D11582
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:
Molecular Weight:
238.24
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
form
powder
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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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K Seligman et al.
Plant & cell physiology, 49(7), 1112-1121 (2008-06-10)
The nitrate reductase (NR)-defective double mutant of Arabidopsis thaliana (nia1 nia2) has previously been shown to present a low endogenous content of NO in its leaves compared with the wild-type plants. In the present study, we analyzed the effect of
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
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)
X Chen et al.
Cell biology international, 25(7), 593-598 (2001-07-13)
A method for the direct measurement of intracellular nitric oxide (NO) production stimulated by penicillin G (PG) in cultured hippocampal neurons with diaminoanthraquinone (DAA) using laser scanning confocal microscopy (LSCM) was developed. Intracellular DAA fluorescence could specifically represent NO production
[Detection of NO-synthase activity of lactobacilli by fluorescent staining].
D R Iarullina et al.
Mikrobiologiia, 76(4), 570-572 (2007-11-03)
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