Title: Galvinoxyl
CAS Registry Number: 2370-18-5
CAS Name: 4-[[3,5-Bis(1,1-dimethylethyl)-4-oxo-2,5-cyclohexadien-1-ylidene]methyl]-2,6-bis(1,1-dimethylethyl)phenoxy
Additional Names: Coppinger's radical; 2,6-di-tert-butyl-a-(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadiene-1-ylidene)-p-tolyloxy radical; 2,6,3¢,5¢-tetra-tert-butyl-4¢-phenoxy-4-methylene-2,5-cyclohexadiene-1-one radical
Molecular Formula: C29H41O2
Molecular Weight: 421.63
Percent Composition: C 82.61%, H 9.80%, O 7.59%
Literature References: Stable phenoxyl radical. Prepn: G. M. Coppinger, J. Am. Chem. Soc. 79, 501 (1957); M. S. Kharasch, B. S. Joshi, J. Org. Chem. 22, 1435 (1957). Radical scavenging study: P. D. Bartlett, T. Funahashi, J. Am. Chem. Soc. 84, 2596 (1962). Electrical properties: D. D. Eley et al., Trans. Faraday Soc. 62, 3192 (1966). Structure determn: D. E. Williams, Mol. Physics 16, 145 (1969). Resonance Raman study: G. N. R. Tripathi, Chem. Phys. Lett. 81, 375 (1981). Theoretical study of magnetic interactions: F. Dietz et al., J. Phys. Chem. B 102, 3912 (1998). Ab initio studies of ferromagnetic properties: S. J. Luo, K. L. Yao, J. Magn. Magnet. Mater. 257, 11 (2003). Use in detection of phospholipid phase transitions: M. A. Singer et al., Anal. Biochem. 94, 322 (1979). Use in measurement of hydrogen-donating activity and antioxidant activity in phenols: H. Shi et al., Methods Enzymol. 335, 157 (2001).
Properties: Deep blue needles from absolute ethanol, mp 157.5° (Kharasch, Joshi). Also reported as dark blue needles from dry ethanol, mp 153° (Eley). Absorption max (iso-octane): 280, 289, 400, 423 nm (e ´103 9.39, 9.4, 24.3, 180.0). Absorption max (benzene): 407 nm, 431 nm (e 30000, 154000). Absorption max (ethanol): 428 nm. Sol in petr ether, benzene, cyclohexane.
Melting point: mp 157.5° (Kharasch, Joshi); mp 153° (Eley)
Absorption maximum: Absorption max (iso-octane): 280, 289, 400, 423 nm (e ´103 9.39, 9.4, 24.3, 180.0); Absorption max (benzene): 407 nm, 431 nm (e 30000, 154000); Absorption max (ethanol): 428 nm
Use: Free radical scavenger. |