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
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
| Molecular Formula | C6H6N2O3 |
| Molecular Weight | 154.1234 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Separation and determination of nitrobenzenes by micellar electrokinetic chromatography and high-performance liquid chromatography. | 2002 Dec 6 |
|
| An animal model assessment of common dye-induced allergic contact dermatitis. | 2007 May-Jun |
|
| Synthesis of novel 7-benzylamino-2H-1,4-benzoxazin-3(4H)-ones as anticonvulsant agents. | 2008 Jun |
|
| Final report on the safety assessment of amino nitrophenols as used in hair dyes. | 2009 Nov-Dec |
|
| Inter-laboratory evaluation of the bioluminescent Salmonella reverse mutation assay using 10 model chemicals. | 2009 Sep |
|
| anticonvulsant and toxicity evaluation of newer 4H-benzo[1,4]oxazin-3-ones: The effect of two hydrogen bonding domains. | 2010 Nov |
|
| Exocrine pancreatic carcinogenesis and autotaxin expression. | 2012 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://monographs.iarc.fr/ENG/Monographs/vol57/mono57-13.pdf https://www.ncbi.nlm.nih.gov/pubmed/12732902
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 00:03:03 GMT 2023
by
admin
on
Sat Dec 16 00:03:03 GMT 2023
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| Record UNII |
0149H05U82
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| Record Status |
Validated (UNII)
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| Record Version |
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