1,2-Benzoquinone

1,2-Benzoquinone, also called ortho-benzoquinone, is an organic compound with formula

C6H4O2. It is one of the two isomers of quinone, the other being 1,4-benzoquinone. It is a red
volatile solid that is soluble in water and ethyl ether. It is rarely encountered because of its
instability, but it is of fundamental interest as the parent compound of many derivatives which
are known.[2]
 1,2-Benzoquinone

Names

Preferred IUPAC name

Cyclohexa-3,5-diene-1,2-dione[1]

Other names
ortho-Benzoquinone

o-Benzoquinone

o-Quinone

Identifiers

CAS Number 583-63-1 (https://commonchemistry.cas.org/deta

il?cas_rn=583-63-1)  

3D model (JSmol) Interactive image (https://chemapps.stolaf.edu/j

mol/jmol.php?model=O%3DC1%2FC%3DC%5CC%
3DC%2FC1%3DO)

Interactive image (https://chemapps.stolaf.edu/j

mol/jmol.php?model=C1%3DCC%28%3DO%29C%
28%3DO%29C%3DC1)

ChEBI CHEBI:17253 (https://www.ebi.ac.uk/chebi/searc

hId.do?chebiId=17253)  

ChemSpider 10941 (https://www.chemspider.com/Chemical-S

tructure.10941.html)  

ECHA InfoCard 100.243.463 (https://echa.europa.eu/substance-i

nformation/-/substanceinfo/100.243.463)

KEGG C02351 (https://www.kegg.jp/entry/C02351)  

PubChem CID 11421 (https://pubchem.ncbi.nlm.nih.gov/compo
und/11421)

UNII SVD1LJ47R7 (https://fdasis.nlm.nih.gov/srs/srsd

irect.jsp?regno=SVD1LJ47R7)  

CompTox Dashboard (EPA) DTXSID60894765 (https://comptox.epa.gov/dash

board/chemical/details/DTXSID60894765)

InChI
InChI=1S/C6H4O2/c7-5-3-1-2-4-6(5)8/h1-4H 
Key: WOAHJDHKFWSLKE-UHFFFAOYSA-N 
InChI=1/C6H4O2/c7-5-3-1-2-4-6(5)8/h1-4H
Key: WOAHJDHKFWSLKE-UHFFFAOYAR

SMILES
O=C1/C=C\C=C/C1=O
C1=CC(=O)C(=O)C=C1

Properties

Chemical formula C6H4O2

Molar mass 108.096 g·mol−1

Density 1.424 g/cm3

Boiling point 213.3 °C (415.9 °F; 486.4 K)

Hazards

Flash point 76.4 °C (169.5 °F; 349.5 K)

Related compounds

Related compounds 1,4-benzoquinone

quinone

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F],
100 kPa).

 verify (https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477202978&page2=
1%2C2-Benzoquinone)  (what is   ?)
Infobox references
Structure

The molecule has C2v symmetry. X-ray crystallography shows that the double bonds are
localized, with alternatingly long and short C-C distances within the ring. The C=O distances of
1.21 Å are characteristic of ketones.[3]

Preparation and occurrence

1,2-Benzoquinone is produced on oxidation of catechol exposed to air in aqueous solution[4] or

by ortho oxidation of a phenol.[4]

It is a precursor to melanin.

A strain of the bacterium Pseudomonas mendocina metabolises benzoic acid, yielding 1,2-
benzoquinone via catechol.[5]

References

1. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue
Book). Cambridge: The Royal Society of Chemistry. 2014. p. 728. doi:10.1039/9781849733069-FP001
(https://doi.org/10.1039%2F9781849733069-FP001) . ISBN 978-0-85404-182-4.

2. Liao, Chun-Chen; Peddinti, Rama Krishna (2002). "Masked o-Benzoquinones in Organic Synthesis".
Accounts of Chemical Research. 35 (10): 856–866. doi:10.1021/ar000194n (https://doi.org/10.1021%
2Far000194n) . PMID 12379138 (https://pubmed.ncbi.nlm.nih.gov/12379138) .

3. MacDonald, Alistair L.; Trotter, James (1973). "Crystal and molecular structure of o-benzoquinone".
Journal of the Chemical Society, Perkin Transactions 2 (4): 476. doi:10.1039/P29730000476 (https://d
oi.org/10.1039%2FP29730000476) .

4. Magdziak, D.; Rodriguez, A. A.; Van De Water, R. W.; Pettus, T. R. R. (2002). "Regioselective oxidation of
phenols to o-quinones with o-iodoxybenzoic acid (IBX)" (https://www.ncbi.nlm.nih.gov/pmc/articles/P
MC1557836) . Org. Lett. 4 (2): 285–288. doi:10.1021/ol017068j (https://doi.org/10.1021%2Fol017
068j) . PMC 1557836 (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1557836) . PMID 11796071
(https://pubmed.ncbi.nlm.nih.gov/11796071) .

5. Chanda Parulekar and Suneela Mavinkurve (2006). "Formation of ortho-benzoquinone from sodium
benzoate by Pseudomonas mendocina P2d" (http://nopr.niscair.res.in/bitstream/123456789/6370/1/I
JEB%2044(2)%20157-162.pdf) (PDF). Indian Journal of Experimental Biology. 44 (2): 157–162.
PMID 16480184 (https://pubmed.ncbi.nlm.nih.gov/16480184) .
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Last edited 9 months ago by DePiep