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

A14498 Diethyl oxalate, 99%

CAS Number
95-92-1
Synonyms
Ethyl oxalate
Oxalic acid diethyl ester

Size Price ($) Quantity Availability
500g 21.22
2500g 73.23
10000g 233.81
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Diethyl oxalate, 99%

MDL
MFCD00009119
EINECS
202-464-1

Chemical Properties

Formula
C6H10O4
Formula Weight
146.14
Melting point
-41°
Boiling Point
184-186°
Flash Point
75°(167°F)
Density
1.077
Refractive Index
1.4100
Sensitivity
Moisture Sensitive
Solubility
Miscible with alcohols, ether and other common organic solvents.

Applications

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.

Notes

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

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H302-H319-H227

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

Precautionary Statements: P210-P280-P264-P270-P305+P351+P338-P301+P312-P337+P313-P330-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. Wash thoroughly after handling. Do not eat, drink or smoke when using this product. 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 or doctor/physician if you feel unwell. If eye irritation persists: Get medical advice/attention. Rinse mouth. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,3125
Beilstein
606350
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2917.11
TSCA
Yes
RTECS
RO2800000

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