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Sigma-Aldrich

3,5-Di-tert-butyl-o-benzoquinone

98%

Synonym(s):

3,5-Bis(1,1-dimethylethyl)-3,5-cyclohexadiene-1,2-dione, 3,5-Di-t-butyl-o-quinone, 3,5-Di-tert-butyl-1,2-benzoquinone, 3,5-Di-tert-butyl-o-quinone, 3,5-Di-tert-butylcyclohexa-3,5-diene-1,2-dione, 3,5-Di-tert-butylquinone, 3,5-Ditert-butylcyclohexa-3,5-diene-1,2-dione, 4,6-Di-tert-butyl-1,2-benzoquinone, 4,6-Di-tert-butyl-o-benzoquinone

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About This Item

Linear Formula:
[(CH3)3C]2C6H2(=O)2
CAS Number:
3383-21-9
Molecular Weight:
220.31
Beilstein:
2047944
EC Number:
222-189-0
MDL number:
MFCD00001647
UNSPSC Code:
12352100
PubChem Substance ID:
24849680
NACRES:
NA.22

Quality Level

100

Assay

98%

form

solid

mp

112-114 °C (lit.)

SMILES string

CC(C)(C)C1=CC(=O)C(=O)C(=C1)C(C)(C)C

InChI

1S/C14H20O2/c1-13(2,3)9-7-10(14(4,5)6)12(16)11(15)8-9/h7-8H,1-6H3

InChI key

NOUZOVBGCDDMSX-UHFFFAOYSA-N

Gene Information

human ... ACHE(43) , BCHE(590) , CES1(1066)

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General description

Reactions of the phosphinidene-bridged complexes [Fe2(η5-C5H5)2(μ-PR)(μ-CO)(CO)2] (R = Cy, Ph) with 3,5-di-tert-butyl-o-benzoquinone has been reported.

Application

3,5-Di-tert-butyl-o-benzoquinone was used in the preparation of benzoxazoles derivative ligands. It was also used in the preparation of 1,4-benzodioxines via hetero Diels Alder reaction with acyclic dienes.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000243793
0000246708
0000234429
MKCG5074
MKBW8205V

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Akira Kotani et al.
Analytical sciences : the international journal of the Japan Society for Analytical Chemistry, 19(11), 1473-1476 (2003-12-03)
A disposable voltammetric cell using three pencil leads as working, reference, and counter electrodes was developed for determining the titratable acidity, i.e. the acid content in vinegar. The materials of the pencil leads were graphite-reinforcement carbons (GRCs). A voltammetric determination
Olga Iasco et al.
Inorganic chemistry, 51(4), 2588-2596 (2012-01-12)
Two benzoxazoles derivative ligands were synthesized from the condensation of 3,5-di-tert-butyl-o-benzoquinone (DTBBQ) with ethanolamine or 1,3-diamino-2-hydroxypropane in methanol. Condensation of DTBBQ with ethanolamine gives the expected 5,7-di-tert-butyl-2-methylenhydroxylbenzoxazole (HL1) while with 1,3-diamino-2-hydroxypropane it gives (2-hydroxyethyl-2-{2,4-bis(1,1-dimethylethyl)-1-phenol-6 amino}-2{5,7-di-tert-butyl-benzoxazole}) (H(2)L2) with only one benzoxazole
M Angeles Alvarez et al.
Dalton transactions (Cambridge, England : 2003), 41(48), 14498-14513 (2012-10-12)
The title complexes reacted readily with the methylating agents MeI and CF(3)SO(3)Me, chalcogens (O(2), S(8)) and borane adducts BH(3)·L (L = THF, N(t)Bu(3), PPh(3)) to initially give the corresponding neutral or cationic derivatives of the type [Fe(2)Cp(2){μ-P(E)R}(μ-CO)(CO)(2)](n) (Cp = η(5)-C(5)H(5);
Norma A Macías-Ruvalcaba et al.
The journal of physical chemistry. B, 110(43), 22043-22047 (2006-10-27)
The electrochemical reduction of 3,5-di-tert-butyl-1,2-benzoquinone, 1, has been studied in acetonitrile with added 2,2,2-trifluoroethanol, 2. At low concentrations of 2 the reaction proceeds by the following pathway: reduction of the quinone (Q) to its anion radical (Q*-) followed by complexation
Hitomi Tanaka et al.
International journal of molecular sciences, 19(10) (2018-09-27)
It is generally considered that eumelanin (EM) is photoprotective while pheomelanin (PM) is phototoxic. A recent study using a mouse model demonstrated that PM produces reactive oxygen species (ROS) that cause DNA damage and eventually lead to melanomagenesis. A biochemical
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