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211311

Sigma-Aldrich

Methyl-p-benzoquinone

98%

Synonym(s):

p-Toluquinone

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100 G
$194.00

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100 G
$194.00

About This Item

Linear Formula:
CH3C6H3(=O)2
CAS Number:
553-97-9
Molecular Weight:
122.12
Beilstein/REAXYS Number:
471387
EC Number:
209-056-2
MDL number:
MFCD00001603
UNSPSC Code:
12162002
PubChem Substance ID:
24852667
NACRES:
NA.23

$194.00

Available to ship onApril 29, 2025Details

Request a Bulk Order

Quality Level

200

assay

98%

form

solid

mp

66-67 °C (lit.)

SMILES string

CC1=CC(=O)C=CC1=O

InChI

1S/C7H6O2/c1-5-4-6(8)2-3-7(5)9/h2-4H,1H3

InChI key

VTWDKFNVVLAELH-UHFFFAOYSA-N

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application

Methyl-p-benzoquinone (MBQ) can be used as a coating that forms an interface between the electrode and lithium (Li) electrolyte for the fabrication of redox flow batteries.[1] It can be reduced during positive electrospray ionization mass spectroscopy (ESI MS) and can be potentially used during corona discharge.[2]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0001444413
1451239
1444413
1436278
MKAA1239

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Thomas Schmitt et al.
Journal of chemical ecology, 30(4), 731-740 (2004-07-21)
2-Methyl-1,4-benzoquinone (toluquinone) and 2-methoxy-3-methyl-1,4-benzoquinone are the most common components of defensive secretions of juliform millipedes (Diplopoda: Juliformia). A natural and a synthetic millipede-defensive secretion composed of these two substances attract dung beetles of a few Onthophagus species (Coleoptera: Scarabaeidae) that
Svetlana Trivić et al.
Bioorganic chemistry, 30(2), 95-106 (2002-05-22)
In this communication, we have described the activation of several xenobiotics by glucose oxidase from Aspergillus niger. The following compounds are readily reduced by d-glucose, in the presence of glucose oxidase: p-nitroso-N,N-dimethylaniline, methyl-1,4-benzoquinone, and 7,7,8,8-tetracyano-quinodimethane. In each case, the products
J F Carroll et al.
Journal of chemical ecology, 31(1), 63-75 (2005-04-21)
Many mammals and birds roll on or rub themselves with millipedes that discharge benzoquinones. Chemicals transferred from millipedes onto the integument of anointing animals are thought to deter ectoparasites. We tested the lone star tick, Amblyomma americanum (L.), for responses
Ann Yezerski et al.
Journal of chemical ecology, 33(6), 1217-1225 (2007-05-03)
Many species of insects are known to produce and secrete benzoquinone derivatives. These compounds are usually defined as "defense chemicals." However, in many cases, it has not been determined what the chemicals are meant to defend against. Tribolium beetles produce
Eduardo Mello De Capitani et al.
Clinical toxicology (Philadelphia, Pa.), 49(3), 187-190 (2011-04-19)
The most important millipede species causing accidents in Brazil is Rhinocricus padbergi (order Spirobolida, family Rhinocricidae), a vegetarian scavenger distributed from Central to South America. Eleven clinical cases of dermal and oral accidental exposures to secretions from Rhinocricus spp. milipedes
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