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D2757

Sigma-Aldrich

2,3-Diaminonaphthalene

≥95% (HPLC), powder

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Synonym(s):
2,3-Naphthalenediamine, DAN
Empirical Formula (Hill Notation):
C10H10N2
CAS Number:
Molecular Weight:
158.20
Beilstein/REAXYS Number:
2206394
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.47

Quality Level

assay

≥95% (HPLC)

form

powder

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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This Item
A1028N625088461
vibrant-m

D2757

2,3-Diaminonaphthalene

vibrant-m

N6250

1,3-Dihydroxynaphthalene

vibrant-m

88461

2,3-Diaminonaphthalene

assay

≥95% (HPLC)

assay

≥97% (HPLC)

assay

≥99%

assay

≥98.0% (HPLC)

storage temp.

room temp

storage temp.

room temp

storage temp.

room temp

storage temp.

-

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

100

application(s)

diagnostic assay manufacturing
hematology
histology

application(s)

diagnostic assay manufacturing
hematology
histology

application(s)

diagnostic assay manufacturing
hematology
histology

application(s)

-

solubility

pyridine: 50 mg/mL

solubility

DMF: 50 mg/mL

solubility

ethanol: 50 mg/mL

solubility

-

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

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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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)
In situ fluorogenic reaction for ratiometric fluorescent detection of alkaline phosphatase activity
Wen, et al.
Analytica Chimica Acta, 1230 (2022)
Naphthalene derivatives. In Wiley-VCH (Ed.), Ullmann?s Encyclopedia of Industrial Chemistry (1st ed.)
G Booth
Ullmann's Encyclopedia of Industrial Chemistry (2000)
Sessler JL, et al.
Anion Receptor Chemistry (2006)
Fluorometric measurement of nitrite/nitrate by 2,3-diaminonaphthalene.
Nussler AK, et al.
Nature Protocols, 1, 2223-2223 (2006)

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