1,2 benzoquinone

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Structural formula
Structural formula of 1,2-benzoquinone
General
Surname 1,2 benzoquinone
other names
  • ortho- quinon
  • o -benzoquinone
  • Cyclohexa-3,5-diene-1,2-dione
Molecular formula C 6 H 4 O 2
Brief description

odorless red solid

External identifiers / databases
CAS number 583-63-1
EC number 812-469-6
ECHA InfoCard 100.243.463
PubChem 11421
Wikidata Q402601
properties
Molar mass 108.10 g mol −1
Physical state

firmly

Melting point

60–70 ° C (decomposition)

solubility

soluble in benzene , ethanol and diethyl ether

safety instructions
GHS labeling of hazardous substances
06 - Toxic or very toxic 07 - Warning 08 - Dangerous to health

danger

H and P phrases H: 301-311-315-319-341-351
P: ?
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1,2-Benzoquinone is a chemical compound from the group of ketones and quinones . It is isomeric to 1,4-benzoquinone .

Occurrence

1,2-Benzoquinone is a precursor to melanin .

Extraction and presentation

1,2-Benzoquinone can be obtained by oxidizing catechol in air or by ortho-oxidizing phenol .

Catechol / 1,2-benzoquinone balance

properties

1,2-Benzoquinone is an unstable, odorless red solid.

Individual evidence

  1. ^ A b c d Mary Eagleson: Concise Encyclopedia Chemistry . Walter de Gruyter, 1994, ISBN 3-11-011451-8 , p. 123 ( limited preview in Google Book search).
  2. Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of 1,2-benzoquinone in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), which was accessed on November 5, 2019, is reproduced from a self-classification by the distributor .
  3. Maurice R. Marshall, Jeongmok Kim and Cheng-I Wei: Enzymatic Browning in Fruits, Vegetables and Seafoods ( Memento of February 9, 2014 in the Internet Archive ), Section 2.3.2.
  4. a b Magdziak, D., Rodriguez, AA; Van De Water, RW; Pettus, TRR: Regioselective oxidation of phenols to o-quinones with o-iodoxybenzoic acid (IBX) . In: Org. Lett. . 4, No. 2, 2002, pp. 285-288. doi : 10.1021 / ol017068j . PMID 11796071 . PMC 1557836 (free full text).
  5. Chanda Parulekar and Suneela Mavinkurve (2006), "Formation of ortho- benzoquinone from sodium benzoate by Pseudomonas mendocina P 2 d". Indian Journal of Experimental Biology, volume 44, pp. 157-162. Online version (PDF; 252 kB) Retrieved on February 4, 2012 (English).