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Sigma-Aldrich

4-tert-Butylcatechol

≥99.0%

Synonym(s):

4-(1,1-Dimethylethyl)benzene-1,2-diol, 4-tert-Butylcatechin, 4-tert-Butylpyrocatechol, 4-TBC, p-tert-Butylcatechol

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About This Item

Linear Formula:
(CH3)3CC6H3-1,2-(OH)2
CAS Number:
98-29-3
Molecular Weight:
166.22
Beilstein:
2043335
EC Number:
202-653-9
MDL number:
MFCD00002201
UNSPSC Code:
12352100
PubChem Substance ID:
57647804
NACRES:
NA.22

Quality Level

100

Assay

≥99.0%

form

powder

bp

285 °C (lit.)

mp

52-55 °C (lit.)
56-58 °C

solubility

methanol: soluble 1 g/10 mL, clear, colorless

SMILES string

CC(C)(C)c1ccc(O)c(O)c1

InChI

1S/C10H14O2/c1-10(2,3)7-4-5-8(11)9(12)6-7/h4-6,11-12H,1-3H3

InChI key

XESZUVZBAMCAEJ-UHFFFAOYSA-N

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General description

4-tert-Butylcatechol,in the presence of O2 catalyzed by tyrosinase, yields 4-tert-butyl-o-benzoquinone. Electrochemical oxidation of 4-tert-Butylcatechol in the presence of 4-hydroxycoumarin as nucleophile has been studied using cyclic voltammetry and controlled-potential coulometry. It undergoes electrochemical trimerization via anodic oxidation and mechanism of trimerization has been studied using cyclic voltammetry and controlled-potential coulometry.

Application

  • Antioxidant source for radical reactions: Research identified 4-tert-Butylcatechol as a viable source of hydrogen atoms in radical reactions, specifically in deiodination processes, expanding its utility in synthetic organic chemistry (Povie et al., 2016).

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Mechanistic study of electrochemical oxidation of 4-tert-butylcatechol: A facile electrochemical method for the synthesis of new trimer of 4-tert-butylcatechol.
Nematollahi D, et al.
Electrochimica Acta, 49(15), 2495-2502 (2004)
Electrochemical study of 3, 4-dihydroxybenzoic acid and 4-tert-butylcatechol in the presence of 4-hydroxycoumarin application to the electro-organic synthesis of coumestan derivatives.
Golabi SM and Nematollahi D.
Journal of Electroanalytical Chemistry, 430(1), 141-146 (1997)
María José Peñalver et al.
Biochimica et biophysica acta, 1597(1), 140-148 (2002-05-16)
The stoichiometry of oxygen consumption during tyrosinase-catalyzed oxidation of an o-diphenol (4-tert-butylcatechol, TBC) and a monophenol (4-tert-butylphenol, TBP) has been determined. At high [substrate]/[enzyme] ratios, in the case of o-diphenols, the stoichiometry of the enzyme-catalyzed reaction was always 1 O(2)/2
Martín A Fernández-Baldo et al.
Talanta, 79(3), 681-686 (2009-07-07)
Botrytis cinerea is a plant-pathogenic fungus that produces the disease known as grey mould in a wide variety of agriculturally important hosts in many countries. This paper describes the development of an immunosensor coupled to carbon-based screen-printed electrodes (SPCE) modified
T Kawashima et al.
The Journal of investigative dermatology, 82(1), 53-56 (1984-01-01)
4-Tertiary butyl catechol (TBC) causes depigmentation in humans and animals and stimulates formation of pheomelanosomes. In this study, we investigated the effects of noncytotoxic doses of TBC on glutathione S-transferase (GST) activity in the skin of Uscd strain mice and
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