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Merck
CN

157457

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24849680
EC Number:
222-189-0
Beilstein/REAXYS Number:
2047944
MDL number:
MFCD00001647
Assay:
98%
Form:
solid

Key Documents

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mp

112-114 °C (lit.)

InChI key

NOUZOVBGCDDMSX-UHFFFAOYSA-N

InChI

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

SMILES string

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

assay

98%

form

solid

Quality Level

100

Gene Information

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

Related Categories

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000246708
0000243793
0000234429
0000243793
0000246708

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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
Hetero Diels-Alder reactions of 3, 5-di-tert-butyl-o-benzoquinone with acyclic dienes: novel synthesis of 1, 4-benzodioxines.
Nair V and Kumar S.
Journal of the Chemical Society. Chemical Communications, 11, 1341-1342 (1994)
Adám Kupán et al.
Journal of inorganic biochemistry, 103(3), 389-395 (2009-01-13)
The attempted alkylation of 1,3-bis(2'-pyridylimino)isoindoline (indH) by the use of n-BuLi and subsequent alkyl halides led to quaternization of the pyridine nitrogens and the zwitterionic monodentate N-ligand (Me(2)ind)I was formed. By the use of the ligand the copper(I) complex [Cu(I)(Me(2)ind)I(2)]
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