Diethyl succinate

Last updated
Diethyl succinate
Diethylsuccinat.svg
Names
Preferred IUPAC name
Diethyl butanedioate
Other names
Diethyl succinate
Butanedioic acid diethyl ester
Clorius
Identifiers
3D model (JSmol)
907645
ChemSpider
ECHA InfoCard 100.004.194 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
RTECS number
  • WM7400000
UNII
  • 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
C8H14O4
Molar mass 174.196 g·mol−1
AppearanceColorless liquid
Density 1.047 g/mL
Melting point −20 °C (−4 °F; 253 K)
Boiling point 218 °C (424 °F; 491 K)
Slightly soluble
Vapor pressure 0.13 mmHg
−105.07·10−6 cm3/mol
Thermochemistry
24.22 kJ/g
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Primary irritant
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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).

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. Et2succinoylsuccinate.svg
Diethylsuccinoylsuccinate, a useful precursor to dyes and pigments, is produced by base-induced condensation of diethyl succinate.

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   978-3-527-30673-2.(subscription required)
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