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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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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.
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)
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
One-pot protocol for J-aggregated anthraimidazolediones catalyzed by phosphotungstic acid in PEG-400 under aerobic condition
Bhattacharyya B, et al.
Royal Society of Chemistry Advances, 6(26), 21907-21916 (2016)
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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