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136883

Sigma-Aldrich

4-Methyl-3,5-dinitrobenzoic acid

98%

Synonym(s):

3,5-Dinitro-4-methylbenzoic acid, 3,5-Dinitro-p-toluic acid

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About This Item

Linear Formula:
(O2N)2C6H2(CH3)CO2H
CAS Number:
16533-71-4
Molecular Weight:
226.14
Beilstein/REAXYS Number:
2507949
EC Number:
240-603-8
MDL number:
MFCD00007175
UNSPSC Code:
12352100
PubChem Substance ID:
24848299
NACRES:
NA.22

Quality Level

100

assay

98%

form

solid

mp

155-158 °C (lit.)

solubility

methanol: soluble 250 mg/10 mL, clear, faintly yellow to yellow

functional group

carboxylic acid
nitro

SMILES string

Cc1c(cc(cc1[N+]([O-])=O)C(O)=O)[N+]([O-])=O

InChI

1S/C8H6N2O6/c1-4-6(9(13)14)2-5(8(11)12)3-7(4)10(15)16/h2-3H,1H3,(H,11,12)

InChI key

LZWWZQXBKVZKIP-UHFFFAOYSA-N

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Application

4-Methyl-3,5-dinitrobenzoic acid was used in characterization of the range of highly polar nitroaromatic compounds in water samples from a trinitrotoluene-contaminated waste disposal site. It was used as starting reagent for the asymmetric synthesis of the benzazocine core of FR900482.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
00416EJ
03221HG
02421LU

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Alfred Preiss et al.
Analytical and bioanalytical chemistry, 389(6), 1979-1988 (2007-10-12)
Leachate and ground water samples from a trinitrotoluene-contaminated waste disposal site near a former ammunitions plant in Stadtallendorf, Germany, were analyzed by liquid chromatography (LC)-mass spectrometry (MS) and LC-NMR hyphenated techniques to comprehensively characterize the range of highly polar nitroaromatic
Barry M Trost et al.
Organic letters, 6(11), 1745-1748 (2004-05-21)
An asymmetric synthesis of the benzazocine core of FR900482 has been achieved in 15 steps from 3,5-dinitro-p-toluic acid. Key features of the synthesis include an enantioselective N-methylephedrine-mediated zinc acetylide addition to a highly enolizable arylacetaldehyde and a novel Pd-catalyzed carbonylative

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