Diethyl phenylmalonate supplier

Name
Diethyl phenylmalonate
EINECS 201-456-5
CAS No. 83-13-6
Article Data74
CAS DataBase
Density 1.111 g/cm³
Solubility immiscible with water
Melting Point 16 °C
Formula C₁₃H₁₆O₄
Boiling Point 301 °C at 760 mmHg
Molecular Weight 236.268
Flash Point 141.8 °C
Transport Information
Appearance clear colourless to yellowish liquid after melting
Safety 23-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Propanedioic acid, phenyl-, diethyl ester;diethyl 2-phenylpropanedioate;Malonic acid, phenyl-, diethyl ester (8CI);Phenylmalonic acid diethyl ester;Malonic acid, phenyl-, diethyl ester;phenyl ethyl malonic acid diethylester;Diethyl phenyl malonate;Phenyldiethylmalonate;
PSA 52.60000
LogP 1.89640

Synthetic route

: 591-50-4
iodobenzene

: 105-53-3
diethyl malonate

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
With barium dihydroxide; sodium tetrachloropalladate(II) In N,N-dimethyl acetamide at 100℃; for 14h;	100%
With N,N'-(1R,2R)-cyclohexane-1,2-diyl-bis-[1-(pyridine-2-yl)methanimine]; 3 A molecular sieve; caesium carbonate; copper(l) iodide In acetonitrile at 70℃; for 30h;	93%
With copper(l) iodide; caesium carbonate In 1,4-dioxane at 70℃; for 2h;	93%

: 108-86-1
bromobenzene

: 105-53-3
diethyl malonate

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
With barium dihydroxide; sodium tetrachloropalladate(II) In N,N-dimethyl acetamide at 100℃; for 14h;	99%
With di-tert-butyl(neopentyl)phosphine; sodium hydride; bis(dibenzylideneacetone)-palladium(0) In toluene; mineral oil at 70℃; for 24h;	89%
With tri-tert-butyl phosphine; sodium hydride; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 70℃; for 1h;	87%

: 108-90-7
chlorobenzene

: 105-53-3
diethyl malonate

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
With barium dihydroxide; sodium tetrachloropalladate(II) In N,N-dimethyl acetamide at 100℃; for 14h;	93%
With potassium phosphate; (1-adamantyl)di(tert-butyl) phosphine; bis(dibenzylideneacetone)-palladium(0) In toluene at 100℃;	85%

: 101-97-3
Ethyl 2-phenylethanoate

polystyrene-o-nitrophenyl ethyl carbonate: polystyrene-o-nitrophenyl ethyl carbonate

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
With polystyrene-trityllithium In tetrahydrofuran Ambient temperature;	92%

: 154377-07-8
diethyl (methylsulfonyl)phenylmalonate

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
Stage #1: diethyl phenyl(methylsulfonyl)malonate With 1,4-diaza-bicyclo[2.2.2]octane In toluene at 20℃; for 8h; Reflux; Stage #2: With water	83%
With 1,4-diaza-bicyclo[2.2.2]octane; water 1.) toluene, reflux, 2.) room temperature; Yield given. Multistep reaction;

: 5256-74-6
1,3-diethyl 2-diazopropanedioate

: 71-43-2
benzene

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid In neat (no solvent) at 60℃; for 0.5h; Temperature; Friedel-Crafts Alkylation;	82%

: 19213-72-0
ethyl 1-imidazolecarboxylate

: 101-97-3
Ethyl 2-phenylethanoate

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
Stage #1: Ethyl 2-phenylethanoate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: ethyl 1-imidazolecarboxylate In tetrahydrofuran at -78 - 20℃;	81%

: 107365-54-8
diethyl 2-chloro-2-phenylmalonate

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
With zinc In water; acetic acid for 4h; Heating;	80%

: 47252-14-2
triphenylbismuth carbonate

: 105-53-3
diethyl malonate

A: 97080-43-8
diethyl 2,2-diphenylmalonate

B: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
In tetrahydrofuran at 67℃; for 11h;	A 77% B 18%
In tetrahydrofuran at 67℃; for 11h;	A 13% B 53%

...Expand

: 5256-74-6
1,3-diethyl 2-diazopropanedioate

: 934-56-5
trimethyl(phenyl)stannane

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
With potassium fluoride; [Rh(OH)(cod)]2; XPhos In tetrahydrofuran; water at 70℃; for 1h; Stille Cross Coupling; Heating; Inert atmosphere;	76%

: 1979-51-7
1,1,3,3,3-pentafluoro-2-phenylpropene

: 141-52-6
sodium ethanolate

A: 90784-42-2
ethyl 3,3,3-trifluoro-2-phenylpropanoate

B: 83-13-6
diethyl 2-phenylmalonate

C: (E)-3-Ethoxy-3-fluoro-2-phenyl-acrylic acid ethyl ester

Conditions

Conditions	Yield
In acetonitrile at 25℃;	A 74% B 4% C 4%

...Expand

: 591-50-4
iodobenzene

: 105-53-3
diethyl malonate

A: 101-97-3
Ethyl 2-phenylethanoate

B: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
With tri-tert-butyl phosphine; caesium carbonate; tris(dibenzylideneacetone)dipalladium (0) In 1,2-dimethoxyethane at 80℃; for 68h;	A 11% B 71%
With sodium hydride; copper(l) iodide In 1,4-dioxane at 101℃; for 5h; Title compound not separated from byproducts;	A 3 % Chromat. B 97 % Chromat.
copper(l) iodide In 1,4-dioxane at 101℃; for 5h; Product distribution; further solvents, catalysts and additives;	A 3 % Chromat. B 97 % Chromat.

...Expand

: 12082-05-2
(η6-fluorobenzene)tricarbonylchromium

: 105-53-3
diethyl malonate

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
With potassium hydroxide; iodine In diethyl ether; dimethyl sulfoxide addn. of C6H5CH(COOC2H5)2 to mixt. of Cr(CO)3-complex/powd. KOH in DMSO (stirring; 20°C, 6 h), diln. with aq. HCl, extn. with Et2O, treating with excess I2 (room temp., 3 h); distn. (reduced pressure); identification by GC and NMR;	66%

: 5256-74-6
1,3-diethyl 2-diazopropanedioate

: 98-80-6
phenylboronic acid

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
With potassium phosphate; chloro(1,5-cyclooctadiene)rhodium(I) dimer In toluene at 80℃; for 10.5h; Inert atmosphere; Sealed tube; chemoselective reaction;	63%

: 5256-74-6
1,3-diethyl 2-diazopropanedioate

: 2996-92-1
phenyl trimethylsiloxane

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
With [Rh(OH)(cod)]2; tetrabutyl ammonium fluoride; tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane; water at 100℃; for 5h; Hiyama Coupling; Inert atmosphere;	62%

: 7147-33-3
2-oxo-3-phenylbutanedioic acid diethyl ester

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
at 170 - 180℃; for 12h;	61%
under 20 - 40 Torr; bei der Destillation;

: (phenylmethylene)bis(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolane)

: 105-58-8
Diethyl carbonate

A: 83-13-6
diethyl 2-phenylmalonate

B: 102-04-5
1,3-Diphenylpropanone

Conditions

Conditions	Yield
With lithium tert-butoxide In tetrahydrofuran at 23℃; for 3h; Glovebox;	A 21% B 33%

...Expand

: 69836-07-3
diethyl α-bromophenylmalonate

: 108-88-3
toluene

A: 108802-89-7
phenyl-p-tolyl-malonic acid diethyl ester

B: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
With antimony pentafluoride 1.) SO2, -65 deg C, 2.) -65 deg C to RT; Yield given. Multistep reaction;	A n/a B 28%

...Expand

: diphenyliodonium tetrafluoroborate

: 105-53-3
diethyl malonate

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 70℃; for 4h; Phenylation;	27%

: 5256-74-6
1,3-diethyl 2-diazopropanedioate

: 71-43-2
benzene

: (1R*,5R*)-diethyl Bicyclo[3.2.0]hepta-2,6-diene-2,6-dicarboxylate

B: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
at 20℃; for 17h; Mechanism; Inert atmosphere; Sealed tube; Photolysis;	A 17% B 18%

...Expand

: 69836-07-3
diethyl α-bromophenylmalonate

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
With antimony pentafluoride; benzene Product distribution; 1.) SO2, -65 deg C; 2.) -65 deg C to RT;	13%

: 56-23-5
tetrachloromethane

: 28383-65-5
ethyl 2-diazo-3-oxo-3-phenylpropanoate

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
Behandeln des Reaktionsproduktes mit verd. Natriumaethylat-Loesung;

: 28383-65-5
ethyl 2-diazo-3-oxo-3-phenylpropanoate

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
at 250℃; under 11 Torr;
With xylene Behandeln des Reaktionsproduktes mit verd. Natriumaethylat-Loesung;
at 250℃; under 11 Torr;

: 101-97-3
Ethyl 2-phenylethanoate

: 95-92-1
oxalic acid diethyl ester

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
With sodium ethanolate Erhitzen des Reaktionsprodukts unter 200 Tor auf 140-150grad;

: 101-97-3
Ethyl 2-phenylethanoate

: 105-58-8
Diethyl carbonate

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
With sodium ethanolate under 125 Torr; unter Entfernen des entstehenden Aethanols;
With sodium hydride In tetrahydrofuran at 0℃; for 4h; Reflux;

: 101-97-3
Ethyl 2-phenylethanoate

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
With ammonia; sodium amide Erwaermen des Reaktionsprodukts mit Kohlensaeure-diaethylester in Aether;
With diethyl ether; potassium at 20℃; Behandlung des Reaktionsprodukts mit Chlorameisensaeure-aethylester;
Multi-step reaction with 2 steps 1: sodium ethanolate 2: 12 h / 170 - 180 °C View Scheme

: 95-92-1
oxalic acid diethyl ester

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
With ethanol; sodium at 60℃; man zersetzt das Natriumsalz mit verd. Schwefelsaeure und erhitzt bei etwa 15 mm auf 175grad;

: 4553-07-5
ethyl phenylcyanoacetate

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
With hydrogenchloride; ethanol

: 64-17-5
ethanol

: 83392-44-3
Phenylmalonic dibromide

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
With 2-oxo-3-trimethyltetrahydro-1,3-oxazole for 0.25h; Ambient temperature; Yield given;

: 1825-62-3
ethyl trimethylsilyl ether

: 83392-44-3
Phenylmalonic dibromide

: 83-13-6
diethyl 2-phenylmalonate

Conditions

Conditions	Yield
In dichloromethane at 15℃; for 15h; Yield given;

: 83-13-6
diethyl 2-phenylmalonate

: 1570-95-2
2-phenylpropane-1, 3-diol

Conditions

Conditions	Yield
With diisobutylaluminium hydride In tetrahydrofuran for 2h; Mechanism; Product distribution; Ambient temperature; other reducing agents, var. time;	100%
With diisobutylaluminium hydride In tetrahydrofuran for 2h; Ambient temperature;	100%
Stage #1: diethyl 2-phenylmalonate With sodium hydroxide In tetrahydrofuran; water at 145℃; under 2280.15 Torr; for 0.933333h; Inert atmosphere; Stage #2: With tetrabutyl-ammonium chloride In tetrahydrofuran; water for 0.183333h; Inert atmosphere; Stage #3: With sodium hydroxide In tetrahydrofuran; water; toluene at 156℃; under 3800.26 Torr; for 3.13333h; Solvent; Temperature; Pressure; Inert atmosphere;	99.6%

: 124-68-5
2-Amino-2-methyl-1-propanol

: 83-13-6
diethyl 2-phenylmalonate

: N,N'-bis(1-hydroxy-2-methylpropan-2-yl)-2-phenylmalonamide

Conditions

Conditions	Yield
With sodium hydride In mineral oil at 160℃; Inert atmosphere;	100%

: 83-13-6
diethyl 2-phenylmalonate

: 69836-07-3
diethyl α-bromophenylmalonate

Conditions

Conditions	Yield
With cetyltrimethylammonim bromide; manganese triacetate In acetic acid at 70℃; for 2h;	99%
Stage #1: diethyl 2-phenylmalonate With sodium hydride In tetrahydrofuran Stage #2: With dibromamine-B In tetrahydrofuran; dichloromethane at 0℃; for 1h;	88%
Stage #1: diethyl 2-phenylmalonate With sodium hydride In tetrahydrofuran at 0℃; Stage #2: With N-Bromosuccinimide In tetrahydrofuran for 0.25h;	63%

: 106-96-7
propargyl bromide

: 83-13-6
diethyl 2-phenylmalonate

: 51632-37-2
diethyl 2-phenyl-2-(prop-2-yn-1-yl)malonate

Conditions

Conditions	Yield
Stage #1: diethyl 2-phenylmalonate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Stage #2: propargyl bromide In tetrahydrofuran; toluene; mineral oil at 0 - 20℃;	99%
(i) NaOEt, EtOH, (ii) /BRN= 605309/; Multistep reaction;

: 83-13-6
diethyl 2-phenylmalonate

: 22225-53-2
α-Amino-α-phenyl-malonsaeure-diaethylester

Conditions

Conditions	Yield
Stage #1: diethyl 2-phenylmalonate With sodium hydride In tetrahydrofuran at 23℃; for 0.25h; Stage #2: With O-(4-nitrobenzoyl) hydroxylamine In tetrahydrofuran at 23℃;	99%
With sodium hydride; O-(2,4-dinitrophenyl)hydroxylamine
(i) NaH, THF, (ii) O-(2,4-dinitro-phenyl)-hydroxylamine; Multistep reaction;

: 83-13-6
diethyl 2-phenylmalonate

: 270921-38-5
(4-methylphenyl)methyl carbonate

: diethyl [(4-methylphenyl)methyl](phenyl)malonate

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; 1,5-cis,cis-cyclooctadiene; [PdCp(η3-C3H5)] In tetrahydrofuran at 80℃;	99%
With 1,1'-bis-(diphenylphosphino)ferrocene; N,O-bis-(trimethylsilyl)-acetamide; {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4; potassium acetate In tetrahydrofuran at 80℃; for 24h;	98%

: 83-13-6
diethyl 2-phenylmalonate

: 270921-39-6
(4-methoxyphenyl)methyl methyl carbonate

: 95002-44-1
diethyl [(4-methoxyphenyl)methyl](phenyl)malonate

Conditions

Conditions	Yield
With 1,1'-bis(diisopropylphosphino)ferrocene; {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4; caesium carbonate In N,N-dimethyl-formamide at 30℃; for 24h; Inert atmosphere;	99%
With 1,1'-bis-(diphenylphosphino)ferrocene; 1,5-cis,cis-cyclooctadiene; [PdCp(η3-C3H5)] In tetrahydrofuran at 80℃; for 3h;	98%
With 1,1'-bis-(diphenylphosphino)ferrocene; N,O-bis-(trimethylsilyl)-acetamide; {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4; potassium acetate In tetrahydrofuran at 80℃; for 4h;	94%

: 83-13-6
diethyl 2-phenylmalonate

: [4-(methoxycarbonyl)phenyl]methyl methyl carbonate

: diethyl [{4-(methoxycarbonyl)phenyl}methyl](phenyl)malonate

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; 1,5-cis,cis-cyclooctadiene; [PdCp(η3-C3H5)] In tetrahydrofuran at 80℃;	99%
With 1,1'-bis-(diphenylphosphino)ferrocene; N,O-bis-(trimethylsilyl)-acetamide; {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4; potassium acetate In tetrahydrofuran at 80℃; for 24h;	86%
With 1,1'-bis(diisopropylphosphino)ferrocene; {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4; caesium carbonate In N,N-dimethyl-formamide at 30℃; for 4h; Inert atmosphere;	84%

: 83-13-6
diethyl 2-phenylmalonate

: methyl 2-naphthalenylmethyl carbonate

: diethyl [(2-naphthyl)methyl](phenyl)malonate

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; [PdCp(η3-C3H5)] In tetrahydrofuran at 80℃; for 1h;	99%

: 83-13-6
diethyl 2-phenylmalonate

: methyl (naphthalen-1-ylmethyl) carbonate

: diethyl [(1-naphthyl)methyl](phenyl)malonate

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; [PdCp(η3-C3H5)] In tetrahydrofuran at 80℃; for 1h;	99%

: 73930-97-9
3-acetoxy-1,3-diphenylpropene

: 83-13-6
diethyl 2-phenylmalonate

: C28H28O4

Conditions

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); C24H31O2P; lithium acetate; bis-(trimethylsilyl)acetamide In dichloromethane at -20℃; for 10h; Inert atmosphere; optical yield given as %ee;	99%

: 23726-00-3
<2H9>trimethylsulphoxonium iodide

: 83-13-6
diethyl 2-phenylmalonate

: diethyl 2-(methyl-d3)-2-phenylmalonate

Conditions

Conditions	Yield
Stage #1: diethyl 2-phenylmalonate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Sealed tube; Stage #2: <2H9>trimethylsulphoxonium iodide In tetrahydrofuran; mineral oil at 80℃; for 8h; Sealed tube;	99%

: 83-13-6
diethyl 2-phenylmalonate

: 74-88-4
methyl iodide

: 34009-61-5
diethyl 2-methyl-2-phenylmalonate

Conditions

Conditions	Yield
Stage #1: diethyl 2-phenylmalonate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: methyl iodide In N,N-dimethyl-formamide for 18h;	98%
With sodium ethanolate In ethanol for 3h; Heating;	81%
Stage #1: diethyl 2-phenylmalonate With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 0 - 20℃; for 36h; Inert atmosphere; Schlenk technique;	75%

: 13326-10-8
benzyl methyl carbonate

: 83-13-6
diethyl 2-phenylmalonate

: 613670-59-0
diethyl 2-benzyl-2-phenylmalonate

Conditions

Conditions	Yield
With 1,1'-bis(diisopropylphosphino)ferrocene; {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4; caesium carbonate In N,N-dimethyl-formamide at 30℃; for 48h; Inert atmosphere;	98%
With 1,1'-bis-(diphenylphosphino)ferrocene; N,O-bis-(trimethylsilyl)-acetamide; {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4; potassium acetate In tetrahydrofuran at 80℃; for 24h;	95%
With 1,1'-bis-(diphenylphosphino)ferrocene; 1,5-cis,cis-cyclooctadiene; [PdCp(η3-C3H5)] In tetrahydrofuran at 80℃;	84%

: 83-13-6
diethyl 2-phenylmalonate

: 73640-03-6
hydroxyphenylmalonic acid diethyl ester

Conditions

Conditions	Yield
With 10% Pd on charcoal; oxygen; triethylamine In ethanol at 20℃; for 6h;	98%
With 5%-palladium/activated carbon; triethylamine In ethanol at 20℃; for 5h; Reagent/catalyst;	98%
With Pd2hpp4; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; oxygen In tetrahydrofuran at 6℃; under 760.051 Torr; for 12h; regioselective reaction;	97%
With iodine; sodium acetate In tetrahydrofuran; water at 35℃; for 5h; Irradiation; Green chemistry;	88%

: 83-13-6
diethyl 2-phenylmalonate

: 131934-09-3, 135765-81-0, 712-41-4
ethyl 2-(hydroxyimino)-2-phenylacetate

Conditions

Conditions	Yield
With sulfuric acid; potassium carbonate; sodium nitrite In ethanol; water at 10℃; for 5h;	97.2%

: 6138-90-5
trans-geranyl bromide

: 83-13-6
diethyl 2-phenylmalonate

: 16725-60-3
(E)-diethyl 2-[3,7-dimethylocta-2,6-dienyl]-2-phenylmalonate

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere;	97%
With sodium ethanolate In ethanol

: 104-94-9
4-methoxy-aniline

: 83-13-6
diethyl 2-phenylmalonate

: 28563-21-5
4-hydroxy-6-methoxy-3-phenyl-2(1H)-quinolinone

Conditions

Conditions	Yield
In diphenylether at 250 - 300℃; for 3h;	97%
	71%
at 260 - 270℃;	71%

: 83-13-6
diethyl 2-phenylmalonate

: methyl (2-methylphenyl)methyl carbonate

: diethyl [(2-methylphenyl)methyl](phenyl)malonate

Conditions

Conditions	Yield
With 1,1'-bis(diisopropylphosphino)ferrocene; {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4; caesium carbonate In N,N-dimethyl-formamide at 50℃; for 24h; Inert atmosphere;	97%
With 1,1'-bis-(diphenylphosphino)ferrocene; 1,5-cis,cis-cyclooctadiene; [PdCp(η3-C3H5)] In tetrahydrofuran at 80℃;	90%

: 87751-69-7
rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene

: 83-13-6
diethyl 2-phenylmalonate

: (S,E)-diethyl 2-(1,3-diphenylallyl)-2-phenylmalonate

Conditions

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide; bis(η3-allyl-μ-chloropalladium(II)); N-[(S)-1-(2-(diphenylphosphino)phenyl)ethyl]-1,7,7-trimethylbicyclo[2,2,1]heptan-2-imine; cesium acetate In toluene at 20℃; enantioselective reaction;	97%
With N,O-bis-(trimethylsilyl)-acetamide; bis(η3-allyl-μ-chloropalladium(II)); (S)-7-(diphenylphosphino)-2′-isopropyl-2,3-dihydro-5′H-spiro[indene-1,4′-oxazole]; potassium acetate In toluene at 0℃; for 5h; Inert atmosphere; Schlenk technique; enantioselective reaction;	91%

: C12H10(2)HF2NO6S

: 83-13-6
diethyl 2-phenylmalonate

: C14H15(2)HF2O4

Conditions

Conditions	Yield
Stage #1: diethyl 2-phenylmalonate With lithium tert-butoxide In acetonitrile at 20℃; for 0.166667h; Stage #2: C12H10(2)HF2NO6S In acetonitrile at 20℃; for 0.166667h;	97%

: (6-methoxynaphthalen-2-yl)methyl 2,3,4,5,6-pentafluorobenzoate

: 83-13-6
diethyl 2-phenylmalonate

: diethyl 2-((6-methoxynaphthalen-2-yl)methyl)-2-phenylmalonate

Conditions

Conditions	Yield
With 2-Picolinic acid; bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)]; caesium carbonate In acetonitrile at 60℃; for 18h; Inert atmosphere;	97%

: 17739-45-6, 59146-56-4
2-(2-bromoethoxy)tetrahydropyran

: 83-13-6
diethyl 2-phenylmalonate

: 106996-59-2
(tetrahydropyrannyl-2 oxy)-2 ethyl phenyl malonate de diethyle

Conditions

Conditions	Yield
With hydrogenchloride In N,N-dimethyl-formamide	96%
With potassium tert-butylate 1.) t-butanol, 70 deg. C, 2 h; 2.) 70 deg C, 10 h; Yield given. Multistep reaction;

: 83-13-6
diethyl 2-phenylmalonate

: 300537-13-7
Diethyl [α-2H]phenylmalonate

Conditions

Conditions	Yield
Stage #1: diethyl 2-phenylmalonate With sodium hydride In tetrahydrofuran for 5h; Metallation; Heating; Stage #2: With diclazuril; water-d2 Substitution; Deuteration; Further stages.;	96%

: 83-13-6
diethyl 2-phenylmalonate

: 270921-40-9
[(4-trifluoromethyl)phenyl]methyl methyl carbonate

: diethyl [{4-(trifluoromethyl)phenyl}methyl](phenyl)malonate

Conditions

Conditions	Yield
With 1,1'-bis(diisopropylphosphino)ferrocene; {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4; caesium carbonate In N,N-dimethyl-formamide at 30℃; for 24h; Inert atmosphere;	96%
With 1,1'-bis-(diphenylphosphino)ferrocene; 1,5-cis,cis-cyclooctadiene; [PdCp(η3-C3H5)] In tetrahydrofuran at 80℃;	90%
With 1,1'-bis-(diphenylphosphino)ferrocene; N,O-bis-(trimethylsilyl)-acetamide; {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4; potassium acetate In tetrahydrofuran at 80℃; for 48h;	78%

: 3749-51-7
4-hydroxy-6-methyl-2-pyridone

: 83-13-6
diethyl 2-phenylmalonate

: 955377-04-5
C15H11NO4

Conditions

Conditions	Yield
In diphenylether Heating;	96%

: 83-13-6
diethyl 2-phenylmalonate

: 41601-44-9
3-amino-4,6-dimethylpyrazolo[3,4-b]pyridine

: 1220996-95-1
4-hydroxy-8,10-dimethyl-3-phenylpyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidin-2(1H)-one

Conditions

Conditions	Yield
In diphenylether at 220 - 250℃;	96%

: 1187617-25-9
(Z)-3-bromo-5-triisopropylsilyl-1,3-pentadiene

: 83-13-6
diethyl 2-phenylmalonate

: 1370439-84-1
diethyl 2-phenyl-2-[5-(triisopropylsilyl)penta-2,3-dienyl]propane-1,3-dioate

Conditions

Conditions	Yield
With (PdAllylCl)2; sodium hydride; 2,2'-bis(diphenylphosphino)biphenyl In tetrahydrofuran at 23℃; for 12h; Inert atmosphere;	96%

Diethyl phenylmalonate Specification

The IUPAC name of Diethyl phenylmalonate is diethyl 2-phenylpropanedioate. With the CAS registry number 83-13-6, it is also named as Phenylmalonic acid diethyl ester. The product's categories are Pharmaceutical Intermediates; C12 to C63; Carbonyl Compounds; Esters. Besides, it is clear colourless to yellowish liquid after melting, which should be stored in dark, dry and sealed place. In addition, its molecular formula is C₁₃H₁₆O₄ and molecular weight is 236.26. When you are using this chemical, please do not breathe vapour. And you should avoid contact with skin and eyes.

The other characteristics of this product can be summarized as: (1)EINECS: 201-456-5; (2)ACD/LogP: 2.71; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 2.71; (5)ACD/LogD (pH 7.4): 2.71; (6)ACD/BCF (pH 5.5): 67.03; (7)ACD/BCF (pH 7.4): 67.02; (8)ACD/KOC (pH 5.5): 706.06; (9)ACD/KOC (pH 7.4): 706.03; (10)#H bond acceptors: 4; (11)#H bond donors: 0; (12)#Freely Rotating Bonds: 7; (13)Index of Refraction: 1.5; (14)Molar Refractivity: 62.51 cm³; (15)Molar Volume: 212.4 cm³; (16)Surface Tension: 38.9 dyne/cm; (17)Density: 1.111 g/cm³; (18)Flash Point: 141.8 °C; (19)Melting Point: 16 °C; (20)Enthalpy of Vaporization: 54.11 kJ/mol; (21)Boiling Point: 301 °C at 760 mmHg; (22)Vapour Pressure: 0.00108 mmHg at 25 °C.

Preparation of Diethyl phenylmalonate: this chemical can be prepared by condensation, acidification and elimination of Ethyl phenylacetate. It is also produced by the reaction of Malonic acid diethyl ester with Bromobenzene.

This reaction needs Ba(OH)₂, Na₂PdCl₄ and N,N-Dimethyl-acetamide at temperature of 100 °C. The reaction time is 14 hours. The yield is 99 %.

Uses of Diethyl phenylmalonate: this chemical is a pharmaceutical intermediate that can be used to produce Phenobarbital. Similarly, it can react with 2-Amino-benzenethiol to get Bis-benzothiazol-2-yl-phenyl-methane.

This reaction needs Polyphosphoric acid at temperature of 80-90 °C for 2 hours. The yield is 92 %.

People can use the following data to convert to the molecule structure.
(1)SMILES: O=C(OCC)C(C(=O)OCC)c1ccccc1
(2)InChI: InChI=1/C13H16O4/c1-3-16-12(14)11(13(15)17-4-2)10-8-6-5-7-9-10/h5-9,11H,3-4H2,1-2H3
(3)InChIKey: FGYDHYCFHBSNPE-UHFFFAOYAH

Product Name

Diethyl phenylmalonate

Synthetic route

Diethyl phenylmalonate Specification

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