Diethyl allylmalonate supplier

Name
Diethyl allylmalonate
EINECS 218-072-9
CAS No. 2049-80-1
Article Data145
CAS DataBase
Density 1.021 g/cm³
Solubility Not miscible or difficult to mix with water.
Melting Point
Formula C₁₀H₁₆O₄
Boiling Point 222.499 °C at 760 mmHg
Molecular Weight 200.235
Flash Point 92.778 °C
Transport Information
Appearance clear colorless to slightly yellow liquid
Safety 26-36-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Malonicacid, allyl-, diethyl ester (6CI,7CI,8CI);Propanedioic acid, 2-propenyl-,diethyl ester (9CI);(2-Propenyl)propanedioic acid diethyl ester;2-Allylmalonic acid diethyl ester;Allylmalonic acid diethyl ester;Diethyl1-butene-4,4-dicarboxylate;Diethyl 2-allyl-1,3-propanedioate;Diethyl2-allylmalonate;Diethyl 2-prop-2-enylmalonate;Diethyl 2-propenylmalonate;Ethyl allylmalonate;NSC 67393;NSC 8777;
PSA 52.60000
LogP 1.30490

Synthetic route

: 106-95-6
allyl bromide

: 105-53-3
diethyl malonate

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

Conditions

Conditions	Yield
With tetrabutyl-ammonium chloride; potassium carbonate In dichloromethane; water at 80℃; for 45h;	100%
	98%
With P(MeNCH2CH2)3N In hexane; acetonitrile at 25℃; for 0.5h;	94%

: 591-87-7
Allyl acetate

: 105-53-3
diethyl malonate

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

Conditions

Conditions	Yield
With palladium diacetate; potassium fluoride on basic alumina for 0.0833333h; Trost-Tsuji reaction; microwave irradiation;	98%
With C29H29N2O2PPd; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h; Reagent/catalyst; Tsuji-Trost Allylation; Schlenk technique; Inert atmosphere;	77%
With potassium fluoride on basic alumina; 1,2-bis-(diphenylphosphino)ethane; bis[1,2-bis(diphenylphosphino)ethane]palladium(0) In tetrahydrofuran for 4.5h; Ambient temperature;	75%

: 107-18-6
allyl alcohol

: 105-53-3
diethyl malonate

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

Conditions

Conditions	Yield
With pyridine; magnesium sulfate; 1,2-(p-MeOC6H4)2cyclobuten[=P(2,4,6-tri-t-BuPh)]2PdOTf at 50℃; for 12h;	92%
With [bis(methyldiphenylsilyl)methyl]diphenylphosphine; pyridine; tetrabutyl ammonium fluoride; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 100℃; for 8h; Tsuji-Trost reaction;	86%

: 591-87-7
Allyl acetate

: 105-53-3
diethyl malonate

A: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

B: 3195-24-2
diallylmalonic acid diethyl ester

Conditions

Conditions	Yield
With C33H33N2O4PPd; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h; Reagent/catalyst; Tsuji-Trost Allylation; Schlenk technique; Inert atmosphere;	A 91% B 8%
With C48H47ClN2P2Pd(1+); potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h; Reagent/catalyst; Tsuji-Trost Allylation; Schlenk technique; Inert atmosphere;	A 22% B 78%
With aluminum oxide; triphenylphosphine; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 40h; Ambient temperature;	A 70% B 15%

...Expand

: 107-05-1
3-chloroprop-1-ene

: 105-53-3
diethyl malonate

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

Conditions

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In acetonitrile at 50℃; for 7h;	87%
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In acetonitrile for 7h;	87%

: 74070-96-5
Phenyl-phosphonothioic acid S-allyl ester O-ethyl ester

: 105-53-3
diethyl malonate

A: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

B: 3195-24-2
diallylmalonic acid diethyl ester

Conditions

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) at 80℃; for 0.666667h; Product distribution;	A 87% B 13%

...Expand

: 16515-85-8
triethyl pent-4-ene-1,2,2-tricarboxylate

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

Conditions

Conditions	Yield
With sodium ethanolate In tetrahydrofuran for 1h; Inert atmosphere;	87%

: 35466-83-2
allyl methyl carbonate

: 105-53-3
diethyl malonate

A: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

B: 3195-24-2
diallylmalonic acid diethyl ester

Conditions

Conditions	Yield
With triphenylphosphine In water at 50℃; for 24h;	A 84% B 4%
With triphenylphosphine; Pd-Gr In tetrahydrofuran; dodecane for 4h; Heating; Title compound not separated from byproducts;	A 41 % Chromat. B 3 % Chromat.
With tris-(dibenzylideneacetone)dipalladium(0); 2,2’-(methylenedisulfanediyl)bis(1,3-benzothiazole) In tetrahydrofuran at 70℃; for 2h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Tsuji-Trost Allylation; chemoselective reaction;

...Expand

: 105-53-3
diethyl malonate

<(C5H5)Co3>Pd(propenyl): <(C5H5)Co3>Pd(propenyl)

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

Conditions

Conditions	Yield
With sodium hydride In toluene at 20℃; for 16h;	82%

: 105-53-3
diethyl malonate

allyl halide: allyl halide

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran	80%

: 34727-00-9
lithium diethyl malonate

tetracarbonyl(ϖ-allyl)manganese: tetracarbonyl(ϖ-allyl)manganese

A: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

B: 3195-24-2
diallylmalonic acid diethyl ester

Conditions

Conditions	Yield
In N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether for 1.5h; -78 deg C -> r.t.; Title compound not separated from byproducts;	A 13% B 76%

...Expand

: 106-95-6
allyl bromide

: 105-53-3
diethyl malonate

A: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

B: 3195-24-2
diallylmalonic acid diethyl ester

Conditions

Conditions	Yield
Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran at 0℃; for 0.25h; Stage #2: allyl bromide In tetrahydrofuran at 0 - 25℃; for 14h; Further stages.;	A 24% B 76%
Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: allyl bromide at 20℃; for 12h; Inert atmosphere;	A 68% B n/a
Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: allyl bromide In tetrahydrofuran at 20℃; for 12h;	A 68% B 12%

...Expand

: 17686-63-4
acetone O-<(allyloxy)-carbonyl>oxime

: 105-53-3
diethyl malonate

A: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

B: 3195-24-2
diallylmalonic acid diethyl ester

Conditions

Conditions	Yield
ethyl-diphenyl-phosphane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran for 1h; Ambient temperature;	A 75% B 3%

...Expand

: 118068-86-3
C12H13NO3

: 105-53-3
diethyl malonate

A: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

B: 3195-24-2
diallylmalonic acid diethyl ester

Conditions

Conditions	Yield
ethyl-diphenyl-phosphane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran for 1.5h; Product distribution; Ambient temperature; variation of allylating agents, solvent, temperature and reaction time.;	A 75% B 14%
ethyl-diphenyl-phosphane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran for 1.5h; Ambient temperature;	A 75% B 14%

...Expand

: 1823-91-2
1-phenylethyl cyanide

: 105-53-3
diethyl malonate

A: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

B: 3195-24-2
diallylmalonic acid diethyl ester

Conditions

Conditions	Yield
With potassium carbonate; Pd(PhCH=CH)2CO>2CO; 1,2-bis-(diphenylphosphino)ethane In N,N-dimethyl-formamide Ambient temperature;	A 74% B 26%

...Expand

: 105-53-3
diethyl malonate

: 762-72-1
allyl-trimethyl-silane

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

Conditions

Conditions	Yield
With ammonium cerium(IV) nitrate In methanol for 4h; Ambient temperature;	74%
With ammonium cerium (IV) nitrate In methanol	57%

: 74070-90-9, 97714-35-7, 97714-36-8
Allyl ethyl phenylphosphonothionate

: 105-53-3
diethyl malonate

A: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

B: 3195-24-2
diallylmalonic acid diethyl ester

C: 74070-96-5
Phenyl-phosphonothioic acid S-allyl ester O-ethyl ester

Conditions

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) at 80℃; for 0.333333h; Product distribution;	A 25% B 2% C 73%

...Expand

: 556-56-9
allyl iodid

: 105-53-3
diethyl malonate

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

Conditions

Conditions	Yield
With cerium oxide nanoparticle In water at 20℃; for 12h; Green chemistry;	72%
Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h; Stage #2: allyl iodid In tetrahydrofuran for 24h; Reflux;

: 107-05-1
3-chloroprop-1-ene

: 105-53-3
diethyl malonate

A: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

B: 3195-24-2
diallylmalonic acid diethyl ester

Conditions

Conditions	Yield
Stage #1: diethyl malonate With potassium tert-butylate In N,N-dimethyl-formamide at 0℃; for 0.0833333h; Stage #2: 3-chloroprop-1-ene In N,N-dimethyl-formamide at 20℃; for 12h;	A 70% B 5%
With potassium hydroxide; polyethylene glycol Alkylation;	A 42.5% B n/a
With potassium hydroxide; water; cetyltrimethylammonim bromide for 1h; Alkylation;	A 30.9% B n/a
With ethanol; sodium

...Expand

: 24850-33-7
allyltributylstanane

: 685-87-0
Diethyl 2-bromomalonate

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

Conditions

Conditions	Yield
With [Cu(2,9-bis(4-methoxyphenyl)-1,10-phenanthroline)2]Cl In acetonitrile for 4.5h; Irradiation; Inert atmosphere;	70%

: 685-87-0
Diethyl 2-bromomalonate

: 762-72-1
allyl-trimethyl-silane

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

Conditions

Conditions	Yield
With fac-tris[2-phenylpyridinato-C2,N]iridium(III) In acetonitrile at 20 - 30℃; for 24h; Inert atmosphere; Irradiation;	70%
With C44H29CuN4O3P(1+)*BF4(1-) In acetonitrile at 20℃; Reagent/catalyst; UV-irradiation;	64%

: 118068-88-5
C10H15NO3

: 105-53-3
diethyl malonate

A: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

B: 3195-24-2
diallylmalonic acid diethyl ester

Conditions

Conditions	Yield
ethyl-diphenyl-phosphane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran for 3h; Ambient temperature;	A 69% B 2%

...Expand

: 50998-68-0
4-nitro-benzaldehyde-(O-allyl-seqtrans-oxime )

: 105-53-3
diethyl malonate

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

Conditions

Conditions	Yield
With sodium diethylmalonate; ethyl-diphenyl-phosphane; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 100℃; for 24h;	67%

: 685-87-0
Diethyl 2-bromomalonate

: potassium trifluoro(prop-1-en-2-yl)borate

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; eosin y In methanol at 20℃; Irradiation;	67%

: 996-82-7, 34727-00-9, 73177-21-6
sodium diethylmalonate

: 29443-23-0
N,N,N-triethylprop-2-en-1-aminium bromide

A: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

B: 3195-24-2
diallylmalonic acid diethyl ester

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 24h; Ambient temperature;	A 62% B 13%

...Expand

: 996-82-7, 34727-00-9, 73177-21-6
sodium diethylmalonate

: 591-87-7
Allyl acetate

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

Conditions

Conditions	Yield
diiron nonacarbonyl In tetrahydrofuran at 20℃; for 120h;	61%

: 107-18-6
allyl alcohol

: 105-53-3
diethyl malonate

A: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

B: 3195-24-2
diallylmalonic acid diethyl ester

Conditions

Conditions	Yield
With acetic acid; tetrakis(triphenylphosphine) palladium(0) at 100℃; for 0.166667h;	A 61% B 30%
With 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) bromide trihydrate; tetrabutylammonium acetate; zinc In N,N-dimethyl acetamide at 50℃; for 66h; Inert atmosphere;	A 45% B 6%
With bis(1,5-cyclooctadiene)nickel (0); 1,4-di(diphenylphosphino)-butane In toluene at 105℃; for 17h; Reagent/catalyst; Temperature; Inert atmosphere; Schlenk technique;	A 20 %Chromat. B 63 %Chromat.

...Expand

: 3195-24-2
diallylmalonic acid diethyl ester

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

Conditions

Conditions	Yield
With iodine In dimethyl sulfoxide at 60℃; for 0.5h; Acidic conditions;	57%
With tris(triphenylphosphine)ruthenium(II) chloride; triethylaluminum In toluene at 20℃; for 36h;	91 % Spectr.
With triethylaluminum; Fe(III)bis(imidazolonyl)pyridine)Cl3 In toluene at 20℃; for 24h;	13 % Spectr.

: 85021-16-5
allyl (N-phenyl)benzimidate

: 105-53-3
diethyl malonate

A: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

B: 3195-24-2
diallylmalonic acid diethyl ester

Conditions

Conditions	Yield
With 1,2-bis-(diphenylphosphino)ethane; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide for 4h; Ambient temperature;	A 55% B 28%

...Expand

: 107-11-9
1-amino-2-propene

: 105-53-3
diethyl malonate

A: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

B: 3195-24-2
diallylmalonic acid diethyl ester

Conditions

Conditions	Yield
With nickel(II) bromide trihydrate; 1,4-di(diphenylphosphino)-butane; zinc In N,N-dimethyl-formamide at 80℃; for 22h; Inert atmosphere;	A 55% B 20%

...Expand

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 13353-23-6
ethyl (±)-4,5-epoxy-2-(ethoxycarbonyl)pentanoate

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 15h; Ambient temperature;	100%
With 3-chloro-benzenecarboperoxoic acid In chloroform for 12h; Ambient temperature;	98%
With potassium peroxymonosulfate sulfate In aq. phosphate buffer; water; ethyl acetate; acetone at 20℃; pH=8;	86%

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 2583-25-7
allylmalonic acid

Conditions

Conditions	Yield
With potassium hydroxide In ethanol	100%
With sodium hydroxide In methanol; dichloromethane at 20℃; for 1h;	87%
With lithium aluminium tetrahydride In tetrahydrofuran	85%

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 1528-30-9
methylenecyclopentane

: 127220-05-7
diethyl 4-methylenespiro<4.4>nonane-2,2-dicarboxylate

Conditions

Conditions	Yield
With copper diacetate; manganese triacetate In acetic acid at 70 - 75℃; for 24h;	100%

: 5332-26-3
N-(bromomethyl)phtalimide

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 1200242-48-3
diethyl 2‐allyl‐2‐phthalimidomethylmalonate

Conditions

Conditions	Yield
Stage #1: (2-propenyl)propanedioic acid diethyl ester With sodium hydride In tetrahydrofuran at 0 - 25℃; Inert atmosphere; Stage #2: N-(bromomethyl)phtalimide In tetrahydrofuran at 0 - 25℃; Inert atmosphere;	100%

: 50-00-0
formaldehyd

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 82515-47-7
diethyl 2-allyl-2-(hydroxymethyl)malonate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water at 0 - 20℃; for 20h;	99%
With sodium hydrogencarbonate In ethanol; water at 0 - 20℃; for 20h;	99%
With potassium carbonate In dimethyl sulfoxide for 168h; Ambient temperature;	13%

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 18495-26-6
1-bromo-2-heptyne

: 191801-57-7
diethyl 2-allyl-2-(hept-2-yn-1-yl)malonate

Conditions

Conditions	Yield
Stage #1: (2-propenyl)propanedioic acid diethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: 1-bromo-2-heptyne In tetrahydrofuran; mineral oil at 0 - 20℃; for 12h; Inert atmosphere;	99%
Stage #1: (2-propenyl)propanedioic acid diethyl ester With sodium hydride In tetrahydrofuran at 20℃; Stage #2: 1-bromo-2-heptyne In tetrahydrofuran at 20℃; for 12h; Further stages.;

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 161678-48-4
Octa-<(3-mercaptopropyl)-silsesquioxan>

: C104H184O44S8Si8

Conditions

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In tetrahydrofuran for 0.5h; UV-irradiation;	98.7%

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: silver allylmalonate

Conditions

Conditions	Yield
With nitric acid; silver nitrate In water	98.5%

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 106-96-7
propargyl bromide

: 101268-55-7
4,4-bis(ethoxycarbonyl)-1-hepten-6-yne

Conditions

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran; hexane; toluene at -78℃; for 1h;	98%
Stage #1: (2-propenyl)propanedioic acid diethyl ester With sodium ethanolate In diethyl ether; ethanol for 0.166667h; Cooling with ice; Inert atmosphere; Stage #2: propargyl bromide In diethyl ether; ethanol at 20℃; for 1h; Cooling with ice; Inert atmosphere;	92%
Stage #1: (2-propenyl)propanedioic acid diethyl ester With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Inert atmosphere; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 0 - 25℃; for 1h; Inert atmosphere;	92%

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 513-81-5
2,3-dimethyl-buta-1,3-diene

: diethyl 2-(4,5-dimethyl-2-methylene-4-hexenyl)malonate

Conditions

Conditions	Yield
With tetrabutylammonium borohydride; zinc(II) iodide; cobalt(II) bromide-[1,2-bis(diphenylphosphino)ethane] In dichloromethane at 40℃; for 20h;	98%
With cobalt(II) bromide-[1,2-bis(diphenylphosphino)ethane]; zinc(II) iodide; zinc In dichloromethane for 20h;	92%
With tetrabutylammonium borohydride; zinc(II) iodide; cobalt(II) bromide-[1,2-bis(diphenylphosphino)ethane] In dichloromethane at 40℃; for 16h;	81%

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 821-10-3
1,4-Dichloro-2-butyne

: 1193378-70-9
tetraethyl dodeca-1,11-dien-6-yne-4,4,9,9-tetracarboxylate

Conditions

Conditions	Yield
Stage #1: (2-propenyl)propanedioic acid diethyl ester With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; Stage #2: 1,4-Dichloro-2-butyne In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃;	98%

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 7022-45-9
2-(methylsulfanyl)benzaldehyde

: 1362860-33-0
1,3-diethyl 2-(4-(2-(methylthio)phenyl)-4-oxobutyl)malonate

Conditions

Conditions	Yield
With C21H44N2P2Rh*C32H12BF24 In acetone at 55℃; for 3h; Inert atmosphere;	98%
With [Rh(η6-C6H5F)(bis(dicyclohexylphosphino)methane)][B(C6H3-3,5-(CF3)2)4] In 1,2-dichloro-ethane at 80℃; for 2h; Inert atmosphere;

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: (Z)-3-fluoro-3-phenylallyl 2,2,2-trifluoroacetate

: diethyl (S)-2-allyl-2-(1-fluoro-1-phenylallyl)malonate

Conditions

Conditions	Yield
Stage #1: (2-propenyl)propanedioic acid diethyl ester With sodium hydride In tetrahydrofuran at 65℃; for 0.166667h; Sealed tube; Stage #2: (Z)-3-fluoro-3-phenylallyl 2,2,2-trifluoroacetate With C51H54IrNO4P(1+)*BF4(1-) In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; enantioselective reaction;	98%

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 74-88-4
methyl iodide

: 53651-72-2
diethyl allylmethylmalonate

Conditions

Conditions	Yield
	97%
With sodium methylate
With sodium ethanolate

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 5292-43-3
bromoacetic acid tert-butyl ester

: 193806-54-1
2-Allyl-2-ethoxycarbonyl-succinic acid 4-tert-butyl ester 1-ethyl ester

Conditions

Conditions	Yield
With sodium hydride	96%
Stage #1: (2-propenyl)propanedioic acid diethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Stage #2: bromoacetic acid tert-butyl ester In tetrahydrofuran; mineral oil at 20℃; for 16h;

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 106-93-4
ethylene dibromide

: 174619-42-2
diethyl (+/-)-(2-bromoethyl)(2-propenyl)propanedioate

Conditions

Conditions	Yield
Stage #1: (2-propenyl)propanedioic acid diethyl ester With sodium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: ethylene dibromide In tetrahydrofuran at 20℃; for 15h;	96%
Stage #1: (2-propenyl)propanedioic acid diethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1.5h; Inert atmosphere; Stage #2: ethylene dibromide In tetrahydrofuran; mineral oil at 20℃; for 15.5h; Inert atmosphere;	96%
Stage #1: (2-propenyl)propanedioic acid diethyl ester With sodium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: ethylene dibromide In tetrahydrofuran at 20℃; for 15h;	81%

: C39H53NO3*C24H32O8*F6P(1-)*H(1+)

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: C40H59NO5*C24H32O8*F6P(1-)*H(1+)

Conditions

Conditions	Yield
Stage #1: (2-propenyl)propanedioic acid diethyl ester With sodium hydride In tetrahydrofuran Stage #2: C39H53NO3C24H32O8F6P(1-)*H(1+) With 1,3-bis-(diphenylphosphino)propane; palladium diacetate In tetrahydrofuran at 20℃; for 20h; Tsuji-Trost allylation;	96%

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 85850-08-4
(Z)-1-bromo-3-methylpent-2-en-4-yne

: 1187458-52-1
2-allyl-2-((Z)-3-methyl-pent-2-en-4-ynyl)-malonic acid diethyl ester

Conditions

Conditions	Yield
Stage #1: (2-propenyl)propanedioic acid diethyl ester With sodium hydride In tetrahydrofuran Inert atmosphere; Stage #2: (Z)-1-bromo-3-methylpent-2-en-4-yne In tetrahydrofuran Inert atmosphere;	96%

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 42201-43-4
2-allyl-1,3-propanediol

Conditions

Conditions	Yield
Stage #1: (2-propenyl)propanedioic acid diethyl ester With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 4.5h; Stage #2: With water; sodium hydroxide In tetrahydrofuran at 0 - 20℃; for 0.166667h;	95%
With lithium aluminium tetrahydride In diethyl ether for 1h; Ambient temperature;	94%
With lithium aluminium tetrahydride In diethyl ether 1.) 1 h, 0 deg C, 2.) 4 h, room temperature;	86%

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 1493-27-2
ortho-nitrofluorobenzene

: diethyl 2-nitrophenyl(2-propenyl)malonate

Conditions

Conditions	Yield
With triethylsilane; t-Bu-P4 In hexane; N,N-dimethyl-formamide at 80℃; for 2h;	95%

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 50-01-1
guanidine hydrochloride

: 97570-29-1
5-allyl-2-aminopyrimidine-4,6-diol

Conditions

Conditions	Yield
Stage #1: (2-propenyl)propanedioic acid diethyl ester; guanidine hydrochloride With sodium In ethanol at 20℃; for 4h; Inert atmosphere; Stage #2: In ethanol for 1h; Inert atmosphere; Reflux;	95%
With sodium In ethanol Inert atmosphere;	95%
With sodium methylate In methanol at 0℃; Reflux;	62.8%
With sodium carbonate In water at 60℃; for 0.5h; Reagent/catalyst; Sonication;	61%
Stage #1: guanidine hydrochloride With sodium ethanolate In ethanol at 0℃; for 0.166667h; Stage #2: (2-propenyl)propanedioic acid diethyl ester In ethanol at 0 - 20℃; for 65h; Stage #3: With hydrogenchloride In ethanol; water	51%

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 20629-39-4, 20629-62-3, 79629-38-2
1,2-dibromo-2-butene

: 1254219-12-9
diethyl 2-allyl-2-((Z)-2-bromo-2-butenyl)malonate

Conditions

Conditions	Yield
With sodium ethanolate In tetrahydrofuran at 20℃; Inert atmosphere;	95%

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 21003-54-3, 23970-90-3, 96725-21-2
(E)-(2,3-dibromoprop-1-enyl)benzene

: 1254219-14-1
diethyl 2-allyl-2-((E)-3-phenyl-2-bromo-2-propenyl)malonate

Conditions

Conditions	Yield
With sodium ethanolate In tetrahydrofuran at 20℃; Inert atmosphere;	95%

: penta-2,3-dien-1-yl methanesulfonate

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 1304145-47-8
diethyl 2-allyl-2-(penta-2,3-dien-1-yl)malonate

Conditions

Conditions	Yield
Stage #1: (2-propenyl)propanedioic acid diethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: penta-2,3-dien-1-yl methanesulfonate In tetrahydrofuran; mineral oil at 21 - 25℃; Inert atmosphere;	95%
Stage #1: (2-propenyl)propanedioic acid diethyl ester With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: penta-2,3-dien-1-yl methanesulfonate In tetrahydrofuran at 0 - 55℃; for 50.0833h;	40%

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 2163-48-6
diethyl propylmalonate

Conditions

Conditions	Yield
With platinum(IV) oxide; hydrogen In ethanol at 20℃; for 4h;	94%
With hydrogen; polymeric rhodium In tetrahydrofuran; ethanol under 760 Torr; for 12h;

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 18495-27-7
1-bromooct-2-yne

: 350248-68-9
(2-octynyl)-(2-propenyl)propanedioic acid diethyl ester

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;	94%
Stage #1: (2-propenyl)propanedioic acid diethyl ester With sodium hydride In tetrahydrofuran at 0 - 20℃; Stage #2: 1-bromooct-2-yne In tetrahydrofuran at 20℃; for 16h; Further stages.;	81%

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: 1794-48-5
1-bromo-3-phenylprop-2-yne

: 143633-91-4
diethyl 2-allyl-2-(3-phenylprop-2-yn-1-yl)malonate

Conditions

Conditions	Yield
Stage #1: (2-propenyl)propanedioic acid diethyl ester With sodium hydride In tetrahydrofuran at 20℃; Stage #2: 1-bromo-3-phenylprop-2-yne In tetrahydrofuran at 20℃; for 12h; Further stages.;	94%
Stage #1: (2-propenyl)propanedioic acid diethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1.5h; Inert atmosphere; Stage #2: 1-bromo-3-phenylprop-2-yne In tetrahydrofuran; mineral oil at 0 - 20℃; for 24h; Inert atmosphere;	79%
With sodium hydride Inert atmosphere;
Stage #1: (2-propenyl)propanedioic acid diethyl ester With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1.5h; Stage #2: 1-bromo-3-phenylprop-2-yne In tetrahydrofuran at 0 - 20℃;

: 2049-80-1
(2-propenyl)propanedioic acid diethyl ester

: (E)-1,1,1-trifluoro-4-phenylbut-3-en-2-yl benzoate

: (S)-diethyl 2-allyl-2-(4,4,4-trifluoro-1-phenylbut-2-en-1-yl)malonate

Conditions

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide; {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4; 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine] In 1,4-dioxane at 60℃; for 24h; Inert atmosphere; enantioselective reaction;	94%

Diethyl allylmalonate Chemical Properties

Molecular structure of Propanedioic acid, 2-(2-propen-1-yl)-, 1,3-diethyl ester (CAS NO.2049-80-1):

IUPAC Name: Diethyl 2-prop-2-enylpropanedioate
Molecular Weight: 200.23164 [g/mol]
Molecular Formula: C₁₀H₁₆O₄
Density: 1.021 g/cm³
Boiling Point: 222.5 °C at 760 mmHg
Flash Point: 92.8 °C
Index of Refraction: 1.439
Molar Refractivity: 51.61 cm³
Molar Volume: 196 cm³
Surface Tension: 31.8 dyne/cm
Enthalpy of Vaporization: 45.9 kJ/mol
Vapour Pressure: 0.101 mmHg at 25 °C
XLogP3: 1.9
H-Bond Acceptor :4
Rotatable Bond Count: 8
Exact Mass: 200.104859
MonoIsotopic Mass: 200.104859
Topological Polar Surface Area: 52.6
Heavy Atom Count: 14
Canonical SMILES: CCOC(=O)C(CC=C)C(=O)OCC
InChI: 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
EINECS: 218-072-9
Product Categories: Pharmaceutical Intermediates; Aromatic Esters; TheMalonateRamificationProducts

Diethyl allylmalonate Uses

Propanedioic acid, 2-(2-propen-1-yl)-, 1,3-diethyl ester (CAS NO.2049-80-1) is used as raw materials for pharmaceutical and pesticide intermediates.

Diethyl allylmalonate Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
HS Code: 29171990

Diethyl allylmalonate Specification

Propanedioic acid, 2-(2-propen-1-yl)-, 1,3-diethyl ester (CAS NO.2049-80-1) is also named as AI3-11069 ; Diethyl 2-(2-propenyl)-1,3-propanedioate ; Diethyl 2-(prop-2-enyl)malonate ; Diethyl 2-allylmalonate ; Diethyl allylmalonate ; Diethyl prop-2-enylpropanedioate ; Ethyl allylmalonate ; Malonic acid, allyl-, diethyl ester ; NSC 67393 ; NSC 8777 ; Propanedioic acid, 2-propenyl-, diethyl ester . Propanedioic acid, 2-(2-propen-1-yl)-, 1,3-diethyl ester (CAS NO.2049-80-1) is clear colorless to slightly yellow liquid.

Product Name

Diethyl allylmalonate

Synthetic route

Diethyl allylmalonate Chemical Properties

Diethyl allylmalonate Uses

Diethyl allylmalonate Safety Profile

Diethyl allylmalonate Specification

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