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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
Pricing and availability is not currently available.

Assay

96%

form

solid

mp

350-351 °C (lit.)

functional group

ketone

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.[1]

Application

6,11-Dihydroxy-5,12-naphthacenedione was used in the synthesis of a tetracene derivative, 5,6,11,12-tetrachlorotetracene.[2] It was also used for the synthesis of (3Z,3′Z)-3,3′-(ethane-1,2-diylidene)bis[isobenzofuran-1(3H)-one].[1] It may be used for the following studies:
  • Synthesis of self-assembled, chair-shaped dirhenium(I) macrocyclic compounds.[3]
  • Synthesis of half-sandwich Ir, Rh-based organometallic molecular boxes.[4]
  • As ligand for the synthesis of supramolecular coordination complexes (SCCs).[5]

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT3286
MKCP2122
MKCJ9632
MKCJ5541
MKBP2227V

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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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