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553-97-9

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553-97-9 Usage

Description

p-Toluquinone, also known as methyl-p-benzoquinone, is a yellow to brownish crystalline powder with unique chemical properties. It is an organic compound that has found various applications in different industries due to its distinctive characteristics.

Uses

Used in Chemical Synthesis:
p-Toluquinone is used as a key intermediate in the synthesis of various organic compounds, such as 2H-indazole-4,7-dione derivatives from 3-phenylsydnone and p-toluquinone. It plays a crucial role in the formation of tetrahedral adducts and facilitates Michael addition reactions with 2-methylcyclopentane-1,3-dione, yielding products in a regiospecific manner.
Used in Energy Storage:
In the energy storage industry, p-Toluquinone is used as a coating material that forms an interface between the electrode and lithium (Li) electrolyte for the fabrication of redox flow batteries. Its application enhances the performance and efficiency of these batteries.
Used in Analytical Chemistry:
p-Toluquinone can be reduced during positive electrospray ionization mass spectroscopy (ESI MS), making it a valuable compound in analytical chemistry for various research and diagnostic applications.
Used in Corona Discharge:
Due to its reductive properties, p-Toluquinone can be potentially used during corona discharge processes, which are essential in various industrial applications, such as air purification and surface treatment.

Synthesis Reference(s)

The Journal of Organic Chemistry, 52, p. 5053, 1987 DOI: 10.1021/jo00231a048Synthetic Communications, 7, p. 467, 1977 DOI: 10.1080/00397917708050782

Safety Profile

Poison by ingestion. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Crystallise p-toluoquinone from heptane or EtOH, dry rapidly (vacuum/P2O5) and stored in a vacuum. [Beilstein 7 IV 2088.]

Check Digit Verification of cas no

The CAS Registry Mumber 553-97-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 3 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 553-97:
(5*5)+(4*5)+(3*3)+(2*9)+(1*7)=79
79 % 10 = 9
So 553-97-9 is a valid CAS Registry Number.
InChI:InChI=1/C7H6O2/c1-5-4-6(8)2-3-7(5)9/h2-4H,1H3

553-97-9 Well-known Company Product Price

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  • TCI America

  • (T1244)  p-Toluquinone  >98.0%(GC)(T)

  • 553-97-9

  • 25g

  • 371.00CNY

  • Detail
  • TCI America

  • (T1244)  p-Toluquinone  >98.0%(GC)(T)

  • 553-97-9

  • 500g

  • 3,620.00CNY

  • Detail
  • Alfa Aesar

  • (36670)  Methyl-p-benzoquinone, 98%   

  • 553-97-9

  • 10g

  • 241.0CNY

  • Detail
  • Alfa Aesar

  • (36670)  Methyl-p-benzoquinone, 98%   

  • 553-97-9

  • 50g

  • 757.0CNY

  • Detail
  • Aldrich

  • (211311)  Methyl-p-benzoquinone  98%

  • 553-97-9

  • 211311-5G

  • 496.08CNY

  • Detail
  • Aldrich

  • (211311)  Methyl-p-benzoquinone  98%

  • 553-97-9

  • 211311-100G

  • 1,587.69CNY

  • Detail

553-97-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-methylcyclohexa-2,5-diene-1,4-dione

1.2 Other means of identification

Product number -
Other names 2-methylbenzoquinone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:553-97-9 SDS

553-97-9Relevant articles and documents

Emitters of chemiluminescence occurring during autoxidation of substituted hydroquinones in water

Kalinichenko,Kalinichenko,Odaryuk,Kanibolotskaya,Shendrik

, p. 1476 - 1480 (2017)

A mathematical processing method for determination of spectral parameters of chemiluminescence emitters during the autoxidation of phenolic compounds in aqueous-alkaline media has been developed. The presence of a single luminescence emitter (the corresponding p-benzoquinone in the triplet state) has been demonstrated in the hydroquinone–oxygen–water system. The emitters spectra have been obtained.

Can Donor Ligands Make Pd(OAc)2a Stronger Oxidant? Access to Elusive Palladium(II) Reduction Potentials and Effects of Ancillary Ligands via Palladium(II)/Hydroquinone Redox Equilibria

Bruns, David L.,Musaev, Djamaladdin G.,Stahl, Shannon S.

supporting information, p. 19678 - 19688 (2020/12/18)

Palladium(II)-catalyzed oxidation reactions represent an important class of methods for selective modification and functionalization of organic molecules. This field has benefitted greatly from the discovery of ancillary ligands that expand the scope, reactivity, and selectivity in these reactions; however, ancillary ligands also commonly poison these reactions. The different influences of ligands in these reactions remain poorly understood. For example, over the 60-year history of this field, the PdII/0 redox potentials for catalytically relevant Pd complexes have never been determined. Here, we report the unexpected discovery of (L)PdII(OAc)2-mediated oxidation of hydroquinones, the microscopic reverse of quinone-mediated oxidation of Pd0 commonly employed in PdII-catalyzed oxidation reactions. Analysis of redox equilibria arising from the reaction of (L)Pd(OAc)2 and hydroquinones (L = bathocuproine, 4,5-diazafluoren-9-one), generating reduced (L)Pd species and benzoquinones, provides the basis for determination of (L)PdII(OAc)2 reduction potentials. Experimental results are complemented by density functional theory calculations to show how a series of nitrogen-based ligands modulate the (L)PdII(OAc)2 reduction potential, thereby tuning the ability of PdII to serve as an effective oxidant of organic molecules in catalytic reactions.

Activated Carbon-Promoted Dehydrogenation of Hydroquinones to Benzoquinones, Naphthoquinones, and Anthraquinones under Molecular Oxygen Atmosphere

Kim, Sanghun,Matsubara, Ryosuke,Hayashi, Masahiko

, p. 2997 - 3003 (2019/03/08)

We found that the activated carbon-molecular oxygen system promotes the conversion of hydroquinones to benzoquinones, naphthoquinones, and anthraquinones, which are often found in natural products and pharmaceuticals. In particular, the one-pot synthesis of naphthoquinones and anthraquinones involving a Diels-Alder reaction is a useful protocol for this purpose.

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