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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

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

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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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
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
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)
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
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