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D11582

Sigma-Aldrich

1,2-Diaminoanthraquinone

Synonym(s):

1,2-Diamino-9,10-anthraquinone

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About This Item

Empirical Formula (Hill Notation):
C14H10N2O2
CAS Number:
1758-68-5
Molecular Weight:
238.24
EC Number:
217-156-2
MDL number:
MFCD00001219
UNSPSC Code:
12352100
PubChem Substance ID:
24893368
NACRES:
NA.22

form

powder

Quality Level

100

mp

289-291 °C (lit.)

SMILES string

Nc1ccc2C(=O)c3ccccc3C(=O)c2c1N

InChI

1S/C14H10N2O2/c15-10-6-5-9-11(12(10)16)14(18)8-4-2-1-3-7(8)13(9)17/h1-6H,15-16H2

InChI key

LRMDXTVKVHKWEK-UHFFFAOYSA-N

Application

1,2-Diaminoanthraquinone (DAQ) can be used as a building block to prepare:
  • Imidazoanthraquinone derivatives via palladium-catalyzed Suzuki–Miyaura and Sonogashira coupling reactions.
  • Anthra[1,2-d]imidazole-6,11-diones by reacting with various aldehydes in the presence of phosphotungstic acid/PEG-400 catalyst.
  • DAQ-containing polymer materials are applicable as solid-state colorimetric sensors for nitrite anion and nitric oxide.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

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
03212JM
00818HM

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María J Marín et al.
Chembiochem : a European journal of chemical biology, 12(16), 2471-2477 (2011-09-29)
Nitric oxide (NO) is involved in many biological processes. Aromatic ortho-diamine derivatives are commonly used in the fluorescence imaging of NO in living cells. ortho-diamino (o-diamino) compounds are believed to react with NO in an oxygenated medium leading to the
Cross-linked poly (2-hydroxyethylmethacrylate) films doped with 1, 2-diaminoanthraquinone (DAQ) as efficient materials for the colorimetric sensing of nitric oxide and nitrite anion
Bru Miriam, et al.
Tetrahedron Letters, 47(11), 1787-1791 (2006)
Francisco Galindo et al.
Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 7(1), 126-130 (2008-01-03)
Spectroscopic analysis of the fluorescent probe 1,2-diaminoanthraquinone () provides information about the mechanism of nitric oxide imaging in living cells. Fluorescent aggregates of a reaction product of are thought to be responsible for the images obtained with confocal fluorescence microscopy.
Synthesis and studies of Imidazoanthraquinone derivatives for applications in organic electronics
Sharma Bharat K, et al.
European Journal of Organic Chemistry, 2017(30), 4389-4400 (2017)
Oliver von Bohlen und Halbach et al.
NeuroImage, 15(3), 633-639 (2002-02-19)
Long-term potentiation (LTP), a model of activity-dependent synaptic plasticity, involves the persistent enhancement of excitatory neurotransmission. Several recent studies have suggested a critical role for nitric oxide (NO) production in hippocampal LTP. However, increase in NO production in living tissue
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