Dimethyl malonate

Structural formula
General
Surname	Dimethyl malonate
other names	Dimethyl malonate
Molecular formula	C 5 H 8 O 4
Brief description	light-, air- and moisture-sensitive colorless liquid with a weak ester-like odor
External identifiers / databases
CAS number 108-59-8 EC number 203-597-8 ECHA InfoCard 100.003.271 PubChem 7943 Wikidata Q4263082
properties
Molar mass	132.12 g mol −1
Physical state	liquid
density	1.15 g cm −3
Melting point	−62 ° C
boiling point	181 ° C
Vapor pressure	0.15 mbar (20 ° C)
solubility	slightly soluble in water (20 ° C)
Refractive index	1.4135 (20 ° C, 589 nm)
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 319 P: 305 + 351 + 338
Toxicological data	5330 mg kg −1 ( LD 50 ,  rat ,  oral ) 5000 mg kg −1 ( LD 50 ,  rabbit ,  transdermal )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Dimethyl malonate is a chemical compound from the group of carboxylic acid esters , more precisely the esters of malonic acid .

Extraction and presentation

Dimethyl malonate can be obtained by reacting formaldehyde dimethyl acetal with carbon monoxide .

${\displaystyle \mathrm {H_{2}C(OCH_{3})_{2}+2\ CO\longrightarrow CH_{2}(CO_{2}CH_{3})_{2}} }$

properties

Dimethyl malonate is a slightly volatile, light-, air- and moisture-sensitive, colorless liquid with a weak ester-like odor that is sparingly soluble in water.

use

Dimethyl malonate is used as the starting material in organic syntheses (e.g. barbituric acid ). It is still used in heating technology as a liquid in heat cost allocators .

safety instructions

The vapors of dimethyl malonate can form an explosive mixture with air ( flash point 69–76 ° C, ignition temperature 440 ° C).

Individual evidence

1. ↑ ^{a b c d e f g h i j k l} Entry on dimethyl malonate in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
2. ↑ Data sheet dimethyl malonate (PDF) from Merck , accessed on February 28, 2013.
3. ^ RA Sheldon: Chemicals from Synthesis Gas: Catalytic Reactions of CO and . Springer, 1983, ISBN 90-277-1489-4 , pp. 207 ( limited preview in Google Book search).
4. ^ Marye Anne Fox, James K. Whitesell: Organic Chemistry . Jones & Bartlett Learning, 2004, ISBN 0-7637-2197-2 , pp. 665,669 ( limited preview in Google Book Search).
5. ^ Ernst-Rudolf Schramek: Pocket book for heating + air conditioning 07/08 . Oldenbourg Industrieverlag, 2007, ISBN 3-8356-3104-7 , p. 303 ( limited preview in Google Book search).