich - 176877

Packaging
5 g in glass bottle

REFERENCES

• Treatment of phthalan with excess Li metal in the presence of 4,4'-Di-tert-butylbiphenyl, B21470, results in opening of the furan ring. Sequential introduction of two different electrophiles can be effected in the resulting bis-benzylic species, consequently phthalan can be regarded as an o-xylene dianion synthon. This approach provides a convenient access to diols and hydroxy acids which can be readily dehydrated to benzo-fused 6- or 7-membered cyclic ethers or lactones: Tetrahedron, 51, 3351 (1995); see also: J. Org. Chem., 61, 4913 (1996); Tetrahedron Lett., 39, 7759 (1998).
• For use in synthesis of nine-membered cyclic dione ethers, see: Synlett, 909 (1993).