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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All Photos(2)
About This Item
Linear Formula:
H2NC6H3(NO2)OH
CAS Number:
Molecular Weight:
154.12
Beilstein:
972974
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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form
solid
mp
198-202 °C (dec.) (lit.)
functional group
nitro
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[1]
- as semipermanent (nonoxidative) hair colorant and as toner in permanent (oxidative) hair dye products[2]
- in synthesis of series of 7-benzylamino-2H-1,4-benzoxazin-3(4H)-ones, anticonvulsant agents[3]
Reactant for:
- Diazotation and coupling reactions
- Preparation of biologically and pharmacologically active molecules
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 2
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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
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
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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