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{{short description|Chemical compound}}
{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 443340025
| Watchedfields = changed
⚫ | ImageFileL1 = Orthobenzoquinone.svg
⚫ | verifiedrevid = 477202978
| ImageSizeL1 = 100px
⚫ | ImageFileL1 = Orthobenzoquinone.svg
| ImageFileR1 = 1,2-benzoquinone-3D-vdW.png | ImageFileR1 = 1,2-benzoquinone-3D-vdW.png
| ImageSizeR1 = 120px
| PIN = Cyclohexa-3,5-diene-1,2-dione<ref name="IUPAC2013_728">{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 728 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>
| IUPACName = cyclohexa-3,5-diene-1,2-dione
| OtherNames = 1,2-benzoquinone, ''o''-benzoquinone, ''o''-quinone | OtherNames = {{bulletedlist|''ortho''-Benzoquinone|''o''-Benzoquinone|''o''-Quinone}}
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C02351 | KEGG = C02351
| InChI = 1/C6H4O2/c7-5-3-1-2-4-6(5)8/h1-4H | InChI = 1/C6H4O2/c7-5-3-1-2-4-6(5)8/h1-4H
Line 17: Line 18:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WOAHJDHKFWSLKE-UHFFFAOYSA-N | StdInChIKey = WOAHJDHKFWSLKE-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 583-63-1 | CASNo = 583-63-1
| PubChem = 11421 | PubChem = 11421
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = SVD1LJ47R7 | UNII = SVD1LJ47R7
| SMILES = O=C1/C=C\C=C/C1=O | SMILES = O=C1/C=C\C=C/C1=O
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17253 | ChEBI = 17253
| ChemSpiderID=10941 | ChemSpiderID =10941
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=6|H=4|O=2
| Formula = C<sub>6</sub>H<sub>4</sub>O<sub>2</sub>
⚫ | Appearance = Red volatile solid
| MolarMass = 108.0964 g/mol
⚫ | Density = 1.424 g/cm{{sup|3}}
⚫ | Appearance =
| MeltingPtC = 60-70
⚫ | Density = 1.256 g/cm3
|MeltingPt_notes=decomposes<ref>{{cite book | last=Eagleson | first=Mary | title=Concise encyclopedia chemistry | publisher=Walter de Gruyter | publication-place=Berlin | date=1994 | isbn=0-89925-457-8 | oclc=29029713|page=123}}</ref>
| MeltingPt =
⚫ | Solubility =
| BoilingPt = 213.3 °C @760 mmHg
⚫ }}
⚫ | Solubility =
⚫ |Section7={{Chembox Hazards
⚫ }}
| MainHazards =
⚫ | Section7 = {{Chembox Hazards
| MainHazards = | FlashPtC = 76.4
| AutoignitionPtC =
| FlashPt = 76.4 °C
⚫ }}
| Autoignition =
⚫ |Section8={{Chembox Related
⚫ }}
⚫ | OtherCompounds = ] <br/> ]
⚫ | Section8 = {{Chembox Related
⚫ }}
⚫ | OtherCpds = ] ]
⚫ }}
}} }}
'''1,2-Benzoquinone''', also called '''''ortho''-benzoquinone''', is an ] with formula {{Chem2|C6H4O2|auto=yes}}. It is one of the two isomers of ], the other being ]. It is a red volatile solid that is soluble in water and ]. It is rarely encountered because of its instability, but it is of fundamental interest as the parent compound of many ] which are known.<ref>{{cite book |doi=10.1002/9780470771297 |title=Quinonoid Compounds: Vol. 1 (1974) |year=1974 |isbn=9780470771297 |editor-last1=Patai |editor-first1=Saul|series=PATAI'S Chemistry of Functional Groups}}</ref><ref>{{cite book |doi=10.1002/9780470771303 |title=Quinonoid Compounds: Vol. 2 (1974) |year=1974 |isbn=9780470771303 |editor-last1=Patai |editor-first1=Saul|series=PATAI'S Chemistry of Functional Groups}}</ref>
'''1,2-Benzoquinone''', also called '''''ortho''-benzoquinone''' or '''cyclohexa-3,5-diene-1,2-dione''', is a ], with formula C<sub>6</sub>H<sub>4</sub>O<sub>2</sub>. It is one of the two isomers of ], the other being ].


==Structure==
1,2-Benzoquinone is produced on oxidation of ] exposed to air in aqueous solution<ref name=mag/><ref name=paru>
The molecule has C{{sub|2v}} 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.<ref>{{cite journal | doi = 10.1039/P29730000476| title = Crystal and molecular structure of o-benzoquinone| journal = Journal of the Chemical Society, Perkin Transactions 2| issue = 4| pages = 476| year = 1973| last1 = MacDonald| first1 = Alistair L.| last2 = Trotter| first2 = James}}</ref>
⚫ Chanda Parulekar and Suneela Mavinkurve (2006), ''Formation of ''ortho''-benzoquinone from sodium benzoate by ''Pseudomonas mendocina'' P<sub>2</sub>d. Indian Journal of Experimental Biology, volume 44, pages 157--162. accessed on 2010-02-04.
⚫ </ref> or by ortho oxidation of a ].<ref name=mag>{{cite journal | author = Magdziak, D., Rodriguez, A. A.; Van De Water, R. W.; Pettus, T. R. R. | title = Regioselective oxidation of phenols to o-quinones with o-iodoxybenzoic acid (IBX) | journal = ] | volume = 4 | issue = 2 | pages = 285–288 | year = 2002 | doi = 10.1021/ol017068j | pmc = 1557836 | pmid=11796071}}</ref>
It is a precursor to ].<ref> Section 2.3.2</ref>
It is a red substance soluble in water and insoluble in ].


==Preparation and reactions==
A strain of the ] '']'' ] ] yielding 1,2-benzoquinone (via cathecol) as the final product.<ref name=paru/>
⚫ 1,2-Benzoquinone is produced on oxidation of ] exposed to air in aqueous solution<ref name=mag/> or by ortho oxidation of a ].<ref name=mag>{{cite journal |author1=Magdziak, D. |author2=Rodriguez, A. A. |author3=Van De Water, R. W. |author4=Pettus, T. R. R. | title = Regioselective oxidation of phenols to o-quinones with o-iodoxybenzoic acid (IBX) | journal = ] | volume = 4 | issue = 2 | pages = 285–288 | year = 2002 | doi = 10.1021/ol017068j | pmc = 1557836 | pmid=11796071}}</ref>


⚫ A strain of the ] '']'' ] ], yielding 1,2-benzoquinone via ].<ref name=paru>{{Cite journal | author = Chanda Parulekar and Suneela Mavinkurve | date = 2006 | title = Formation of ''ortho''-benzoquinone from sodium benzoate by ''Pseudomonas mendocina'' P<sub>2</sub>d | journal = Indian Journal of Experimental Biology | volume = 44 | issue = 2 | pages = 157–162 | url = http://nopr.niscair.res.in/bitstream/123456789/6370/1/IJEB%2044(2)%20157-162.pdf | pmid = 16480184}}</ref>
⚫ == See also ==

⚫ * ]
Ortho-quinones are widely used in ].<ref>{{cite journal | doi = 10.1021/ar000194n| pmid = 12379138| title = Masked o-Benzoquinones in Organic Synthesis| journal = Accounts of Chemical Research| volume = 35| issue = 10| pages = 856–866| year = 2002| last1 = Liao| first1 = Chun-Chen| last2 = Peddinti| first2 = Rama Krishna}}</ref>
* ] (o-bromanil)
==Occurrence of ''ortho''-quinones==
* ] (o-chloranil)
] is effected in nature by the action of an orthoquinone called lysyl tyrosylquinone.|center|420 px]]
* ]
4,5-Dimethyl-1,2-benzoquinone, also a red solid, is a well behaved synthetic ''ortho''-quinone.<ref>{{cite journal| vauthors = Teuber HJ | title = Use of Dipotassium Nitrosodisulfonate (Frémy's Salt): 4,5-Dimethyl-''o''-Benzoquinone | doi= 10.15227/orgsyn.052.0088| volume= 52 | page= 88 | year = 1972|journal=Org. Synth.}}</ref>
* ]

The biological pigment ] is rich in ''ortho''-quinones.

Finally, the enzyme ] ] (TTQ), ] (CTQ), ] (LTQ) and ] (PQQ) contain the ''ortho''-quinone moiety in their chemical structure.<ref>{{cite journal |doi=10.1021/ja0214274 |title=Synthesis and Characterization of Model Compounds of the Lysine Tyrosyl Quinone Cofactor of Lysyl Oxidase |year=2003 |last1=Mure |first1=Minae |last2=Wang |first2=Sophie X. |last3=Klinman |first3=Judith P. |journal=Journal of the American Chemical Society |volume=125 |issue=20 |pages=6113–6125 |pmid=12785842}}</ref><!--this ref to be replaced by review-->

⚫ ==See also==
⚫ *]


== References == == References ==
{{reflist}} {{reflist}}


{{DEFAULTSORT:Benzoquinone, 1,2-}} {{DEFAULTSORT:Benzoquinone, 1, 2-}}
] ]
]

{{ketone-stub}}


]
] ]
]
]

Latest revision as of 13:17, 23 January 2025

Chemical compound
1,2-Benzoquinone
Names
Preferred IUPAC name Cyclohexa-3,5-diene-1,2-dione
Other names
  • ortho-Benzoquinone
  • o-Benzoquinone
  • o-Quinone
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.243.463 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H4O2/c7-5-3-1-2-4-6(5)8/h1-4HKey: WOAHJDHKFWSLKE-UHFFFAOYSA-N
  • InChI=1/C6H4O2/c7-5-3-1-2-4-6(5)8/h1-4HKey: 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
Appearance Red volatile solid
Density 1.424 g/cm
Melting point 60–70 °C (140–158 °F; 333–343 K) decomposes
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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.

Preparation and reactions

1,2-Benzoquinone is produced on oxidation of catechol exposed to air in aqueous solution or by ortho oxidation of a phenol.

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

Ortho-quinones are widely used in organic synthesis.

Occurrence of ortho-quinones

The oxidation of lysyl side chains is effected in nature by the action of an orthoquinone called lysyl tyrosylquinone.

4,5-Dimethyl-1,2-benzoquinone, also a red solid, is a well behaved synthetic ortho-quinone.

The biological pigment melanin is rich in ortho-quinones.

Finally, the enzyme cofactors tryptophan tryptophylquinone (TTQ), cysteine tryptophylquinone (CTQ), lysine tyrosylquinone (LTQ) and pyrroloquinoline quinone (PQQ) contain the ortho-quinone moiety in their chemical structure.

See also

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. ISBN 978-0-85404-182-4.
  2. Eagleson, Mary (1994). Concise encyclopedia chemistry. Berlin: Walter de Gruyter. p. 123. ISBN 0-89925-457-8. OCLC 29029713.
  3. Patai, Saul, ed. (1974). Quinonoid Compounds: Vol. 1 (1974). PATAI'S Chemistry of Functional Groups. doi:10.1002/9780470771297. ISBN 9780470771297.
  4. Patai, Saul, ed. (1974). Quinonoid Compounds: Vol. 2 (1974). PATAI'S Chemistry of Functional Groups. doi:10.1002/9780470771303. ISBN 9780470771303.
  5. 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.
  6. ^ 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)". Org. Lett. 4 (2): 285–288. doi:10.1021/ol017068j. PMC 1557836. PMID 11796071.
  7. Chanda Parulekar and Suneela Mavinkurve (2006). "Formation of ortho-benzoquinone from sodium benzoate by Pseudomonas mendocina P2d" (PDF). Indian Journal of Experimental Biology. 44 (2): 157–162. PMID 16480184.
  8. 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. PMID 12379138.
  9. Teuber HJ (1972). "Use of Dipotassium Nitrosodisulfonate (Frémy's Salt): 4,5-Dimethyl-o-Benzoquinone". Org. Synth. 52: 88. doi:10.15227/orgsyn.052.0088.
  10. Mure, Minae; Wang, Sophie X.; Klinman, Judith P. (2003). "Synthesis and Characterization of Model Compounds of the Lysine Tyrosyl Quinone Cofactor of Lysyl Oxidase". Journal of the American Chemical Society. 125 (20): 6113–6125. doi:10.1021/ja0214274. PMID 12785842.
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