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366765

Sigma-Aldrich

Methyl 2-methyl-3-nitrobenzoate

97%

Synonym(s):

Methyl 3-nitro-o-toluate

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About This Item

Linear Formula:
CH3C6H3(NO2)CO2CH3
CAS Number:
59382-59-1
Molecular Weight:
195.17
Beilstein:
1964020
MDL number:
MFCD00082564
UNSPSC Code:
12352100
PubChem Substance ID:
24862702
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

mp

62-65 °C (lit.)

SMILES string

COC(=O)c1cccc(c1C)[N+]([O-])=O

InChI

1S/C9H9NO4/c1-6-7(9(11)14-2)4-3-5-8(6)10(12)13/h3-5H,1-2H3

InChI key

CRZGFIMLHZTLGT-UHFFFAOYSA-N

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Application

Methyl 2-methyl-3-nitrobenzoate may be used in the synthesis of:
  • methyl indole-4-carboxylate
  • 5-aminoisoquinolin-1(2H)-one
  • 5-nitroisocoumarin
  • substituted nitrostyrene benzoic acids, via reaction with aromatic aldehydes in the presence of DBU in DMSO
  • 4-(hydroxymethyl)-1-tosylindole, via Batcho-Leimgruber modification of the Reissert indole synthesis
  • [2-(4-fluorophenyl)-1H-indol-4-yl]-1-pyrrolidinylmethanone

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M C McDonald et al.
British journal of pharmacology, 130(4), 843-850 (2000-06-24)
Poly (ADP-ribose) synthetase (PARP) is a nuclear enzyme activated by strand breaks in DNA, which are caused inter alia by reactive oxygen species (ROS). Here we report on (i) a new synthesis of a water-soluble and potent PARP inhibitor, 5-aminoisoquinolinone
Synthesis of 2-Arylindole-4-Carboxylic Amides:[2-(4-Fluorophenyl)-1H-Indol-4-YL]-1-Pyrrolidinylmethanone.
Kuethe JT and Beutner GL.
Organic Syntheses, 92-104 (2009)
A N Brubaker et al.
Journal of medicinal chemistry, 29(8), 1528-1531 (1986-08-01)
Three 7-methyl-1,4-dioxa-7-azaspiro[4.5]decanes that contained either the benzyl, 3-indolylmethyl, or 4-indolylmethyl group at the 6-position were synthesized via alkylation of the pyrrolidine enamine of the key intermediate, ethyl 3-oxopiperidine-1-carboxylate. The spirodecane derivatives were evaluated for in vivo central and peripheral dopamine
Preparation of 2-arylindole-4-carboxylic amide derivatives.
Kuethe JT and Davies LW.
Tetrahedron, 62(49), 11381-11390 (2006)
The Chemistry of Indoles. XII. A Facile Route to 5-Nitroisocoumarins and Methyl Indole-4-carboxylate.
<BIG>Masanori S, et al. </BIG>
Chemical & Pharmaceutical Bulletin, 29(1), 249-253 (1981)

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