Diethyl succinate

Diethyl succinate
Names
Preferred IUPAC name
Diethyl butanedioate
Other names
Diethyl succinate
Butanedioic acid diethyl ester
Clorius
Identifiers
CAS Number
  • 123-25-1 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
 907645
ChemSpider
  • 13865630
ECHA InfoCard 100.004.194 Edit this at Wikidata
PubChem CID
  • 31249
RTECS number
  • WM7400000
UNII
  • ELP55C13DR checkY
CompTox Dashboard (EPA)
  • DTXSID601022558 DTXSID2038732, DTXSID601022558 Edit this at Wikidata
InChI
  • InChI=1/C8H14O4/c1-3-11-7(9)5-6-8(10)12-4-2/h3-6H2,1-2H3
  • CCOC(=0)CCC(=0)OCC
Properties
Chemical formula
 C8H14O4
Molar mass 174.196 g·mol−1
Appearance Colorless liquid
Density 1.047 g/mL
Melting point −20 °C (−4 °F; 253 K)
Boiling point 218 °C (424 °F; 491 K)
Solubility in water
 Slightly soluble
Vapor pressure 0.13 mmHg
Magnetic susceptibility (χ)
 -105.07·10−6 cm3/mol
Thermochemistry
Std enthalpy of
combustion (ΔcH⦵298)
 24.22 kJ/g
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Primary irritant
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Flash point 90.56 °C (195.01 °F; 363.71 K)
Explosive limits 1.1-6.5%
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

Diethyl succinate is the diethyl ester of succinate.

It is a colorless liquid with the formula (CH2CO2Et)2 (Et = ethyl). The organic molecule contains two ester groups. This ester is a versatile chemical intermediate. A colorless liquid, diethyl succinate is formed by Fischer esterification of succinic acid and ethanol.

Reactions

Being a diester, diethyl succinate is a particularly versatile building block. It participates in acyloin condensation to give 2-hydroxycyclobutanone.[1] Via condensation with oxalate esters, it serves as a precursor to ketoglutaric acid.[2] It is a reagent in the Stobbe condensation.

Diethylsuccinoylsuccinate, a useful precursor to dyes and pigments, is produced by base-induced condensation of diethyl succinate.[3]

References

  1. ^ Bloomfield, Jordan J.; Nelke, Janice M. (1977). "Acyloin Condensation in Which Chlorotrimethylsilane is Used as a Trapping Agent: 1,2-Bis(Trimethylsilyloxy)Cyclobutene and 2-Hydroxycyclobutanone". Organic Syntheses. 57: 1. doi:10.15227/orgsyn.057.0001.
  2. ^ Bottorff, E. M.; Moore, L. L. (1964). "α-Ketoglutaric Acid". Organic Syntheses. 44: 67. doi:10.15227/orgsyn.044.0067.
  3. ^ Hunger, K.; Herbst, W. (2012). "Pigments, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a20_371. ISBN 978-3527306732.(subscription required)