Dimethyl malonate supplier

Name
Dimethyl malonate
EINECS 203-597-8
CAS No. 108-59-8
Article Data112
CAS DataBase
Density 1.156 g/cm³
Solubility negligible
Melting Point -62 °C(lit.)
Formula C₅H₈O₄
Boiling Point 177.1 °C at 760 mmHg
Molecular Weight 132.116
Flash Point 90 °C
Transport Information
Appearance liquid
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Malonicacid, dimethyl ester (6CI,8CI);Propanedioic acid, dimethyl ester (9CI);Dimethyl 1,3-propanedioate;Dimethyl propanedioate;Methylmalonate;NSC 620046;Dimethyl Malonate (DMM);Dimethyl malonate;
PSA 52.60000
LogP -0.27750

Synthetic route

: 67-56-1
methanol

: 141-82-2
malonic acid

: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
With boron trifluoride at 65℃; for 0.333333h;	100%
zirconium(IV) oxide; molybdenum at 84.85℃; for 6h; Esterification;	95%
iodine for 15h; Heating;	94%

: 141-82-2
malonic acid

: 616-38-6
carbonic acid dimethyl ester

: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
With sulfuric acid at 80 - 85℃; for 2h; Neat (no solvent);	99.8%

: 16695-14-0
Malonic acid monomethyl ester

: 79-22-1
methyl chloroformate

A: 108-59-8
malonic acid dimethyl ester

B CO2: CO2

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 4℃; for 0.5h;	A 95% B n/a

...Expand

: 16695-14-0
Malonic acid monomethyl ester

: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
	95%

Co2 (CO)8: Co2 (CO)8

: 96-34-4
methyl chloroacetate

: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
With sodium methylate In methanol	91%
With sodium hydroxide In methanol	87%

: 13750-34-0
N--p-toluolsulfonamid

A: 84274-88-4
N--p-toluolsulfonamid

B: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
With sodium methylate; malonic acid dimethyl ester In methanol for 8h; Ambient temperature;	A 90% B 84%

: 96-34-4
methyl chloroacetate

: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
With potassium methanolate In methanol; Co2 (CO)8	90%

: 67-56-1
methanol

: dicobalt(η2-(C,C)-ketene)(CO)7

A: 79-20-9
acetic acid methyl ester

B: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
With carbon monoxide In methanol Carbonylation at 50 atm.;	A 77% B 7%

...Expand

: 109-84-2
2-hydroxyethylhydrazine

: dimethyl 3-(t-butylimino)-2,2-dimethylpropylidenemalonate

A: 7,7-dimethyl-2,3,7,7a-tetrahydropyrazolo<5,1-b>oxazole

B: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
In methanol for 8h; Heating;	A 75% B 73%

...Expand

: 67-56-1
methanol

: 75-09-2
dichloromethane

: 201230-82-2
carbon monoxide

A: 109-87-5
Dimethoxymethane

B: 79-20-9
acetic acid methyl ester

C: 6290-49-9
methyl methoxyacetate

D: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
With Methyl formate; sodium methylate; Co2(CO)6{P(C4H9-n)3}2 at 80℃; under 11250.9 Torr; for 15h; electrolysis;	A 8% B n/a C 3% D 74.5%
With Methyl formate; sodium methylate; Co2(CO)6{P(C4H9-n)3}2 at 80℃; under 11250.9 Torr; for 15h; Product distribution; Mechanism; electrolysis, var. of catalyst, its reduction method, ratio;	A 8% B n/a C 3% D 74.5%
With sodium hydroxide; carbon-doped cobalt at 80℃; under 23560 Torr; for 1h;	A 1.2 % Chromat. B 7.5 % Chromat. C 1.9 % Chromat. D 28.8 % Chromat.

...Expand

: dimethyl 3-(t-butylimino)-2,2-dimethylpropylidenemalonate

: 40440-12-8
(3-hydroxypropyl)hydrazine

A: 3,3-dimethyl-3,3a,6,7-tetrahydro-5H-pyrazolo<5,1-b><1,3>oxazine

B: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
In methanol for 8h; Heating;	A 74% B 70%

...Expand

: 42287-37-6
1-hydrazinyl-2-methylpropan-2-ol

: dimethyl 3-(t-butylimino)-2,2-dimethylpropylidenemalonate

A: 2,2,7,7-tetramethyl-2,3,7,7a-tetrahydropyrazolo<5,1-b>oxazole

B: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
In methanol for 8h; Heating;	A 71% B 68%

...Expand

: 84157-94-8
4-hydroxybutylhydrazine

: dimethyl 3-(t-butylimino)-2,2-dimethylpropylidenemalonate

A: 3,3-dimethyl-3,3a,5,6,7,8-hexahydropyrazolo<5,1-b><1,3>oxazepine

B: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
In methanol for 8h; Heating;	A 69% B 67%

...Expand

: 67-56-1
methanol

: 109-77-3
malononitrile

A: 105-34-0
methyl 2-cyanoacetate

B: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate for 68h; Heating;	A 68% B 28%

...Expand

: dimethyl 3-(t-butylimino)-2,2-dimethylpropylidenemalonate

: 3-hydrazino-2,2-dimethyl-1-propanol

A: 90832-25-0
3,3,6,6-tetramethyl-3,3a,6,7-tetrahydro-5H-pyrazolo<5,1-b><1,3>oxazine

B: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
In methanol for 8h; Heating;	A 67% B 63%

...Expand

: 74-87-3
methylene chloride

: 141-95-7
sodium malonate

: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
tetrahexylammonium bromide at 125℃; for 4h;	67%
tetrabutylammomium bromide at 125℃; for 5h;	64%
tetrabutylammomium bromide at 100℃; for 4h;	58%

: 67-56-1
methanol

: 108-13-4
malonodiamide

: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
With Amberlyst 15 at 60℃; for 24h;	63%

: 67-56-1
methanol

: 1165952-92-0
cyclohexa-1,4-diene

A: 7424-91-1
methyl 3,3-dimethoxypropionate

B: 102-52-3
malonaldehydebis(dimethylacetal)

C: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
With hydrogenchloride; ozone -40 deg C, then ca. 30 min reflux; Yields of byproduct given;	A 60% B n/a C n/a
With hydrogenchloride; ozone at -40℃; -40 deg C, then ca. 30 min reflux; Yield given;	A 60% B n/a C n/a
With hydrogenchloride; ozone at -40℃; Product distribution;	A 60% B n/a C n/a

...Expand

: 141-82-2
malonic acid

: 74-88-4
methyl iodide

: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 2h;	54%

: 96-32-2
bromoacetic acid methyl ester

: 3-(methoxycarbonyl)oxazolidin-2-one

: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
With zinc In tetrahydrofuran 1) 30 deg C, 2 h, 2) reflux, 18 h;	53%

: 201230-82-2
carbon monoxide

: 124-41-4
sodium methylate

: 96-32-2
bromoacetic acid methyl ester

A: 6290-49-9
methyl methoxyacetate

B: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
iron pentacarbonyl In tetrahydrofuran at 55℃; under 3800 Torr;	A n/a B 45%

...Expand

: 6773-29-1
dimethyl diazomalonate

: 120-92-3
cyclopentanone

A: 111209-96-2
3-(1,1-Bismethoxycarbonylmethyl)cyclopent-1-one

B: 2-(Cyclopent-1-enyloxy)-malonic acid dimethyl ester

C: 168566-72-1
1,3-dimethyl 2-(2-oxocyclopentyl)propanedioate

D: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
benzophenone for 10h; Irradiation; Further byproducts given;	A 9% B 15% C 39% D 28%

...Expand

: 6773-29-1
dimethyl diazomalonate

: 78-93-3
butanone

A: methyl 2-(methoxycarbonyl)-3-methyl-4-oxopentanonate

B: 2-ethyl-2-methyl-5-(methoxycarbonyl)-1,3-dioxolan-4-one

C: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
benzophenone for 14h; Product distribution; Irradiation;	A 31% B 8% C 26%
for 14h; Irradiation;	A 31% B 8% C 26%

...Expand

: 67-56-1
methanol

: 22692-28-0
1,3-difluoro-1,1,3,3-tetranitropropane

: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
at 60℃; for 3h;	30%

: 6773-29-1
dimethyl diazomalonate

: 67-64-1
acetone

A: 34259-29-5
dimethyl 2-hydroxymalonate

B: 24889-15-4
methyl 2-(methoxycarbonyl)-4-oxopentanonate

C: 62609-79-4
methyl 2,2-dimethyl-5-oxo-1,3-dioxolane-4-carboxylate

D: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
benzophenone for 10h; Irradiation;	A 25% B 5% C 25% D 2%

...Expand

: 868-26-8
dimethyl 2-bromomalonate

: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); H2B(μ-3,5-dimethylpyrazole)2BH2 In toluene at 85℃; for 1h; Inert atmosphere;	25%
With 5-Hexen-1-ol; C30H26N6Ru(2+)*2Cl(1-); triethylamine In N,N-dimethyl-formamide Inert atmosphere; Irradiation;
With 1,2,3,4-tetrakis(carbazol-9-yl)-5,6-dicyanobenzene; triethylamine In 1-methyl-pyrrolidin-2-one at 20℃; for 0.166667h; Inert atmosphere; Irradiation;	48 %Chromat.

: 5018-30-4
dimethyl methoxymalonate

: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
In ethanol for 2h; UV-irradiation;	21%

: 6773-29-1
dimethyl diazomalonate

: 75-07-0
acetaldehyde

A: 60187-67-9
dimethyl acetamidomalonate

B: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
benzophenone for 8h; Irradiation;	A 3% B 15%

...Expand

: 6773-29-1
dimethyl diazomalonate

: 28569-96-2
1,2,2-trimethyl-bicyclo{1.1.0}butane

A: 80530-76-3
1,1-dicarbomethoxy-3,3,4-trimethylpenta-1,4-diene

B: 108-59-8
malonic acid dimethyl ester

Conditions

Conditions	Yield
for 10h; Irradiation; Further byproducts given;	A 14.2% B n/a

...Expand

: 100-52-7
benzaldehyde

: 108-59-8
malonic acid dimethyl ester

: 6626-84-2
dimethyl 2-benzylidenepropanedioate

Conditions

Conditions	Yield
With rac-Pro-OH In dimethyl sulfoxide at 20℃; for 16h; Knoevenagel condensation;	100%
With piperidine; acetic acid In benzene Knoevenagel Condensation; Dean-Stark; Reflux; Inert atmosphere;	99%
With amino-tagged Zr based metal organic frame work(UiO-66-NH-RNH2) In toluene at 23℃; for 2h; Knoevenagel Condensation;	99%

: 552-89-6
2-nitro-benzaldehyde

: 108-59-8
malonic acid dimethyl ester

: 65974-52-9
dimethyl 2-[(2-nitrophenyl)methylidene]malonate

Conditions

Conditions	Yield
With piperidine; acetic acid In benzene at 80℃; for 15h; Knoevenagel Condensation; Microwave irradiation;	100%
With piperidin-1-ium piperidine-1-carboxylate In neat (no solvent) at 25℃; Knoevenagel Condensation;	87%
With potassium carbonate In acetic anhydride at 80℃; for 4h;	86%

: 108-59-8
malonic acid dimethyl ester

: 42937-74-6
dimethyl 2-(hydroxyimino)malonate

Conditions

Conditions	Yield
With acetic acid; sodium nitrite In water at 0 - 20℃;	100%
With acetic acid; sodium hydroxide; sodium nitrite In water at 5 - 20℃; for 24h;	95%
With hydrogenchloride; 1-(4-(nitrosooxy)butyl)-3-methylimidazolium chloride; water at 20℃;	94%

: 292638-85-8
acrylic acid methyl ester

: 108-59-8
malonic acid dimethyl ester

: 80269-67-6
trimethyl 4-oxocyclohexane-1,1,3-tricarboxylate

Conditions

Conditions	Yield
With sodium hydride	100%
With sodium methylate In methanol for 1h; Heating;
With sodium In methanol; water

: 590-86-3
isovaleraldehyde

: 108-59-8
malonic acid dimethyl ester

: 53618-21-6
dimethyl 2-(3-methylbutylidene)malonate

Conditions

Conditions	Yield
With chromatorex NH In toluene at 70℃; Reagent/catalyst; Temperature; Knoevenagel Condensation; Flow reactor; Molecular sieve;	100%
With L-proline In dimethyl sulfoxide at 20℃; Reagent/catalyst; Knoevenagel Condensation;	97%
With rac-Pro-OH In dimethyl sulfoxide at 20℃; for 16h; Knoevenagel condensation;	92%

: 930-68-7
cyclohexenone

: 108-59-8
malonic acid dimethyl ester

: 33646-18-3
dimethyl 2-(3-oxocyclohexyl)malonate

Conditions

Conditions	Yield
(anthracenebisresorcinol(4-):2La(3+))polymer In benzene at 20℃; for 48h; Michael addition;	100%
at 20℃; for 12h; Michael addition; Electrolysis;	98%
Stage #1: malonic acid dimethyl ester at 20℃; Electrolysis; Stage #2: cyclohexenone at 20℃; for 12h; Michael addition;	98%

: 108-59-8
malonic acid dimethyl ester

: 6773-29-1
dimethyl diazomalonate

Conditions

Conditions	Yield
With 4-acetamidobenzenesulfonyl azide; triethylamine In acetonitrile Inert atmosphere;	100%
With 4-acetamidobenzenesulfonyl azide; triethylamine In acetonitrile at 20℃; for 24h; Inert atmosphere;	99%
With 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 20℃; for 1h;	99%

: 100-39-0
benzyl bromide

: 108-59-8
malonic acid dimethyl ester

: 49769-78-0
2-benzyl-malonic acid dimethyl ester

Conditions

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide; toluene at 18℃; for 3h;	100%
With sodium hydride In tetrahydrofuran at 20℃; for 2h;	82%
Stage #1: malonic acid dimethyl ester With sodium hydride In tetrahydrofuran; paraffin oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: benzyl bromide In tetrahydrofuran; paraffin oil at 20℃; for 2h; Inert atmosphere;	78%

: 37622-92-7
1-(p-toluenesulfonyl)-1H-imidazole-4(5)-carboxaldehyde

: 108-59-8
malonic acid dimethyl ester

: 139285-01-1
dimethyl 1(p-toluenesulfonyl)-1H-imidazol-4(5)-ylmethylenemalonate

Conditions

Conditions	Yield
With piperidine; acetic acid In benzene at 40℃; for 3h;	100%

: 76644-52-5, 76704-31-9, 14447-34-8, 62247-41-0
rac-3-acetoxycyclohexene

: 108-59-8
malonic acid dimethyl ester

: 34939-28-1
dimethyl 2-(cyclohex-2-en-1-yl)malonate

Conditions

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0); N,O-bis-(trimethylsilyl)-acetamide; N,N'-bis(diphenylphosphino)-N,N'-dimethylethane-1,2-diamine In tetrahydrofuran at 20℃; for 0.85h; Product distribution; var. ligand: dppb, var. chiral ligands (R,R)-DIOP, S,S-BPPM, etc.):ee = 5-40percent;	100%
With bis(1,5-cyclooctadiene)nickel (0); N,O-bis-(trimethylsilyl)-acetamide; N,N'-bis(diphenylphosphino)-N,N'-dimethylethane-1,2-diamine In tetrahydrofuran at 20℃; for 0.85h;	100%
Stage #1: malonic acid dimethyl ester With sodium hydride In tetrahydrofuran at 20℃; for 0.25h; Metallation; Stage #2: rac-3-acetoxycyclohexene With tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In tetrahydrofuran for 4h; Alkylation; deacetoxylation; Heating;	92%

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

: 108-59-8
malonic acid dimethyl ester

: 177468-91-6
(E)-dimethyl (1,3-diphenylprop-2-en-1-yl)propanedioate

Conditions

Conditions	Yield
With benzenesulfonamide; potassium acetate; [(η3-C3H5)Pd(SC6F4H-4)(P(C6H4OMe-4)3)] In dichloromethane at 20℃; for 4h;	100%
With caesium carbonate; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; bis(2,6-diisopropylphenyl)imidazolium salt In tetrahydrofuran at 50℃; for 10h; Tsuji-Trost reaction;	100%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; caesium carbonate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran at 50℃; for 10h;	100%

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

: 108-59-8
malonic acid dimethyl ester

: 95071-02-6, 96482-67-6, 131065-36-6, 148553-10-0, 96482-64-3
dimethyl 2-[(E)-(S)-1,3-diphenylallyl]-malonate

Conditions

Conditions	Yield
Stage #1: malonic acid dimethyl ester With 15-crown-5; sodium hydride In acetonitrile at 20℃; for 0.5h; Metallation; Stage #2: rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene; chiral 2-(phosphinoaryl)pyridine palladium In acetonitrile at 0℃; for 1h; Alkylation;	100%
With chiral 1-dinaphthoazepino-2-dinaphthophosphepinoethane*BH3; potassium acetate; bis-(trimethylsilyl)acetamide; palladium diacetate In dichloromethane at 20℃; for 6h;	100%
With bis(η3-allyl-μ-chloropalladium(II)); C28H36N4O4P2; tetrabutylammomium bromide; potassium carbonate In dichloromethane at 20℃; for 18h; Tsuji-Trost reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	100%

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

: 108-59-8
malonic acid dimethyl ester

: 95071-02-6, 96482-64-3, 131065-36-6, 148553-10-0, 96482-67-6
(R)-methyl 2-carbomethoxy-3,5-diphenylpent-4-enoate

Conditions

Conditions	Yield
With 1,2-bis[(R)-dinaphthoazepino]ethane ligand; potassium acetate; bis-(trimethylsilyl)acetamide; [(ν3-allyl)PdCl]2 In dichloromethane at 20℃; for 2h;	100%
With bis(η3-allyl-μ-chloropalladium(II)); C2-symmetric chiral P; potassium acetate; bis-(trimethylsilyl)acetamide In dichloromethane for 0.5h; Ambient temperature;	99%
With benzenesulfonamide; (C6H13)4N(+); bis(η3-allyl-μ-chloropalladium(II)); (R,S)-phosphinooxazoline In acetonitrile	99%

: 111014-37-0
methyl (E)-2-carbomethoxy-2-<(E)-4-chloro-2-butenyl>-8-<(tetrahydro-2H-pyran-2-yl)oxy>-6-octenoate

: 108-59-8
malonic acid dimethyl ester

: 111014-38-1
methyl (E),(E)-2,7,7-tricarbomethoxy-13-<(tetrahydro-2H-pyran-2-yl)oxy>-4,11-tridecadienoate

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide for 1.5h; Heating;	100%

: 111014-39-2
methyl 2-carbomethoxy-2-<(Z)-4-chloro-2-butenyl>-8-<(tetrahydro-2H-pyran-2-yl)oxy>-6-octynoate

: 108-59-8
malonic acid dimethyl ester

: 111014-40-5
methyl (Z)-2,7,7-tricarbomethoxy-13-<(tetrahydro-2H-pyran-2-yl)oxy>-4-tridecen-11-ynoate

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide for 1.5h; Heating;	100%

: 114939-22-9
2-((Z)-4-Chloro-but-2-enyl)-2-[8-(tetrahydro-pyran-2-yloxy)-oct-6-ynyl]-malonic acid dimethyl ester

: 108-59-8
malonic acid dimethyl ester

: 114939-30-9
(Z)-2,7-Bis-methoxycarbonyl-2-[8-(tetrahydro-pyran-2-yloxy)-oct-6-ynyl]-oct-4-enedioic acid dimethyl ester

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide for 1.5h; Heating;	100%

: 145471-52-9
12-Benzyl-6,7,12,12b-tetrahydro-1H-indolo[2,3-a]quinolizine-4-thione

: 108-59-8
malonic acid dimethyl ester

: 145471-53-0
2-((2R,12bS)-12-Benzyl-4-thioxo-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl)-malonic acid dimethyl ester

Conditions

Conditions	Yield
With caesium carbonate In tetrahydrofuran at 20℃; for 5h;	100%

: 169308-84-3
2,2,2-Trichloro-acetimidic acid 2-cyclopropylidene-ethyl ester

: 108-59-8
malonic acid dimethyl ester

: 130715-11-6
dimethyl (2-cyclopropylideneethyl)malonate

Conditions

Conditions	Yield
With sodium hydride; bis(dibenzylideneacetone)-palladium(0); bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran for 18h; Ambient temperature;	100%

: 20657-21-0
3-acetoxycyclopent-1-ene

: 108-59-8
malonic acid dimethyl ester

A: 155057-81-1
dimethyl (S)-cyclopent-2-enylmalonate

B: dimethyl (1R)-(cyclopent-2-en-1-yl)malonate

Conditions

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide; potassium acetate; bis(η3-allyl-μ-chloropalladium(II)); (Sp)-1-[(1R)-(1-(5-chloro-3H-isobenzofuran-1-ylideneamino)-ethyl)]-2-(diphenylphosphino)-ferrocene In dichloromethane at 20℃; for 16h;	A n/a B 100%
With n-butyllithium; (1S,2R,3S,5R)-3-diphenylphosphinopinan-10-oic acid Pd In tetrahydrofuran at 25℃; for 12h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With sodium hydride; bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran at 20℃; for 0.166667h; Product distribution; other solvent, time and temperature;

...Expand

: 105-34-0
methyl 2-cyanoacetate

: 108-59-8
malonic acid dimethyl ester

A: 6914-71-2
dimethyl 1,1-cyclopropanedicarboxylate

B: 38806-09-6
1-acetylcyclopropanecarboxylic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate; 18-crown-6 ether In butanone for 3h; Heating;	A 100% B 75%

...Expand

: 106-96-7
propargyl bromide

: 108-59-8
malonic acid dimethyl ester

: 63104-44-9
dimethyl 2,2-di(prop-2-ynyl)malonate

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran; toluene Alkylation;	100%
Stage #1: malonic acid dimethyl ester With sodium hydride In dimethyl sulfoxide; mineral oil at 0 - 20℃; for 0.5h; Stage #2: propargyl bromide In tetrahydrofuran; mineral oil at 0 - 20℃; for 1.5h;	100%
With sodium hydride In tetrahydrofuran Heating;	98%

: 820-71-3
methallyl acetate

: 108-59-8
malonic acid dimethyl ester

: 74793-47-8
dimethyl 2,2-di(2-methylallyl)malonate

Conditions

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0); N,O-bis-(trimethylsilyl)-acetamide; 1,3-bis-(diphenylphosphino)propane In tetrahydrofuran at 20℃; for 2h;	100%

: 107-13-1
acrylonitrile

: 108-59-8
malonic acid dimethyl ester

: dimethyl 2,2-bis(2-cyanoethyl)malonate

Conditions

Conditions	Yield
With 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane hydroxide at 20℃; for 0.0166667h; Reagent/catalyst; Time; Michael Addition; Green chemistry;	100%
With tetrabutylammomium bromide; potassium carbonate In hexane Michael condensation; Reflux;	92%
With 1-butyl-3-methylimidazolium hydroxide at 20℃; for 3h; Michael addition;	82%

: 826-13-1
2-cycloheptenyl acetate

: 108-59-8
malonic acid dimethyl ester

A: dimethyl (R)-cyclohept-2-enylmalonate

B: dimethyl (S)-cyclohept-2-enylmalonate

Conditions

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide; sodium acetate; bis(η3-allyl-μ-chloropalladium(II)); (Sp)-1-[(1R)-(1-(5-chloro-3H-isobenzofuran-1-ylideneamino)-ethyl)]-2-(diphenylphosphino)-ferrocene In dichloromethane at 20℃; for 16h;	A 100% B n/a
With benzenesulfonamide; N-(2-diphenylphosphino)benzyl-3,5-dihydro-4H-dinaphth<2,1-c:1',2'-e>azepine; In dichloromethane for 18h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With sodium hydride; bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran at 20℃; for 0.0833333h; Product distribution; other solvent, time and temperature; various chiral ligands;

...Expand

: 826-13-1
2-cycloheptenyl acetate

: 108-59-8
malonic acid dimethyl ester

: dimethyl (R)-cyclohept-2-enylmalonate

Conditions

Conditions	Yield
Stage #1: 2-cycloheptenyl acetate With bis(η3-allyl-μ-chloropalladium(II)); (Sp)-1-[(1R)-(1-(5-chloro-3H-isobenzofuran-1-ylideneamino)-ethyl)]-2-(diphenylphosphanyl)ferrocene In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: malonic acid dimethyl ester With N,O-bis-(trimethylsilyl)-acetamide; sodium acetate In dichloromethane at 20℃; for 16h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	100%
With sodium hydride; bis(η3-allyl-μ-chloropalladium(II)); <1-((4S)-4-tert-butyl-4,5-dihydroo; xazol-2-yl)-2-<(biphenyl-2-yl)phenylphosphanyl>cyclopentadienyl>Mn(CO)3 In N,N-dimethyl-formamide at 0℃; for 1.25h;	86%
With N,O-bis-(trimethylsilyl)-acetamide; bis(η3-allyl-μ-chloropalladium(II)); C40H47O5PSSi2; potassium acetate In dichloromethane at 23℃; for 6h; Inert atmosphere; Schlenk technique; enantioselective reaction;	86%

: 108-59-8
malonic acid dimethyl ester

: 203207-92-5
(2R,4S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-1,4-bis-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyridine

: 2-[(2R,4S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyridin-4-yl]-malonic acid dimethyl ester

Conditions

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide; tin(IV) chloride In dichloromethane at -78 - -20℃;	100%

: 108-59-8
malonic acid dimethyl ester

: (2S,4S)-2-Methyl-1,4-bis-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyridine

: 2-[(S)-2-Methyl-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-pyridin-4-yl]-malonic acid dimethyl ester

Conditions

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide; tin(IV) chloride In dichloromethane at -78 - -20℃;	100%

: 156-87-6
propan-1-ol-3-amine

: 108-59-8
malonic acid dimethyl ester

: 53828-48-1
N,N'-bis(3-hydroxypropyl)propanediamide

Conditions

Conditions	Yield
at 160℃; for 1h;	100%

: 2700-22-3
Benzylidenemalononitrile

: 108-59-8
malonic acid dimethyl ester

: dimethyl 3,3-dicyano-2-phenylpropane-1,1-dicarboxylate

Conditions

Conditions	Yield
With triethylamine In diethyl ether Michael addition;	100%
With sodium methylate In methanol for 1h;	63%

Dimethyl malonate Consensus Reports

Reported in EPA TSCA Inventory.

Dimethyl malonate Specification

Dimethyl malonate, with the CAS NO.108-59-8, is a diester derivative of malonic acid. It is a common reagent for organic synthesis. It is used in the malonic ester synthesis. It is also called Dimethyl ester of malonic acid; Dimethyl propanedioate; dimethyl1,3-propanedioate; dimethylpropanedioate; MALONIC ACID,BIS-METHYL ESTER; MALONIC ACID DIMETHYL ESTER; METHYL MALONATE. Dimethyl malonate should be stored in a cool, dry place. Keep container closed when not in use.

Physical properties about Dimethyl malonate are: (1)ACD/LogP: -0.36; (2)ACD/LogD (pH 5.5): -0.36; (3)ACD/LogD (pH 7.4): -0.36; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 15.19; (7)ACD/KOC (pH 7.4): 15.18; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 4; (10)Index of Refraction: 1.402; (11)Molar Refractivity: 28.763 cm³; (12)Molar Volume: 118.034 cm³; (13)Polarizability: 11.403 10-24cm³; (14)Surface Tension: 31.9130001068115 dyne/cm; (15)Density: 1.119 g/cm³; (16)Flash Point: 90 °C; (17)Enthalpy of Vaporization: 41.338 kJ/mol; (18)Boiling Point: 177.071 °C at 760 mmHg; (19)Vapour Pressure: 1.05900001525879 mmHg at 25°C

You can still convert the following datas into molecular structure
(1)InChI=1S/C5H8O4/c1-8-4(6)3-5(7)9-2/h3H2,1-2H3;
(2)InChIKey=BEPAFCGSDWSTEL-UHFFFAOYSA-N;
(3)SmilesC(C(OC)=O)C(OC)=O;

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rabbit	LD50	skin	> 5gm/kg (5000mg/kg)		Food and Cosmetics Toxicology. Vol. 17, Pg. 363, 1979.
rat	LD50	oral	5331mg/kg (5331mg/kg)		Food and Cosmetics Toxicology. Vol. 17, Pg. 363, 1979.

Product Name

Dimethyl malonate

Synthetic route

Dimethyl malonate Consensus Reports

Dimethyl malonate Specification

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