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2,4-Dimethyl-6-tert-butylphenol

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2,4-Dimethyl-6-tert-butylphenol
Names
Preferred IUPAC name 2-tert-Butyl-4,6-dimethylphenol
Other names 2,4-Dimethyl-6-tert-butylphenol
6-tert-Butyl-2,4-dimethylphenol
2-(tert-Butyl)-4,6-dimethylphenol
2-tert-Butyl-4,6-dimethyl phenol
6-t-Butyl-2,4-xylenol
2-(1,1-Dimethylethyl)-4,6-dimethyl-phenol
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.015.940 Edit this at Wikidata
EC Number
  • 217-533-1
PubChem CID
UNII
UN number 2430
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C12H18O/c1-8-6-9(2)11(13)10(7-8)12(3,4)5/h6-7,13H,1-5H3Key: OPLCSTZDXXUYDU-UHFFFAOYSA-N
  • InChI=1/C12H18O/c1-8-6-9(2)11(13)10(7-8)12(3,4)5/h6-7,13H,1-5H3Key: OPLCSTZDXXUYDU-UHFFFAOYAT
SMILES
  • CC(C)(C)c1c(O)c(C)cc(C)c1
  • Oc1c(cc(cc1C(C)(C)C)C)C
Properties
Chemical formula C12H18O
Melting point 21 to 23 °C (70 to 73 °F; 294 to 296 K)
Boiling point 248 to 249 °C (478 to 480 °F; 521 to 522 K)
Hazards
GHS labelling:
Pictograms GHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Signal word Danger
Hazard statements H301, H302, H310, H315, H319, H373, H411
Precautionary statements P260, P262, P264, P270, P273, P280, P301+P310, P301+P312, P302+P350, P302+P352, P305+P351+P338, P310, P314, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

2,4-Dimethyl-6-tert-butylphenol is the organic compound with the formula Me2(tert-Bu)C6H2OH (Me = methyl, tert-Bu = tertiary butyl). It is a colorless oil that is classified as an alkylated phenol.

Preparation, reactions, uses

It is used as an antioxidant, e.g. to prevent gumming in fuels, and as an ultraviolet stabilizer. It is used in jet fuels, gasolines, and avgas.

It is prepared by alkylation of xylenol with isobutylene. This alkylation provides a means to separate 2,4-xylenol from 2,5-xylenol since 2,4-dimethyl-6-tert-butylphenol is insoluble in 10% NaOH but 2,5-dimethyl-6-tert-butylphenol is soluble. Subsequent to separation, the tert-butyl group can be removed in strong acid.

Tradenames

One of its trade names is Topanol A. It is found in antioxidant mixtures AO-30, AO-31, AO-32, IONOL K72, IONOL K78, IONOL K98, and others.

See also

References

  1. ^ Fiege H (2000). "Cresols and Xylenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_025. ISBN 3-527-30673-0.
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