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Merck
CN

303585

2-Amino-5-nitrophenol

Synonym(s):

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

Linear Formula:
H2NC6H3(NO2)OH
CAS Number:
121-88-0
Molecular Weight:
154.12
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24858130
EC Number:
204-503-8
Beilstein/REAXYS Number:
972974
MDL number:
MFCD00007692
Form:
solid

Key Documents

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InChI key

DOPJTDJKZNWLRB-UHFFFAOYSA-N

InChI

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

SMILES string

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

form

solid

mp

198-202 °C (dec.) (lit.)

functional group

nitro

Quality Level

100

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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

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
MKCT6907
MKCJ2766
MKBR4582V
MKBH9458V
MKBF0521V

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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
2-Amino-5-nitrophenol.
IARC monographs on the evaluation of carcinogenic risks to humans, 57, 177-184 (1993-01-01)
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
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
Weixia Zhu et al.
Se pu = Chinese journal of chromatography, 30(9), 870-875 (2013-01-05)
An analytical method was developed for the simultaneous determination of 11 aminophenols in direct and oxidized hair dyes by high performance liquid chromatography (HPLC). The samples were extracted with methanol using sodium bisulfite for anti-oxidation. The purification was carried out
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