Benzanthrone

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title: "Benzanthrone" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["fluorescent-dyes", "ketones", "polycyclic-aromatic-compounds"] topic_path: "general/fluorescent-dyes" source: "https://en.wikipedia.org/wiki/Benzanthrone" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 432993859 | ImageFile = Benzanthrone.svg | ImageSize = 180px | ImageName = Skeletal formula of benzanthrone | ImageFile1 = Benzanthrone-3D-balls.png | ImageSize1 = | ImageName1 = Ball-and-stick model | PIN = 7H-Benzo[de]anthracen-7-one | OtherNames = Benzanthrenone 1,9-Benzanthrone MS-Benzanthrone Mesobenzanthrone Naphtanthrone 7H-Benz(de)anthracene-7-one 7-Oxobenz(de)anthracene |Section1={{Chembox Identifiers | ChemSpiderID_Ref = | ChemSpiderID = 6442 | ChEMBL_Ref = | ChEMBL = 1607517 | 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 | InChIKey = HUKPVYBUJRAUAG-UHFFFAOYAL | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = HUKPVYBUJRAUAG-UHFFFAOYSA-N | CASNo_Ref = | CASNo = 82-05-3 | SMILES = O=C3c4c(c2cccc1cccc3c12)cccc4 | PubChem = 6697 | EINECS = 201-393-3 | UNNumber = 2811 | UNII = LP5P3RR8QN | ChEBI = 93350 |Section2={{Chembox Properties | C=17 | H=10 | O=1 | Appearance = Light yellow to brown-green solid | Density = | MeltingPtC = 170 | MeltingPt_notes = | BoilingPt = | Solubility = Insoluble |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = | GHSPictograms = | GHSSignalWord = Warning | HPhrases = | PPhrases =

Benzanthrone (BZA) is a polycyclic aromatic hydrocarbon. It is a yellow solid. Its derivatives are used as a dyestuff intermediate for anthraquinone-based dyes. 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.

Safety

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

References

References

  1. (1934). "Benzanthrone". Organic Syntheses.
  2. (2005). "Anthraquinone Dyes and Intermediates".
  3. (1999). "Benzanthrone". National Academies Press (US).
  4. (1999). "Toxicity of Military Smokes and Obscurants".

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fluorescent-dyesketonespolycyclic-aromatic-compounds