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163821

Sigma-Aldrich

3-Methoxy-2-nitrobenzaldehyde

≥97%

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About This Item

Linear Formula:
CH3OC6H3(NO2)CHO
CAS Number:
Molecular Weight:
181.15
Beilstein:
1959385
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥97%

form

solid

mp

97-101 °C (lit.)

SMILES string

[H]C(=O)c1cccc(OC)c1[N+]([O-])=O

InChI

1S/C8H7NO4/c1-13-7-4-2-3-6(5-10)8(7)9(11)12/h2-5H,1H3

InChI key

GDTUACILWWLIJF-UHFFFAOYSA-N

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General description

3-Methoxy-2-nitrobenzaldehyde undergoes 1,4-diazabicyclo[2.2.2]octane-catalyzed reaction with methyl vinyl ketone (MVK) to afford normal Baylis-Hillman adduct, the MVK dimer and a pair of diastereomeric bis-(MVK)Baylis-Hillman adducts.

Application

3-Methoxy-2-nitrobenzaldehyde was used in the synthesis of 8-hydroxyquinazoline, methy-3-methoxyanthranilate and 3-methoxy-2-nitrobenzylidenebisformamide.

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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Elucidation of the complex Baylis-Hillman reaction of 3-methoxy-2-nitrobenzaldehyde with methyl vinyl ketone.
Idahosa KC, et al.
South African Journal of Chemistry, 64, 144-150 (2011)
972. Analogues of 8-hydroxyquinoline having additional cyclic nitrogen atoms. Part I. Preparative.
Albert A and Hampton A.
Journal of the Chemical Society, 4985-4993 (1952)

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