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  • Diethyl methylmalonate CAS 609-08-5 Methylmalonic acid diethyl ester Ethyl methylmalonate CAS no 609-08-5 Diethyl 2-methylmalonate Propanedioicacid, 2-methyl-, 1,3-diethyl ester

    Cas No: 609-08-5

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609-08-5 Usage

Chemical Properties

Clear liquid

Uses

Different sources of media describe the Uses of 609-08-5 differently. You can refer to the following data:
1. Diethyl methylmalonate is used as intermediate for the syntheses of pharmaceuticals, e.g. non-steroidal anti-inflammatory agents with 2-acrylpropionic acid structures acrylpropionic acid structure. It is also used in the flavour and fragrance industries. Product Data Sheet
2. Diethyl methylmalonate was used to investigate the effect of direct supplementation of the medium with di-ester of methylmalonate on erythromycin fermentation in Saccharopolyspora erythraea mutB strain.

General Description

Diethyl methylmalonate reacts with 2-cyclohexenone under abnormal Michael conditions form 2-(3-oxocyclohexyl)-2-cyclohexenone. It causes the alkylation of poly(chloromethylstyrene) during pahse transfer catalysis.

Check Digit Verification of cas no

The CAS Registry Mumber 609-08-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,0 and 9 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 609-08:
(5*6)+(4*0)+(3*9)+(2*0)+(1*8)=65
65 % 10 = 5
So 609-08-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H14O4/c1-4-11-7(9)6(3)8(10)12-5-2/h6H,4-5H2,1-3H3

609-08-5 Well-known Company Product Price

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  • Alfa Aesar

  • (A12078)  Diethyl methylmalonate, 99%   

  • 609-08-5

  • 50g

  • 180.0CNY

  • Detail
  • Alfa Aesar

  • (A12078)  Diethyl methylmalonate, 99%   

  • 609-08-5

  • 250g

  • 594.0CNY

  • Detail
  • Alfa Aesar

  • (A12078)  Diethyl methylmalonate, 99%   

  • 609-08-5

  • 1000g

  • 2219.0CNY

  • Detail

609-08-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Diethyl Methylmalonate

1.2 Other means of identification

Product number -
Other names Propanedioic acid, methyl-, diethyl ester

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:609-08-5 SDS

609-08-5Synthetic route

diethyl malonate
105-53-3

diethyl malonate

methyl iodide
74-88-4

methyl iodide

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With P(MeNCH2CH2)3N In hexane; acetonitrile at 25℃; for 0.5h;98%
With sodium In ethanol at 80℃; for 10h; Inert atmosphere;97%
With (3S,4S)-1-benzyl-3,4-pyrrolidin-diol-onium iodide; potassium carbonate In N,N-dimethyl-formamide for 2.5h; Ambient temperature;96%
ethanol
64-17-5

ethanol

2-methylmalononitrile
3696-36-4

2-methylmalononitrile

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With sulfuric acid In tetrahydrofuran at 60 - 70℃;97.51%
2-cyanopropanoic acid
632-07-5

2-cyanopropanoic acid

ethanol
64-17-5

ethanol

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With sulfuric acid at 20 - 80℃; for 4h; Temperature;91.2%
at 20 - 65℃; for 3h; Temperature; Large scale;
diethyl malonate
105-53-3

diethyl malonate

methyl iodide
74-88-4

methyl iodide

A

2,2-dimethylmalonic acid diethyl ester
1619-62-1

2,2-dimethylmalonic acid diethyl ester

B

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 4h; Ambient temperature;A 5%
B 90%
With sodium hydride 1.) DMSO, cooling, 10 min, 2.) overnight; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
diethyl allylmethylmalonate
53651-72-2

diethyl allylmethylmalonate

naphthalen-2-ylzinc(II) bromide

naphthalen-2-ylzinc(II) bromide

A

2-allylnaphthalene
2489-87-4

2-allylnaphthalene

B

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
Stage #1: diethyl allylmethylmalonate; naphthalen-2-ylzinc(II) bromide With dibromobis(triphenylphosphine)nickel(II); magnesium bromide In tetrahydrofuran; toluene at 20 - 60℃; Inert atmosphere;
Stage #2: With ammonium chloride In tetrahydrofuran; water; toluene
A 89%
B 95 %Spectr.
methyl bromide
74-83-9

methyl bromide

diethyl malonate
105-53-3

diethyl malonate

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 3h; Heating;85%
With sodium ethanolate In ethanol
Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
Stage #2: methyl bromide In tetrahydrofuran at 0℃; for 8h; Inert atmosphere;
diethyl malonate
105-53-3

diethyl malonate

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
In acetoacetic acid methyl ester82.6%
diethyl allylmethylmalonate
53651-72-2

diethyl allylmethylmalonate

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With titanium(IV) isopropylate; isopropylmagnesium chloride In diethyl ether at -50 - -40℃; for 1h; deallylation;81%
diethyl α-(chloro)-methylmalonate
29263-82-9

diethyl α-(chloro)-methylmalonate

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With zinc In water; acetic acid for 4h; Heating;80%
2-methyl-2-trimethylsilanylethynyl-malonic acid diethyl ester

2-methyl-2-trimethylsilanylethynyl-malonic acid diethyl ester

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With titanium(IV) isopropylate; isopropylmagnesium chloride In diethyl ether at -50 - -40℃; for 1h; dealkynylation;80%
diethylaminomethyl-methyl-malonic acid diethyl ester
80073-77-4

diethylaminomethyl-methyl-malonic acid diethyl ester

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran at 20℃;77%
C15H21NO4
1187336-84-0

C15H21NO4

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran Reflux;74%
2-(3-Methoxy-phenoxymethylene)-malonic acid diethyl ester

2-(3-Methoxy-phenoxymethylene)-malonic acid diethyl ester

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol under 2100.2 Torr; for 1.5h;68%
ethanol
64-17-5

ethanol

methyl-propanedioic acid
516-05-2

methyl-propanedioic acid

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With thionyl chloride at 30 - 70℃; for 6h; Temperature;65.5%
diethyl 2-methyl-2-(3-phenylprop-2-yn-1-yl)malonate

diethyl 2-methyl-2-(3-phenylprop-2-yn-1-yl)malonate

A

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

B

ethyl 4-(ethoxycarbonyl)-2-methyl-5-phenyl-4-(E)-pentenoate

ethyl 4-(ethoxycarbonyl)-2-methyl-5-phenyl-4-(E)-pentenoate

Conditions
ConditionsYield
With titanium(IV) isopropylate; isopropylmagnesium chloride In diethyl ether at -45℃; for 1h;A 31 % Spectr.
B 46%
With titanium(IV) isopropylate; isopropylmagnesium chloride In diethyl ether at -50 - -40℃; for 1h; Rearrangement; depropargylation;A 31%
B 46%
diethyl methyl(2-nonynyl)malonate

diethyl methyl(2-nonynyl)malonate

A

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

B

ethyl 4-(ethoxycarbonyl)-2-methyl-5-(E)-undecenoate

ethyl 4-(ethoxycarbonyl)-2-methyl-5-(E)-undecenoate

Conditions
ConditionsYield
With titanium(IV) isopropylate; isopropylmagnesium chloride In diethyl ether at -45℃; for 1h;A 34 % Spectr.
B 45%
With titanium(IV) isopropylate; isopropylmagnesium chloride In diethyl ether at -50 - -40℃; for 1h; Rearrangement; depropargylation;A 34%
B 45%
diethyl 2-(but-2-yn-1-yl)-2-methylmalonate
182809-41-2

diethyl 2-(but-2-yn-1-yl)-2-methylmalonate

A

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

B

ethyl 4-(ethoxycarbonyl)-2-methyl-4-(E)-hexenoate

ethyl 4-(ethoxycarbonyl)-2-methyl-4-(E)-hexenoate

Conditions
ConditionsYield
With titanium(IV) isopropylate; isopropylmagnesium chloride In diethyl ether at -45℃; for 1h;A 32 % Spectr.
B 42%
With titanium(IV) isopropylate; isopropylmagnesium chloride In diethyl ether at -50 - -40℃; for 1h; Rearrangement; depropargylation;A 32%
B 42%
4-O,O-t-butyl 1-ethyl 2-(ethoxycarbonyl)monoperoxybutanedioate
89317-62-4

4-O,O-t-butyl 1-ethyl 2-(ethoxycarbonyl)monoperoxybutanedioate

A

ethyl 3-(t-butoxy)-2-(ethoxycarbonyl)propionate
91368-88-6

ethyl 3-(t-butoxy)-2-(ethoxycarbonyl)propionate

B

diethyl (cyclohexylmethyl)propanedioate
29805-59-2

diethyl (cyclohexylmethyl)propanedioate

C

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

D

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

E

2-(tert-butoxy)butanedioic acid diethyl ester

2-(tert-butoxy)butanedioic acid diethyl ester

Conditions
ConditionsYield
In cyclohexane Ambient temperature; Irradiation; photolysis of further t-butyl percarboxylates in various solvents;A 40.8%
B n/a
C 1.3%
D 37%
E 1.7%
dipropionatopalladium(II)

dipropionatopalladium(II)

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With carbon monoxide; triethylamine In acetonitrile Ambient temperature;38%
1,2-epoxy-7-methoxy-8-methyl-1,2,3,4-tetrahydro-naphthalene
27982-94-1

1,2-epoxy-7-methoxy-8-methyl-1,2,3,4-tetrahydro-naphthalene

2-((1S,2S)-2-Hydroxy-7-methoxy-8-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-propionic acid
27767-56-2

2-((1S,2S)-2-Hydroxy-7-methoxy-8-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-propionic acid

B

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With sodium In benzene for 30h; Heating;A 32%
B 30%
methyl bromide
74-83-9

methyl bromide

sodium diethylmalonate
996-82-7

sodium diethylmalonate

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

diethyl ether
60-29-7

diethyl ether

ethyl γ-benzoyl-α-ethoxycarbonyl-α-methyl-β-phenylbutyrate
77670-31-6

ethyl γ-benzoyl-α-ethoxycarbonyl-α-methyl-β-phenylbutyrate

sodium ethanolate
141-52-6

sodium ethanolate

A

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

B

1,3-diphenyl-propen-3-one
614-47-1

1,3-diphenyl-propen-3-one

diethyl aminomethylenemalonate
6296-99-7

diethyl aminomethylenemalonate

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With ethanol; nickel at 100 - 125℃; Hydrogenation;
ethanol
64-17-5

ethanol

diethyl bromomethylmalonate
29263-94-3

diethyl bromomethylmalonate

sodium ethyl acetylacetate enolate
1007476-32-5

sodium ethyl acetylacetate enolate

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

ethanol
64-17-5

ethanol

methyl-malonyl bromide
98020-11-2

methyl-malonyl bromide

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

diethyl methylenemalonate
3377-20-6

diethyl methylenemalonate

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With diethyl ether; nickel Hydrogenation.unter Druck;
With ethanol; nickel Hydrogenation.unter Druck;
With n-butylmercuric chloride; sodium thiosulfate; HSiPh3 1.) DMSO, 12 h, 2.) DMSO; Yield given. Multistep reaction;
ethyl 2-diazo-3-oxobutanoate
2009-97-4

ethyl 2-diazo-3-oxobutanoate

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With ethanol Irradiation.mit UV-Licht;
diethyl oxalpropionate
759-65-9

diethyl oxalpropionate

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
bei der Destillation;
diethyl 2-(hydroxymethylene)malonate
20734-18-3

diethyl 2-(hydroxymethylene)malonate

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

Conditions
ConditionsYield
With ethanol; nickel at 100 - 125℃; Hydrogenation;
sodium ethanolate
141-52-6

sodium ethanolate

ethyl acetoacetate
141-97-9

ethyl acetoacetate

diethyl malonate
105-53-3

diethyl malonate

methyl iodide
74-88-4

methyl iodide

A

2-acetylpropanoic acid ethyl ester
609-14-3

2-acetylpropanoic acid ethyl ester

B

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

monoethyl methylmalonate
2985-33-3

monoethyl methylmalonate

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 0 - 20℃; for 2h;100%
With sodium hydroxide In tetrahydrofuran at 0℃; for 1.5h;96%
Stage #1: Diethyl methylmalonate With potassium hydroxide; water In tetrahydrofuran at 0℃; for 1h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran at 0℃; Product distribution / selectivity;
96%
1,3-dibromo-propane
109-64-8

1,3-dibromo-propane

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

heptane-2,2,6,6-tetracarboxylic acid tetraethyl ester
33524-34-4

heptane-2,2,6,6-tetracarboxylic acid tetraethyl ester

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 24℃; Substitution; Heating;100%
(i) NaH, benzene, (ii) /BRN= 635662/; Multistep reaction;
N-ethoxycarbonylaziridine
671-51-2

N-ethoxycarbonylaziridine

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

3-Methyl-2-oxo-3-pyrrolidincarbonsaeure-ethylester
79232-62-5

3-Methyl-2-oxo-3-pyrrolidincarbonsaeure-ethylester

Conditions
ConditionsYield
With triethylamine for 120h; Ambient temperature;100%
ethyl bromoacetate
105-36-2

ethyl bromoacetate

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

triethyl propane-1,2,2-tricarboxylate
39994-45-1

triethyl propane-1,2,2-tricarboxylate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 2h; Ambient temperature;100%
2-Bromo-4'-phenylacetophenone
135-73-9

2-Bromo-4'-phenylacetophenone

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

2-(2-Biphenyl-4-yl-2-oxo-ethyl)-2-methyl-malonic acid diethyl ester
88598-79-2

2-(2-Biphenyl-4-yl-2-oxo-ethyl)-2-methyl-malonic acid diethyl ester

Conditions
ConditionsYield
With sodium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide for 2h; Ambient temperature;100%
allyl bromide
106-95-6

allyl bromide

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

diethyl allylmethylmalonate
53651-72-2

diethyl allylmethylmalonate

Conditions
ConditionsYield
Stage #1: Diethyl methylmalonate With sodium ethanolate In ethanol for 0.333333h;
Stage #2: allyl bromide In ethanol for 12h;
100%
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at 20℃; for 1.5h;99%
Stage #1: Diethyl methylmalonate With sodium hydride In N,N-dimethyl-formamide at 0 - 50℃;
Stage #2: allyl bromide In N,N-dimethyl-formamide at 20 - 50℃;
96%
ethyl (1-13C)-bromoacetate
61203-71-2

ethyl (1-13C)-bromoacetate

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

Triethyl (1-C=O-13C)-1,1,2-propanetricarboxylate
157246-97-4

Triethyl (1-C=O-13C)-1,1,2-propanetricarboxylate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran for 2h; Ambient temperature;100%
With sodium hydride 1.) THF, 2.) THF; Multistep reaction;
formaldehyd
50-00-0

formaldehyd

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

2-(hydroxymethyl)-2-methylpropanedioic acid diethyl ester
72999-08-7

2-(hydroxymethyl)-2-methylpropanedioic acid diethyl ester

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethanol; water at 0 - 20℃; for 20h;100%
With sodium hydrogencarbonate In ethanol; water at 0 - 20℃; for 20h;100%
With triethylamine In water; N,N-dimethyl-formamide at 40 - 50℃; for 2h;88%
1-Bromo-2-butyne
3355-28-0

1-Bromo-2-butyne

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

diethyl 2-(but-2-yn-1-yl)-2-methylmalonate
182809-41-2

diethyl 2-(but-2-yn-1-yl)-2-methylmalonate

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;100%
Stage #1: Diethyl methylmalonate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: 1-Bromo-2-butyne In tetrahydrofuran at -78℃; for 1h;
97.6%
Stage #1: Diethyl methylmalonate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: 1-Bromo-2-butyne In tetrahydrofuran at -78 - 20℃;
97.6%
2-(Trimethylsilyl)ethanol
2916-68-9

2-(Trimethylsilyl)ethanol

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

2-methyl-malonic acid bis-(2-trimethylsilanyl-ethyl) ester

2-methyl-malonic acid bis-(2-trimethylsilanyl-ethyl) ester

Conditions
ConditionsYield
With sodium hydride In toluene for 14h; Heating;100%
rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene
87751-69-7

rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

diethyl 2-((E)-(S)-1,3-diphenyl-allyl)-α-methylmalonate

diethyl 2-((E)-(S)-1,3-diphenyl-allyl)-α-methylmalonate

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)); chiral sulfideoxathiane ligand; potassium acetate; N,O-bis-(trimethylsilyl)-acetamide In dichloromethane at 0℃; for 48h;100%
With N,O-bis-(trimethylsilyl)-acetamide; chiral sulfideoxathiane ligand; potassium acetate; bis(η3-allyl-μ-chloropalladium(II)) In dichloromethane at 0℃; for 48h;100%
Stage #1: rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene With (S)-7,7'-bis[di(3,5-dimethyl-4-methoxyphenyl)-phosphino]-1,1'-spirobiindane; bis(η3-allyl-μ-chloropalladium(II)) In 1,4-dioxane at 20℃; for 0.166667h;
Stage #2: Diethyl methylmalonate With diethylzinc In 1,4-dioxane; hexane at 20℃; for 3h; Further stages.;
96%
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;95%
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;93%
(S)-tert-leucinol
112245-13-3

(S)-tert-leucinol

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

N1,N3-bis[(S)-1-hydroxy-3,3-dimethylbutan-2-yl]malonamide
909713-82-2

N1,N3-bis[(S)-1-hydroxy-3,3-dimethylbutan-2-yl]malonamide

Conditions
ConditionsYield
at 110℃; for 72h;100%
In toluene at 120℃;82%
at 120℃; for 72h; Schlenk technique; Inert atmosphere;
at 120℃; for 72h; Schlenk technique; Inert atmosphere;
Allyl acetate
591-87-7

Allyl acetate

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

diethyl allylmethylmalonate
53651-72-2

diethyl allylmethylmalonate

Conditions
ConditionsYield
Stage #1: Diethyl methylmalonate With sodium hydride In tetrahydrofuran at 25℃; for 0.5h;
Stage #2: Allyl acetate With 1,4-di(diphenylphosphino)-butane; bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran at 55℃; for 3h; Further stages.;
100%
With potassium carbonate; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;100 %Chromat.
With 1-ethyl-2,3-dimethylimidazolium tetrafluoroborate; potassium carbonate; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) In dichloromethane at 20℃; for 18 - 24h; Tsuji-Trost Allylation;
Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

4-benzyloxybenzyl chloride
836-42-0

4-benzyloxybenzyl chloride

diethyl 2-(4-(benzyloxy)benzyl)-2-methylmalonate
144871-72-7

diethyl 2-(4-(benzyloxy)benzyl)-2-methylmalonate

Conditions
ConditionsYield
In tetrahydrofuran; water; ethyl acetate100%
Stage #1: Diethyl methylmalonate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃;
Stage #2: 4-benzyloxybenzyl chloride In tetrahydrofuran; mineral oil Reflux;
91%
2-Amino-2-methyl-1-propanol
124-68-5

2-Amino-2-methyl-1-propanol

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

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

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

Conditions
ConditionsYield
With sodium hydride In mineral oil at 160℃; Inert atmosphere;100%
With sodium hydride at 140℃; for 4h; Inert atmosphere;95%
Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

cinnamyl halide

cinnamyl halide

2-methyl-2-(3-phenyl-2-propenyl)malonic acid diethyl ester
156382-65-9

2-methyl-2-(3-phenyl-2-propenyl)malonic acid diethyl ester

Conditions
ConditionsYield
Stage #1: Diethyl methylmalonate With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere;
Stage #2: cinnamyl halide In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
100%
Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

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

1-bromo-3-phenylprop-2-yne

diethyl 2-methyl-2-(3-phenylprop-2-yn-1-yl)malonate

diethyl 2-methyl-2-(3-phenylprop-2-yn-1-yl)malonate

Conditions
ConditionsYield
Stage #1: Diethyl methylmalonate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.666667h;
Stage #2: 1-bromo-3-phenylprop-2-yne In tetrahydrofuran at -78 - 20℃;
100%
2-bromo-butyryl bromide
26074-52-2

2-bromo-butyryl bromide

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

C12H19BrO5

C12H19BrO5

Conditions
ConditionsYield
Stage #1: Diethyl methylmalonate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1.33333h; Inert atmosphere;
Stage #2: 2-bromo-butyryl bromide In tetrahydrofuran; mineral oil at 0 - 20℃; for 17h; Inert atmosphere;
100%
3,5-dibromophenylamidine hydrochloride

3,5-dibromophenylamidine hydrochloride

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

2-(3,5-dibromophenyl)-4,6-dihydroxy-5-methylpyrimidine

2-(3,5-dibromophenyl)-4,6-dihydroxy-5-methylpyrimidine

Conditions
ConditionsYield
With sodium methylate In methanol at 70℃; for 24h; Inert atmosphere; Cooling with ice;100%
2,4-Difluoronitrobenzene
446-35-5

2,4-Difluoronitrobenzene

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

diethyl 2-(3-fluoro-4-nitrophenyl)-2-methyl-malonate
78543-06-3

diethyl 2-(3-fluoro-4-nitrophenyl)-2-methyl-malonate

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide for 5h;99.75%
With sodium hydroxide In N,N-dimethyl-formamide at 25 - 30℃; for 4h;91%
Stage #1: Diethyl methylmalonate With sodium hydride In dimethyl sulfoxide at 15℃;
Stage #2: 2,4-Difluoronitrobenzene In dimethyl sulfoxide at 15℃; for 0.5h;
87%
Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

2-methyl-malonamide
1113-63-9

2-methyl-malonamide

Conditions
ConditionsYield
With ammonia In methanol for 168h; Ambient temperature;99.7%
With MH3 gas In methanol at 110℃; for 16h;98%
With ammonia; sodium methylate In methanol for 120h; Ambient temperature;95%
1-Bromotetradecane
112-71-0

1-Bromotetradecane

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

methyl-tetradecyl-malonic acid diethyl ester
114289-75-7

methyl-tetradecyl-malonic acid diethyl ester

Conditions
ConditionsYield
99%
(i) Na, (ii) /BRN= 1742640/; Multistep reaction;
With sodium ethanolate 1.) ethanol, reflux, 15 min, 2.) ethanol, reflux, overnight; Multistep reaction;
iodoform
75-47-8

iodoform

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

2-diiodomethyl-2-methyl-malonic acid diethyl ester
311807-55-3

2-diiodomethyl-2-methyl-malonic acid diethyl ester

Conditions
ConditionsYield
Stage #1: Diethyl methylmalonate In diethyl ether for 0.5h;
Stage #2: With sodium hydride In diethyl ether for 1.5h; Reflux;
Stage #3: iodoform for 12h; Reflux;
99%
With sodium hydride In diethyl ether Reflux;99%
Stage #1: Diethyl methylmalonate With sodium hydride In diethyl ether; mineral oil at 40℃; for 3h; Inert atmosphere;
Stage #2: iodoform In diethyl ether; mineral oil for 24h; Inert atmosphere; Reflux;
80%
Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

methyl-propanedioic acid
516-05-2

methyl-propanedioic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 1h; Ambient temperature;99%
With potassium hydroxide In water at 0 - 20℃; for 60h;71%
With potassium hydroxide In ethanol; water for 4h; Heating;
1,8-bis(bromomethyl)naphthalene
2025-95-8

1,8-bis(bromomethyl)naphthalene

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

2-[8-(2,2-bis-ethoxycarbonyl-propyl)-naphthalen-1-ylmethyl]-2-methyl-malonic acid diethyl ester
849706-62-3

2-[8-(2,2-bis-ethoxycarbonyl-propyl)-naphthalen-1-ylmethyl]-2-methyl-malonic acid diethyl ester

Conditions
ConditionsYield
Stage #1: Diethyl methylmalonate With sodium In ethanol at 20℃; for 0.5h;
Stage #2: 1,8-bis(bromomethyl)naphthalene In ethanol for 3h; Heating;
99%
phenylacetylene
536-74-3

phenylacetylene

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

2-methyl-2-(1-phenylvinyl)malonic acid diethyl ester
35293-95-9

2-methyl-2-(1-phenylvinyl)malonic acid diethyl ester

Conditions
ConditionsYield
indium(III) triflate at 140℃; for 16h;99%
With indium(III) triflate99%
With indium(III) bromide In o-xylene at 130℃;92%
1-Iodooctane
629-27-6

1-Iodooctane

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

methyloctylpropanedioic acid diethyl ester
98061-08-6

methyloctylpropanedioic acid diethyl ester

Conditions
ConditionsYield
Stage #1: Diethyl methylmalonate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: 1-Iodooctane In N,N-dimethyl-formamide at 0 - 20℃;
99%
methanesulfonic acid 3-(anthracen-9-ylmethoxy)propyl ester
877995-16-9

methanesulfonic acid 3-(anthracen-9-ylmethoxy)propyl ester

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

diethyl 2-{3-[(anthracen-9-yl)methoxy]propyl}-2-methylmalonate
929210-63-9

diethyl 2-{3-[(anthracen-9-yl)methoxy]propyl}-2-methylmalonate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 60℃;99%
ortho-nitrofluorobenzene
1493-27-2

ortho-nitrofluorobenzene

Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

diethyl methyl(2-nitrophenyl)malonate
71127-36-1

diethyl methyl(2-nitrophenyl)malonate

Conditions
ConditionsYield
With triethylsilane; t-Bu-P4 In hexane; N,N-dimethyl-formamide at 80℃; for 1h;99%
Diethyl methylmalonate
609-08-5

Diethyl methylmalonate

acrolein
107-02-8

acrolein

diethyl 2-methyl-2-(3-oxopropyl)malonate
3576-11-2

diethyl 2-methyl-2-(3-oxopropyl)malonate

Conditions
ConditionsYield
With 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In dichloromethane at 20℃; Michael addition; Inert atmosphere;99%

609-08-5Relevant articles and documents

Synthesis, Electronic Spectroscopy, and Photochemistry of Methacrolein Oxide: A Four-Carbon Unsaturated Criegee Intermediate from Isoprene Ozonolysis

Vansco, Michael F.,Marchetti, Barbara,Trongsiriwat, Nisalak,Bhagde, Trisha,Wang, Guanghan,Walsh, Patrick J.,Klippenstein, Stephen J.,Lester, Marsha I.

, p. 15058 - 15069 (2019)

Ozonolysis of isoprene, one of the most abundant volatile organic compounds in the earth's atmosphere, generates the four-carbon unsaturated methacrolein oxide (MACR-oxide) Criegee intermediate. The first laboratory synthesis and direct detection of MACR-oxide is achieved through reaction of photolytically generated, resonance-stabilized iodoalkene radicals with oxygen. MACR-oxide is characterized on its first π? a? πelectronic transition using a ground-state depletion method. MACR-oxide exhibits a broad UV-visible spectrum peaked at 380 nm with weak oscillatory structure at long wavelengths ascribed to vibrational resonances. Complementary theory predicts two strong ?€? a? πtransitions arising from extended conjugation across MACR-oxide with overlapping contributions from its four conformers. Electronic promotion to the 11π? state agrees well with experiment, and results in nonadiabatic coupling and prompt release of O 1D products observed as anisotropic velocity-map images. This UV-visible detection scheme will enable study of its unimolecular and bimolecular reactions under thermal conditions of relevance to the atmosphere.

Preparation of mono-substituted malonic acid half oxyesters (SMAHOs)

Condon, Sylvie,Le Gall, Erwan,Pichon, Christophe,Presset, Marc,Xavier, Tania

supporting information, p. 2085 - 2094 (2021/09/02)

The use of mono-substituted malonic acid half oxyesters (SMAHOs) has been hampered by the sporadic references describing their preparation. An evaluation of different approaches has been achieved, allowing to define the best strategies to introduce diversity on both the malonic position and the ester function. A classical alkylation step of a malonate by an alkyl halide followed by a monosaponification gave access to reagents bearing different substituents at the malonic position, including functionalized derivatives. On the other hand, the development of a monoesterification step of a substituted malonic acid derivative proved to be the best entry for diversity at the ester function, rather than the use of an intermediate Meldrum acid. Both these transformations are characterized by their simplicity and efficiency, allowing a straightforward access to SMAHOs from cheap starting materials.

Apple flavor compound, preparation method thereof and food additive

-

Paragraph 0064-0066; 0081; 0082; 0086; 0090; 0091, (2020/07/13)

The invention relates to an apple flavor compound, a preparation method thereof and a food additive. The apple flavor compound has a structural formula shown as the specification, the apple flavor compound can be named as 1-(1-(1-(3, 3-dimethylcyclohexyl)ethyl)3-ethyl malonic acid malonate. Experiments prove that the compound has obvious mature sweet apple fragrance, can be used in food additiveswith apple fragrance, and provides a new source for the apple flavor compound.

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