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161195

Sigma-Aldrich

2-Methoxy-5-nitroaniline

98%

Synonym(s):

5-Nitro-o-anisidine

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About This Item

Linear Formula:
CH3OC6H3(NO2)NH2
CAS Number:
99-59-2
Molecular Weight:
168.15
EC Number:
202-770-5
MDL number:
MFCD00007261
UNSPSC Code:
12352100
PubChem Substance ID:
24849912
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.[1]

Application

2-Methoxy-5-nitroaniline was used in the synthesis of 5-(9-acridinylamino)-p-anisidines via reaction with 9-anilinoacridines.[2] It was also used in the synthesis of disazo disperse dyes containing nitro and methoxy groups, used for the dyeing of polyester fibre.[3]

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

246.2 °F - closed cup

flash_point_c

119 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
S76153V
S76153
11328DJ
S50182
S31215

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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
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
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
Valeriy A Bacherikov et al.
Bioorganic & medicinal chemistry, 13(23), 6513-6520 (2005-09-06)
A series of 5-(9-acridinylamino)anisidines were synthesized by condensing methoxy-substituted 1,3-phenylenediamines (10 and 11) with 9-chloroacridine derivatives to form 5-(9-acridinylamino)-m-anisidines (AMAs, 14a-e) and 5-(9-acridinylamino)-o-anisidines (AOAs, 15a-e). 5-(9-Acridinylamino)-p-anisidines (APAs, 17a-e) were synthesized by reacting 2-methoxy-5-nitroaniline (12) with 9-anilinoacridines, followed by reduction. The
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