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161195

Sigma-Aldrich

2-Methoxy-5-nitroaniline

98%

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Synonym(s):
5-Nitro-o-anisidine
Linear Formula:
CH3OC6H3(NO2)NH2
CAS Number:
Molecular Weight:
168.15
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

98%

mp

117-119 °C (lit.)

SMILES string

COc1ccc(cc1N)[N+]([O-])=O

InChI

1S/C7H8N2O3/c1-12-7-3-2-5(9(10)11)4-6(7)8/h2-4H,8H2,1H3

InChI key

NIPDVSLAMPAWTP-UHFFFAOYSA-N

General description

2-Methoxy-5-nitroaniline is an aromatic metabolite of 2,4-dinitroanisole.

Application

2-Methoxy-5-nitroaniline was used in the synthesis of 5-(9-acridinylamino)-p-anisidines via reaction with 9-anilinoacridines. It was also used in the synthesis of disazo disperse dyes containing nitro and methoxy groups, used for the dyeing of polyester fibre.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 2

Flash Point(F)

246.2 °F

Flash Point(C)

119 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Jidong Liang et al.
Journal of hazardous materials, 262, 281-287 (2013-09-18)
2,4-Dinitroanisole (DNAN) is an insensitive munitions compound considered to replace conventional explosives such as 2,4,6-trinitrotoluene (TNT). DNAN undergoes facile microbial reduction to 2-methoxy-5-nitroaniline (MENA) and 2,4-diaminoanisole (DAAN). This study investigated the inhibitory effect of DNAN, MENA, and DAAN toward various
5-Nitro-ortho-anisidine.
IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans, 27, 133-139 (1982-04-01)
C Sawyer et al.
Biometrics, 40(1), 27-40 (1984-03-01)
An index of carcinogenic potency for chemicals tested in chronic animal experiments is described. By analogy with the well-known 'lethal dose 50' (LD50) of quantal bioassay, a 'tumorigenic dose 50' (TD50) may be defined (in the absence both of tumors
Disperse dyes derived from 2-methoxy-5-nitroaniline.
Otutu JO and Osabohien E.
Orient. J. Chem., 25(4), 863-863 (2009)
Changjin Ou et al.
Physical chemistry chemical physics : PCCP, 17(34), 22072-22078 (2015-08-04)
Reductive degradation of three typical multi-substituted nitroaromatic pollutants by zero valent iron was comprehensively compared in terms of performance, kinetics, toxicity and mechanisms in this study. The results showed that 0.5 mM 2,4-dinitrochlorobenzene (DNCB), 2,4-dinitroanisole (DNAN) and 2,4-dinitrophenol (DNP) could

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