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424757

Sigma-Aldrich

trans-4-Methyl-β-nitrostyrene

98%

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Linear Formula:
CH3C6H4CH=CHNO2
CAS Number:
Molecular Weight:
163.17
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

form

solid

mp

102-104 °C (lit.)

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

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1 of 4

This Item
400017424749399299
trans-4-Methyl-β-nitrostyrene 98%

424757

trans-4-Methyl-β-nitrostyrene

trans-4-Bromo-β-nitrostyrene 99%

400017

trans-4-Bromo-β-nitrostyrene

trans-β-Methyl-β-nitrostyrene 99%

424749

trans-β-Methyl-β-nitrostyrene

trans-4-Methoxy-β-nitrostyrene 99%

399299

trans-4-Methoxy-β-nitrostyrene

form

solid

form

solid

form

solid

form

-

mp

102-104 °C (lit.)

mp

148-150 °C (lit.)

mp

63-65 °C (lit.)

mp

86-88 °C (lit.)

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

-

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

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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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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