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Ethyl Oxalate

Catalog Number
ACMA00016963
Product Name
Ethyl Oxalate
Category
Polymers
Description
Ethyl oxalate appears as a colorless liquid. Slightly denser than water and insoluble in water. Hence sinks in water. May irritate skin and mucous membranes; may be mildly toxic by ingestion; may emit irritating fumes in a fire. Vapors are much heavier than air. Used as a solvent for plastics and in the manufacture of perfumes and pharmaceuticals.;Liquid
IUPAC Name
diethyl oxalate
Molecular Weight
146.14g/mol
Molecular Formula
C6H10O4
Canonical SMILES
CCOC(=O)C(=O)OCC
InChI
InChI=1S/C6H10O4/c1-3-9-5(7)6(8)10-4-2/h3-4H2,1-2H3
InChI Key
WYACBZDAHNBPPB-UHFFFAOYSA-N
Boiling Point
185.7 °C;185.7 °C @ 760 MM HG
Melting Point
-40.6 °C;-38.5 °C
Flash Point
168 °F (NFPA, 2010);168 °F CC
Density
1.0785 @ 20 °C/4 °C
Solubility
0.25 M;SPARINGLY SOL IN WATER WHICH DECOMP IT GRADUALLY; MISCIBLE WITH USUAL ORG SOLVENTS;SOL IN ALL PROPORTIONS IN ALCOHOL, ETHER, ACETONE;MISCIBLE WITH ETHYL ACETATE
Application
Ethyl oxalate serves as a versatile compound with a wide range of applications across the pharmaceutical, plastics, and dye industries. It acts as an intermediary in the synthesis of numerous active pharmaceutical ingredients (APIs), such as azathioprine and sulfamethoxazole, and is pivotal in manufacturing other drugs like phenylpenicillin derivatives and chloroquine lactate. Additionally, ethyl oxalate finds utility as a solvent for cellulose esters, ethers, resins, and lacquers, especially in electronic applications. It is also engaged in various chemical reactions, including transesterification with phenol to produce diphenyl oxalate, and plays a role in Claisen condensation to prepare glyoxalyl derivatives. Furthermore, it is instrumental in synthesizing compounds used in the creation of heterocyclic structures and is involved in the microemulsion process to develop zinc oxide nanoparticles. The compound's ability to absorb moisture and its slow decomposition profile underpin its significance in these diverse applications.
Color/Form
COLORLESS, OILY LIQUID
Complexity
114
Covalently-Bonded Unit Count
1
EC Number
202-464-1
Exact Mass
146.057909g/mol
Formal Charge
0
Heavy Atom Count
10
Log P
0.56 (LogP)
Monoisotopic Mass
146.057909g/mol
NSC Number
8851
Odor
AROMATIC ODOR
Other Experimental
CAN REACT WITH OXIDIZING MATERIALS
Refractive Index
INDEX OF REFRACTION: 1.4101 @ 20 °C/D; SADTLER REFERENCE NUMBER: 5267 (IR, PRISM); MAX ABSORPTION (ALCOHOL): 225 NM (LOG E= 2.6)
Rotatable Bond Count
5
Stability
UNSTABLE
UNII
860M3ZWF6J
UN Number
2525;2525;2525
Vapor Density
5.04
Vapor Pressure
0.41 mmHg;1 MM HG @ 47 °C
XLogP3
0.6
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