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TERT-BUTYL ETHYL MALONATE

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TERT-BUTYL ETHYL MALONATE Basic information

Product Name:
TERT-BUTYL ETHYL MALONATE
Synonyms:
  • ETHYL TERT-BUTYL MALONATE
  • Malonic acid 1-ethyl 3-tert-butyl ester
  • Malonic acid 1-tert-butyl 3-ethyl ester
  • 1-tert-Butyl 3-ethyl malonate
  • Propanedioic acid, 1,1-dimethylethyl ethyl ester
  • TERT-BUTYL ETHYL MALONATE
  • T-BUTYL ETHYL MALONATE
  • tert-Buty ethyl malonate
CAS:
32864-38-3
MF:
C9H16O4
MW:
188.22
EINECS:
251-269-8
Product Categories:
  • C8 to C9
  • Carbonyl Compounds
  • Esters
Mol File:
32864-38-3.mol
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TERT-BUTYL ETHYL MALONATE Chemical Properties

Boiling point:
83-85 °C/8 mmHg (lit.)
Density 
0.994 g/mL at 25 °C (lit.)
refractive index 
n20/D 1.416(lit.)
Flash point:
189 °F
storage temp. 
Inert atmosphere,Room Temperature
form 
clear liquid
pka
11.86±0.46(Predicted)
color 
Colorless to Almost colorless
Water Solubility 
Miscible with most common solvents. Immiscible with water.
BRN 
1776681
InChIKey
OCOBFMZGRJOSOU-UHFFFAOYSA-N
CAS DataBase Reference
32864-38-3(CAS DataBase Reference)
NIST Chemistry Reference
tert-Butyl ethyl malonate(32864-38-3)
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Safety Information

Safety Statements 
23-24/25
RIDADR 
NA 1993 / PGIII
WGK Germany 
3
HS Code 
29171900

MSDS

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TERT-BUTYL ETHYL MALONATE Usage And Synthesis

Chemical Properties

Clear colorless liquid

Uses

tert-Butyl ethyl malonate is used in the preparation of polar ester-functionalized aliphatic polysulfone. It is also a useful reagent for organic synthesis.

Uses

tert-Butyl ethyl malonate was used in the synthesis of polar ester-functionalized aliphatic polysulfone with remarkable thermal stability.

Synthesis Reference(s)

The Journal of Organic Chemistry, 39, p. 2114, 1974 DOI: 10.1021/jo00928a032

Purification Methods

A likely impurity is monoethyl malonate; check IR for OH bands at 3330 br cm-1 . To ca 50g of ester add ice cold NaOH (50g in 200mL of H2O and 200g of ice). Swirl a few times (filter off ice if necessary), place it in a separating funnel and extract with 2 x 75mL of Et2O. Dry the extract (MgSO4) (since traces of acid decompose the t-Bu group of the ester, the distillation flask has to be washed with aqueous NaOH, rinsed with H2O and allowed to dry). Addition of some K2CO3 or MgO before distilling is recommended to inhibit decomposition. Distil it under reduced pressure through a 10cm Vigreux column (p 11). Decomposition is evidenced by severe foaming due to autocatalytic decomposition and cannot be prevented from accelerating except by stopping the distillation and rewashing the distillation flask with alkali again. [Breslow et al. J Am Chem Soc 66 1287 1944, Hauser et al. J Am Chem Soc 64 2714 1942, Strube Org Synth Coll Vol IV 417 1963, Stube Org Synth 37 35 1957, Beilstein 2 IV 1884.]

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