Benzanthrone

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Benzanthrone
Skeletal formula of benzanthrone Benzanthrone.svg
Skeletal formula of benzanthrone
Ball-and-stick model Benzanthrone-3D-balls.png
Ball-and-stick model
Names
Preferred IUPAC name
7H-Benzo[de]anthracen-7-one
Other names
Benzanthrenone
1,9-Benzanthrone
MS-Benzanthrone
Mesobenzanthrone
Naphtanthrone
7H-Benz(de)anthracene-7-one
7-Oxobenz(de)anthracene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.268 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-393-3
PubChem CID
UNII
UN number 2811
  • InChI=1S/C17H10O/c18-17-14-8-2-1-7-12(14)13-9-3-5-11-6-4-10-15(17)16(11)13/h1-10H Yes check.svgY
    Key: HUKPVYBUJRAUAG-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C17H10O/c18-17-14-8-2-1-7-12(14)13-9-3-5-11-6-4-10-15(17)16(11)13/h1-10H
    Key: HUKPVYBUJRAUAG-UHFFFAOYAL
  • O=C3c4c(c2cccc1cccc3c12)cccc4
Properties
C17H10O
Molar mass 230.266 g·mol−1
AppearanceLight yellow to brown-green solid
Melting point 170 °C (338 °F; 443 K)
Insoluble
Hazards
GHS labelling:
‹ The template below ( GHS exclamation mark ) is being considered for mergingwith GHS pictogram. See templates for discussion to help reach a consensus. ›
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Benzanthrone (BZA) is a polycyclic aromatic ketone. It is a yellow solid. [1] Its derivatives are used as a dyestuff intermediate for anthraquinone-based dyes. [2] Dehydrogenative coupling gives violanthrone. It is prepared by reduction of anthroquinone to anthrone followed by alkylation with a mixture of glycerol and sulfuric acid.

Contents

It is a basic substance with fluorescent and luminescent properties. It can be used for photosensitization, and as a charge transport material. It is also used in pyrotechnics industry, mainly as a component of some older formulations of green and yellow colored smokes, often together with Vat Yellow 4; its US military specification is MIL-D-50074D. [3]

Safety

Benzanthrone causes itching and burning sensations on exposed skin, together with erythema, dermatitis, and skin pigmentation. [4]

See also

References

  1. ↑ Macleod, L. C.; Allen, C. F. H. (1934). "Benzanthrone". Organic Syntheses. 14: 4. doi: 10.15227/orgsyn.014.0004 .
  2. ↑ Bien, H.-S.; Stawitz, J.; Wunderlich, K. (2005). "Anthraquinone Dyes and Intermediates". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_355. ISBN   978-3-527-30673-2.
  3. ↑ Benzanthrone. National Academies Press (US). 1999.
  4. ↑ "Appendix A: Benzanthrone". Toxicity of Military Smokes and Obscurants. Vol. 3. 1999.
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