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D2757

Sigma-Aldrich

2,3-Diaminonaphthalene

≥95% (HPLC), powder

Synonym(s):

2,3-Naphthalenediamine, DAN

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About This Item

Empirical Formula (Hill Notation):
C10H10N2
CAS Number:
771-97-1
Molecular Weight:
158.20
Beilstein/REAXYS Number:
2206394
EC Number:
212-241-0
MDL number:
MFCD00004116
UNSPSC Code:
12171500
PubChem Substance ID:
24893709
NACRES:
NA.47

Quality Level

100

assay

≥95% (HPLC)

form

powder

color

off-white to dark beige, to Dark Brown

mp

198-200 °C

solubility

pyridine: 50 mg/mL

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

SMILES string

Nc1cc2ccccc2cc1N

InChI

1S/C10H10N2/c11-9-5-7-3-1-2-4-8(7)6-10(9)12/h1-6H,11-12H2

InChI key

XTBLDMQMUSHDEN-UHFFFAOYSA-N

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General description

2,3-Diaminonaphthalene is also known as 2,3-Naphthalenediamine or DAN. It is one of the isomers of naphthalene bearing two amino groups, which are also called naphthalenediamines. They are usually prepared by reducing the nitronaphthalene derivative and aminating the subsequent hydroxynaphthalene derivative.

Application

  • 2,3-Diaminonaphthalene (DAN) has been used for the fluorometric measurement of nitrite/nitrate.
  • DAN has been used to develop a solid phase extraction-multisyringe flow injection system to spectrophotometrically detect the presence of selenium.
  • It has been employed in a study to develop a colorimetric assay for the detection of methylglyoxal.
  • It has also been used in a study to develop a novel ratiometric fluorescent probe for the in-situ detection of alkaline phosphatase activity.

Biochem/physiol Actions

2,3-Diaminonaphthalene (DAN) is used in the nitrite detection test, where it reacts with nitrite to form fluorescent 1H-naphthotriazol.
DAN also reacts with selenite to form 4,5-benzopiazselenol which is detectable via absorptiometry or fluorometry.

pictograms

Exclamation markHealth hazard
GHS07,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1A - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Fluorometric measurement of nitrite/nitrate by 2,3-diaminonaphthalene.
Nussler AK, et al.
Nature Protocols, 1, 2223-2223 (2006)
Sessler JL, et al.
Anion Receptor Chemistry (2006)
N R Neng et al.
Journal of chromatography. A, 1169(1-2), 47-52 (2007-09-25)
Stir bar sorptive extraction with in-situ derivatization using 2,3-diaminonaphthalene (DAN) followed by liquid desorption and high performance liquid chromatography with diode array detection (SBSE(DAN)in-situ-LD-HPLC-DAD) was developed for the determination of glyoxal (Gly) and methylglyoxal (MGly) in environmental and biological matrices.
Maria De Lucia et al.
Chemical research in toxicology, 21(12), 2407-2413 (2009-06-24)
With a view to elucidating the structural requisites for effective antinitrosating properties in plant polyphenolics and their metabolites, we have undertaken a comparative investigation of the nitrite scavenging effects of representative catechol derivatives of dietary relevance in the 2,3-diaminonaphthalene (DAN)
A M Serra et al.
Talanta, 81(1-2), 572-577 (2010-03-02)
In the present work, a solid phase extraction (SPE) is hyphenated with an automatic MSFIA system to improve the selenite determination based on the reaction of selenite with aromatic o-diamines (such as 2,3-diaminonaphthalene (DAN)) to form the piazselenol complex. This
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