2,6-Di-tert-butylphenol is an organic compound with the structural formula 2,6-((CH3)3C)2C6H3OH. This colorless solid alkylated phenol and its derivatives are used industrially as UV stabilizers and antioxidants for hydrocarbon-based products ranging from petrochemicals to plastics. Illustrative of its usefulness, it prevents gumming in aviation fuels.
|Preferred IUPAC name
Ethyl AN 701
Irganox L 140
3D model (JSmol)
|UN number||2430, 3077|
CompTox Dashboard (EPA)
|Molar mass||206.329 g·mol−1|
|Appearance||Low-melting colourless solid|
|Melting point||34 to 37 °C (93 to 99 °F; 307 to 310 K)|
|Boiling point||253 °C (487 °F; 526 K)|
|GHS Signal word||Warning|
|H315, H319, H400, H410|
|P264, P273, P280, P302+352, P305+351+338, P321, P332+313, P337+313, P362, P391, P501|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
- C6H5OH + 2 CH2=C(CH3)2 → ((CH3)3C)2C6H3OH
Its dominant use is as an antioxidant.
2,6-di-tert-butylphenol is a precursor to more complex compounds used as antioxidants and light-protection agents for the stabilization for polymers. Of particular note is methyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate (CAS# 6386-38-5), which is formed by the Michael addition of methyl methacrylate. This compound is used as a feedstock in the synthesis of more complex antioxidants such as Irganox 1098. 2,6-Di-tert-butylphenol is also used in the synthesis of CGP-7930, probucol, and nicanartine.
Safety and regulation
The LD50 is 9200 mg/kg, indicating a low toxicity.
2,6-Di-tert-butylphenol is covered by the U.S. Department of Transportation Code of Federal Regulations 49 CFR 172.101, Appendix B (20 Dec 2004). This substance is designated by the U.S. Department of Transportation (DOT) as a marine pollutant.
- Peter P. Klemchuk (2005). "Antioxidants". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_091.
- Helmut Fiege; Heinz-Werner Voges; Toshikazu Hamamoto; Sumio Umemura; Tadao Iwata; Hisaya Miki; Yasuhiro Fujita; Hans-Josef Buysch; Dorothea Garbe (2002). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313.