Diethylmalonat

Bezeichnung:Diethylmalonat

CAS-Nr105-53-3

Englisch Name:Diethyl malonate

CBNumberCB8852658

SummenformelC7H12O4

Molgewicht160.17

MOL-Datei105-53-3.mol

Synonyma

Diethylmalonat

Diethylmalonat physikalisch-chemischer Eigenschaften

Schmelzpunkt	-51--50 °C (lit.)
Siedepunkt	199 °C (lit.)
Dichte	1.055 g/mL at 25 °C (lit.)
Dampfdichte	5.52 (vs air)
Dampfdruck	1 mm Hg ( 40 °C)
Brechungsindex	n20/D 1.413(lit.)
FEMA	2375 \| DIETHYL MALONATE
Flammpunkt	212 °F
storage temp.	Store below +30°C.
Löslichkeit	20.8g/l (External MSDS)
pka	13.5(at 25℃)
Aggregatzustand	Liquid
Farbe	colourless liquid
Geruch (Odor)	Sweet ester odor
Explosionsgrenze	0.8-12.8%(V)
Geruchsart	fruity
Wasserlöslichkeit	Miscible with ethyl alcohol, ether, chloroform and benzene. Slightly miscible with water.
Merck	14,3823
JECFA Number	614
BRN	774687
Dielectric constant	7.9（21℃）
Stabilität	Stable. Combustible. Incompatible with strong oxidizing agents,
InChIKey	IYXGSMUGOJNHAZ-UHFFFAOYSA-N
LogP	0.96 at 20℃
CAS Datenbank	105-53-3(CAS DataBase Reference)
NIST chemische Informationen	Propanedioic acid, diethyl ester(105-53-3)
EPA chemische Informationen	Diethyl malonate (105-53-3)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38-36
S-Sätze:	24/25-26
WGK Germany	1
RTECS-Nr.	OO0700000
Selbstentzündungstemperatur	435 °C DIN 51794
Hazard Note	Irritant
TSCA	Yes
HS Code	29171910
Giftige Stoffe Daten	105-53-3(Hazardous Substances Data)
Toxizität	LD50 orally in Rabbit: 15720 mg/kg LD50 dermal Rabbit > 16000 mg/kg

Gefahreninformationscode (GHS)

Diethyl malonate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S24/25:Berührung mit den Augen und der Haut vermeiden.
Aussehen Eigenschaften
C7H12O4; Diethylmalonat, Ethylmalonat, Malonester. Farblose Flüssigkeit mit aromatischem Geruch.
Gefahren für Mensch und Umwelt
Brennbar.
Reizt die Augen und die Haut
LD₅₀ (oral, Ratte): 15000 mg/kg
Schutzmaßnahmen und Verhaltensregeln
Geeignete Schutzhandschuhe als kurzzeitiger Spritzschutz.
Verhalten im Gefahrfall
Mit flüssigkeitsbindendem Material, z.B. Rench Rapid aufnehmen. Der Entsorgung zuführen. Nachreinigen.
Kohlendioxid, Pulver, Schaum.
Brennbar.
Erste Hilfe
Nach Hautkontakt: Mit reichlich Wasser abwaschen.
Nach Augenkontakt: Mit reichlich Wasser bei geöffnetem Lidspalt mindestens 10 Minuten ausspülen. Augenarzt hinzuziehen.
Nach Einatmen: Frischluft.
Nach Verschlucken: Reichlich Wasser trinken lassen. Erbrechen auslösen. Arzt hinzuziehen.
Nach Kleidungskontakt: Kontaminierte Kleidung entfernen.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Als halogenfreie, organische Lösemittelabfälle.
Beschreibung
Diethyl malonate is a diester derivative of malonic acid, a dicarboxylic acid with two carboxyl groups (-COO-) separated by one methylene group (-CH2-). Diethyl malonate is formed by the replacement of the hydroxyl groups (-OH) of malonic acid with ethoxy groups (-OCH2CH3). The hydrogen atoms on the methylene carbon between the two carboxyl groups make this compound acidic. Because of its unique structure, diethyl malonate is reactive and functions as a reagent for organic synthesis and to make products such as barbiturates, pigments, and agrochemicals. Volatile esters are known to have fruity scents and are often used as fragrances and flavorings. Diethyl malonate is a volatile diester that occurs naturally in fruits such as grapes, strawberries, guava, melon, pineapple, and blackberries.
Chemische Eigenschaften
Diethyl malonate has a faint, pleasant, aromatic odor.
Occurrence
Reported found in pineapple, bilberry, Cape gooseberry, cognac, malt whiskey, apple brandy, grape brandy, port, cider, sherry and red, white, strawberry and bilberry wines.
Verwenden
Diethyl Malonate occurs naturally in grapes and strawberries. It is used in the preparation of barbiturates, artificial flavourings, vitamin B1, and vitamin B6 as well as in perfumes.
Verwenden
Diethyl malonate is used in organic synthesis for the preparation of alpha-aryl malonates, mono-substituted and di-substituted acetic acid, barbiturates and artificial flavorings. It is also involved in the synthesis of pharmaceuticals like chloroquine, butazolidin and barbital. It acts as intermediate in the synthesis of vitamin B1, vitamin B6, non-steroidal anti-inflammatory agents agrochemicals and perfumes. In Knoevenagel condensation reaction, it reacts with benzaldehyde to get diethyl benzylidenemalonate.
Verwenden
manufacture of barbiturates.
Definition
ChEBI: Ethyl malonate is a dicarboxylic acid.
synthetische
Reacting chloroacetic acid to cyanoacetic acid using sodium cyanide and subsequent saponification; malonic acid is finally esterified by azeotropic distillation with ethanol in benzene
Taste threshold values
Taste characteristics at 50 ppm: sweet and fruity with apple and pineapple nuances.
Synthesis Reference(s)
The Journal of Organic Chemistry, 46, p. 3151, 1981 DOI: 10.1021/jo00328a041
Tetrahedron Letters, 36, p. 3997, 1995 DOI: 10.1016/0040-4039(95)00697-B
Allgemeine Beschreibung
Diethyl malonate is diethyl ester of malonic acid. Acylation of diethyl malonate using magnesium chloride and triethylamine is reported. K₂CO₃-catalyzed 1,4-addition reaction of diethyl malonate with various substituted 1,2-allenic ketones yields polyfunctionalized β,γ-unsaturated enones.
Sicherheitsprofil
Mildly toxic by ingestion. A skin irritant. Combustible liquid when exposed to heat or flame; can react with oxidizing materials. To fight fire, use water to blanket fire, foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.
Stoffwechsel
When the ester was fed to chicks at a level of 5% in the diet, 32% of the energy from diethyl malonate was available (Yoshida et al. 1970). Hydrolysis of diethyl malonate would produce ethanol and malonic acid, which is a relatively strong acid and acts as an inhibitor of enzymes, including succinic dehydrogenase (Fassett, 1963). Malonic acid injected into rats or rabbits is excreted largely unchanged, but also causes increased excretion of citric and a-ketoglutaric acids (Krebs, Salvin & Johnson, 1938). Some malonate may be metabolized through the tricarboxylic acid cycle, with decarboxylation to acetate followed by transformation to succinate, which has been detected in rat urine (Lee & Lifson, 1951). Diethyl malonate was hydrolysed by adipose-tissue lipase (Lynn & Perryman, 1960) and to the monoester by α-chymotrypsin (Cohen & Crossely, 1964). It was oxidized in 110 min to the extent of 34% by the homogenized mycelium of urethane-grown Streptomyces nitrifica (Schatz, Trelawny, Schatz & Mohan, 1957).
läuterung methode
If too impure (IR, NMR) the ester (250g) is heated on a steam bath for 36hours with absolute EtOH (125mL) and conc H2SO4 (75mL), then fractionally distilled under reduced pressure. Otherwise fractionally distil it under reduced pressure and collect the steady boiling middle fraction. [Beilstein 2 IV 1881.]

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