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924-44-7

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924-44-7 Usage

Uses

Ethyl glyoxylate is widely used as an intermediate in the synthesis of pharmaceuticals (high reactivity of aldehyde function). It is used in the synthesis of a biodegradable polymer, poly(ethyl glyoxylate). It is actively involved in the Friedel-Crafts alkylation reactions with thiophenes to give the corresponding secondary alcohols.

Definition

ChEBI: The ethyl ester of glyoxylic acid.

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 2223, 1983 DOI: 10.1016/S0040-4039(00)81889-4

Check Digit Verification of cas no

The CAS Registry Mumber 924-44-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,2 and 4 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 924-44:
(5*9)+(4*2)+(3*4)+(2*4)+(1*4)=77
77 % 10 = 7
So 924-44-7 is a valid CAS Registry Number.
InChI:InChI=1/C4H6O3/c1-2-7-4(6)3-5/h3H,2H2,1H3

924-44-7SDS

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 ethyl glyoxylate

1.2 Other means of identification

Product number -
Other names ethyl 2-oxoacetate

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:924-44-7 SDS

924-44-7Synthetic route

Diethylamino-selenoxo-acetic acid ethyl ester
160594-74-1

Diethylamino-selenoxo-acetic acid ethyl ester

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 3h;100%
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

Conditions
ConditionsYield
With sodium periodate In dichloromethane; water Heating;94%
With sodium periodate In water at 0℃; for 0.25h;66%
With periodic acid In diethyl ether at 20℃; for 1h;
Ethyl diethoxyacetate
6065-82-3

Ethyl diethoxyacetate

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

Conditions
ConditionsYield
Stage #1: Ethyl diethoxyacetate; 2,2-dihydroxyacetic acid With toluene-4-sulfonic acid at 90℃; for 27h;
Stage #2: With phosphorus pentoxide at 90 - 100℃; for 2h;
90%
diethyl (2S,3S)-tartrate
13811-71-7

diethyl (2S,3S)-tartrate

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

Conditions
ConditionsYield
With periodic acid In diethyl ether; water for 1h; Inert atmosphere;82%
With periodic acid In diethyl ether at 0 - 20℃; for 3h; Inert atmosphere; Cooling with ice;80%
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

Conditions
ConditionsYield
With aluminum oxide; tetrabutylammomium bromide; oxygen; cyclohexene In acetonitrile Hg cathode, Pt anode, -1.0 V vs SCE;72%
N-(ethoxy carbonyl methoxy)-phthalimide
5251-81-0

N-(ethoxy carbonyl methoxy)-phthalimide

A

phthalimide
136918-14-4

phthalimide

B

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

Conditions
ConditionsYield
at 400℃; under 0.01 Torr; for 2.77778E-06h; Kinetics; Temperature;A 57%
B 22%
ethyl acrylate
140-88-5

ethyl acrylate

A

formaldehyd
50-00-0

formaldehyd

B

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

Conditions
ConditionsYield
With ozone at 20.84℃; under 760 Torr; Kinetics; Darkness;A 45%
B 53%
Diethyl tartrate
408332-88-7

Diethyl tartrate

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

Conditions
ConditionsYield
In water periodate oxidation;50%
With lead(IV) acetate; acetic acid at 40 - 50℃;
With periodic acid
ethyl 3-ethoxypropionate
763-69-9

ethyl 3-ethoxypropionate

A

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

B

3-oxo-propionic acid ethyl ester
34780-29-5

3-oxo-propionic acid ethyl ester

C

acetaldehyde
75-07-0

acetaldehyde

D

3-Formyloxy-propionic acid ethyl ester

3-Formyloxy-propionic acid ethyl ester

E

formic acid ethyl ester
109-94-4

formic acid ethyl ester

Conditions
ConditionsYield
With dodecane; methyl nitrite; nitrogen(II) oxide at 23.9℃; under 760 Torr; Rate constant; Product distribution; Mechanism; Irradiation;A 25%
B 4.8%
C 4.9%
D 30%
E 37%
(+/-)-diethyl tartrate
57968-71-5

(+/-)-diethyl tartrate

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

Conditions
ConditionsYield
With sodium bismuthate; phosphoric acid; water at 40℃;
With lead dioxide; acetic acid
ethyl 2-hydroxyacetate
623-50-7

ethyl 2-hydroxyacetate

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

Conditions
ConditionsYield
bei laengerem Durchleiten von Luft in der Waerme und am Licht;
hydroxy-sulfanediyldi-acetic acid diethyl ester

hydroxy-sulfanediyldi-acetic acid diethyl ester

A

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

B

ethyl 2-sulfanylacetate
623-51-8

ethyl 2-sulfanylacetate

Conditions
ConditionsYield
zerfaellt in der Waerme;
ethyl acetoacetate
141-97-9

ethyl acetoacetate

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

Conditions
ConditionsYield
bei der Ozonspaltung;
ethyl 3-oxo-3-phenylpropionate
94-02-0

ethyl 3-oxo-3-phenylpropionate

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

Conditions
ConditionsYield
bei der Ozonspaltung;
tetrachloromethane
56-23-5

tetrachloromethane

1,3-dioxo-indan-2-carboxylic acid ethyl ester
3457-77-0

1,3-dioxo-indan-2-carboxylic acid ethyl ester

A

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

B

methylammonium carbonate
15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

C

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
at -20℃; bei der Ozonspaltung;
diethyl (2R,3R)-tartrate
87-91-2

diethyl (2R,3R)-tartrate

lead(IV) tetraacetate
546-67-8

lead(IV) tetraacetate

acetic acid
64-19-7

acetic acid

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

Conditions
ConditionsYield
at 18℃; Geschwindigkeit;
dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

ethyl bromoacetate
105-36-2

ethyl bromoacetate

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

diethyl (2E)-3-methyl-2-pentenedioate
1466-21-3

diethyl (2E)-3-methyl-2-pentenedioate

ethyl acetate
141-78-6

ethyl acetate

A

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

B

ethyl acetoacetate
141-97-9

ethyl acetoacetate

Conditions
ConditionsYield
Liefert bei der Ozonisierung ein oeliges Ozonid,das bei mehrstuendiger Einw. von Wasser;
4-methyl-3-phenyl-pentenedioic acid diethyl ester
872269-25-5

4-methyl-3-phenyl-pentenedioic acid diethyl ester

ethyl acetate
141-78-6

ethyl acetate

A

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

B

oxalic acid
144-62-7

oxalic acid

C

propionic acid
802294-64-0

propionic acid

D

ethyl 2-benzoylpropionate
10488-87-6

ethyl 2-benzoylpropionate

Conditions
ConditionsYield
at 0℃; beim Ozonisieren und Zersetzen des Ozonids mit Wasser; substance of bp 5-6: 165-166 degree;
ethyl bromoacetate
105-36-2

ethyl bromoacetate

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

Conditions
ConditionsYield
With dimethyl sulfoxide at 70℃;
With trimethylamine-N-oxide In chloroform
oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

Conditions
ConditionsYield
With sodium amalgam; ethanol
durch elektrolytische Reduktion;
ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

Conditions
ConditionsYield
With potassium fluoride
diethyl oxaloacetate
108-56-5

diethyl oxaloacetate

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

Conditions
ConditionsYield
bei der Ozonspaltung;
3,4-dimethyl-pentenedioic acid diethyl ester

3,4-dimethyl-pentenedioic acid diethyl ester

methyl iodide
74-88-4

methyl iodide

A

2-acetylpropanoic acid ethyl ester
609-14-3

2-acetylpropanoic acid ethyl ester

B

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

C

ethyl acetoacetate
141-97-9

ethyl acetoacetate

Conditions
ConditionsYield
Das Kaliumverbindung reagiert,bei der Ozonspaltung des erhaltenen Produkts;
ethyl 2-ethoxyglycolate
49653-17-0

ethyl 2-ethoxyglycolate

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

Conditions
ConditionsYield
Heating;
acid;
3-tert-Butyl-4,4-dimethyl-penten-(2)-saeure-ethylester
83720-78-9

3-tert-Butyl-4,4-dimethyl-penten-(2)-saeure-ethylester

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

Conditions
ConditionsYield
With ozone In ethyl acetate
Propionic acid (1R,2R)-1,2-dihydroxy-2-propionyloxy-ethyl ester

Propionic acid (1R,2R)-1,2-dihydroxy-2-propionyloxy-ethyl ester

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

Conditions
ConditionsYield
With sodium bismuthate; phosphoric acid
Diethyl maleate
141-05-9

Diethyl maleate

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

Conditions
ConditionsYield
With dimethylsulfide; ozone 1.) CH2Cl2, -78 deg C, 2.25 h, 2.) 25 deg C, overnight; Yield given. Multistep reaction;
With potassium permanganate at 40℃;47.9 % Chromat.
With ozone In dichloromethane at -78℃;
ethyl (dimethylsulfuranylidene)acetate
7380-81-6

ethyl (dimethylsulfuranylidene)acetate

A

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

B

dimethylsulfone
67-71-0

dimethylsulfone

C

ethyl 2-(dimethyl(oxo)-λ6-sulfaneylidene)acetate
19956-89-9

ethyl 2-(dimethyl(oxo)-λ6-sulfaneylidene)acetate

D

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
With triphenyl phosphite ozonide In dichloromethane 1.) -78 deg C to -60 deg C, 3 h, 2.) -60 deg C to 20 deg C;
acetaldehyde
75-07-0

acetaldehyde

3-Methyl-5-(toluene-4-sulfonyl)-4-p-tolyl-1,5-dihydro-pyrrol-2-one
152656-88-7

3-Methyl-5-(toluene-4-sulfonyl)-4-p-tolyl-1,5-dihydro-pyrrol-2-one

A

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

B

(Z)-5-ethylidene-1,5-dihydro-3-methyl-4-(p-tolyl)-2H-pyrrol-2-one

(Z)-5-ethylidene-1,5-dihydro-3-methyl-4-(p-tolyl)-2H-pyrrol-2-one

Conditions
ConditionsYield
With tributylphosphine; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran Ambient temperature; Yield given. Yields of byproduct given;
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

ethyl 2-(hydroxyimino)acetate
31767-14-3, 31767-15-4, 37858-07-4

ethyl 2-(hydroxyimino)acetate

Conditions
ConditionsYield
With hydroxylamine hydrochloride; triethylamine In water; toluene; acetonitrile at 20℃; for 1h;100%
Stage #1: glyoxylic acid ethyl ester With hydroxylamine hydrochloride In water; toluene; acetonitrile at 20℃; for 0.0833333h;
Stage #2: With triethylamine In water; toluene; acetonitrile at 20℃;
97%
With hydroxylamine hydrochloride; triethylamine In water; toluene; acetonitrile at 20℃; for 1.5h; Inert atmosphere;95%
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

(S)-1-phenyl-ethylamine
2627-86-3

(S)-1-phenyl-ethylamine

ethyl <(S)-1-phenylethyl>iminoethanoate
37662-06-9

ethyl <(S)-1-phenylethyl>iminoethanoate

Conditions
ConditionsYield
In toluene for 0.333333h; Heating;100%
In toluene at 110℃; under 760.051 Torr;100%
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

(R)-1-phenyl-ethyl-amine
3886-69-9

(R)-1-phenyl-ethyl-amine

((R)-1-phenyl-ethylimino)-acetic acid ethyl ester
37662-05-8

((R)-1-phenyl-ethylimino)-acetic acid ethyl ester

Conditions
ConditionsYield
In toluene for 0.333333h; Heating;100%
In toluene Heating;100%
In toluene at 15 - 25℃;95%
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

(+/-)-ethyl 2-cyano-2-hydroxyacetate
137622-41-4

(+/-)-ethyl 2-cyano-2-hydroxyacetate

Conditions
ConditionsYield
With sodium acetate buffer In ethanol; water for 0.166667h; Ambient temperature;100%
With sodium acetate; acetic acid In ethanol for 0.166667h; Ambient temperature;1.29 g
Stage #1: glyoxylic acid ethyl ester With copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 0.25h;
Stage #2: trimethylsilyl cyanide In dichloromethane at 20℃; for 18h;
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

5-methylhex-4-en-1-amine
115610-15-6

5-methylhex-4-en-1-amine

Ethyl (5-methyl-4-hexenylimino)acetate
125718-51-6

Ethyl (5-methyl-4-hexenylimino)acetate

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane at 0℃;100%
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

p-toluidine
106-49-0

p-toluidine

ethyl 2-(4-methylphenylimino)acetate
121641-60-9

ethyl 2-(4-methylphenylimino)acetate

Conditions
ConditionsYield
With sodium sulfate In dichloromethane for 0.5h;100%
With magnesium sulfate In toluene at 25℃; for 0.5h;100%
for 1h; Green chemistry;75%
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

4-chloro-aniline
106-47-8

4-chloro-aniline

(4-chloro-phenylimino)-acetic acid ethyl ester
121641-61-0

(4-chloro-phenylimino)-acetic acid ethyl ester

Conditions
ConditionsYield
With magnesium sulfate In toluene at 25℃; for 0.5h;100%
With sodium sulfate In toluene at 110℃; for 0.5h;
With sodium sulfate In toluene
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

4-methoxy-aniline
104-94-9

4-methoxy-aniline

ethyl (4-methoxyphenylimino)acetate
124156-21-4

ethyl (4-methoxyphenylimino)acetate

Conditions
ConditionsYield
With sodium sulfate In dichloromethane for 0.5h;100%
With magnesium sulfate In toluene at 25℃; for 0.5h;100%
With magnesium sulfate In dichloromethane; toluene for 3h; Inert atmosphere; Reflux;100%
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

4-methoxy-aniline
104-94-9

4-methoxy-aniline

ethyl (E)-2-(p-methoxyphenylimino)acetate
115276-75-0, 124156-21-4, 120419-96-7

ethyl (E)-2-(p-methoxyphenylimino)acetate

Conditions
ConditionsYield
With silica gel In dichloromethane; toluene for 20h; sonication;100%
Stage #1: glyoxylic acid ethyl ester; 4-methoxy-aniline In dichloromethane; toluene at 20℃; for 2h; Schlenk technique; Inert atmosphere;
Stage #2: In toluene for 3h; Schlenk technique; Inert atmosphere; Molecular sieve;
100%
In toluene for 22h; Inert atmosphere; Molecular sieve;100%
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

aniline
62-53-3

aniline

ethyl 2-(phenylimino)acetate
121642-09-9, 84484-31-1

ethyl 2-(phenylimino)acetate

Conditions
ConditionsYield
With magnesium sulfate In toluene at 25℃; for 0.5h;100%
With magnesium sulfate In toluene at 20℃; for 1.5h; Inert atmosphere;99%
With sodium sulfate In toluene for 0.5h; Ambient temperature;
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

(R)-1-phenyl-ethyl-amine
3886-69-9

(R)-1-phenyl-ethyl-amine

<(R)-(1-phenylethyl)imino>acetic acid ethyl ester
851389-20-3

<(R)-(1-phenylethyl)imino>acetic acid ethyl ester

Conditions
ConditionsYield
In toluene for 1.5h; Heating;100%
With molecular sieve In dichloromethane at 0℃;
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

5-chloro-2-iodoaniline
6828-35-9

5-chloro-2-iodoaniline

ethyl-(5-chloro-2-iodophenylimino)acetate

ethyl-(5-chloro-2-iodophenylimino)acetate

Conditions
ConditionsYield
With magnesium sulfate In toluene at 120℃; for 2h; Condensation;100%
In toluene Heating;
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

(+/-)-2-(2-aminopropyl)-2-methyl-1,3-dioxane
246042-05-7

(+/-)-2-(2-aminopropyl)-2-methyl-1,3-dioxane

[(E)-1-Methyl-2-(2-methyl-[1,3]dioxan-2-yl)-ethylimino]-acetic acid ethyl ester

[(E)-1-Methyl-2-(2-methyl-[1,3]dioxan-2-yl)-ethylimino]-acetic acid ethyl ester

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane Condensation; Heating;100%
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

rac-methylbenzylamine
618-36-0

rac-methylbenzylamine

N-[(1-methyl)phenylmethyl]imino-acetic acid ethyl ester
35823-28-0

N-[(1-methyl)phenylmethyl]imino-acetic acid ethyl ester

Conditions
ConditionsYield
In toluene Heating;100%
With magnesium sulfate In dichloromethane
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

4-fluoroaniline
371-40-4

4-fluoroaniline

(4-fluoro-phenylimino)-acetic acid ethyl ester
1001011-80-8

(4-fluoro-phenylimino)-acetic acid ethyl ester

Conditions
ConditionsYield
With magnesium sulfate In toluene at 25℃; for 0.5h;100%
In toluene at 3 - 18℃;40%
In dichloromethane; toluene for 2h; Heating;
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

isopropenylbenzene
98-83-9

isopropenylbenzene

(R)-(-)-2-hydroxy-4-phenyl-pent-4-enoic acid ethyl ester
208242-81-3

(R)-(-)-2-hydroxy-4-phenyl-pent-4-enoic acid ethyl ester

Conditions
ConditionsYield
With 4 A molecular sieve; immobilized chiral bis(binaphthoxide)-based Ti In diethyl ether; toluene at 20℃; for 72h;100%
Stage #1: With titanium(IV) isopropylate; (R)-1,1'-Bi-2-naphthol In toluene at 20℃; for 0.5h; Inert atmosphere;
Stage #2: With 3,3',5,5'-tetramethyl-2,2',6,6'-tetrahydroxy biphenyl In diethyl ether; toluene at 60℃; for 0.5h; Inert atmosphere;
Stage #3: glyoxylic acid ethyl ester; isopropenylbenzene In diethyl ether; toluene at 0℃; for 30h; Inert atmosphere;
99%
With titanium(IV) isopropylate; (R)-6,6'-diiodo-2,2'-dihydroxy-1,1'-binaphthalene In dichloromethane; toluene at 0℃; for 48h;98%
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

(1-p-tolylvinyl)carbamic acid benzyl ester
697301-74-9

(1-p-tolylvinyl)carbamic acid benzyl ester

(S)-4-[(Z)-Benzyloxycarbonylimino]-2-hydroxy-4-p-tolyl-butyric acid ethyl ester

(S)-4-[(Z)-Benzyloxycarbonylimino]-2-hydroxy-4-p-tolyl-butyric acid ethyl ester

Conditions
ConditionsYield
With (1R,2R)-N,N'-di(4'-bromobenzylidene)-1,2-diaminocyclohexane In dichloromethane at 0℃; for 1h;100%
tetrakis(acetonitrile)copper(I) perchlorate; (1R,2R)-N,N'-bis(5-bromobenzylidene)diiminocyclohexane In dichloromethane at 0℃; for 1h; Product distribution / selectivity;100%
2-azetidinone
930-21-2

2-azetidinone

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

ethyl 2-hydroxy-2-(2-oxo-azetidin-1-yl)acetate
701910-95-4

ethyl 2-hydroxy-2-(2-oxo-azetidin-1-yl)acetate

Conditions
ConditionsYield
In toluene for 3h; Heating;100%
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

ethyl 2-cinnamamido-2-hydroxyacetate
863036-86-6

ethyl 2-cinnamamido-2-hydroxyacetate

Conditions
ConditionsYield
In tetrahydrofuran; toluene at 80℃; Inert atmosphere;100%
In tetrahydrofuran at 20℃;65%
In toluene Inert atmosphere; Reflux;
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

2,4-Xylidine
95-68-1

2,4-Xylidine

ethyl 2-(2,4-dimethylphenylimino)acetate
868374-14-5

ethyl 2-(2,4-dimethylphenylimino)acetate

Conditions
ConditionsYield
With sodium sulfate In dichloromethane for 0.5h;100%
In methanol; toluene at 70℃; for 7h;47%
With magnesium sulfate In toluene; acetonitrile for 1h; Inert atmosphere;
6-methylnicotinic acid
3222-47-7

6-methylnicotinic acid

glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

6-[(1E)-3-ethoxy-3-oxoprop-1-en-1-yl]nicotinic acid
1018673-98-7

6-[(1E)-3-ethoxy-3-oxoprop-1-en-1-yl]nicotinic acid

Conditions
ConditionsYield
With acetic anhydride In toluene at 20 - 130℃; for 20h;100%
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

1-methoxy-3-<(trimethylsilyl)oxy>01,3-butadiene
59414-23-2

1-methoxy-3-<(trimethylsilyl)oxy>01,3-butadiene

4-oxo-3,4-dihydro-2H-pyran-2-carboxylic acid ethyl ester
287193-06-0

4-oxo-3,4-dihydro-2H-pyran-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
With zinc(II) chloride In tetrahydrofuran; toluene at 20℃; for 0.5h;100%
With zinc(II) chloride In tetrahydrofuran; benzene at 20℃; for 72h;75%
zinc(II) chloride In tetrahydrofuran; benzene at 20℃; for 72h;75%
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

(1-phenylvinyl)carbamic acid benzyl ester
697301-71-6

(1-phenylvinyl)carbamic acid benzyl ester

(S)-4-[(Z)-Benzyloxycarbonylimino]-2-hydroxy-4-phenyl-butyric acid ethyl ester

(S)-4-[(Z)-Benzyloxycarbonylimino]-2-hydroxy-4-phenyl-butyric acid ethyl ester

Conditions
ConditionsYield
C22H26N2; tetrakis(acetonitrile)copper(I) perchlorate In dichloromethane at 0℃; for 1h; Product distribution / selectivity;100%
tetrakis(acetonitrile)copper(I) perchlorate; N,N'-bis-(4-methyl-benzylidene)-cyclohexane-1,2-diamine In dichloromethane at 0℃; for 1h; Product distribution / selectivity;98%
C22H26N2; tetrakis(acetonitrile)copper(I) perchlorate In dichloromethane at 0℃; for 1h; Product distribution / selectivity;97%
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

N-amino-(4-nitrophenyl)carboxamide
636-97-5

N-amino-(4-nitrophenyl)carboxamide

ethyl (2E)-[(4-nitrobenzoyl)hydrazono]ethanoate
1062747-45-8

ethyl (2E)-[(4-nitrobenzoyl)hydrazono]ethanoate

Conditions
ConditionsYield
In ethanol; toluene at 80℃; Inert atmosphere;100%
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

ethyl 2-(benzo[1,3]dioxol-5-ylimino)acetate

ethyl 2-(benzo[1,3]dioxol-5-ylimino)acetate

Conditions
ConditionsYield
With magnesium sulfate In toluene at 25℃; for 0.5h;100%
In toluene at 23℃; for 1h; Molecular sieve; Inert atmosphere;
In dichloromethane for 0.333333h; Inert atmosphere;
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

(E)-3-(3-(benzyloxy)-4-methoxyphenyl)acrylamide
1198115-94-4

(E)-3-(3-(benzyloxy)-4-methoxyphenyl)acrylamide

(E)-ethyl 2-(3-(3-(benzyloxy)-4-methoxyphenyl)acrylamido)-2-hydroxyacetate
1198115-95-5

(E)-ethyl 2-(3-(3-(benzyloxy)-4-methoxyphenyl)acrylamido)-2-hydroxyacetate

Conditions
ConditionsYield
In tetrahydrofuran; toluene at 80℃; Inert atmosphere;100%
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

diethyl carbamoylmethylphosphonate
5464-68-6

diethyl carbamoylmethylphosphonate

ethyl 2-(2-(diethoxyphosphoryl)acetamido)-2-hydroxyacetate
1198115-97-7

ethyl 2-(2-(diethoxyphosphoryl)acetamido)-2-hydroxyacetate

Conditions
ConditionsYield
In tetrahydrofuran; toluene at 80℃; Inert atmosphere;100%
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

Chloroacetamide
79-07-2

Chloroacetamide

ethyl 2-(2-chloroacetamido)-2-hydroxyacetate
1198115-96-6

ethyl 2-(2-chloroacetamido)-2-hydroxyacetate

Conditions
ConditionsYield
In tetrahydrofuran; toluene at 80℃; Inert atmosphere;100%
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

2,2-dimethylpropionamide
754-10-9

2,2-dimethylpropionamide

methyl 2-hydroxy-2-pivalamidoacetate
1242425-51-9

methyl 2-hydroxy-2-pivalamidoacetate

Conditions
ConditionsYield
In toluene Inert atmosphere; Radiolysis;100%

924-44-7Relevant articles and documents

Friedel-Crafts reactions in water of carbonyl compounds with heteroaromatic compounds

Zhuang, Wei,Jorgensen, Karl Anker

, p. 1336 - 1337 (2002)

The development of Friedel-Crafts reaction in H2O of carbonyl compounds is presented; a series of different heteroaromatic compounds react with ethyl glyoxylate to give the Friedel-Crafts addition adducts in good yields in various H2O solutions.

Asymmetric Catalytic Aza-Diels–Alder/Ring-Closing Cascade Reaction Forming Bicyclic Azaheterocycles by Trienamine Catalysis

Li, Yang,Barl?se, Casper,J?rgensen, Julie,Carlsen, Bj?rn Drei?,J?rgensen, Karl Anker

supporting information, p. 38 - 41 (2017/01/09)

An asymmetric catalytic aza-Diels–Alder/ring-closing cascade reaction between acylhydrazones and in situ formed trienamines is presented. The reaction proceeds through a formal aza-Diels–Alder cycloaddition, followed by a ring-closing reaction forming the hemiaminal ring leading to chiral bicyclic azaheterocycles in moderate to good yield (up to 71 %), good enantio- (up to 92 % ee) and diastereoselectivity (up to >20:1 d.r.). Furthermore, transformations are presented to show the potential application of the formed product.

Synthesis, structure and antiproliferative activity of chiral polyamines based on a 2-azanorbornane skeleton

Kamińska, Karolina,Wojaczyńska, El?bieta,Wietrzyk, Joanna,Turlej, Eliza,B?a?ejczyk, Agnieszka,Wieczorek, Robert

, p. 753 - 758 (2016/07/29)

A series of enantiopure 2-azanorbornane-based amines were prepared via a stereoselective aza-Diels–Alder reaction and further modifications of the obtained cycloadduct. In particular, derivatives containing two bicyclic moieties linked by [Formula presented] fragments were synthesized. Two dimeric derivatives exhibited a significant antiproliferative activity against selected cell lines, comparable to cisplatin in certain cases.

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