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409715

Sigma-Aldrich

6,11-Dihydroxy-5,12-naphthacenedione

96%

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About This Item

Empirical Formula (Hill Notation):
C18H10O4
CAS Number:
1785-52-0
Molecular Weight:
290.27
MDL number:
MFCD00192048
UNSPSC Code:
12352100
PubChem Substance ID:
24865669
NACRES:
NA.22

Assay

96%

form

solid

mp

350-351 °C (lit.)

SMILES string

Oc1c2C(=O)c3ccccc3C(=O)c2c(O)c4ccccc14

InChI

1S/C18H10O4/c19-15-9-5-1-2-6-10(9)16(20)14-13(15)17(21)11-7-3-4-8-12(11)18(14)22/h1-8,19-20H

InChI key

QECAURYYBPUIFF-UHFFFAOYSA-N

Related Categories

General description

Crystallographic analysis of 6,11-dihydroxy-5,12-naphthacenedione has been reported. Study indicates the presence of (3Z,3′Z)-3,3′-(ethane-1,2-diylidene)bis[isobenzofuran-1(3H)-one] as impurity.

Application

6,11-Dihydroxy-5,12-naphthacenedione was used in the synthesis of a tetracene derivative, 5,6,11,12-tetrachlorotetracene. It was also used for the synthesis of (3Z,3′Z)-3,3′-(ethane-1,2-diylidene)bis[isobenzofuran-1(3H)-one]. It may be used for the following studies:
  • Synthesis of self-assembled, chair-shaped dirhenium(I) macrocyclic compounds.
  • Synthesis of half-sandwich Ir, Rh-based organometallic molecular boxes.
  • As ligand for the synthesis of supramolecular coordination complexes (SCCs).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P261 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Dibyendu Bhattacharya et al.
Inorganic chemistry, 49(22), 10264-10272 (2010-10-16)
Self-assembled, chair-shaped dirhenium(I) macrocyclic compounds featuring the two different bis-chelating quinone dianions (1, L = dhnq(2-); 2, L = dhaq(2-); H(2)dhnq = 6,11-dihydroxy-5,12-naphthacenedione; H(2)dhaq = 1,4-dihydroxy-9,10-anthraquinone) that interface with two fac-Re(CO)(3) cores and a ditopic semirigid N-donor 1,4-bis(5,6-dimethylbenzimidazol-1-ylmethyl)naphthalene (L' =
(3Z, 3'Z)-3, 3'-(Ethane-1, 2-diylidene) bis [isobenzofuran-1 (3H)-one].
Ono K, et al.
Acta Crystallographica Section E, Structure Reports Online, 65(9), 2118-2118 (2009)
5, 6, 11, 12-Tetrachlorotetracene, a tetracene derivative with p-stacking structure: The synthesis, crystal structure and transistor properties.
Chi X, et al.
Organic Electronics, 9(2), 234-240 (2008)
Ying-Feng Han et al.
Dalton transactions (Cambridge, England : 2003), 39(16), 3976-3984 (2010-04-08)
Reactions of [Cp*MCl(mu-Cl)](2) (M = Ir or Rh) with 6,11-dihydroxy-5,12-naphthacenedione (H(2)DHNA) in the presence of base, gave the corresponding binuclear complexes [Cp*(2)M(2)(mu-DHNA)Cl(2)] (M = Ir (1a); M = Rh (1b)), respectively. Treatment of 1a or 1b with bidentate ligands (L)
Synthesis of rhenium-based M 2 LL'-type supramolecular coordination complexes from flexible ligands.
Shankar B, et al.
Journal of Organometallic Chemistry, 743, 109-113 (2013)

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