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2999-46-4 - Ethyl isocyanoacetate, 98% - Isocyanoacetic acid ethyl ester - L15379 - Alfa Aesar

L15379 Ethyl isocyanoacetate, 98%

Número CAS
2999-46-4
Nombre Alternativo
Isocyanoacetic acid ethyl ester

Tamaño Precio ($) Cantidad Disponibilidad
1g 31,60
5g 85,40
25g 294,00
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Ethyl isocyanoacetate, 98%

MDL
MFCD00000007
EINECS
221-077-9

Propiedades químicas

Fórmula
CNCH2CO2CH2CH3
Peso molecular
113.12
Punto de ebullición
194-196°
Punto de inflamabilidad
84°(183°F)
Densidad
1.035
Índice de refracción
1.4220
Sensibilidad
Moisture & Light Sensitive
Solubilidad
Miscible with organic solvents. Slightly miscible with water.

Aplicaciones

Ethyl isocyanoacetate is used in the syntheses of 7-aza-tetrahydroindoles, oxazolines, benzodiazepines, imidazoles and oxazoles. For example, it is involved in the synthesis of 1H-indole-2-carboxylate by condensing with 2-bromo benzenealdehyde using CuI as a catalyst. It is a precursor used in the preparation of ethyl thiazole-4-carboxylate upon reaction with O-ethyl thioformate.

Notas

Store in cool place. Moisture and light sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents and strong bases.

Referencias documentales

Base-catalyzed Michael addition to nitroalkenes provides a route to substituted pyrroles, valuable as intermediates for porphyrin synthesis: J. Chem. Soc., Chem. Commun., 1098 (1985); Tetrahedron, 46, 7483, 7587 (1990); Org. Synth. Coll., 9, 242 (1998).

The method has been extended to nitroaromatics, leading to pyrroles and porphyrins fused with aromatic rings: J. Chem. Soc., Perkin 1, 417 (1996).

The terminal carbon also undergoes nucleophilic attack on an acyl chloride to give an ɑ-keto imidoyl chloride, which cyclizes in base to a 2-acyl-5-ethoxy oxazole: Synth. Commun., 26, 1149 (1996).

Kondratov, I. S.; Dolovanyuk, V. G.; Tolmachova, N. A.; Gerus, I. I.; Bergander, K.; Fröhlich, R.; Haufe, G. Reactions of β-alkoxyvinyl polyfluoroalkyl ketones with ethyl isocyanoacetate and its use for the synthesis of new polyfluoroalkyl pyrroles and pyrrolidines. Org. Biomol. Chem. 2012, 10 (44), 8778-8785.

Baumann, M.; Garcia, A. M. R.; Baxendale, I. R. Flow synthesis of ethyl isocyanoacetate enabling the telescoped synthesis of 1, 2, 4-triazoles and pyrrolo-[1, 2-c] pyrimidines. Org. Biomol. Chem. 2015, 13 (14), 4231-4239.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H227-H302-H312-H332-H315-H319-H335

Combustible liquid. Harmful if swallowed. Harmful in contact with skin. Harmful if inhaled. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Indicaciones de precaución: P210u-P261-P280-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Otras referencias

Beilstein
3588613
Clase de peligro
6.1
Grupo de embalaje
III
Código de tarifa arancelaria unificado
2929.90
TSCA
No

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