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Assay
98%
form
solid
mp
102-104 °C (lit.)
functional group
amine
nitro
storage temp.
2-8°C
SMILES string
[H]\C(=C(\[H])[N+]([O-])=O)c1ccc(C)cc1
InChI
1S/C9H9NO2/c1-8-2-4-9(5-3-8)6-7-10(11)12/h2-7H,1H3/b7-6+
InChI key
JSPNBERPFLONRX-VOTSOKGWSA-N
General description
trans-4-Methyl-β-nitrostyrene ((E)-1-methyl-4-(2-nitrovinyl)benzene) is a nitrolefin. Its asymmetric Michael addition with benzaldehyde in the presence of silylated pyrrolidine catalyst has been reported. Its hydrogenation in the presence of Pd(II) complexes of (Z)-2-((quinolin-3-ylimino)methyl)phenol as catalyst has been studied.
Application
trans-4-Methyl-β-nitrostyrene may be used as a reagent in the synthesis of N-benzylpyrrolomorphinans and 4-oxo-2-aryl-4H-chromene-3-carboxylate derivatives.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Pd (II) complexes based on quinoline derivative: Structural characterization and their role as a catalyst for hydrogenation of (E)-1-methyl-4-(2-nitrovinyl) benzene.
Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 123, 1-6 (2014)
Journal of medicinal chemistry, 45(2), 537-540 (2002-01-11)
A new method for the preparation of N-benzylpyrrolomorphinans has been developed. Thus Michael reaction of the benzylimines of oxycodones and oxymorphones with nitrostyrenes gave a series of 4'-aryl-N-benzylpyrrolomorphinans. These were selective delta antagonists of much higher in vitro potency (with
Silylated pyrrolidines as catalysts for asymmetric Michael additions of aldehydes to nitroolefins.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(42), 12549-12552 (2010-09-30)
The Journal of organic chemistry, 77(15), 6495-6504 (2012-07-20)
The unusual alcohol mediated formation of 4-oxo-2-aryl-4H-chromene-3-carboxylate (flavone-3-carboxylate) derivatives from 4-hydroxycoumarins and β-nitroalkenes in an alcoholic medium is described. The transformation occurs via the in situ formation of a Michael adduct, followed by the alkoxide ion mediated rearrangement of the
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