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Sigma-Aldrich

p-Benzoquinone dioxime

technical, ≥90% (TLC)

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About This Item

Linear Formula:
C6H4(=NOH)2
CAS Number:
105-11-3
Molecular Weight:
138.12
Beilstein/REAXYS Number:
2043234
EC Number:
203-271-5
MDL number:
MFCD00063636
UNSPSC Code:
12352100
PubChem Substance ID:
57646983
NACRES:
NA.22

grade

technical

assay

≥90% (TLC)

form

solid

mp

243 °C (dec.) (lit.)

solubility

dioxane: soluble 0.1 g/10 mL, clear

SMILES string

O\N=C1/C=C\C(C=C1)=N\O

InChI

1S/C6H6N2O2/c9-7-5-1-2-6(8-10)4-3-5/h1-4,9-10H/b7-5-,8-6+

InChI key

LNHURPJLTHSVMU-CGXWXWIYSA-N

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General description

The electrochemical behaviour of p-benzoquinone dioxime on modified Pt electrodes has been studied in aqueous HClO4 solutions by employing cyclic voltammetric and rotating-disc or ring-disc techniques.

Application

p-Benzoquinone dioxime was used in oxidative regeneration of a variety of carbonyl compounds from their oximes using superoxide ion generated in situ by the phase transfer reaction between potassium superoxide and 18-crown-6.

Biochem/physiol Actions

p-Benzoquinone dioxime is sex-specific rat carcinogen inducing tumours of the urinary bladder in female rats and is a direct-acting mutagen in Salmonella typhimurium TA982.

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Carc. 2 - Expl. 1.1 - Eye Irrit. 2 - Flam. Sol. 2 - Muta. 2 - Skin Sens. 1A

Storage Class

1 - Explosive hazardous materials

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
430826/2
426485/1
421459/1
418790/1
418387/1

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para-Benzoquinone dioxime.
IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans, 29, 185-191 (1982-05-01)
Oxidative regeneration of carbonyl compounds from their oximes using in situ generated superoxide.
Singh KN, et al
Indian J. Chem. B, 45(11), 2552-2552 (2006)
Bacchetta Loretta et al.
Journal of food science and technology, 56(8), 3627-3634 (2019-08-16)
Opuntia ficus indica by-products can be exploited as sources of high-value components for applications in food and other industries. The aim of the present work is to elucidate and optimize the mucilage extraction process from cladodes. The effect of five
1,4-Benzoquinone dioxime.
IARC monographs on the evaluation of carcinogenic risks to humans, 71 Pt 3, 1251-1254 (1999-09-07)
C Westmoreland et al.
Environmental and molecular mutagenesis, 19(1), 71-76 (1992-01-01)
P-Benzoquinone dioxime (BQD) appears to be a sex-specific rat carcinogen inducing tumours of the urinary bladder in female rats. The present paper shows that BQD is a direct-acting mutagen in Salmonella typhimurium TA98, confirming published data. In contrast to this
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