5018-30-4

Basic information

• Product Name: DIMETHYL METHOXYMALONATE
• Synonyms: DIMETHYL METHOXYMALONATE;DIMETHYL 2-METHOXYMALONATE;METHOXYMALONIC ACID DIMETHYL ESTER;2-Methoxy-malonicaciddimethylester;Dimethyltartronate;Methoxymalonsαuredimethylester;Propanedioicacid,methoxy-,dimethylester;Dimethylmethoxymalonate99%
• CAS NO: 5018-30-4
• Molecular Formula: C₆H₁₀O₅
• Molecular Weight: 162.14
• EINECS: 225-697-0
• Mol File: 5018-30-4.mol
• Article Data: 12

Chemical Properties

• Melting Point: 11-12 °C
• Boiling Point: 96-97 °C (8.3 mmHg)
• Flash Point: 105 °C
• Appearance: clear colourless liquid after melting
• Density: 1.18
• Vapor Pressure: 0.145mmHg at 25°C
• Refractive Index: 1.4225-1.4245
• Storage Temp.: 0-6°C
• PKA: 13.05±0.46(Predicted)
• BRN: 1772841
• CAS DataBase Reference: DIMETHYL METHOXYMALONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL METHOXYMALONATE(5018-30-4)
• EPA Substance Registry System: DIMETHYL METHOXYMALONATE(5018-30-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• Hazardous Substances Data: 5018-30-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron, 52, p. 5799, 1996 DOI: 10.1016/0040-4020(96)00231-1

InChI:InChI=1/C6H10O5/c1-9-4(5(7)10-2)6(8)11-3/h4H,1-3H3

Synthetic route

chloropentamethoxycyclopropane (84212-88-4) → dimethyl methoxymalonate (5018-30-4)

Conditions	Yield
With silver perchlorate In methanol	85%

methanol (67-56-1) + dimethyl diazomalonate (6773-29-1) → dimethyl methoxymalonate (5018-30-4)

Conditions	Yield
dirhodium tetraacetate In dichloromethane at 18 - 20℃; for 48h;	70%
With dirhodium tetraacetate In dichloromethane at 20℃; for 48h; Inert atmosphere;	70%
With copper(l) iodide; phosphorous acid trimethyl ester
copper In toluene

C8H16O5(1+)*AlBr3Cl(1-) → dimethyl methoxymalonate (5018-30-4)

Conditions	Yield
With sodium methylate In methanol; dichloromethane-d2	60%

methanol (67-56-1) + dimethyl diazomalonate (6773-29-1) → dimethyl 2-hydroxymalonate (34259-29-5) + dimethyl methoxymalonate (5018-30-4) + methyl 2-(methoxycarbonyl)-4-oxopentanonate (24889-15-4) + methyl 2,2-dimethyl-5-oxo-1,3-dioxolane-4-carboxylate (62609-79-4)

Conditions	Yield
In acetone for 10h; Irradiation;	A 24% B 1% C 0.5% D 31%

dimethyl diazomalonate (6773-29-1) + acetone (67-64-1) → dimethyl 2-hydroxymalonate (34259-29-5) + dimethyl methoxymalonate (5018-30-4) + methyl 2-(methoxycarbonyl)-4-oxopentanonate (24889-15-4) + methyl 2,2-dimethyl-5-oxo-1,3-dioxolane-4-carboxylate (62609-79-4)

Conditions	Yield
for 10h; Product distribution; Irradiation; reaction in the presence of benzophenone;	A 24% B 1% C 0.5% D 31%
for 10h; Irradiation;	A 24% B 1% C 0.5% D 31%

dimethyl diazomalonate (6773-29-1) + pentan-3-one (96-22-0) → dimethyl 2-hydroxymalonate (34259-29-5) + dimethyl methoxymalonate (5018-30-4) + methyl 2-(methoxycarbonyl)-5-oxoheptanoate (37069-22-0) + methyl 2-(methoxycarbonyl)-3-oxoheptanoate (111209-93-9) + 2,2-diethyl-5-(methoxycarbonyl)-1,3-dioxolan-4-one

Conditions	Yield
for 10h; Product distribution; Irradiation; reaction in the presence of benzophenone;	A 21% B 0.6% C 3.8% D 4.7% E 13%

dimethyl 3-methoxy-2-oxo-1,4-butanedioate (36797-93-0) → dimethyl methoxymalonate (5018-30-4)

diazomethane (186581-53-3, 908094-01-9) + dimethyl diazomalonate (6773-29-1) → dimethyl methoxymalonate (5018-30-4)

Conditions	Yield
(i) (irradiation), THF, H2O, (ii) /BRN= 102415/; Multistep reaction;

diazomethane (186581-53-3, 908094-01-9) + diethyl methoxymalonate (40924-27-4) → dimethyl methoxymalonate (5018-30-4)

Conditions	Yield
(i) aq. NaOH, (ii) /BRN= 102415/; Multistep reaction;

Dimethyl oxalate (553-90-2) + methyl methoxyacetate (6290-49-9) → dimethyl methoxymalonate (5018-30-4)

Conditions	Yield
With sodium methylate In benzene

methyl methoxyacetate (6290-49-9) → dimethyl methoxymalonate (5018-30-4)

trimethylene oxide (503-30-0) + methanol (67-56-1) + dimethyl diazomalonate (6773-29-1) → dimethyl methoxymalonate (5018-30-4) + (3-Methoxypropoxy)malonsaeure-dimethylester (133649-65-7) + 2-Oxetanylmalonsaeure-dimethylester (133649-63-5) + Tetrahydrofuran-2,2-dicarbonsaeure-dimethylester (133649-64-6)

Conditions	Yield
at 0℃; Irradiation; Yield given. Yields of byproduct given;

methanol (67-56-1) + dibenzyl 2-methoxymalonate (138434-87-4) → dimethyl methoxymalonate (5018-30-4) + (+)-methoxy benzyl methyl malonate (138434-85-2, 138434-89-6) + (-)-methoxy benzyl methyl malonate (138434-85-2, 138434-89-6)

Conditions	Yield
In hexane at 40℃; lipase from Candida cylindracea; stopped at 50percent conversion; Title compound not separated from byproducts;

chloropentamethoxycyclopropane (84212-88-4) → dimethyl methoxymalonate (5018-30-4) + methyl 2,2,3,3-tetramethoxypropanoate (92095-79-9)

Conditions	Yield
With tert.-butyl lithium; oxygen 1.) ether, -78 deg C, 20 min, 2.) ether, -78 deg C, 3 h -> room temperature; Yield given. Multistep reaction. Yields of byproduct given;

methyl methoxyacetate (6290-49-9) + carbonic acid dimethyl ester (616-38-6) → dimethyl methoxymalonate (5018-30-4)

Conditions	Yield
With sodium methylate for 2h; Heating;	18.3 g

methyl trimethoxyacrylate → dimethyl methoxymalonate (5018-30-4)

Conditions	Yield
With silver perchlorate In methanol

dimethyl diazomalonate (6773-29-1) + trimethyl orthoformate (149-73-5) → dimethyl methoxymalonate (5018-30-4) + methyl 2-carbomethoxy-2,3,3-trimethoxypropanoate (88969-16-8)

Conditions	Yield
copper(II) bis(trifluoromethanesulfonate) at 50℃; for 4h; also with Rh2(OAc)4 as catalyst;	A 20 % Chromat. B 46 % Chromat.
copper(II) bis(trifluoromethanesulfonate) at 50℃; for 4h; Product distribution; also with Rh2(OAc)4 as catalyst;	A 20 % Chromat. B 46 % Chromat.
copper(II) bis(trifluoromethanesulfonate) at 50℃; for 4h;	A 20 % Chromat. B 46 % Chromat.

methanol (67-56-1) + dibenzyl 2-methoxymalonate (138434-87-4) → dimethyl methoxymalonate (5018-30-4) + (R)-(+)-benzyl,methyl 2-methoxymalonate + (S)-(-)-benzyl,methyl 2-methoxymalonate (138434-85-2)

Conditions	Yield
In hexane at 40℃; for 0.75h; lipase from Candida cylindracea; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

dimethyl 3-methoxy-2-oxo-1,4-butanedioate (36797-93-0) → dimethyl methoxymalonate (5018-30-4) + CO

Conditions	Yield
Destillation;

malonic acid dimethyl ester (108-59-8) → dimethyl methoxymalonate (5018-30-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: TsN3, Et3N / acetonitrile 2: (i) (irradiation), THF, H2O, (ii) /BRN= 102415/ View Scheme
Multi-step reaction with 2 steps 1: TsN3, Et3N / acetonitrile 2: Cu / toluene View Scheme

methanol (67-56-1) + benzothiophenium bismethoxycarbonylmethylide (72932-82-2) → dimethyl methoxymalonate (5018-30-4) + malonic acid dimethyl ester (108-59-8)

Conditions	Yield
In acetonitrile UV-irradiation;

methanol (67-56-1) + benzothiophenium bismethoxycarbonylmethylide (72932-82-2) → dimethyl methoxymalonate (5018-30-4) + malonic acid dimethyl ester (108-59-8) + Benzo[b]thiophene (95-15-8)

Conditions	Yield
In acetonitrile Quantum yield; UV-irradiation;

methanol (67-56-1) + dibenzothiophenium bismethoxycarbonylmethylide (34297-79-5) → dibenzothiophene (132-65-0) + dimethyl methoxymalonate (5018-30-4) + malonic acid dimethyl ester (108-59-8)

Conditions	Yield
In acetonitrile Quantum yield; UV-irradiation;

methanol (67-56-1) + dibenzothiophenium bismethoxycarbonylmethylide (34297-79-5) → dimethyl methoxymalonate (5018-30-4) + malonic acid dimethyl ester (108-59-8)

Conditions	Yield
In acetonitrile UV-irradiation;
With benzophenone Inert atmosphere; UV-irradiation;	A 9 %Chromat. B 57 %Chromat.

methanol (67-56-1) + thiophenium bis(methoxycarbonyl)methylide (63196-84-9) → thiophene (188290-36-0) + dimethyl (2-thienyl)propanedioate (66946-94-9) + dimethyl methoxymalonate (5018-30-4) + malonic acid dimethyl ester (108-59-8)

Conditions	Yield
In acetonitrile Quantum yield; UV-irradiation;

methanol (67-56-1) + thiophenium bis(methoxycarbonyl)methylide (63196-84-9) → dimethyl (2-thienyl)propanedioate (66946-94-9) + dimethyl methoxymalonate (5018-30-4) + malonic acid dimethyl ester (108-59-8)

Conditions	Yield
In acetonitrile UV-irradiation;

methanol (67-56-1) + C9H8Br2O4S (1107692-57-8) → dimethyl methoxymalonate (5018-30-4)

Conditions	Yield
at 80℃; Inert atmosphere;

methanol (67-56-1) + C9H8Br2O4S (1107692-57-8) → dimethyl methoxymalonate (5018-30-4) + malonic acid dimethyl ester (108-59-8)

Conditions	Yield
Inert atmosphere; UV-irradiation;	A 86.5 %Chromat. B 9.4 %Chromat.

methanol (67-56-1) + dimethylmalonate-3,4-dibromothiophene-S,C-ylide (1107692-58-9) → dimethyl methoxymalonate (5018-30-4)

Conditions	Yield
at 80℃; Inert atmosphere;

dimethyl methoxymalonate (5018-30-4) → methoxymalonic acid (57584-77-7)

Conditions	Yield
With water; sodium hydroxide at 65℃;	100%
With potassium hydroxide In methanol Heating;	1.28 g

2-bromo-5-bromomethylpyridine (101990-45-8) + dimethyl methoxymalonate (5018-30-4) → dimethyl [(6-bromopyridin-3-yl)methyl](methoxy)malonate (784149-99-1)

Conditions	Yield
With potassium tert-butylate In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 3.5h;	100%

dimethyl methoxymalonate (5018-30-4) + diguanidine carbonate (593-85-1) → 2-amino-5-methoxypyrimidine-4,6-diol (98142-98-4)

Conditions	Yield
Stage #1: diguanidine carbonate With ethanol; sodium at 80℃; for 0.5h; Inert atmosphere; Stage #2: dimethyl methoxymalonate at 80℃; for 2h;	100%

dimethyl methoxymalonate (5018-30-4) + methyl (naphthalen-1-ylmethyl) carbonate → dimethyl methoxy[(1-naphthyl)methyl]malonate

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

dimethyl methoxymalonate (5018-30-4) + sodium methylate (124-41-4) + urea (57-13-6) → 6-hydroxy-5-methoxy-1H-pyrimidine-2,4-dione (60703-43-7)

Conditions	Yield
Stage #1: dimethyl methoxymalonate; sodium methylate; urea In ethanol at 100℃; for 4h; Stage #2: With hydrogenchloride In ethanol; water pH=3 - 4;	99%

formaldehyd (50-00-0) + dimethyl methoxymalonate (5018-30-4) → dimethyl 2-(hydroxymethyl)-2-methoxymalonate (1620016-98-9)

Conditions	Yield
With sodium hydrogencarbonate In ethanol; water at 0 - 20℃; for 20h;	98%
With sodium hydrogencarbonate In ethanol; water at 0 - 20℃; for 20h;	98%

bis(1,1-dimethylethyl) [[(8-aminooctyl)imino]methylene]biscarbamate (160677-42-9) + dimethyl methoxymalonate (5018-30-4) → 1-(1,1-Dimethylethyl) 16-methyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]-15-methoxy-14-oxo-2,4,13-triazahexadec-2-enedioate (170368-22-6) + 1-(1,1-Dimethylethyl) 16-ethyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]-15-phenylmethoxy-14-oxo-2,4,13-triazahexadec-2-enedioate (170367-46-1)

Conditions	Yield
	A 95% B n/a

dimethyl methoxymalonate (5018-30-4) + (4-methoxyphenyl)methyl methyl carbonate (270921-39-6) → dimethyl methoxy[(4-methoxyphenyl)methyl]malonate

Conditions	Yield
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;	94%
With 1,1'-bis-(diphenylphosphino)ferrocene; 1,5-cis,cis-cyclooctadiene; [PdCp(η3-C3H5)] In tetrahydrofuran at 80℃;	90%
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;	90%

dimethyl methoxymalonate (5018-30-4) + methyl (2-methylphenyl)methyl carbonate → dimethyl methoxy[(2-methylphenyl)methyl]malonate

Conditions	Yield
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;	92%

dimethyl methoxymalonate (5018-30-4) + Di-tert-butyl acetylenedicarboxylate (66086-33-7) + triphenylphosphine (603-35-0) → 2,3-di-tert-butyl 1,1-dimethyl 1-methoxy-3-(1,1,1-triphenyl-λ5-phosphanylidene)-1,1,2,3-propanetetracarboxylate

Conditions	Yield
In toluene for 5h; Heating;	92%

dimethyl methoxymalonate (5018-30-4) → 2-methylglycerol (761-06-8)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 120℃; for 6h; Inert atmosphere; Cooling with ice;	91.67%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 16h; Cooling with ice; Inert atmosphere;	91.67%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 16h; Inert atmosphere; Cooling with ice;	91.67%

dimethyl methoxymalonate (5018-30-4) + benzhydrilium tetrafluoroborate → dimethyl 2-(bis(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)methyl)-2-methoxymalonate

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide at 20℃; Inert atmosphere;	91%

dimethyl methoxymalonate (5018-30-4) + dimethyl acetylenedicarboxylate (762-42-5) + triphenylphosphine (603-35-0) → tetramethyl 3-(1,1,1-triphenyl-λ5-phosphanylidene)-1-propene-1,1,2,3-tetracarboxylate

Conditions	Yield
In dichloromethane at 20℃; for 24h;	90%

dimethyl methoxymalonate (5018-30-4) + benzyl methyl carbonate (13326-10-8) → dimethyl O-methylbenzyltartronate (124604-07-5)

Conditions	Yield
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;	88%

dimethyl methoxymalonate (5018-30-4) + (4-hydroxyphenyl)methanol (623-05-2) → 2-(4-hydroxy-benzyl)-2-methoxy-malonic acid dimethyl ester (848245-33-0)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 3h; Heating / reflux;	88%

2-(6-aminohexyl)-1,3-diBocguanidine (160677-41-8) + dimethyl methoxymalonate (5018-30-4) → 1-(1,1-Dimethylethyl) 14-methyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]-13-methoxy-12-oxo-2,4,11-triazatetradec-2-enedioate (160677-53-2) + 3-<<(1,1-dimethylethoxy)carbonyl>amino>-20-<(1,1-dimethylethoxy)carbonyl>-12,14-dioxo-2,4,11,15,20,24-hexaazapentacosenedioic acid, bis(1,1-dimethylethyl)ester (160677-45-2)

Conditions	Yield
	A n/a B 87%

dimethyl methoxymalonate (5018-30-4) → dimethyl 2-fluoro-2-methoxymalonate (181762-19-6)

Conditions	Yield
With sodium hydride; Selectfluor In tetrahydrofuran for 0.333333h; Ambient temperature;	86%
With sodium hydride; fluorine In acetonitrile 1.) r.t., 1 h, 2.) -15 deg C, 1 h;	51 % Spectr.

dimethyl methoxymalonate (5018-30-4) + diphenylmethyl methyl carbonate (85926-25-6) → dimethyl (diphenylmethyl)methoxymalonate

Conditions	Yield
With sodium carbonate; [Pd(ϖ-C3H5)(cod)]BF4 In N,N-dimethyl-formamide at 120℃; for 24h;	86%

dimethyl methoxymalonate (5018-30-4) + propargyl bromide (106-96-7) → dimethyl 2-methoxy-2-(2-propynyl)malonate (507471-59-2)

Conditions	Yield
Stage #1: dimethyl methoxymalonate With n-butyllithium In hexane; tert-butyl alcohol for 0.25h; Stage #2: propargyl bromide In hexane; toluene; tert-butyl alcohol at 20℃; for 20h;	84%

dimethyl methoxymalonate (5018-30-4) + benzyl alcohol (100-51-6) → (S)-(-)-benzyl,methyl 2-methoxymalonate (138434-85-2)

Conditions	Yield
In hexane at 40℃; for 3.5h; lipase from Candida cylindracea;	83%

dimethyl methoxymalonate (5018-30-4) + [(4-trifluoromethyl)phenyl]methyl methyl carbonate (270921-40-9) → dimethyl methoxy[{4-(trifluoromethyl)phenyl}methyl]malonate

Conditions	Yield
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;	83%

dimethyl methoxymalonate (5018-30-4) + tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate (155396-71-7) → 2-(tert-butoxycarbonylamino-phenyl-methyl)-2-methoxy-malonic acid dimethyl ester

Conditions	Yield
With potassium carbonate In acetonitrile at 30℃; for 24h;	83%

dimethyl methoxymalonate (5018-30-4) + p-methoxybenzyl acetate (104-21-2) → dimethyl methoxy[(4-methoxyphenyl)methyl]malonate

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; potassium carbonate; {(η4-1,5-cyclooctadiene)Pd(η3-allyl)}BF4 In tert-Amyl alcohol at 80℃; for 48h;	83%

dimethyl methoxymalonate (5018-30-4) + Fe(CO)2(P(C6H5)3)(C5H6CH3)(1+)*PF6(1-)=[Fe(CO)2(P(C6H5)3)(C5H6CH3)]PF6 (161730-33-2, 193425-61-5, 164576-60-7) → Fe(CO)2(P(C6H5)3)(CH2(CH)4(CH3)(C(OCH3)(COOCH3)2)) + Fe(CO)2(P(C6H5)3)(CH3(CH)4CH2(C(OCH3)(COOCH3)2))

Conditions	Yield
With LDA In tetrahydrofuran stirring dimethyl methoxymalonate with LDAi at -78°C, addn. of Fe-complex, warming to 0°C, stirring for 2.5 h; addn. of H2O, extn. into ether, drying of org. layer (MgSO4), evapn., chromy. (SiO2, hexanes/EtOAc=15:1); elem. anal.;	A 83% B 9%

Phenylselenyl chloride (5707-04-0) + dimethyl methoxymalonate (5018-30-4) → dimethyl 2-methoxy-2-phenylselenopropanedioate

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 2h;	82%

dimethyl methoxymalonate (5018-30-4) + propynoic acid methyl ester (922-67-8) + triphenylphosphine (603-35-0) → trimethyl 3-(1,1,1-triphenyl-λ5-phosphanylidene)-1-propene-1,1,2-tricarboxylate

Conditions	Yield
In dichloromethane at 20℃; for 24h;	82%

dimethyl methoxymalonate (5018-30-4) + phenylacetylene (536-74-3) → 2-methoxy-2-(1-phenylvinyl)malonic acid dimethyl ester

Conditions	Yield
With indium(III) chloride at 140℃;	81%

dimethyl methoxymalonate (5018-30-4) + triphenylphosphine (603-35-0) + acetylenedicarboxylic acid diethyl ester (762-21-0) → 2,2-diethyl 1,1-dimethyl 3-(1,1,1-triphenyl-λ5-phosphanylidene)-1-propene-1,1,2,3-tetracarboxylate

Conditions	Yield
In dichloromethane at 20℃; for 24h;	81%

3-[3-(benzyloxy)phenylthio]-6-vinyl-1-chlorobenzene (1023648-20-5) + dimethyl methoxymalonate (5018-30-4) → 2-(2-{4-[3-(benzyloxy)phenylthio]-2-chlorophenyl}ethyl)-2-methoxymalonic acid dimethyl ester (1023648-23-8)

Conditions	Yield
Stage #1: dimethyl methoxymalonate With caesium carbonate In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: 3-[3-(benzyloxy)phenylthio]-6-vinyl-1-chlorobenzene In dimethyl sulfoxide at 20 - 35℃; Further stages.;	79%

Upstream product

• 36797-93-0 dimethyl 3-methoxy-2-oxo-1,4-butanedioate 
• 186581-53-3 diazomethane 
• 6773-29-1 dimethyl diazomalonate 
• 40924-27-4 diethyl methoxymalonate 
• 503-30-0 trimethylene oxide 
• 67-56-1 methanol 
• 72932-82-2 benzothiophenium bismethoxycarbonylmethylide 
• 34297-79-5 dibenzothiophenium bismethoxycarbonylmethylide 
• 63196-84-9 thiophenium bis(methoxycarbonyl)methylide 
• 66946-86-9 2,5-dichlorothiophenium-1-bis(methoxycarbonyl)methylide 
• 97580-07-9 C₉H₈Cl₂O₄Se 
• 1107692-62-5 C₂₄H₂₀O₇S 
• 1107692-61-4 C₁₇H₁₂Br₂O₄S 
• 1107692-60-3 C₁₇H₁₃BrO₄S 

Downstream Products

• 40924-27-4 diethyl methoxymalonate 
• 1126320-77-1 2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-methoxy-pyrimidine-4,6-diol 
• 89280-05-7 C₅H₇N₃O₃ 
• 1620016-99-0 dimethyl 2-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxymalonate 
• 1303588-01-3 2-(3-fluorophenyl)-5-ethoxypyrimidin-4,6-diol 
• 5193-84-0 4,6-Dihydroxy-5-methoxypyrimidine 
• 108-59-8 malonic acid dimethyl ester 
• 1023648-23-8 2-(2-{4-[3-(benzyloxy)phenylthio]-2-chlorophenyl}ethyl)-2-methoxymalonic acid dimethyl ester 
• 170368-22-6 1-(1,1-Dimethylethyl) 16-methyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]-15-methoxy-14-oxo-2,4,13-triazahexadec-2-enedioate 

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The pentamethoxyallyl cation is readily generated from pentamethoxychlorocyclopropane by treatment with AlBr3 or SnCl4 in CD2Cl2 or with SnCl4 in SO2.

On the most powerful chemical traps for bis(methoxycarbonyl)carbene (=2-methoxy-1-(methoxycarbonyl)-2-oxoethylidene)

The efficiency and validity of different chemical substrates for trapping bis(methoxycarbonyl)carbene (=2-methoxy-1-(methoxycarbonyl)-2-oxoethylidene; 1) is dependent on the conditions of carbene generation. On conventional photolysis of dimethyldiazomalonate (=2-diazopropanedioic acid dimethyl ester; 2) by long-wave UV light (through a Pyrex filter, λ > 290 nm), the most powerful trap for carbene 1 in the series of substrates Me2S, MeOH, cyclohexane, and pyridine is Me2S (with an efficiency ratio of ca. 6 :4 : 2 : 1, resp.). When short-wave decomposition of diazomalonate 2 is employed (through a quartz filter, λ > 210 nm), more reliable and useful chemical traps for bis(methoxycarbonyl)carbene (1) are pyridine and cyclohexane, whose adducts with 1 are rather stable under short-wave-irradiation conditions. Application of alcohols for the trapping of 1 proves to be preferential when simultaneous monitoring of carbene and oxoketene formation during photolysis is necessary.

Catalytic decomposition of 5-diazo-2,2-dimethyl-1,3-dioxane-4,6-dione and its analogs

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