1,2-naphthoquinone

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Structural formula
Structural formula of 1,2-naphthoquinone
General
Surname 1,2-naphthoquinone
other names
  • 1,2-naphthalenedione
  • Naphthalene-1,2-dione
  • o-naphthoquinone
  • β-naphthoquinone
Molecular formula C 10 H 6 O 2
Brief description

golden yellow to brown odorless solid

External identifiers / databases
CAS number 524-42-5
EC number 208-360-2
ECHA InfoCard 100.007.602
PubChem 10667
Wikidata Q171721
properties
Molar mass 158.16 g mol −1
Physical state

firmly

density

1.45 g cm −3

Melting point

145–147 ° C (decomposition)

solubility
  • practically insoluble in water
  • Easily soluble in alcohol, ether and benzene
safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302-315-319-335
P: 280-301 + 330 + 331-312-302 + 352-332 + 313-337 + 313
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1,2-Naphthoquinone is a chemical compound from the quinone group . It is one of the isomeric naphthoquinones to which z. B. also include 1,4-naphthoquinone and 2,6-naphthoquinone .

Occurrence

1,2-naphthoquinone is a component of tobacco smoke .

Extraction and presentation

1,2-naphthoquinone can be prepared by oxidation of 1-amino-2-naphthol with iron (III) chloride are obtained.

Another production process is a multistage reaction starting from the diazotization of sulfanilic acid .

properties

1,2-Naphthoquinone is a flammable, hardly flammable, golden yellow to brown, odorless solid that is practically insoluble in water. It decomposes when heated above 145–147 ° C. The compound is an important metabolite of naphthalene and was found in diesel soot.

use

1,2-Naphthoquinone is used as an intermediate in the manufacture of dyes.

Individual evidence

  1. a b c d e f g h Entry on 1,2-naphthoquinone in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
  2. a b c d RÖMPP Lexikon Chemie, 10th edition, 1996-1999 Volume 4: M - Pk . Georg Thieme Verlag, 2014, ISBN 3-13-200031-0 , p. 1992 ( limited preview in Google Book Search).
  3. Alan Rodgman, Thomas A. Perfetti: The Chemical Components of Tobacco and Tobacco Smoke, Second Edition . CRC Press, 2016, ISBN 978-1-4665-1552-9 , pp. 637 ( limited preview in Google Book search).
  4. WLF Armarego: Purification of Laboratory Chemicals . Butterworth-Heinemann, 2017, ISBN 978-0-12-805456-7 , pp. 1144 ( limited preview in Google Book search).
  5. ^ VK Ahluwalia: Intermediates for Organic Synthesis . IK International Pvt Ltd, 2010, ISBN 978-81-88237-33-3 ( limited preview in Google Book Search).
  6. Data sheet 1,2-naphthoquinone, 97% from Sigma-Aldrich , accessed on September 26, 2017 ( PDF ).