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  • 5018-30-4 Structure
  • Basic information

    1. Product Name: DIMETHYL METHOXYMALONATE
    2. Synonyms: DIMETHYL METHOXYMALONATE;DIMETHYL 2-METHOXYMALONATE;METHOXYMALONIC ACID DIMETHYL ESTER;2-Methoxy-malonicaciddimethylester;Dimethyltartronate;Methoxymalonsαuredimethylester;Propanedioicacid,methoxy-,dimethylester;Dimethylmethoxymalonate99%
    3. CAS NO:5018-30-4
    4. Molecular Formula: C6H10O5
    5. Molecular Weight: 162.14
    6. EINECS: 225-697-0
    7. Product Categories: N/A
    8. Mol File: 5018-30-4.mol
    9. Article Data: 12
  • Chemical Properties

    1. Melting Point: 11-12 °C
    2. Boiling Point: 96-97 °C (8.3 mmHg)
    3. Flash Point: 105 °C
    4. Appearance: clear colourless liquid after melting
    5. Density: 1.18
    6. Vapor Pressure: 0.145mmHg at 25°C
    7. Refractive Index: 1.4225-1.4245
    8. Storage Temp.: 0-6°C
    9. Solubility: N/A
    10. PKA: 13.05±0.46(Predicted)
    11. BRN: 1772841
    12. CAS DataBase Reference: DIMETHYL METHOXYMALONATE(CAS DataBase Reference)
    13. NIST Chemistry Reference: DIMETHYL METHOXYMALONATE(5018-30-4)
    14. EPA Substance Registry System: DIMETHYL METHOXYMALONATE(5018-30-4)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 24/25-36-26
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 5018-30-4(Hazardous Substances Data)

5018-30-4 Usage

Synthesis Reference(s)

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

Check Digit Verification of cas no

The CAS Registry Mumber 5018-30-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,0,1 and 8 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 5018-30:
(6*5)+(5*0)+(4*1)+(3*8)+(2*3)+(1*0)=64
64 % 10 = 4
So 5018-30-4 is a valid CAS Registry Number.
InChI:InChI=1/C6H10O5/c1-9-4(5(7)10-2)6(8)11-3/h4H,1-3H3

5018-30-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Methoxymalonic Acid Dimethyl Ester

1.2 Other means of identification

Product number -
Other names DiMethyl MethoxyMalonate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5018-30-4 SDS

5018-30-4Synthetic route

chloropentamethoxycyclopropane
84212-88-4

chloropentamethoxycyclopropane

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

Conditions
ConditionsYield
With silver perchlorate In methanol85%
methanol
67-56-1

methanol

dimethyl diazomalonate
6773-29-1

dimethyl diazomalonate

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

Conditions
ConditionsYield
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-)

C8H16O5(1+)*AlBr3Cl(1-)

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

Conditions
ConditionsYield
With sodium methylate In methanol; dichloromethane-d260%
methanol
67-56-1

methanol

dimethyl diazomalonate
6773-29-1

dimethyl diazomalonate

A

dimethyl 2-hydroxymalonate
34259-29-5

dimethyl 2-hydroxymalonate

B

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

C

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

methyl 2-(methoxycarbonyl)-4-oxopentanonate

D

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

methyl 2,2-dimethyl-5-oxo-1,3-dioxolane-4-carboxylate

Conditions
ConditionsYield
In acetone for 10h; Irradiation;A 24%
B 1%
C 0.5%
D 31%
dimethyl diazomalonate
6773-29-1

dimethyl diazomalonate

acetone
67-64-1

acetone

A

dimethyl 2-hydroxymalonate
34259-29-5

dimethyl 2-hydroxymalonate

B

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

C

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

methyl 2-(methoxycarbonyl)-4-oxopentanonate

D

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

methyl 2,2-dimethyl-5-oxo-1,3-dioxolane-4-carboxylate

Conditions
ConditionsYield
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

dimethyl diazomalonate

pentan-3-one
96-22-0

pentan-3-one

A

dimethyl 2-hydroxymalonate
34259-29-5

dimethyl 2-hydroxymalonate

B

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

C

methyl 2-(methoxycarbonyl)-5-oxoheptanoate
37069-22-0

methyl 2-(methoxycarbonyl)-5-oxoheptanoate

D

methyl 2-(methoxycarbonyl)-3-oxoheptanoate
111209-93-9

methyl 2-(methoxycarbonyl)-3-oxoheptanoate

E

2,2-diethyl-5-(methoxycarbonyl)-1,3-dioxolan-4-one

2,2-diethyl-5-(methoxycarbonyl)-1,3-dioxolan-4-one

Conditions
ConditionsYield
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 3-methoxy-2-oxo-1,4-butanedioate

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

dimethyl diazomalonate
6773-29-1

dimethyl diazomalonate

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

Conditions
ConditionsYield
(i) (irradiation), THF, H2O, (ii) /BRN= 102415/; Multistep reaction;
diethyl methoxymalonate
40924-27-4

diethyl methoxymalonate

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

Conditions
ConditionsYield
(i) aq. NaOH, (ii) /BRN= 102415/; Multistep reaction;
Dimethyl oxalate
553-90-2

Dimethyl oxalate

methyl methoxyacetate
6290-49-9

methyl methoxyacetate

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

Conditions
ConditionsYield
With sodium methylate In benzene
methyl methoxyacetate
6290-49-9

methyl methoxyacetate

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

trimethylene oxide
503-30-0

trimethylene oxide

methanol
67-56-1

methanol

dimethyl diazomalonate
6773-29-1

dimethyl diazomalonate

A

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

B

(3-Methoxypropoxy)malonsaeure-dimethylester
133649-65-7

(3-Methoxypropoxy)malonsaeure-dimethylester

C

2-Oxetanylmalonsaeure-dimethylester
133649-63-5

2-Oxetanylmalonsaeure-dimethylester

D

Tetrahydrofuran-2,2-dicarbonsaeure-dimethylester
133649-64-6

Tetrahydrofuran-2,2-dicarbonsaeure-dimethylester

Conditions
ConditionsYield
at 0℃; Irradiation; Yield given. Yields of byproduct given;
methanol
67-56-1

methanol

dibenzyl 2-methoxymalonate
138434-87-4

dibenzyl 2-methoxymalonate

A

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

(+)-methoxy benzyl methyl malonate
138434-85-2, 138434-89-6

(+)-methoxy benzyl methyl malonate

(-)-methoxy benzyl methyl malonate
138434-85-2, 138434-89-6

(-)-methoxy benzyl methyl malonate

Conditions
ConditionsYield
In hexane at 40℃; lipase from Candida cylindracea; stopped at 50percent conversion; Title compound not separated from byproducts;
chloropentamethoxycyclopropane
84212-88-4

chloropentamethoxycyclopropane

A

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

B

methyl 2,2,3,3-tetramethoxypropanoate
92095-79-9

methyl 2,2,3,3-tetramethoxypropanoate

Conditions
ConditionsYield
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

methyl methoxyacetate

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

Conditions
ConditionsYield
With sodium methylate for 2h; Heating;18.3 g
methyl trimethoxyacrylate

methyl trimethoxyacrylate

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

Conditions
ConditionsYield
With silver perchlorate In methanol
dimethyl diazomalonate
6773-29-1

dimethyl diazomalonate

trimethyl orthoformate
149-73-5

trimethyl orthoformate

A

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

B

methyl 2-carbomethoxy-2,3,3-trimethoxypropanoate
88969-16-8

methyl 2-carbomethoxy-2,3,3-trimethoxypropanoate

Conditions
ConditionsYield
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

methanol

dibenzyl 2-methoxymalonate
138434-87-4

dibenzyl 2-methoxymalonate

A

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

B

(R)-(+)-benzyl,methyl 2-methoxymalonate

(R)-(+)-benzyl,methyl 2-methoxymalonate

C

(S)-(-)-benzyl,methyl 2-methoxymalonate
138434-85-2

(S)-(-)-benzyl,methyl 2-methoxymalonate

Conditions
ConditionsYield
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 3-methoxy-2-oxo-1,4-butanedioate

A

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

B

CO

CO

Conditions
ConditionsYield
Destillation;
malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

Conditions
ConditionsYield
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

methanol

benzothiophenium bismethoxycarbonylmethylide
72932-82-2

benzothiophenium bismethoxycarbonylmethylide

A

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

B

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

Conditions
ConditionsYield
In acetonitrile UV-irradiation;
methanol
67-56-1

methanol

benzothiophenium bismethoxycarbonylmethylide
72932-82-2

benzothiophenium bismethoxycarbonylmethylide

A

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

B

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

C

Benzo[b]thiophene
95-15-8

Benzo[b]thiophene

Conditions
ConditionsYield
In acetonitrile Quantum yield; UV-irradiation;
methanol
67-56-1

methanol

dibenzothiophenium bismethoxycarbonylmethylide
34297-79-5

dibenzothiophenium bismethoxycarbonylmethylide

A

dibenzothiophene
132-65-0

dibenzothiophene

B

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

C

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

Conditions
ConditionsYield
In acetonitrile Quantum yield; UV-irradiation;
methanol
67-56-1

methanol

dibenzothiophenium bismethoxycarbonylmethylide
34297-79-5

dibenzothiophenium bismethoxycarbonylmethylide

A

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

B

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

Conditions
ConditionsYield
In acetonitrile UV-irradiation;
With benzophenone Inert atmosphere; UV-irradiation;A 9 %Chromat.
B 57 %Chromat.
methanol
67-56-1

methanol

thiophenium bis(methoxycarbonyl)methylide
63196-84-9

thiophenium bis(methoxycarbonyl)methylide

A

thiophene
188290-36-0

thiophene

B

dimethyl (2-thienyl)propanedioate
66946-94-9

dimethyl (2-thienyl)propanedioate

C

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

D

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

Conditions
ConditionsYield
In acetonitrile Quantum yield; UV-irradiation;
methanol
67-56-1

methanol

thiophenium bis(methoxycarbonyl)methylide
63196-84-9

thiophenium bis(methoxycarbonyl)methylide

A

dimethyl (2-thienyl)propanedioate
66946-94-9

dimethyl (2-thienyl)propanedioate

B

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

C

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

Conditions
ConditionsYield
In acetonitrile UV-irradiation;
methanol
67-56-1

methanol

C9H8Br2O4S
1107692-57-8

C9H8Br2O4S

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

Conditions
ConditionsYield
at 80℃; Inert atmosphere;
methanol
67-56-1

methanol

C9H8Br2O4S
1107692-57-8

C9H8Br2O4S

A

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

B

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

Conditions
ConditionsYield
Inert atmosphere; UV-irradiation;A 86.5 %Chromat.
B 9.4 %Chromat.
methanol
67-56-1

methanol

dimethylmalonate-3,4-dibromothiophene-S,C-ylide
1107692-58-9

dimethylmalonate-3,4-dibromothiophene-S,C-ylide

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

Conditions
ConditionsYield
at 80℃; Inert atmosphere;
dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

methoxymalonic acid
57584-77-7

methoxymalonic acid

Conditions
ConditionsYield
With water; sodium hydroxide at 65℃;100%
With potassium hydroxide In methanol Heating;1.28 g
2-bromo-5-bromomethylpyridine
101990-45-8

2-bromo-5-bromomethylpyridine

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

dimethyl [(6-bromopyridin-3-yl)methyl](methoxy)malonate
784149-99-1

dimethyl [(6-bromopyridin-3-yl)methyl](methoxy)malonate

Conditions
ConditionsYield
With potassium tert-butylate In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 3.5h;100%
dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

diguanidine carbonate
593-85-1

diguanidine carbonate

2-amino-5-methoxypyrimidine-4,6-diol
98142-98-4

2-amino-5-methoxypyrimidine-4,6-diol

Conditions
ConditionsYield
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

dimethyl methoxymalonate

methyl (naphthalen-1-ylmethyl) carbonate

methyl (naphthalen-1-ylmethyl) carbonate

dimethyl methoxy[(1-naphthyl)methyl]malonate

dimethyl methoxy[(1-naphthyl)methyl]malonate

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; [PdCp(η3-C3H5)] In tetrahydrofuran at 80℃; for 1h;99%
dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

sodium methylate
124-41-4

sodium methylate

urea
57-13-6

urea

6-hydroxy-5-methoxy-1H-pyrimidine-2,4-dione
60703-43-7

6-hydroxy-5-methoxy-1H-pyrimidine-2,4-dione

Conditions
ConditionsYield
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

formaldehyd

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

dimethyl 2-(hydroxymethyl)-2-methoxymalonate
1620016-98-9

dimethyl 2-(hydroxymethyl)-2-methoxymalonate

Conditions
ConditionsYield
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

bis(1,1-dimethylethyl) [[(8-aminooctyl)imino]methylene]biscarbamate

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

A

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-methyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]-15-methoxy-14-oxo-2,4,13-triazahexadec-2-enedioate

B

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

1-(1,1-Dimethylethyl) 16-ethyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]-15-phenylmethoxy-14-oxo-2,4,13-triazahexadec-2-enedioate

Conditions
ConditionsYield
A 95%
B n/a
dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

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

(4-methoxyphenyl)methyl methyl carbonate

dimethyl methoxy[(4-methoxyphenyl)methyl]malonate

dimethyl methoxy[(4-methoxyphenyl)methyl]malonate

Conditions
ConditionsYield
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

dimethyl methoxymalonate

methyl (2-methylphenyl)methyl carbonate

methyl (2-methylphenyl)methyl carbonate

dimethyl methoxy[(2-methylphenyl)methyl]malonate

dimethyl methoxy[(2-methylphenyl)methyl]malonate

Conditions
ConditionsYield
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

dimethyl methoxymalonate

Di-tert-butyl acetylenedicarboxylate
66086-33-7

Di-tert-butyl acetylenedicarboxylate

triphenylphosphine
603-35-0

triphenylphosphine

2,3-di-tert-butyl 1,1-dimethyl 1-methoxy-3-(1,1,1-triphenyl-λ5-phosphanylidene)-1,1,2,3-propanetetracarboxylate

2,3-di-tert-butyl 1,1-dimethyl 1-methoxy-3-(1,1,1-triphenyl-λ5-phosphanylidene)-1,1,2,3-propanetetracarboxylate

Conditions
ConditionsYield
In toluene for 5h; Heating;92%
dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

2-methylglycerol
761-06-8

2-methylglycerol

Conditions
ConditionsYield
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

dimethyl methoxymalonate

benzhydrilium tetrafluoroborate

benzhydrilium tetrafluoroborate

dimethyl 2-(bis(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)methyl)-2-methoxymalonate

dimethyl 2-(bis(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)methyl)-2-methoxymalonate

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide at 20℃; Inert atmosphere;91%
dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

triphenylphosphine
603-35-0

triphenylphosphine

tetramethyl 3-(1,1,1-triphenyl-λ5-phosphanylidene)-1-propene-1,1,2,3-tetracarboxylate

tetramethyl 3-(1,1,1-triphenyl-λ5-phosphanylidene)-1-propene-1,1,2,3-tetracarboxylate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 24h;90%
dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

benzyl methyl carbonate
13326-10-8

benzyl methyl carbonate

dimethyl O-methylbenzyltartronate
124604-07-5

dimethyl O-methylbenzyltartronate

Conditions
ConditionsYield
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

dimethyl methoxymalonate

(4-hydroxyphenyl)methanol
623-05-2

(4-hydroxyphenyl)methanol

2-(4-hydroxy-benzyl)-2-methoxy-malonic acid dimethyl ester
848245-33-0

2-(4-hydroxy-benzyl)-2-methoxy-malonic acid dimethyl ester

Conditions
ConditionsYield
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

2-(6-aminohexyl)-1,3-diBocguanidine

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

A

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

1-(1,1-Dimethylethyl) 14-methyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]-13-methoxy-12-oxo-2,4,11-triazatetradec-2-enedioate

B

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

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

Conditions
ConditionsYield
A n/a
B 87%
dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

dimethyl 2-fluoro-2-methoxymalonate
181762-19-6

dimethyl 2-fluoro-2-methoxymalonate

Conditions
ConditionsYield
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

dimethyl methoxymalonate

diphenylmethyl methyl carbonate
85926-25-6

diphenylmethyl methyl carbonate

dimethyl (diphenylmethyl)methoxymalonate

dimethyl (diphenylmethyl)methoxymalonate

Conditions
ConditionsYield
With sodium carbonate; [Pd(ϖ-C3H5)(cod)]BF4 In N,N-dimethyl-formamide at 120℃; for 24h;86%
dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

propargyl bromide
106-96-7

propargyl bromide

dimethyl 2-methoxy-2-(2-propynyl)malonate
507471-59-2

dimethyl 2-methoxy-2-(2-propynyl)malonate

Conditions
ConditionsYield
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

dimethyl methoxymalonate

benzyl alcohol
100-51-6

benzyl alcohol

(S)-(-)-benzyl,methyl 2-methoxymalonate
138434-85-2

(S)-(-)-benzyl,methyl 2-methoxymalonate

Conditions
ConditionsYield
In hexane at 40℃; for 3.5h; lipase from Candida cylindracea;83%
dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

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

[(4-trifluoromethyl)phenyl]methyl methyl carbonate

dimethyl methoxy[{4-(trifluoromethyl)phenyl}methyl]malonate

dimethyl methoxy[{4-(trifluoromethyl)phenyl}methyl]malonate

Conditions
ConditionsYield
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

dimethyl methoxymalonate

tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate
155396-71-7

tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate

2-(tert-butoxycarbonylamino-phenyl-methyl)-2-methoxy-malonic acid dimethyl ester

2-(tert-butoxycarbonylamino-phenyl-methyl)-2-methoxy-malonic acid dimethyl ester

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 30℃; for 24h;83%
dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

p-methoxybenzyl acetate
104-21-2

p-methoxybenzyl acetate

dimethyl methoxy[(4-methoxyphenyl)methyl]malonate

dimethyl methoxy[(4-methoxyphenyl)methyl]malonate

Conditions
ConditionsYield
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

dimethyl methoxymalonate

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)(C5H6CH3)(1+)*PF6(1-)=[Fe(CO)2(P(C6H5)3)(C5H6CH3)]PF6

Fe(CO)2(P(C6H5)3)(CH2(CH)4(CH3)(C(OCH3)(COOCH3)2))

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))

Fe(CO)2(P(C6H5)3)(CH3(CH)4CH2(C(OCH3)(COOCH3)2))

Conditions
ConditionsYield
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

Phenylselenyl chloride

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

dimethyl 2-methoxy-2-phenylselenopropanedioate

dimethyl 2-methoxy-2-phenylselenopropanedioate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 2h;82%
dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

propynoic acid methyl ester
922-67-8

propynoic acid methyl ester

triphenylphosphine
603-35-0

triphenylphosphine

trimethyl 3-(1,1,1-triphenyl-λ5-phosphanylidene)-1-propene-1,1,2-tricarboxylate

trimethyl 3-(1,1,1-triphenyl-λ5-phosphanylidene)-1-propene-1,1,2-tricarboxylate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 24h;82%
dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

phenylacetylene
536-74-3

phenylacetylene

2-methoxy-2-(1-phenylvinyl)malonic acid dimethyl ester

2-methoxy-2-(1-phenylvinyl)malonic acid dimethyl ester

Conditions
ConditionsYield
With indium(III) chloride at 140℃;81%
dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

triphenylphosphine
603-35-0

triphenylphosphine

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

2,2-diethyl 1,1-dimethyl 3-(1,1,1-triphenyl-λ5-phosphanylidene)-1-propene-1,1,2,3-tetracarboxylate

2,2-diethyl 1,1-dimethyl 3-(1,1,1-triphenyl-λ5-phosphanylidene)-1-propene-1,1,2,3-tetracarboxylate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 24h;81%
3-[3-(benzyloxy)phenylthio]-6-vinyl-1-chlorobenzene
1023648-20-5

3-[3-(benzyloxy)phenylthio]-6-vinyl-1-chlorobenzene

dimethyl methoxymalonate
5018-30-4

dimethyl methoxymalonate

2-(2-{4-[3-(benzyloxy)phenylthio]-2-chlorophenyl}ethyl)-2-methoxymalonic acid dimethyl ester
1023648-23-8

2-(2-{4-[3-(benzyloxy)phenylthio]-2-chlorophenyl}ethyl)-2-methoxymalonic acid dimethyl ester

Conditions
ConditionsYield
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%

5018-30-4Relevant articles and documents

The Pentamethoxyallyl Cation

Moss, Robert A.,Guo, Wenjeng,Hagedorn, Alfred,Beveridge, Richard

, p. 1102 - 1103 (1982)

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)

Shevchenko, Vladimir V.,Zhegalova, Natalya G.,Borzenko, Andey O.,Nikolaev, Valerij A.

experimental part, p. 501 - 509 (2009/02/07)

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

Shevchenko,Shakhmin,Nikolaev

, p. 1741 - 1744 (2007/10/03)

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