Benzanthrone

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
CAS Number	82-05-3^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:93350
ChEMBL	ChEMBL1607517^N
ChemSpider	6442^Y
ECHA InfoCard	100.001.268
EC Number	201-393-3
PubChem CID	6697
UNII	LP5P3RR8QN
UN number	2811
CompTox Dashboard (EPA)	DTXSID8052566
InChI 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^Y Key: HUKPVYBUJRAUAG-UHFFFAOYSA-N^Y 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
SMILES O=C3c4c(c2cccc1cccc3c12)cccc4
Properties
Chemical formula	C17H10O
Molar mass	230.266 g·mol^−1
Appearance	Light yellow to brown-green solid
Melting point	170 °C (338 °F; 443 K)
Solubility in water	Insoluble
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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). N verify (what is ^YN ?) Infobox references

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

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

See also

• 3-Nitrobenzanthrone

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.

External links

• National Pollutant Inventory - Polycyclic Aromatic Hydrocarbon Fact Sheet