Benzanthrone

Benzanthrone (BZA) is a polycyclic aromatic hydrocarbon. 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.

Benzanthrone
Skeletal formula of benzanthrone
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
EC Number
  • 201-393-3
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 checkY
    Key: HUKPVYBUJRAUAG-UHFFFAOYSA-N checkY
  • 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
Appearance Light yellow to brown-green solid
Melting point 170 °C (338 °F; 443 K)
Insoluble
Hazards
GHS labelling:
GHS07: Exclamation mark
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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Infobox references

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.
  3. Benzanthrone. National Academies Press (US). 1999.
  4. "Appendix A: Benzanthrone". Toxicity of Military Smokes and Obscurants. Vol. 3. 1999.
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