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Key Documents

281670

Sigma-Aldrich

4-Nitrocinnamaldehyde, predominantly trans

98%

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About This Item

Linear Formula:
O2NC6H4CH=CHCHO
CAS Number:
Molecular Weight:
177.16
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

assay

98%

form

solid

mp

140-143 °C (lit.)

storage temp.

2-8°C

SMILES string

[H]C(=O)\C=C\c1ccc(cc1)[N+]([O-])=O

InChI

1S/C9H7NO3/c11-7-1-2-8-3-5-9(6-4-8)10(12)13/h1-7H/b2-1+

InChI key

ALGQVMMYDWQDEC-OWOJBTEDSA-N

General description

Reduction of trans-4-nitrocinnamaldehyde using the polymer-supported Hantzsch 1,4-dihydropyridine ester and a catalytic amount of HCl has been investigated.

Application

4-Nitrocinnamaldehyde has been used in the preparation of 2, 2′-[(E)-3-(4-nitrophenyl) prop-2-ene-1,1-diyl] bis(3-hydroxy-5, 5-dimethylcyclohex-2-en-1-one).

Pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

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


Certificates of Analysis (COA)

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Polymer-Supported Hantzsch 1, 4-Dihydropyridine Ester: An Efficient Biomimetic Hydrogen Source.
He R, et al.
Advanced Synthesis & Catalysis, 350(1), 54-60 (2008)
Joo Hwan Cha et al.
Acta crystallographica. Section E, Structure reports online, 68(Pt 8), o2510-o2510 (2012-08-21)
In the title compound, C(25)H(29)NO(6), each of the cyclo-hexenone rings adopts a half-chair conformation. The hy-droxy and carbonyl O atoms face each other and are oriented to allow for the formation of two intra-molecular O-H⋯O hydrogen bonds. In the crystal
E Eder et al.
Mutagenesis, 6(4), 261-269 (1991-07-01)
Seventeen cinnamaldehydes, cinnamic acids, 2-furylacroleins and related compounds were tested in the Salmonella preincubation reversion assay and in the SOS chromotest. Of eight compounds containing nitrogroups, seven were clearly mutagenic in the presence of S9 mix and six in its
I Baburina et al.
Biochemistry, 37(5), 1245-1255 (1998-03-07)
The residue C221 on pyruvate decarboxylase (EC. 4.1.1.1) from Saccharomyces cerevisiae has been shown to be the site where the substrate activation cascade is triggered [Baburina et al. (1994) Biochemistry 33, 5630-5635] and is located on the beta domain [Arjunan

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