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303585

Sigma-Aldrich

2-Amino-5-nitrophenol

Sinónimos:

2-Hydroxy-4-nitroaniline, 3-Hydroxy-4-aminonitrobenzene, 3-Nitro-6-aminophenol, 5-Nitro-2-amino-1-hydroxybenzene, 5-Nitro-2-aminophenol, NSC 7087

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About This Item

Fórmula lineal:
H2NC6H3(NO2)OH
Número de CAS:
121-88-0
Peso molecular:
154.12
Beilstein/REAXYS Number:
972974
EC Number:
204-503-8
MDL number:
MFCD00007692
UNSPSC Code:
12352100
PubChem Substance ID:
24858130
NACRES:
NA.22

form

solid

Quality Level

100

mp

198-202 °C (dec.) (lit.)

SMILES string

Nc1ccc(cc1O)[N+]([O-])=O

InChI

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

InChI key

DOPJTDJKZNWLRB-UHFFFAOYSA-N

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Application

2-Amino-5-nitrophenol was used:
  • as starting material in the synthesis of series of (Z)-2-(substituted aryl)-N-(3-oxo-4-(substituted carbamothioyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl) hydrazine carboxamides
  • as semipermanent (nonoxidative) hair colorant and as toner in permanent (oxidative) hair dye products
  • in synthesis of series of 7-benzylamino-2H-1,4-benzoxazin-3(4H)-ones, anticonvulsant agents
Reactant for:
  • Diazotation and coupling reactions
  • Preparation of biologically and pharmacologically active molecules

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 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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USP

1597005

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2-Amino-4-methylphenol 97%

Sigma-Aldrich

144908

2-Amino-4-methylphenol

3-Aminophenol 98%

Sigma-Aldrich

100242

3-Aminophenol

2,6-Diaminopyridine 98%

Sigma-Aldrich

D24404

2,6-Diaminopyridine

Nadeem Siddiqui et al.
Archiv der Pharmazie, 343(11-12), 657-663 (2010-11-27)
A series of (Z)-2-(substituted aryl)-N-(3-oxo-4-(substituted carbamothioyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl) hydrazine carboxamides (6a-r) was synthesized using 2-amino-5-nitrophenol as a starting material. All the synthesized compounds possessed two hydrogen-bonding domains and their effect on the activity was studied thereof. The anticonvulsant activity was assessed by
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
F Chen et al.
Cancer letters, 126(1), 67-74 (1998-05-01)
Two hair dye components, carcinogenic 4-nitro-2-aminophenol and 5-nitro-2-aminophenol, induced Cu(II)-dependent DNA cleavage frequently at thymine and guanine residues in DNA fragments obtained from the c-Ha-ras-1 protooncogene. When the p53 tumor suppressor gene was used, 4-nitro-2-aminophenol caused Cu(II)-dependent piperidine-labile sites at
2-Amino-5-nitrophenol.
IARC monographs on the evaluation of carcinogenic risks to humans, 57, 177-184 (1993-01-01)
Zhong-Tai Piao et al.
European journal of medicinal chemistry, 43(6), 1216-1221 (2007-10-24)
A series of 7-benzylamino-2H-1,4-benzoxazin-3(4H)-ones were synthesized using 2-amino-5-nitrophenol as a starting material. Their anticonvulsant activities were evaluated by the maximal electroshock test (MES test) and their neurotoxicity was evaluated by the rotarod neurotoxicity test (Tox.). The MES test showed that
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