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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

Signal Word

Warning

Hazard Statements

H315,H319,H335

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCS5853
MKCM2811
MKCF2467
MKCB3146V
MKBW1957V

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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.
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
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)
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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