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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:
2804307
EC Number:
210-060-1
MDL number:
MFCD00010875
UNSPSC Code:
12352100
PubChem Substance ID:
24857893
NACRES:
NA.22

Quality Level

100

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

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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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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