2,4-Di-tert-butylphenol

2,4-Di-tert-butylphenol

Names
Other names 2,4-Bis(1,1-dimethylethyl)phenol 2,4-Bis(tert-butyl)phenol 2,4-Di-tert-butylhydroxybenzene 2,4-Di-tert-butylphenol
Identifiers
CAS Number	96-76-4
3D model (JSmol)	Interactive image
ChEBI	CHEBI:89188
ChEMBL	ChEMBL29873
ChemSpider	7037
ECHA InfoCard	100.002.303
EC Number	202-532-0
PubChem CID	7311
UNII	FOB94G6HZT
CompTox Dashboard (EPA)	DTXSID2026602
InChI InChI=1S/C14H22O/c1-13(2,3)10-7-8-12(15)11(9-10)14(4,5)6/h7-9,15H,1-6H3 Key: ICKWICRCANNIBI-UHFFFAOYSA-N
SMILES CC(C)(C)c1ccc(O)c(c1)C(C)(C)C
Properties
Chemical formula	C14H22O
Molar mass	206.329 g·mol−1
Appearance	White crystalline solid
Odor	phenolic, medical
Density	0.887
Melting point	56.8 °C (134.2 °F; 329.9 K)
Boiling point	264.2 °C (507.6 °F; 537.3 K)
Solubility in water	33 mg/L at 25 °C, pH 6 - 7
Vapor pressure	5 Pa @ 38°C
Acidity (pKa)	11.6
Hazards
GHS labelling: [1]
Pictograms
Signal word	Warning
Hazard statements	H315, H318, H410
Precautionary statements	P264, P273, P280, P302+P352, P305+P351+P338, P310, P332+P313, P362, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2,4-Di-tert-butylphenol (2,4-DTBP) is a white solid with a phenolic odour. It is primarily used as a raw material for the production of several commercially important antioxidants and phenolic benzotriazole-type UV absorbers. It also finds use as a starting material in the synthesis of agrochemicals, fragrances and catalysts (i.e. Jacobsen's catalyst).

Despite its toxicity against most tested organisms, it is made by a wide range of living organisms: 169 species of bacteria, fungi, plants, and animals. ^[2]

Synthesis

The butylation of phenol is typically achieved by a Friedel–Crafts alkylation with isobutylene catalysed by a strong acid. These acids can be either liquids like triflic acid, or solid acids such as zeolites. The isobutylene can be generated in situ by the dehydration of tert-butyl alcohol or methyl tert-butyl ether, which being liquids are simpler to handle than the highly flammable isobutylene gas. ^[3]

Applications

2,4-DTBP is used in the production of antioxidants like tris(2,4-di-tert-butylphenyl)phosphite.

See also

• 2,6-Di-tert-butylphenol

References

1. "Registration Dossier - ECHA". echa.europa.eu. Retrieved 31 August 2024.
2. Zhao, F; Wang, P; Lucardi, RD; Su, Z; Li, S (6 January 2020). "Natural Sources and Bioactivities of 2,4-Di-Tert-Butylphenol and Its Analogs". Toxins. 12 (1): 35. doi: 10.3390/toxins12010035 . PMC   7020479 . PMID   31935944.
3. Yadav, Ganapati D; Doshi, Nirav S (September 2002). "Alkylation of phenol with methyl-tert-butyl ether and tert-butanol over solid acids: efficacies of clay-based catalysts". Applied Catalysis A: General. 236 (1–2): 129–147. Bibcode:2002AppCA.236..129Y. doi:10.1016/S0926-860X(02)00300-9.