Galvinoxyl

Galvinoxyl
Names
	Preferred IUPAC name 4-[(3,5-Di-tert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-2,6-di-tert-butylphenoxyl
Identifiers
CAS Number	2370-18-5;
3D model (JSmol)	Interactive image;
ChemSpider	52083310;
ECHA InfoCard	100.017.395
EC Number	219-133-2;
PubChem CID	2723634;
UNII	W07Q6T5546;
CompTox Dashboard (EPA)	DTXSID401015731 ;
	InChI InChI=1S/C29H41O2/c1-26(2,3)20-14-18(15-21(24(20)30)27(4,5)6)13-19-16-22(28(7,8)9)25(31)23(17-19)29(10,11)12/h13-17H,1-12H3 Key: GNZDAXRYGVFYPU-UHFFFAOYSA-N;
	SMILES CC(C)(C)C1=CC(=CC(=C1[O])C(C)(C)C)C=C2C=C(C(=O)C(=C2)C(C)(C)C)C(C)(C)C;
Properties
Chemical formula	C29H41O2
Molar mass	421.645 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Galvinoxyl is a commercially available radical scavenger.^[1] It finds use both as a probe for studying radical reactions and as an inhibitor of radical polymerization. It may be synthesized by oxidation of the parent phenol with lead dioxide or potassium hexacyanoferrate(III). Its radical structure is confirmed by the loss of the O–H stretch in the IR spectrum and by electron spin resonance; it is stable even in the presence of oxygen.^[2]^[3]

References

^ RajanBabu, T. V. (2001). "Galvinoxyl". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rg001.
^ Coppinger, Galvin M. (1957). "A Stable Phenoxy Radical Inert to Oxygen". J. Am. Chem. Soc. 79 (2): 501. doi:10.1021/ja01559a073.
^ Kharasch, M. S.; Joshi, B. S. (1957). "Reactions of Hindered Phenols. II. Base-Catalyzed Oxidations of Hindered Phenols". J. Am. Chem. Soc. 22 (11): 1439. doi:10.1021/jo01362a034.