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424757

Sigma-Aldrich

trans-4-Methyl-β-nitrostyrene

98%

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About This Item

Linear Formula:
CH3C6H4CH=CHNO2
CAS Number:
5153-68-4
Molecular Weight:
163.17
MDL number:
MFCD00024828
UNSPSC Code:
12352100
PubChem Substance ID:
24866588
NACRES:
NA.22

Quality Level

100

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCM2811
MKCF2467
MKCB3146V
MKBW1957V
MKBV9949V

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Silylated pyrrolidines as catalysts for asymmetric Michael additions of aldehydes to nitroolefins.
Ralph Husmann et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(42), 12549-12552 (2010-09-30)
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.
Azam M, et al.
Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 123, 1-6 (2014)
Sanjay K Srivastava et al.
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
Manoj R Zanwar et al.
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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