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.

Related Research Articles

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<span class="mw-page-title-main">Knorr pyrrole synthesis</span> Chemical reaction

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<span class="mw-page-title-main">Trifluoromethanesulfonic anhydride</span> Chemical compound

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<span class="mw-page-title-main">Dimethyl acetylenedicarboxylate</span> Chemical compound

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<span class="mw-page-title-main">Dimethyl oxalate</span> Chemical compound

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<span class="mw-page-title-main">Stobbe condensation</span>

The Stobbe condensation entails the reaction of an aldehyde or ketone with an ester of succinic acid to generate alkylidene succinic acid or related derivatives. The reaction consumes one equivalent of metal alkoxide. Commonly, diethylsuccinate is a component of the reaction. The usual product is salt of the half-ester. The Stobbe condensation is named after its discoverer, Hans Stobbe, whose work involved the sodium ethoxide-induced condensation of acetone and diethyl succinate.

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<span class="mw-page-title-main">Ethyl propionate</span> Chemical compound

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<span class="mw-page-title-main">Diethylphosphite</span> Chemical compound

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<span class="mw-page-title-main">Diethyl oxomalonate</span> Chemical compound

Diethyl oxomalonate is the diethyl ester of mesoxalic acid (ketomalonic acid), the simplest oxodicarboxylic acid and thus the first member (n = 0) of a homologous series HOOC–CO–(CH2)n–COOH with the higher homologues oxalacetic acid (n = 1), α-ketoglutaric acid (n = 2) and α-ketoadipic acid (n = 3) (the latter a metabolite of the amino acid lysine). Diethyl oxomalonate reacts because of its highly polarized keto group as electrophile in addition reactions and is a highly active reactant in pericyclic reactions such as the Diels-Alder reactions, cycloadditions or ene reactions. At humid air, mesoxalic acid diethyl ester reacts with water to give diethyl mesoxalate hydrate and the green-yellow oil are spontaneously converted to white crystals.

<span class="mw-page-title-main">Diethylsuccinoylsuccinate</span> Chemical compound

Diethylsuccinoylsuccinate is an organic compound with the formula [CH2C(OH)=C(CO2Et)]2 (Et = ethyl). A tetrasubstituted derivative of 1,4-cyclohexadiene, the compound is the enol tautomer of the corresponding cyclohexadione. It is produced by base-induced condensation of diethyl succinate:

<span class="mw-page-title-main">1-Hexyne</span> Chemical compound

1-Hexyne is a hydrocarbon consisting of a straight six-carbon chain having a terminal alkyne. Its molecular formula is HC2C4H9. A colorless liquid, it is one of three isomers of hexyne. It is used as a reagent in organic synthesis.

<i>tert</i>-Butyl nitrite Chemical compound

tert-Butyl nitrite is an organic compound with the formula (CH3)3CONO. A colorless liquid, it is the tert-butyl ester of nitrous acid. It is typically employed as a solution with tert-butyl alcohol.

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)
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