Anthrol

From Wikipedia, the free encyclopedia
Anthrol
Identifiers
3D model (JSmol)
1869102
ChEBI
ChEMBL
ChemSpider
EC Number
  • 1-: 275-152-6
185412
KEGG
UNII
  • 1-: InChI=1S/C14H10O/c15-14-7-3-6-12-8-10-4-1-2-5-11(10)9-13(12)14/h1-9,15H
    Key: MUVQKFGNPGZBII-UHFFFAOYSA-N
  • 2-: InChI=1S/C14H10O/c15-14-6-5-12-7-10-3-1-2-4-11(10)8-13(12)9-14/h1-9,15H
    Key: BQBWUVWMUXGILF-UHFFFAOYSA-N
  • 9-: InChI=1S/C14H10O/c15-14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-9,15H
    Key: AUKRYONWZHRJRE-UHFFFAOYSA-N
  • 1,2-: InChI=1S/C14H10O2/c15-13-6-5-11-7-9-3-1-2-4-10(9)8-12(11)14(13)16/h1-8,15-16H
    Key: UTCOUOISVRSLSH-UHFFFAOYSA-N
  • 1,2,3-: InChI=1S/C14H10O3/c15-12-7-10-5-8-3-1-2-4-9(8)6-11(10)13(16)14(12)17/h1-7,15-17H
    Key: SLOLMTWBBAFOKJ-UHFFFAOYSA-N
  • 1-: C1=CC=C2C=C3C(=CC2=C1)C=CC=C3O
  • 2-: C1=CC=C2C=C3C=C(C=CC3=CC2=C1)O
  • 9-: C1=CC=C2C(=C1)C=C3C=CC=CC3=C2O
  • 1,2-: C1=CC=C2C=C3C(=CC2=C1)C=CC(=C3O)O
  • 1,2,3-: C1=CC=C2C=C3C(=CC2=C1)C=C(C(=C3O)O)O
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Anthrols (sometimes called anthranols) are the hydroxylated derivatives of anthracene. For the monohydroxo derivatives, three isomers are possible: 1-anthrol, 2-anthrol, and 9-anthrol. The latter exists as a minor tautomer of 9-anthrone. Despite their simplicity, these compounds have little commercial value. 1- and 2-substituted anthracenes typically are prepared via the hydroxy anthroquinones, which means that the preparation of these derivatives is arduous.[1]

Name CAS m.p. Structure
1-anthrol, 1-hydroxyanthracene 610-50-4 150 °C 302 °F 1-anthrol.svg
2-anthrol, 2-hydroxyanthracene 613-14-9 166 °C 331 °F 2-anthrol.svg
9-anthrol, 9-hydroxyanthracene[2] 529-86-2 152 °C 306 °F 9-anthrol.svg

References[edit]

  1. ^ Ray, Debdas; Belin, Colette; Hui, Fei; Fabre, Bruno; Hapiot, Philippe; Bassani, Dario M. (2011). "Direct formation of fullerene monolayers using [4+2] Diels–Alder cycloaddition" (PDF). Chemical Communications. 47 (9): 2547–9. doi:10.1039/C0CC04899B. PMID 21221431.
  2. ^ Ośmiałowski, Borys; Raczyńska, Ewa D.; Krygowski, Tadeusz M. (2006). "Tautomeric Equilibria and Pi Electron Delocalization for Some Monohydroxyarenes Quantum Chemical Studies". The Journal of Organic Chemistry. 71 (10): 3727–3736. doi:10.1021/jo052615q. PMID 16674042.