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

L15379 Ethyl isocyanoacetate, 98%

Codice CAS
2999-46-4
Sinonimi
Isocyanoacetic acid ethyl ester

Dimensioni Prezzo ($) Quantità Disponibilità
5g 86,21
25g 296,64
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Ethyl isocyanoacetate, 98%

MDL
MFCD00000007
EINECS
221-077-9

Proprietà chimiche

Formula
CNCH2CO2CH2CH3
Peso formula
113.12
Punto di ebollizione
194-196°
Punto di infiammabilità
84°(183°F)
Densità
1.035
Indice di rifrazione
1.4220
Sensibilità
Moisture & Light Sensitive
Solubilità
Miscible with organic solvents. Slightly miscible with water.

Applicazioni

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.

Note

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.

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H331-H302-H312-H315-H319-H335-H227

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

Dichiarazioni precauzionali: P210-P261-P280-P305+P351+P338-P304+P340-P311-P362-P301+P312-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. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Call a POISON CENTER or doctor/physician. Take off contaminated clothing and wash before reuse. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
3588613
Classe di rischio
6.1
Gruppo di imballaggio
III
Codice tariffe armonizzato
2929.90
TSCA
No

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