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297003

Sigma-Aldrich

2-Amino-3-nitrophenol

98%

Synonym(s):

2-Hydroxy-6-nitroaniline

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About This Item

Linear Formula:
H2NC6H3(NO2)OH
CAS Number:
603-85-0
Molecular Weight:
154.12
Beilstein/REAXYS Number:
2804307
EC Number:
210-060-1
MDL number:
MFCD00010875
UNSPSC Code:
12352100
PubChem Substance ID:
24857893
NACRES:
NA.22

assay

98%

form

solid

mp

212-213 °C (lit.)

SMILES string

Nc1c(O)cccc1[N+]([O-])=O

InChI

1S/C6H6N2O3/c7-6-4(8(10)11)2-1-3-5(6)9/h1-3,9H,7H2

InChI key

KUCWUAFNGCMZDB-UHFFFAOYSA-N

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Application

2-Amino-3-nitrophenol has been used:
  • as semipermanent (nonoxidative) hair colorant and as toner in permanent (oxidative) hair dye products
  • as matrix during visible matrix-assisted laser desorption/ionization (VIS-MALDI) mass spectrometry
  • in preparation of 1,3-benzoxazole-4,7-dione

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Regioselective preparation of 5-amino-and 6-amino-1, 3-benzoxazole-4, 7-diones from symmetrical diaminophenol and aminoresorcinol.
Brehu L, et al.
Tetrahedron Letters, 46(9), 1437-1440 (2005)
Christina L Burnett et al.
International journal of toxicology, 28(6 Suppl 2), 217S-251S (2010-01-30)
2-Amino-3-nitrophenol, 2-amino-4-nitrophenol, 2-amino-5-nitrophenol, 4-amino-3-nitrophenol, 4-amino-2-nitrophenol, 2-amino-4-nitrophenol sulfate, 3-nitro-p-hydroxyethylaminophenol, and 4-hydroxypropylamino-3-nitrophenol are substituted aromatic compounds used as semipermanent (nonoxidative) hair colorants and as toners in permanent (oxidative) hair dye products. All ingredients in this group except 2-amino-4-nitrophenol sulfate, 2-amino-5-nitrophenol, and 4-amino-2-nitrophenol
Lee Chuin Chen et al.
Rapid communications in mass spectrometry : RCM, 21(24), 4129-4134 (2007-11-21)
Visible matrix-assisted laser desorption/ionization (VIS-MALDI) was performed using 2-amino-3-nitrophenol as matrix. The matrix is of near-neutral pH, and has an optical absorption band in the near-UV and visible region. A frequency-doubled Nd:YAG laser operated at 532 nm wavelength was used

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