Benzanthrone
Names | |
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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)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.001.268 |
EC Number |
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PubChem CID
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UNII | |
UN number | 2811 |
CompTox Dashboard (EPA)
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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: | |
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 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.
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
[edit]Benzanthrone causes itching and burning sensations on exposed skin, together with erythema, dermatitis, and skin pigmentation.[4]
See also
[edit]References
[edit]- ^ Macleod, L. C.; Allen, C. F. H. (1934). "Benzanthrone". Organic Syntheses. 14: 4. doi:10.15227/orgsyn.014.0004.
- ^ 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 978-3527306732.
- ^ Benzanthrone. National Academies Press (US). 1999.
- ^ "Appendix A: Benzanthrone". Toxicity of Military Smokes and Obscurants. Vol. 3. 1999.