CAS 2049-80-1 Diethyl allylmalonate (HCID 74900)

Names & identifiers

Preferred name: Diethyl allylmalonate
IUPAC: diethyl 2-prop-2-enylpropanedioate
English name: Diethyl allylmalonate
Molecular formula: C10H16O4
Molecular weight: 200.23

Names & synonyms

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

Show more names

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

Database identifiers

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

Properties

Computed structural properties

XLogP: 1.9
Topological polar surface area: 52.6 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 8
Heavy atoms: 14
Formal charge: 0
Complexity: 192

Experimental & physicochemical properties

SpringerMaterials PropertiesDiamagnetic susceptibility

Physicochemical properties

Boiling point: 222 · 222-223 °C(lit.)
Density: 1.015 g/mL · 1.015 g/mL at 25 °C(lit.)
refractive index: 20 · n20/D 1.431(lit.)
Flash point: 160 °F · 160 °F
storage temp.: 30 °C · Store below +30°C.
form: Liquid
pka: 12.63 · 12.63±0.46(Predicted)
color: Clear colorless to slightly yellow
Water Solubility: 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 DataBase Reference: 2049 · 2049-80-1(CAS DataBase Reference)
FDA UNII: 5 ETZ38HUJ · M5ETZ38HUJ
NIST Chemistry Reference: 2 · Propanedioic acid, 2-propenyl-, diethyl ester(2049-80-1)
EPA Substance Registry System: 2 · Propanedioic acid, 2-propenyl-, diethyl ester (2049-80-1)
UNSPSC Code: 12162002 · 12162002
NACRES: 23 · NA.23
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 335 · H335-H227-H315-H319
Precautionary statements: 210 · P210-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P370+P378-P403+P235-P501-P210e-P261-P280a-P305+P351+P338-P405-P501a
PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36-37/39
RIDADR: 1993 · NA 1993 / PGIII
WGK Germany: 3 · 3
TSCA: TSCA listed
HS Code: 29171990 · 29171990
Storage Class: 10 · 10 - Combustible liquids

Safety & regulation

GHS classification

GHS Classification · 5 items

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.

Hazard information

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%)

Safety data

PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
tsca: TSCA listed
ridadr: NA 1993 / PGIII
hs_code: 29171990
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36-37/39
Storage Class: 10 - Combustible liquids
Hazard statements: H335-H227-H315-H319
Precautionary statements: P210-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P370+P378-P403+P235-P501-P210e-P261-P280a-P305+P351+P338-P405-P501a

Chemistry & industry

Uses & manufacturing

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

Applications

UsesDiethyl 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.

Preparation methods · 1 item

PreparationDiethyl 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.