Chemistry:Diethyl succinate

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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
RTECS number
  • WM7400000
UNII
Properties
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)
Slightly soluble
Vapor pressure 0.13 mmHg
-105.07·10−6 cm3/mol
Thermochemistry
24.22 kJ/g
Hazards
Main hazards Primary irritant
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
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

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. thumb|222px|left|[[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). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a20_371. (Subscription content?)