diethyl oxalate

• ChemBase ID: 123357
• Molecular Formular: C6H10O4
• Molecular Mass: 146.1412
• Monoisotopic Mass: 146.0579088
• SMILES: C(=O)(C(=O)OCC)OCC
• 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
• InChIKey: WYACBZDAHNBPPB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl oxalate
• IUPAC Traditional name: ethyl oxalate
• Synonyms: diethyl oxalate; Diethyl oxalate; Ethyl oxalate; Oxalic acid diethyl ester; 草酸二乙酯

Database IDs

• CAS Number: 95-92-1
• EC Number: 202-464-1
• MDL Number: MFCD00009119
• Beilstein Number: 606350
• Merck Index: 143125
• PubChem SID: 162217710; 24886868; 24873338; 24848078
• PubChem CID: 7268

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.2083191
• LogD (pH = 7.4): 1.2083191
• Log P: 1.2083191
• Molar Refractivity: 33.474 cm^3
• Polarizability: 13.4318905 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -41 °C(lit.); -41 to -39°C
• Boiling Point: 184-186°C; 185 °C(lit.)
• Flash Point: 167 °F; 75 °C; 75°C(167°F)
• Density: 1.076 g/mL at 25 °C(lit.); 1.077
• Refractive Index: 1.4100; n20/D 1.410; n20/D 1.410(lit.)
• Vapor Pressure: 1 mmHg ( 47 °C)
• Vapor Density: 5.03 (vs air)

Safety Information

• Storage Warning: Moisture Sensitive
• RTECS: RO2800000
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 2525; UN2525
• German water hazard class: 1
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 22-36
• Safety Statements: 23
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H319; H302-H319-H227
• GHS Precautionary statements: P210-P280-P305+P351+P338-P301+P312-P403+P235-P501A; P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2525 6.1/PG 3

Product Information

• Purity: ≥99%; ≥99.0% (GC); ≥99.7% (GC); 99%
• Grade: analytical standard; purum
• Shelf Life: (limited shelf life, expiry date on the label)
• Linear Formula: C2H5OCOCOOC2H5

DETAILS

Sigma Aldrich - 135364

Packaging
1, 3 kg in glass bottle
25 g in glass bottle

REFERENCES

• Base-promoted condensation with ketones, esters, nitriles, etc. yields ɑ-ethoxalyl derivatives, which with aldehydes, e.g. formaldehyde, yield ɑ?-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).
• 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).
• With the benzylic phosphoranes, gives stereoselectively (Z)-3-aryl-2-ethoxyacrylates: Synthesis, 958 (1989).