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Details

Stereochemistry ACHIRAL
Molecular Formula C6H6N2O3
Molecular Weight 154.1234
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2-AMINO-5-NITROPHENOL

SMILES

NC1=C(O)C=C(C=C1)[N+]([O-])=O

InChI

InChIKey=DOPJTDJKZNWLRB-UHFFFAOYSA-N
InChI=1S/C6H6N2O3/c7-5-2-1-4(8(10)11)3-6(5)9/h1-3,9H,7H2

HIDE SMILES / InChI
2-Amino-5-nitrophenol is produced from 2-aminophenol by reaction with acetic anhydride to form 2-methylbenzoxazole, which is nitrated and hydrolysed to form 2-amino5-nitrophenol. It was first sythesized by Kaltwasser and Oehrn In 1920. 2-Amino-5-nitrophenol is used as an intermediate in the manufacture of several azo dyes, including CI Solvent Red 8, which is used for colouring synthetic resins, lacquers, inks and wood stains. 2-Amino-5-nitrophenol is also used in many countries as a dye in semi-permanent hair colouring products to produce red and gold-blond shades. These products are generally shampooed into the hair, lathered and then allowed to remain in contact with the hair and scalp for 30-45 min. For this application, 2-amino-5-nitrophenol is mixed (at levels up to 0.5 %) with a blend of several other dyes in a shampoo base to produce the final colour or tint desired. It has been used (and still is to a limited extent) in permanent hair colouring products. The use of 2-amino-5-nitrophenol in cosme tic products is prohibited in the European Economic Community.

Originator

Curator's Comment: 2-Amino-5-nitrophenol was first sythesized by Kaltwasser and Oehrn In 1920.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct

Sample Use Guides

In Vivo Use Guide
Curator's Comment: The LD50 of 2-amino-5-nitrophenol in rats has been reported to be greater than 4000 mg/kg bw by oral administration and greater than 800 mg/kg bw by intraperitoneal injection
Mice: Groups of 50 male and 50 female B6C3F1 mice, seven to eight weeks of age, were administered 0, 400 or 800 mg/kg bw 2-amino-5-nitrophenol (98% pure) by gavage in corn oil (10 ml/kg) on five days a week for up to 103 weeks and were kiled at 112 weeks of age. The mean body weights of high-dose males were 8- 11 % lower than those of vehicle controls from week 29 to week 74, whereas those of low-dose males were greater than those of vehicle controls throughout most of the study. The mean body weights of low-dose and high-dose female mice were 5-9 and 8-13 % lower than those of vehicle controls from week 69 to the end of the study, respectively. Survival of high-dose males after week 20 and of females after week 22 was reduced compared with that of controls.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: The dose range-finding assays were performed to select the concentration that induced an inhibition of cell growth by more than 80%. Two independent studies were performed to assess cytotoxicity, the acute WST-1 colorimetric test and the colony-formation efficiency (CFE) test. In both cell lines of BALB/3T3 and HaCaT, CFE test appeared to be more sensitive to test article treatment than the WST-1 colorimetric test.
In 2-Amino-5-nitrophenol-treated Balb/3T3 cells significant growth inhibition could be observed in CFE test with LC90 < 0.05 mM
Name Type Language
2-AMINO-5-NITROPHENOL
HSDB   INCI  
INCI  
Official Name English
AMINO-5-NITROPHENOL, 2-
Systematic Name English
PHENOL, 2-AMINO-5-NITRO-
Systematic Name English
RODOL YBA
Brand Name English
5-NITRO-2-AMINOPHENOL
Systematic Name English
5-NITRO-2-AMINO-1-HYDROXYBENZENE
Systematic Name English
2-AMINO-5-NITROPHENOL [IARC]
Common Name English
3-HYDROXY-4-AMINONITROBENZENE
Systematic Name English
2-HYDROXY-4-NITROANILINE
Systematic Name English
URSOL YELLOW BROWN A
Brand Name English
C.I. 76535
Code English
NSC-7087
Code English
3-NITRO-6-AMINOPHENOL
Systematic Name English
2-AMINO-5-NITROPHENOL [INCI]
Common Name English
2-AMINO-5-NITROPHENOL [HSDB]
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID1020063
Created by admin on Sat Dec 16 00:03:03 GMT 2023 , Edited by admin on Sat Dec 16 00:03:03 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-503-8
Created by admin on Sat Dec 16 00:03:03 GMT 2023 , Edited by admin on Sat Dec 16 00:03:03 GMT 2023
PRIMARY
CAS
121-88-0
Created by admin on Sat Dec 16 00:03:03 GMT 2023 , Edited by admin on Sat Dec 16 00:03:03 GMT 2023
PRIMARY
HSDB
4168
Created by admin on Sat Dec 16 00:03:03 GMT 2023 , Edited by admin on Sat Dec 16 00:03:03 GMT 2023
PRIMARY
FDA UNII
0149H05U82
Created by admin on Sat Dec 16 00:03:03 GMT 2023 , Edited by admin on Sat Dec 16 00:03:03 GMT 2023
PRIMARY
NSC
7087
Created by admin on Sat Dec 16 00:03:03 GMT 2023 , Edited by admin on Sat Dec 16 00:03:03 GMT 2023
PRIMARY
PUBCHEM
4984721
Created by admin on Sat Dec 16 00:03:03 GMT 2023 , Edited by admin on Sat Dec 16 00:03:03 GMT 2023
PRIMARY