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D2757

Sigma-Aldrich

2,3-Diaminonaphthalene

≥95% purity (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:
2206394
EC Number:
212-241-0
MDL number:
MFCD00004116
UNSPSC Code:
12171500
PubChem Substance ID:
24893709
NACRES:
NA.47

product name

2,3-Diaminonaphthalene, ≥95% (HPLC), powder

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

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H302,H315,H319,H335,H350

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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In situ fluorogenic reaction for ratiometric fluorescent detection of alkaline phosphatase activity
Wen, et al.
Analytica Chimica Acta, 1230 (2022)
Solid phase extraction ? Multisyringe flow injection system for the spectrophotometric determination of selenium with 2,3-diaminonaphthalene
Serra, et al.
Talanta, 81 (2010)
Bio-inspired Maillard-Like reactions enable a simple and sensitive assay for colorimetric detection of methylglyoxal
Wang, et al.
Journal of the Chemical Society. Chemical Communications, 55 (2015)
Raluca Petrican et al.
NeuroImage, 123, 80-88 (2015-08-26)
Current evidence suggests that two spatially distinct neuroanatomical networks, the dorsal attention network (DAN) and the default mode network (DMN), support externally and internally oriented cognition, respectively, and are functionally regulated by a third, frontoparietal control network (FPC). Interactions among
Jingqi Tian et al.
The Analyst, 136(11), 2221-2224 (2011-04-01)
In this Communication, we report on the first preparation of conjugation polymer poly(2,3-diaminonaphthalene) (PDAN) microspheres via chemical oxidation polymerization of 2,3-diaminonaphthalene (DAN) monomers by ammonium persulfate (APS) at room temperature. We further demonstrate the use of PDAN microspheres as a
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