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496-14-0 - Phthalan, 98% - 1,3-Dihydrobenzo[c]furan - 1,3-Dihydroisobenzofuran - A10217 - Alfa Aesar

A10217 Phthalan, 98%

CAS Number
496-14-0
Synonyms
1,3-Dihydrobenzo[c]furan
1,3-Dihydroisobenzofuran

Size Price ($) Quantity Availability
5g 37.68
25g 141.74
100g 400.00
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Phthalan, 98%

MDL
MFCD00005932
EINECS
207-815-2

Chemical Properties

Formula
C8H8O
Formula Weight
120.15
Boiling Point
192°
Flash Point
63°(145°F)
Density
1.094
Refractive Index
1.5460
Solubility
Low aqueous solubility.

Applications

Phthalan is used in the synthesis of nine-membered cyclic dione ethers. It is used along with excess Li metal in the presence of 4,4'-Di-tert-butyl­biphenyl­, B21470, results in opening of the furan ring. It is used in the synthesis of functionalized benzylic alcohols.

Notes

Store away from oxidizing agents. Store in a cool, dry condition in well sealed containers.

Literature References

Katsuhiko Tomooka; Lan-Fang Wang; Fumiaki Okazaki; Takeshi Nakai. External chiral ligand-induced enantioselective lithiation/SE2 reactions of isochroman and phthalan. Tetrahedron Letters. 2000, 41 6121-6125.

Bondoc E.; Sakurai S.; Morris K.; Chiang WY.; Laane J. Fluorescence and electronic absorption spectra of phthalan: Two-dimensional vibrational potential energy surface for the ring-puckering and flapping in the S-1(pi,pi(*)) state. Journal of Chemical Physics. 2000, 112 (15), 6700-6706.

For use in synthesis of nine-membered cyclic dione ethers, see: Synlett, 909 (1993).

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).

GHS Hazard and Precautionary Statements

Hazard Statements: H227

Combustible liquid.

Precautionary Statements: P210-P280-P370+P378a-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. In case of fire: Use for extinction: CO2, powder or water spray. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
111932
Harmonized Tariff Code
2932.99
TSCA
No

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