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95-92-1 - Diethyl oxalate, 99% - Ethyl oxalate - Oxalic acid diethyl ester - A14498 - Alfa Aesar

A14498 Diethyl oxalate, 99%

Codice CAS
95-92-1
Sinonimi
Ethyl oxalate
Oxalic acid diethyl ester

Dimensioni Prezzo ($) Quantità Disponibilità
500g 21,30
2500g 73,60
10000g 235,00
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Diethyl oxalate, 99%

MDL
MFCD00009119
EINECS
202-464-1

Proprietà chimiche

Formula
C6H10O4
Peso formula
146.14
Punto di fusione
-41°
Punto di ebollizione
184-186°
Punto di infiammabilità
75°(167°F)
Densità
1.077
Indice di rifrazione
1.4100
Sensibilità
Moisture Sensitive
Solubilità
Miscible with alcohols, ether and other common organic solvents.

Applicazioni

Diethyl oxalate is used to prepare active pharmaceutical ingredients (API), plastics and dyestuff intermediates. It is also used as a solvent for cellulose esters, ethers, resins, perfumes and lacquers for electronics. It is involved in the transesterification reaction with phenol to get dipheny oxalate. It is also involved in the Claisen condensation ketosteroids to prepare glyoxalyl derivatives. Further, it is used to prepare sym-1,4-diphenyl-1,4-dihydro-1,2,4,5-polytetrazine. In addition to this, it is utilized in the microemulsion synthesis of zinc oxide nanoparticles.

Note

Incompatible with strong oxidizing agents, reducing agents, acids and bases. Moisture sensitive.

Letteratura

Base-promoted condensation with ketones, esters, nitriles, etc. yields ɑ-ethoxalyl derivatives, which with aldehydes, e.g. formaldehyde, yield ɑß-unsaturated compounds: J. Org. Chem., 42, 1180 (1977). Condensation with the activated methyl group of o-nitrotoluenes can lead to indole-2-carboxylic acid ethyl ester: Org. Synth. Coll., 5, 567 (1973), or to o-nitrophenylacetic acids which can be converted to indole-2-acetic acid esters: Org. Synth. Coll., 9, 601 (1998).

With the benzylic phosphoranes, gives stereoselectively (Z)-3-aryl-2-ethoxyacrylates: Synthesis, 958 (1989).

Reaction with Grignard reagents at low temperatures gives ɑ-keto esters: Synth. Commun., 11, 943 (1981); Org. Prep. Proced. Int., 21, 501 (1989). Similarly, vinyl Grignards give 2-oxo-3-alkenoic acids: Synthesis, 564 (1988).

Ding, J.; Zhang, J.; Zhang, C.; Liu, K.; Xiao, H.; Kong, F.; Chen, J. Hydrogenation of diethyl oxalate over Cu/SiO2 catalyst with enhanced activity and stability: Contribution of the spatial restriction by varied pores of support. Appl. Catal., A 2015, 508, 68-79.

Afrooz, M.; Dehghani, H. First application of diethyl oxalate as efficient additive in high performance dye-sensitized solar cells based on iodide/triiodide electrolyte. Electrochim. Acta 2015, 174, 521-531.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H227-H302-H319

Combustible liquid. Harmful if swallowed. Causes serious eye irritation.

Dichiarazioni precauzionali: P210u-P280a-P305+P351+P338-P301+P312a-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Call a POISON CENTER/doctor if you feel unwell. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Merck
14,3125
Beilstein
606350
Classe di rischio
6.1
Gruppo di imballaggio
III
Codice tariffe armonizzato
2917.11
TSCA
Yes
RTECS
RO2800000

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