Anthracene-9-carbaldehyde

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Anthracene-9-carbaldehyde
Anthracene-9-carbaldehyde.png
Names
Preferred IUPAC name
Anthracene-9-carbaldehyde
Other names
9-Anthraldehyde, 9-Anthracenaldehyde, Anthracene-9-carbaldehyde
Identifiers
3D model (JSmol)
639167
ChemSpider
EC Number
  • 211-383-0
UNII
  • 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
  • C1=CC=C2C(=C1)C=C3C=CC=CC3=C2C=O
Properties
C15H10O
Molar mass 206.244 g·mol−1
Appearance yellow solid
Melting point 104 °C (219 °F; 377 K)
Hazards
GHS labelling:
GHS08: Health hazard
Warning
H302, H312, H315, H319, H332, H335
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).

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[edit]

  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.