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Sigma-Aldrich

5-Methoxy-2-nitrobenzoic acid

97%

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About This Item

Linear Formula:
CH3OC6H3(NO2)CO2H
CAS Number:
1882-69-5
Molecular Weight:
197.14
MDL number:
MFCD00151836
UNSPSC Code:
12352100
PubChem Substance ID:
24864416
NACRES:
NA.22

Assay

97%

mp

125-130 °C (lit.)

functional group

carboxylic acid
nitro

SMILES string

COc1ccc(c(c1)C(O)=O)[N+]([O-])=O

InChI

1S/C8H7NO5/c1-14-5-2-3-7(9(12)13)6(4-5)8(10)11/h2-4H,1H3,(H,10,11)

InChI key

URADKXVAIGMTEG-UHFFFAOYSA-N

General description

5-Methoxy-2-nitrobenzoic acid is a substituted 2-nitrobenzoic acid. It has been reported to be one of the microbial degradation metabolite of cypermethrin, a synthetic pyrethroid pesticide.

Application

5-Methoxy-2-nitrobenzoic acid may be used as starting material in the synthesis of the following:
  • dictyoquinazol A, a neuroprotective compound
  • 5-methoxyantranilic acid by catalytic reduction
  • pyrrolobenzodiazepines
5-Methoxy-2-nitrobenzoic acid may be used in the synthesis of the following N-phenylethyl-2-nitrobenzamides:
  • N-phenylethyl-5-methoxy-2-nitrobenzamide
  • N-(4-methoxyphenylethyl)-5-methoxy-2-nitrobenzamide
  • N-(3,4-dimethoxyphenylethyl)-5-methoxy-2-nitrobenzamide
  • N-(phenethyl)-5-chloro-2-nitrobenzamide
  • N-(3,4-dimethoxyphenethyl)-5-chloro-2-nitrobenzamide

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
S37679
10617EE
13113CE
06229PD
08327LC

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Total synthesis of neuroprotective dictyoquinazol A, B, and C.
Oh CH and Song CH.
Synthetic Communications, 37(19), 3311-3317 (2007)
Synthesis of pyrrolobenzodiazepines via the PIFA oxidation of amines. Synthesis of 8-deoxy DC-81.
Kraus GA and Melekhov A.
Tetrahedron, 54(39), 11749-11754 (1998)
A Novel Synthesis of 5, 6-Dihydroindazolo [3,2-a] isoquinolines and Their Relative Compounds via Tin (II) Chloride Dihydrate as Reducing Agent.
Kuo CY and Wu MJ.
J. Chin. Chem. Soc., 52(5), 965-974 (2005)
Yin LB, et al.
Biodegradation of Hazardous and Special Products (Intech), 1-16 (2013)
Derivatives of 6-methoxy-2-mercaptoquinazole-4-one as compounds with potential anti-tubercularactivity.
Murav'eva KM, et al.
Pharmaceutical Chemistry Journal, 1(8), 456-458 (1967)

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