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133-13-1

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133-13-1 Usage

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

Diethyl Ethylmalonate is used in the synthesis of HIV-1 reverse transcriptase inhibitors. Also used in the preparation of Peloruside A, a novel antimitotic agent used as a potential anti-cancer agent.

Check Digit Verification of cas no

The CAS Registry Mumber 133-13-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 3 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 133-13:
(5*1)+(4*3)+(3*3)+(2*1)+(1*3)=31
31 % 10 = 1
So 133-13-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H16O4/c1-4-7(8(10)12-5-2)9(11)13-6-3/h7H,4-6H2,1-3H3

133-13-1 Well-known Company Product Price

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  • Alfa Aesar

  • (B24077)  Diethyl ethylmalonate, 99%   

  • 133-13-1

  • 100g

  • 276.0CNY

  • Detail
  • Alfa Aesar

  • (B24077)  Diethyl ethylmalonate, 99%   

  • 133-13-1

  • 500g

  • 882.0CNY

  • Detail

133-13-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Diethyl ethylmalonate

1.2 Other means of identification

Product number -
Other names diethyl 2-ethylpropanedioate

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:133-13-1 SDS

133-13-1Synthetic route

ethyl iodide
75-03-6

ethyl iodide

diethyl malonate
105-53-3

diethyl malonate

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

Conditions
ConditionsYield
With P(MeNCH2CH2)3N In hexane; acetonitrile at 25℃; for 0.5h;92%
With silver(l) oxide
With ethanol; magnesium ethylate
ethyl bromide
74-96-4

ethyl bromide

diethyl malonate
105-53-3

diethyl malonate

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

Conditions
ConditionsYield
With potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride In N,N-dimethyl-formamide at 60℃; for 4h;90%
With potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride In N,N-dimethyl-formamide at 60℃; for 4h; Product distribution; other solvent, other temperature, other reaction time;90%
With sodium acetylide In benzene at 20 - 25℃; for 0.5h; further reagent (sodium phenylacetylide);89%
diethyl cyclopropane-1,1-dicarboxylate
1559-02-0

diethyl cyclopropane-1,1-dicarboxylate

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

Conditions
ConditionsYield
With samarium diiodide; tris(dibenzoylmethano)iron(III); tert-butyl alcohol In tetrahydrofuran for 0.5h; Ambient temperature;89%
With hydrogen; palladium on activated charcoal In methanol Product distribution;
With (5,10,15,20-tetrakis-4-tolylporphyrinato)(methyl)rhodium(III); isopropyl alcohol In benzene-d6 at 200℃; for 48h; Darkness; Sealed tube; regioselective reaction;14 %Spectr.
diethyl ethylidenemalonate
1462-12-0

diethyl ethylidenemalonate

BuMnCl
88626-90-8

BuMnCl

A

diethyl (1-methyl-pentyl)malonate
82297-04-9

diethyl (1-methyl-pentyl)malonate

B

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

Conditions
ConditionsYield
In tetrahydrofuran at -30℃; for 2h;A 87%
B 6%
diethyl ethylidenemalonate
1462-12-0

diethyl ethylidenemalonate

butyl-iodo-manganese
62485-87-4

butyl-iodo-manganese

A

diethyl (1-methyl-pentyl)malonate
82297-04-9

diethyl (1-methyl-pentyl)malonate

B

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

Conditions
ConditionsYield
In diethyl ether at -30℃; for 2h;A 83%
B 11%
diethyl ethylidenemalonate
1462-12-0

diethyl ethylidenemalonate

C12H27Mn(1-)*Cl(1-)*Mg(2+)

C12H27Mn(1-)*Cl(1-)*Mg(2+)

A

diethyl (1-methyl-pentyl)malonate
82297-04-9

diethyl (1-methyl-pentyl)malonate

B

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

Conditions
ConditionsYield
In tetrahydrofuran at -30℃; for 2h;A 82%
B 12%
diethyl ethylidenemalonate
1462-12-0

diethyl ethylidenemalonate

C12H27Mn

C12H27Mn

A

diethyl (1-methyl-pentyl)malonate
82297-04-9

diethyl (1-methyl-pentyl)malonate

B

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

Conditions
ConditionsYield
In tetrahydrofuran at -30℃; for 2h;A 82%
B 8%
diethyl ethylidenemalonate
1462-12-0

diethyl ethylidenemalonate

lithium tri-n-butylmanganate

lithium tri-n-butylmanganate

A

diethyl (1-methyl-pentyl)malonate
82297-04-9

diethyl (1-methyl-pentyl)malonate

B

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

Conditions
ConditionsYield
In tetrahydrofuran at -30℃; for 2h;A 80%
B 7%
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

diethyl ethylidenemalonate
1462-12-0

diethyl ethylidenemalonate

methylaluminum dichloride
917-65-7

methylaluminum dichloride

A

diethyl isopropylmalonate
759-36-4

diethyl isopropylmalonate

B

diethyl (1-methyl-pentyl)malonate
82297-04-9

diethyl (1-methyl-pentyl)malonate

C

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

Conditions
ConditionsYield
Stage #1: n-butyllithium; methylaluminum dichloride In hexane; toluene at -40℃; for 1h; Substitution;
Stage #2: With boron trifluoride diethyl etherate In hexane; toluene for 1h; Addition;
Stage #3: diethyl ethylidenemalonate In hexane; toluene at -40℃; for 18h; Reduction; Michael addition;
A 7 % Chromat.
B 74%
C 6 % Chromat.
diethyl ethylidenemalonate
1462-12-0

diethyl ethylidenemalonate

C3H7ClMn
105486-13-3

C3H7ClMn

A

diethyl 2-(3-methylbutan-2-yl)malonate
759-29-5

diethyl 2-(3-methylbutan-2-yl)malonate

B

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

Conditions
ConditionsYield
In tetrahydrofuran at -30℃; for 2h;A 70%
B 11%
bronidox
30007-47-7

bronidox

C9H15LiO4

C9H15LiO4

A

5-(1,3-dioxa-5-cyclohexylidene)-1,3-dioxane
86251-75-4

5-(1,3-dioxa-5-cyclohexylidene)-1,3-dioxane

B

5-nitro-5-(5-nitro-1,3-dioxa-5-cyclohexyl)-1,3-dioxacyclohexane
86251-74-3

5-nitro-5-(5-nitro-1,3-dioxa-5-cyclohexyl)-1,3-dioxacyclohexane

C

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

D

diethyl ethyl(5-nitro-1,3-dioxan-5-yl)malonate

diethyl ethyl(5-nitro-1,3-dioxan-5-yl)malonate

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 12h; Yield given;A n/a
B 11%
C n/a
D 67%
In dimethyl sulfoxide at 20℃; for 12h;A n/a
B 11%
C n/a
D 67%
diethyl ethylidenemalonate
1462-12-0

diethyl ethylidenemalonate

tert.-butyl lithium
594-19-4

tert.-butyl lithium

methylaluminum dichloride
917-65-7

methylaluminum dichloride

A

diethyl isopropylmalonate
759-36-4

diethyl isopropylmalonate

B

diethyl 2-(3,3-dimethylbutan-2-yl)malonate
125001-54-9

diethyl 2-(3,3-dimethylbutan-2-yl)malonate

C

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

Conditions
ConditionsYield
Stage #1: tert.-butyl lithium; methylaluminum dichloride In hexane; toluene; pentane at -40℃; for 1h; Substitution;
Stage #2: With boron trifluoride diethyl etherate In hexane; toluene; pentane for 1h; Addition;
Stage #3: diethyl ethylidenemalonate In hexane; toluene; pentane at -40℃; Reduction; Michael addition;
A 2 % Chromat.
B 66%
C 6 % Chromat.
hex-3-yne
928-49-4

hex-3-yne

diethyl ethylidenemalonate
1462-12-0

diethyl ethylidenemalonate

A

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

B

diethyl (E-2-ethyl-1-methyl-pent-2-enyl)malonate

diethyl (E-2-ethyl-1-methyl-pent-2-enyl)malonate

Conditions
ConditionsYield
Stage #1: hex-3-yne With diisobutylaluminium hydride In n-heptane; toluene at 50℃; for 3h; Addition;
Stage #2: diethyl ethylidenemalonate In n-heptane; toluene at -40℃; for 18h; Michael addition;
A 21 % Chromat.
B 43%
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%
diethyl ethylidenemalonate
1462-12-0

diethyl ethylidenemalonate

t-butylmanganese chloride
125001-53-8

t-butylmanganese chloride

A

diethyl 2-(3,3-dimethylbutan-2-yl)malonate
125001-54-9

diethyl 2-(3,3-dimethylbutan-2-yl)malonate

B

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

Conditions
ConditionsYield
In tetrahydrofuran at -30℃; for 2h;A 10%
B 40%
diethyl ethylidenemalonate
1462-12-0

diethyl ethylidenemalonate

A

diethyl 2-(3,3-dimethylbutan-2-yl)malonate
125001-54-9

diethyl 2-(3,3-dimethylbutan-2-yl)malonate

B

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

Conditions
ConditionsYield
With t-butylmanganese chloride In tetrahydrofuran at -30℃; for 2h; var. organomanganeses.;A 10%
B 40%
2-Ethyl-2-(2-phenylsulfanyl-acetyl)-malonic acid diethyl ester
93845-20-6

2-Ethyl-2-(2-phenylsulfanyl-acetyl)-malonic acid diethyl ester

A

diethyl (acetyl)ethylmalonate
3378-01-6

diethyl (acetyl)ethylmalonate

B

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

Conditions
ConditionsYield
With nickel In acetoneA 20%
B 24%
2-acetylpropanoic acid ethyl ester
609-14-3

2-acetylpropanoic acid ethyl ester

ethyl 2-bromopropanedioic acid diethyl ester
29237-78-3

ethyl 2-bromopropanedioic acid diethyl ester

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

ethyl bromide
74-96-4

ethyl bromide

sodium diethylmalonate
996-82-7

sodium diethylmalonate

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

diethyl sulfate
64-67-5

diethyl sulfate

sodium diethylmalonate
996-82-7

sodium diethylmalonate

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

2-Ethyl-3-oxo-succinic acid diethyl ester
26103-77-5

2-Ethyl-3-oxo-succinic acid diethyl ester

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

Conditions
ConditionsYield
at 160℃;
ethanol
64-17-5

ethanol

2-ethyl-3-oxo-acrylic acid ethyl ester
24489-48-3

2-ethyl-3-oxo-acrylic acid ethyl ester

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

ethanol
64-17-5

ethanol

propane-1,1,1-tricarboxylic acid triethyl ester
16515-91-6

propane-1,1,1-tricarboxylic acid triethyl ester

sodium ethanolate
141-52-6

sodium ethanolate

A

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

B

Diethyl carbonate
105-58-8

Diethyl carbonate

ethanol
64-17-5

ethanol

ethyl-malonyl bromide
98024-97-6

ethyl-malonyl bromide

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

ethanol
64-17-5

ethanol

1,3-diethyl-2,4-dioxo-cyclobutane-1,3-dicarboxylic acid diethyl ester
36832-92-5

1,3-diethyl-2,4-dioxo-cyclobutane-1,3-dicarboxylic acid diethyl ester

sodium ethanolate
141-52-6

sodium ethanolate

A

monoethyl DL-ethyl-malonate
69923-74-6, 2985-34-4

monoethyl DL-ethyl-malonate

B

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

2-ethyl-3-oxo-acrylic acid ethyl ester
24489-48-3

2-ethyl-3-oxo-acrylic acid ethyl ester

sodium methylate
124-41-4

sodium methylate

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

diethyl ethylidenemalonate
1462-12-0

diethyl ethylidenemalonate

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

Conditions
ConditionsYield
With diethyl ether; nickel under 73550.8 - 95616 Torr;
With ethanol; nickel under 73550.8 - 95616 Torr;
With palladium Hydrogenation;
ethyl propionyl-2-diazoacetate
2009-98-5

ethyl propionyl-2-diazoacetate

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

Conditions
ConditionsYield
at 250℃;
ethyl bromide
74-96-4

ethyl bromide

sodium ethanolate
141-52-6

sodium ethanolate

ethyl acetoacetate
141-97-9

ethyl acetoacetate

diethyl malonate
105-53-3

diethyl malonate

A

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

B

ethyl 2-ethyl-3-oxobutanoate
607-97-6

ethyl 2-ethyl-3-oxobutanoate

sodium diethylmalonate
996-82-7, 34727-00-9, 73177-21-6

sodium diethylmalonate

ethyl iodide
75-03-6

ethyl iodide

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

Conditions
ConditionsYield
With diethyl ether
With ethanol
ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

monoethyl DL-ethyl-malonate
69923-74-6, 2985-34-4

monoethyl DL-ethyl-malonate

Conditions
ConditionsYield
Stage #1: ethyl diethyl malonate With potassium hydroxide; water In ethanol
Stage #2: With hydrogenchloride In water pH=2;
100%
With hydrogenchloride; potassium hydroxide 1.) EtOH, room temp.; overnight;95%
With potassium hydroxide In ethanol for 24h; Ambient temperature;73%
linolenyl tosylate
66605-62-7

linolenyl tosylate

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

ethyl (all-Z)-2-ethyl-2-ethoxycarbonyl-11,14,17-eicosatrienoate
1022975-94-5

ethyl (all-Z)-2-ethyl-2-ethoxycarbonyl-11,14,17-eicosatrienoate

Conditions
ConditionsYield
Stage #1: ethyl diethyl malonate With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; for 0.5h;
Stage #2: linolenyl tosylate With sodium iodide In tetrahydrofuran; N,N-dimethyl-formamide at 70℃; for 2h;
100%
1-(methyl)-thiourea
598-52-7

1-(methyl)-thiourea

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

5-ethyl-1-methyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

5-ethyl-1-methyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

Conditions
ConditionsYield
With sodium methylate In methanol for 16h; Reflux;99%
benzyl 2-fluoro-5-nitrobenzyl(methyl)carbamate
1508298-05-2

benzyl 2-fluoro-5-nitrobenzyl(methyl)carbamate

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

diethyl 2-(2-((((benzyloxy)carbonyl)(methyl)amino)methyl)-4-nitrophenyl)-2-ethylmalonate
1508295-78-0

diethyl 2-(2-((((benzyloxy)carbonyl)(methyl)amino)methyl)-4-nitrophenyl)-2-ethylmalonate

Conditions
ConditionsYield
Stage #1: ethyl diethyl malonate With sodium hydride In dimethyl sulfoxide at 20℃; for 0.333333h;
Stage #2: benzyl 2-fluoro-5-nitrobenzyl(methyl)carbamate In dimethyl sulfoxide at 65℃;
98%
ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

4-Allyloxymethylbenzyl chloride
350671-26-0

4-Allyloxymethylbenzyl chloride

Diethyl 2-(4-allyloxymethylbenzyl)-2-ethylmalonate
350671-27-1

Diethyl 2-(4-allyloxymethylbenzyl)-2-ethylmalonate

Conditions
ConditionsYield
Stage #1: ethyl diethyl malonate With potassium tert-butylate In toluene for 0.5h; Heating;
Stage #2: 4-Allyloxymethylbenzyl chloride In toluene for 6.5h; Heating;
97.7%
ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

epichlorohydrin
106-89-8

epichlorohydrin

2-carbethoxy-2-ethyl-4-(chloromethyl)butyrolactone
94958-06-2

2-carbethoxy-2-ethyl-4-(chloromethyl)butyrolactone

Conditions
ConditionsYield
With potassium tert-butylate for 12h; Heating;97%
With ethanol; sodium ethanolate Behandeln des Reaktionsgemisches mit wss. Salzsaeure;
ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

2-nitro-N-(phenyl-λ3-iodaneylidene)benzenesulfonamide
149552-41-0

2-nitro-N-(phenyl-λ3-iodaneylidene)benzenesulfonamide

C15H18N2O8S

C15H18N2O8S

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 18h;97%
2-Methylpyrimido<1,6-a>benzimidazole-1,3-(2H,5H)-dione
94447-78-6

2-Methylpyrimido<1,6-a>benzimidazole-1,3-(2H,5H)-dione

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

4-Hydroxy-2-methyl-5-ethyl-1H,6H-2,6a,10b-triazafluoranthene-1,3,6(2H)-trione
136296-03-2

4-Hydroxy-2-methyl-5-ethyl-1H,6H-2,6a,10b-triazafluoranthene-1,3,6(2H)-trione

Conditions
ConditionsYield
With trichlorophenol at 280℃; for 0.5h;96%
tetrabutylammonium chloride monohydrate

tetrabutylammonium chloride monohydrate

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

diethyl 2-chloro-2-ethylmalonate
29263-83-0

diethyl 2-chloro-2-ethylmalonate

Conditions
ConditionsYield
With potassium carbonate In tetrachloromethane96%
acrylonitrile
107-13-1

acrylonitrile

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

diethyl 2-(2-cyanoethyl)-2-ethylmalonate
10444-12-9

diethyl 2-(2-cyanoethyl)-2-ethylmalonate

Conditions
ConditionsYield
With potassium tert-butylate In tert-butyl alcohol at 0 - 25℃; for 1h;95%
With potassium carbonate In tetrahydrofuran; 1,2-dimethoxyethane at 65℃; for 8h;92%
With 1,4-dioxane; N-benzyl-trimethylammonium hydroxide at 30 - 40℃;
ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

2-ethyl-1,3-propandiol
2612-29-5

2-ethyl-1,3-propandiol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 72h; Reflux;95%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 72h; Inert atmosphere; Reflux;95%
With lithium aluminium tetrahydride for 14h; Reflux; Inert atmosphere;95%
ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

ethylmalonic acid
601-75-2

ethylmalonic acid

Conditions
ConditionsYield
With sodium hydroxide In water for 2h; Heating;95%
With potassium hydroxide In water for 2h; Heating;94%
With potassium hydroxide; water ueber mehrere Stufen;
4-(bromomethyl)-4'-methyl-2,2'-bipyridine dihydrobromide
118724-31-5

4-(bromomethyl)-4'-methyl-2,2'-bipyridine dihydrobromide

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

2-ethyl-2-(4'-methyl-[2,2']bipyridinyl-4-ylmethyl)-malonic acid diethyl ester

2-ethyl-2-(4'-methyl-[2,2']bipyridinyl-4-ylmethyl)-malonic acid diethyl ester

Conditions
ConditionsYield
Stage #1: ethyl diethyl malonate With sodium hydride In N,N-dimethyl-formamide for 0.5h; Metallation;
Stage #2: 4-(bromomethyl)-4'-methyl-2,2'-bipyridine dihydrobromide In N,N-dimethyl-formamide for 5h; Alkylation;
95%
2-propynyl chloride
624-65-7

2-propynyl chloride

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

diethyl 2-ethyl-2-(1-propyn-3-yl)malonate
84928-67-6

diethyl 2-ethyl-2-(1-propyn-3-yl)malonate

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h;95%
[N-(p-tolylsulfonyl)imino]phenyliodinane
55962-05-5

[N-(p-tolylsulfonyl)imino]phenyliodinane

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

diethyl 2-(1-(4-methylphenylsulfonamido)ethyl)malonate
1373511-56-8

diethyl 2-(1-(4-methylphenylsulfonamido)ethyl)malonate

Conditions
ConditionsYield
With 1,10-Phenanthroline; 2,6-di-tert-butyl-4-methyl-phenol; copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 18h; Molecular sieve; Inert atmosphere;95%
[N-(p-tolylsulfonyl)imino]phenyliodinane
55962-05-5

[N-(p-tolylsulfonyl)imino]phenyliodinane

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

A

diethyl ethylidenemalonate
1462-12-0

diethyl ethylidenemalonate

B

diethyl 2-(1-(4-methylphenylsulfonamido)ethyl)malonate
1373511-56-8

diethyl 2-(1-(4-methylphenylsulfonamido)ethyl)malonate

Conditions
ConditionsYield
With 1,10-Phenanthroline; copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 4h; Molecular sieve; Inert atmosphere;A 2%
B 95%
6-(difluoro(phenylsulfonyl)methyl)phenanthridine

6-(difluoro(phenylsulfonyl)methyl)phenanthridine

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

diethyl 2-(difluoro(phenanthridin-6-yl)methyl)-2-ethylmalonate

diethyl 2-(difluoro(phenanthridin-6-yl)methyl)-2-ethylmalonate

Conditions
ConditionsYield
Stage #1: ethyl diethyl malonate With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 0.5h; Schlenk technique; Inert atmosphere;
Stage #2: 6-(difluoro(phenylsulfonyl)methyl)phenanthridine In dimethyl sulfoxide at 20℃; for 24h; Schlenk technique; Inert atmosphere;
95%
4-hydroxy-1,6-dimethylpyridin-2(1H)-one
6052-75-1

4-hydroxy-1,6-dimethylpyridin-2(1H)-one

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

C12H13NO4
955377-05-6

C12H13NO4

Conditions
ConditionsYield
In diphenylether Heating;94%
para-bromobenzenethiol
106-53-6

para-bromobenzenethiol

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

diethyl 2-((4-bromophenyl)thio)-2-ethylmalonate

diethyl 2-((4-bromophenyl)thio)-2-ethylmalonate

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 6h;94%
With caesium carbonate In N,N-dimethyl-formamide at 20℃;89%
2,6-Diaminopyridine
141-86-6

2,6-Diaminopyridine

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

7-amino-3-ethyl-1,2-dihydro-4-hydroxy-2-oxo-1,8-naphthyridine
120537-85-1

7-amino-3-ethyl-1,2-dihydro-4-hydroxy-2-oxo-1,8-naphthyridine

Conditions
ConditionsYield
In diphenylether for 0.5h; Heating;93%
benzalacetophenone
94-41-7

benzalacetophenone

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

ethyl-2-carbethoxy-3,6-diphenyl-2-ethyl-5-oxopentanoate
75919-29-8

ethyl-2-carbethoxy-3,6-diphenyl-2-ethyl-5-oxopentanoate

Conditions
ConditionsYield
With triethylamine In dichloromethane under 7500600 Torr; for 70h; Ambient temperature;93%
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride for 2h; Ambient temperature;75%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 30℃; under 10000 Torr; for 48h;35%
2-bromonicotinonitrile
20577-26-8

2-bromonicotinonitrile

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

2-(ethyl malonic acid diethyl ester), 3-cyano pyridine
86369-45-1

2-(ethyl malonic acid diethyl ester), 3-cyano pyridine

Conditions
ConditionsYield
With potassium tert-butylate; ammonium chloride In ammonia for 0.166667h; Irradiation;92%
1-bromomethyl-2-[(phenylsulfonyl)methyl]benzene
88116-02-3

1-bromomethyl-2-[(phenylsulfonyl)methyl]benzene

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

4-Benzenesulfonyl-2-ethyl-3-oxo-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester
88116-04-5

4-Benzenesulfonyl-2-ethyl-3-oxo-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran Ambient temperature;92%
ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

benzyl alcohol
100-51-6

benzyl alcohol

dibenzyl ethylmalonate
74254-53-8

dibenzyl ethylmalonate

Conditions
ConditionsYield
With sodium methylate In toluene for 5h; Heating;92%
2-guanidinobenzimidazole
5418-95-1

2-guanidinobenzimidazole

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

2-(1H-Benzoimidazol-2-ylamino)-5-ethyl-6-hydroxy-3H-pyrimidin-4-one

2-(1H-Benzoimidazol-2-ylamino)-5-ethyl-6-hydroxy-3H-pyrimidin-4-one

Conditions
ConditionsYield
In diphenylether at 200 - 220℃;92%
1-bromo-6-benzyloxyhexane
54247-27-7

1-bromo-6-benzyloxyhexane

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

diethyl 2-(6-(benzyloxy)hexyl)-2-ethylmalonate
1416792-20-5

diethyl 2-(6-(benzyloxy)hexyl)-2-ethylmalonate

Conditions
ConditionsYield
Stage #1: ethyl diethyl malonate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1.5h; Inert atmosphere;
Stage #2: 1-bromo-6-benzyloxyhexane In N,N-dimethyl-formamide; mineral oil at 20℃; for 3.5h; Inert atmosphere;
91%
Stage #1: ethyl diethyl malonate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1.5h; Inert atmosphere;
Stage #2: 1-bromo-6-benzyloxyhexane In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 3.5h; Inert atmosphere;
91%
5-oxabicyclo<2.2.0>hex-2-en-6-one
22980-23-0

5-oxabicyclo<2.2.0>hex-2-en-6-one

ethyl diethyl malonate
133-13-1

ethyl diethyl malonate

cis-4-(1-ethoxy-2-(ethoxycarbonyl)-1-oxobutan-2-yl)cyclobut-2-enecarboxylic acid

cis-4-(1-ethoxy-2-(ethoxycarbonyl)-1-oxobutan-2-yl)cyclobut-2-enecarboxylic acid

Conditions
ConditionsYield
Stage #1: ethyl diethyl malonate With sodium hydride In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #2: 5-oxabicyclo<2.2.0>hex-2-en-6-one With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; diethyl ether at 0℃; Inert atmosphere;
Stage #3: With hydrogenchloride In water pH=Ca. 2; Inert atmosphere; diastereoselective reaction;
90%

133-13-1Relevant articles and documents

-

Bailey,Hermes

, p. 1254 (1964)

-

-

Suga et al.

, p. 2920,2921, 2923 (1969)

-

Synthesis of Cyclopentenones through Rhodium-Catalyzed C-H Annulation of Acrylic Acids with Formaldehyde and Malonates

Yu, Shuling,Hong, Chao,Liu, Zhanxiang,Zhang, Yuhong

supporting information, p. 5054 - 5059 (2021/07/20)

An efficient rhodium-catalyzed protocol for the synthesis of cyclopentenones based on a three-component reaction of acrylic acids, formaldehyde, and malonates via vinylic C-H activation is reported. Exploratory studies showed that 5-alkylation of as-prepared cyclopentenones could be realized smoothly by the treatment of a variety of alkyl halides with a Na2CO3/MeOH solution. Excess formaldehyde and malonate led to a multicomponent reaction that afforded the multisubstituted cyclopentenones through a Michael addition.

Nano-K2CO3: Preparation, characterization and evaluation of reactive activities

Li, Jun-Zhang,Fan, Shi-Ming,Sun, Xuan-Fei,Liu, Shouxin

, p. 1865 - 1869 (2016/01/20)

A novel base, nano-K2CO3, was easily prepared by ultrafine wet milling. The surface properties and the reactive activities of nano-K2CO3 were characterized. It was found that such a base showed higher basicity than normal K2CO3 and could replace sodium (or potassium) alkoxide to carry out monoalkylation and oximation of active methylene compounds. The nano-K2CO3 could be regenarated and reused 10 times without loss of its reactive activity.

Copper(II) triflate catalyzed amination and aziridination of 2-Alkyl substituted 1,3-dicarbonyl compounds

Ton, Thi My Uyen,Tejo, Ciputra,Tiong, Diane Ling Ying,Chan, Philip Wai Hong

experimental part, p. 7344 - 7350 (2012/06/16)

A method to prepare α-acyl-β-amino acid and 2,2-diacyl aziridine derivatives efficiently from Cu(OTf)2 + 1,10-phenanthroline (1,10-phen)-catalyzed amination and aziridination of 2-alkyl substituted 1,3-dicarbonyl compounds with PhI=NTs is described. By taking advantage of the orthogonal modes of reactivity of the substrate through slight modification of the reaction conditions, a divergence in product selectivity was observed. In the presence of 1.2 equiv of the iminoiodane, amination of the allylic C-H bond of the enolic form of the substrate, formed in situ through coordination to the Lewis acidic metal catalyst, was found to selectively occur and give the β-aminated adduct. On the other hand, increasing the amount of the nitrogen source from 1.2 to 2-3 equiv was discovered to result in preferential formal aziridination of the C-C bond of the 2-alkyl substituent of the starting material and formation of the aziridine product.

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