Anthracene-9-carbaldehyde

Anthracene-9-carbaldehyde
Names
	Preferred IUPAC name Anthracene-9-carbaldehyde
	Other names 9-Anthraldehyde, 9-Anthracenaldehyde, Anthracene-9-carbaldehyde
Identifiers
CAS Number	642-31-9 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	639167
ChemSpider	62710;
ECHA InfoCard	100.010.349
EC Number	211-383-0;
PubChem CID	69504;
UNII	353S277YHY ;
CompTox Dashboard (EPA)	DTXSID9060940 ;
	InChI InChI=1S/C15H10O/c16-10-15-13-7-3-1-5-11(13)9-12-6-2-4-8-14(12)15/h1-10H Key: YMNKUHIVVMFOFO-UHFFFAOYSA-N;
	SMILES C1=CC=C2C(=C1)C=C3C=CC=CC3=C2C=O;
Properties
Chemical formula	C15H10O
Molar mass	206.244 g·mol−1
Appearance	yellow solid
Melting point	104 °C (219 °F; 377 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H315, H319, H332, H335
Precautionary statements	P261, P264, P270, P271, P280, P301 P312, P302 P352, P304 P312, P304 P340, P305 P351 P338, P312, P321, P322, P330, P332 P313, P337 P313, P362, P363, P403 P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Anthracene-9-carbaldehyde is the most common monoaldehyde derivative of anthracene. It is a yellow solid that is soluble in common organic solvents. It is prepared by Vilsmeier formylation of anthracene.^[1]^[2] The compound is also used as a building block for supramolecular assemblies.^[3] Hydrogenation of 9-anthracenecarboxaldehyde gives 9-anthracenemethanol.

References

^ Fieser, L. F.; Hartwell, J. L.; Jones, J. E.; Wood, J. H.; Bost, R. W. (1940). "9-Anthraldehyde; 2-Ethoxy-1-Naphthaldehyde". Organic Syntheses. 20: 11. doi:10.15227/orgsyn.020.0011.
^ Jones, Gurnos; Stanforth, Stephen P. (1996). "The Vilsmeier Reaction of Fully Conjugated Carbocycles and Heterocycles". Organic Reactions. pp. 1–330. doi:10.1002/0471264180.or049.01. ISBN 0471264180.
^ Lindsey, Jonathan S.; Wagner, Richard W. (1989). "Investigation of the Synthesis of ortho-Substituted Tetraphenylporphyrins". The Journal of Organic Chemistry. 54 (4): 828–836. doi:10.1021/jo00265a021.

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[1] Fieser, L. F.; Hartwell, J. L.; Jones, J. E.; Wood, J. H.; Bost, R. W. (1940). "9-Anthraldehyde; 2-Ethoxy-1-Naphthaldehyde". Organic Syntheses. 20: 11. doi:10.15227/orgsyn.020.0011.

[2] Jones, Gurnos; Stanforth, Stephen P. (1996). "The Vilsmeier Reaction of Fully Conjugated Carbocycles and Heterocycles". Organic Reactions. pp. 1–330. doi:10.1002/0471264180.or049.01. ISBN 0471264180.

[3] Lindsey, Jonathan S.; Wagner, Richard W. (1989). "Investigation of the Synthesis of ortho-Substituted Tetraphenylporphyrins". The Journal of Organic Chemistry. 54 (4): 828–836. doi:10.1021/jo00265a021.

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