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 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	907645
ChemSpider	13865630;
ECHA InfoCard	100.004.194
PubChem CID	31249;
RTECS number	WM7400000;
UNII	ELP55C13DR ;
CompTox Dashboard (EPA)	DTXSID2038732 ;
	InChI InChI=1/C8H14O4/c1-3-11-7(9)5-6-8(10)12-4-2/h3-6H2,1-2H3;
	SMILES 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)	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[edit]

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[edit]

^ 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.
^ Bottorff, E. M.; Moore, L. L. (1964). "α-Ketoglutaric Acid". Organic Syntheses. 44: 67. doi:10.15227/orgsyn.044.0067.
^ 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)

[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.

[Ullmann-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)

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