Diethyl allylmalonate (HCID 74900)

Namen und Bezeichner

Bevorzugter Name: Diethyl allylmalonate
IUPAC: diethyl 2-prop-2-enylpropanedioate
Lokaler Name: Diethylallylmalonat
Englischer Name: Diethyl allylmalonate
Summenformel: C10H16O4
Molmasse: 200.23

Namen und Synonyme

Diethyl allylmalonate2049-80-1diethyl 2-prop-2-enylpropanedioatePropanedioic acid, 2-(2-propen-1-yl)-, 1,3-diethyl esterM5ETZ38HUJ2-allylmalonic acid diethyl esterNSC-8777EINECS 218-072-9NSC-67393AI3-11069DTXSID30883787RefChem:133399

Weitere Namen anzeigen

NSC 8777Diethyl allylDiethyl allylmaloteALLYLDIETHYLMALONATEDiethyl allyimalonateDiethyl allylmalonate,97%Allylmalonic acid diethyl

DTXCID901023274218-072-9GDWAYKGILJJNBB-UHFFFAOYSA-NInChI=1/C10H16O4/c1-4-7-8(9(11)13-5-2)10(12)14-6-3/h4,8H,1,5-7H2,2-3HDiethyl 2-allylmalonateEthyl allylmalonateAllylmalonic acid diethyl esterDiethyl prop-2-enylpropanedioate

Datenbank-Bezeichner

CAS: 2049-80-1
PubChem CID: 74900
DTXSID: DTXSID30883787
UNII: M5ETZ38HUJ
EC Number: 218-072-9
Nikkaji: J26.303F

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 1,9
Polarare Oberfläche (TPSA): 52,6 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 4
Frei drehbare Bindungen: 8
Schwere Atome: 14
Formalladung: 0
Komplexität: 192

Experimentelle und physikochemische Eigenschaften

SpringerMaterials PropertiesDiamagnetic susceptibility

Physikochemische Eigenschaften

Siedepunkt: 222 · 222-223 °C(lit.)
Dichte: 1.015 g/mL · 1.015 g/mL at 25 °C(lit.)
Brechungsindex: 20 · n20/D 1.431(lit.)
Flammpunkt: 160 °F · 160 °F
storage temp.: 30 °C · Store below +30°C.
Aggregatzustand: Liquid
pka: 12.63 · 12.63±0.46(Predicted)
Farbe: Clear colorless to slightly yellow
Wasserlöslichkeit: Not miscible or difficult to mix with water.
BRN: 1709466 · 1709466
InChI: 1S/C10H16O4/c1-4-7-8(9(11)13-5-2)10(12)14-6-3/h4,8H,1,5-7H2,2-3H3
InChIKey: GDWAYKGILJJNBB-UHFFFAOYSA-N
SMILES: CCOC(=O)C(CC=C)C(=O)OCC
LogP: 1.99 · 1.990 (est)
CAS Datenbank: 2049 · 2049-80-1(CAS DataBase Reference)
NIST chemische Informationen: 2 · Propanedioic acid, 2-propenyl-, diethyl ester(2049-80-1)
EPA chemische Informationen: 2 · Propanedioic acid, 2-propenyl-, diethyl ester (2049-80-1)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 2.4% (1 of 41) of reports.

Warning

H315 (97.6%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory InformationChemical: Propanedioic acid, 2-propenyl-, diethyl ester

Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia

Hazard Classes and CategoriesSkin Irrit. 2 (97.6%)

Sicherheitsdaten

wgk: 3
tsca: TSCA listed
ridadr: NA 1993 / PGIII
hs_code: 29171990
risk_code: 36/37/38
hazard_code: Xi
safety_code: 26-36-37/39
Speicherklasse: 10 - Combustible liquids

Chemie und Industrie

Verwendung und Herstellung

General Manufacturing InformationPropanedioic acid, 2-(2-propen-1-yl)-, 1,3-diethyl ester: INACTIVE

Anwendungen

VerwendenDiethyl allylmalonate is an important intermediates in syntheses of vitamins B1 and B6, barbiturates, non-steroidal anti-inflammatory agents, other numerous pharmaceuticals, agrochemicals and flavors and fragrances compounds.

Darstellung · 1 Eintrag

synthetischeDiethyl allyl malonate is obtained by reacting diethyl malonate with allyl bromide. Under nitrogen atmosphere, to a 500 mL three-neck round bottom flask was added diethyl malonate (20 g), anhydrous potassium carbonate (43 g) and anhydrous CH3CN (200 mL). The reaction mixture was stirred at room temperature for 10 minutes, then allyl bromide (23 g) was slowly added to the reaction mixture at room temperature. The reaction mixture was heated to 80°C for 24 hours. The reaction mixture was cooled to room temperature and filtered through a bed of celite. The celite bed was washed with acetonitrile (100 mL) and the combined filtrates were concentrated to give diethyl allylmalonate (24 g) as a colorless liquid.