4-Nitrocinamaldehído, predominantemente trans, 98 %, Thermo Scientific Chemicals
4-Nitrocinamaldehído, predominantemente trans, 98 %, Thermo Scientific Chemicals
4-Nitrocinamaldehído, predominantemente trans, 98 %, Thermo Scientific Chemicals
Thermo Scientific Chemicals

4-Nitrocinamaldehído, predominantemente trans, 98 %, Thermo Scientific Chemicals

 
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Cantidad:
5 g
25 g
50 g
Número de catálogo A11467.06
también denominado A11467-06
Precio (EUR)
83,00
Each
Cantidad:
5 g
Pedido a granel o personalizado
Precio (EUR)
83,00
Each
Identificadores químicos
CAS1734-79-8
IUPAC Name(2E)-3-(4-nitrophenyl)prop-2-enal
Molecular FormulaC9H7NO3
InChI KeyALGQVMMYDWQDEC-OWOJBTEDSA-N
SMILES[O-][N+](=O)C1=CC=C(C=CC=O)C=C1
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EspecificacionesSpecification SheetHoja de especificaciones
Assay (GC)≥97.5%
Appearance (Color)White to yellow to orange
FormPowder
Free acid (titration)≤1.5%
Doebner-Miller reaction the 4- nitrocinnamaldehyde and 2-methylaniline in concentrated HC1 give the corresponding 8-methyl-2-phenylquinoline (3: R = 4'-N02) directly. The asymmetric Friedel-Crafts-type alkylation in aqueous media reaction of 4-Nitrocinnamaldehydr with N-methyl indole using trifluoroacetic acid (TFA) salt of the PEG-PS-supported prolyl peptide having the polyleucine tether as a catalyst. 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).

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Aplicaciones
En la reacción de Doebner-Miller, el 4-nitrocinamaldehído y la 2-metilanilina en HC1 concentrado dan la correspondiente 8-metil-2-fenilquinolina (3: R = 4′-N02) directamente. La alquilación asimétrica de tipo Friedel-Crafts en la reacción acuosa media de 4-nitrocinamaldehído con indol de N-metilo mediante sal de ácido trifluoroacético (TFA) del péptido prolílico soportado por PEG-PS que tiene la unión de polileucina como catalizador. El 4-nitrocinamaldehído se ha utilizado en la preparación de 2, 2′-[(E)-3-(4-nitrofenil) prop-2-ene-1,1-diil] bis(3-hidroxi-5, 5-dimetilciclohex-2-en-1-ona).

Solubilidad
Insoluble en agua.

Notas
Sensible al aire. Almacenar en un lugar fresco. Mantener el recipiente bien cerrado en un lugar seco y bien ventilado. Almacenar alejado de agentes oxidantes fuertes y del aire.
RUO – Research Use Only

General References:

  1. Graham J. Atwell,; Bruce C. Baguley,; William A. Denny. Potential antitumor agents. 57. 2-Phenylquinoline-8-carboxamides as minimal DNA-intercalating antitumor agents with in vivo solid tumor activity . J. Med. Chem. 1989, 32(2),396-401.
  2. Kengo Akagawa,; Takuhiro Yamashita,; Seiji Sakamoto,; Kazuaki Kudo. Friedel-Crafts-type alkylation in aqueous media using resin-supported peptide catalyst having polyleucine. Tetrahedron Letters. 2009, 50 (40) ,5602-5604.