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144320

Sigma-Aldrich

4-Hydroxy-3-nitrobenzaldehyde

97%

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About This Item

Linear Formula:
HOC6H3(NO2)CHO
CAS Number:
3011-34-5
Molecular Weight:
167.12
Beilstein:
2047884
EC Number:
221-141-6
MDL number:
MFCD00007117
UNSPSC Code:
12352100
PubChem Substance ID:
24848648
NACRES:
NA.22

Quality Level

100

Assay

97%

mp

140-142 °C (lit.)

functional group

aldehyde
nitro

SMILES string

[H]C(=O)c1ccc(O)c(c1)[N+]([O-])=O

InChI

1S/C7H5NO4/c9-4-5-1-2-7(10)6(3-5)8(11)12/h1-4,10H

InChI key

YTHJCZRFJGXPTL-UHFFFAOYSA-N

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General description

4-Hydroxy-3-nitrobenzaldehyde reacts with 3-bromo­benzohydrazide in methanol to yield (E)-3-bromo-N′-(4-hydroxy-3-nitrobenzylidene)benzohydrazide.

Application

4-Hydroxy-3-nitrobenzaldehyde was used in the synthesis of:
  • 4-hydroxy-3-nitrocinnamic acid
  • solvated benzohydrazone derivatives: N′-(4-hydroxy-3-nitrobenzylidene)-3-methylbenzohydrazide-methanol-water

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
STBL4748
STBJ3519
STBG5545V
STBG4857V
STBD8590V

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Guo-Biao Cao et al.
Acta crystallographica. Section E, Structure reports online, 65(Pt 8), o1725-o1725 (2009-01-01)
The title compound, C(14)H(10)BrN(3)O(4), was synthesized by the reaction of 4-hydr-oxy-3-nitro-benzaldehyde with an equimolar quantity of 3-bromo-benzohydrazide in methanol. The mol-ecule displays an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 4.6 (2)°. The
Yasuko Sakihama et al.
FEBS letters, 553(3), 377-380 (2003-10-24)
Peroxynitrite (ONOO(-)), a reactive nitrogen species, is capable of nitrating tyrosine residue of proteins. Here we show in vitro evidence that plant phenolic compounds can also be nitrated by an ONOO(-)-independent mechanism. In the presence of NaNO(2), H(2)O(2), and horseradish
Characterization and crystal structures of solvated N'-(4-hydroxy-3-nitrobenzylidene)-3-methylbenzohydrazide and N'-(4-dimethyl-aminobenzylidene)-3-methylbenzohydrazide.
Ma, J-J.
Journal of Structural Chemistry, 54(6), 1145-1150 (2013)

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