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Ethyl diazoacetate
Cas No: 623-73-4
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
Ethyl Diazoacetate
Cas No: 623-73-4
USD $ 150.0-150.0 / Kilogram 1 Kilogram 10 Metric Ton/Month Hebei yanxi chemical co.,LTD. Contact Supplier
Amadis Chemical offer CAS#623-73-4;CAT#A833745
Cas No: 623-73-4
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Diazoacetic acid ethyl ester
Cas No: 623-73-4
No Data No Data No Data Chemwill Asia Co., Ltd. Contact Supplier
CAS NO.623-73-4 Acetic acid, 2-diazo-,ethyl ester
Cas No: 623-73-4
USD $ 50.0-100.0 / Gram 1 Gram 10000 Metric Ton/Month Wuhan Monad Medicine Tech Co.,LTD Contact Supplier
Acetic acid, 2-diazo-,ethyl ester
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Ethyl diazoacetate
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USD $ 1.0-1.0 / Kilogram 1 Kilogram 1000 Kilogram/Month Career Henan Chemical Co Contact Supplier
Ethyl diazoacetate
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ISO 9001 National Research Platform CAS No. 623-73-4
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Acetic acid, 2-diazo-,ethyl ester
Cas No: 623-73-4
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623-73-4 Usage

Purification Methods

It is a very volatile yellow oil with a strong pungent odour. EXPLOSIVE [distillation even under reduced pressure is dangerous and may result in an explosion — TAKE ALL THE NECESSARY PRECAUTIONS IF DISTILLATION IS TO BE CARRIED OUT]. It explodes in contact with conc H2SO4-trace acid causes rapid decomposition. It is slightly soluble in H2O, but is miscible with EtOH, *C6H6, pet ether and Et2O. To purify, dissolve it in Et2O [using CH2Cl2 instead of Et2O, protects the ester from acid], wash it with 10% aqueous Na2CO3, dry (MgSO4), filter and repeat as many times as possible until the Et2O layer loses its yellow colour, then remove the solvent below 20o (vacuum). Note that prolonged heating may lead to rapid decomposition and low yields. It can also be purified by steam distillation under reduced pressure but with considerable loss in yield. Place the residual oil in a brown bottle, keep below 10o, and use as soon as possible without distilling. For preparing esters usually the ethereal solution is used directly without purification. [Womack & Nelson Org Synth Coll Vol III 392 1955, UV: Miller & White J Am Chem Soc 79 5974 1957, Fieser 1 367 1967, Beilstein 3 IV 1495.]

Uses

Reagent for ruthenium-catalyzed asymmetric cyclopropanation of alkenes.1
InChI:InChI=1/C4H6N2O2/c1-2-8-4(7)3-6-5/h3H,2H2,1H3/b4-3+

623-73-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethyl diazoacetate

1.2 Other means of identification

Product number -
Other names (E)-2-diazonio-1-ethoxyethenolate

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:623-73-4 SDS

623-73-4Synthetic route

glycine ethyl ester hydrochloride
623-33-6

glycine ethyl ester hydrochloride

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

Conditions
ConditionsYield
With hydrogenchloride; sodium sulfite; sodium nitrite In dichloromethane; water at 3℃; for 4h; pH=4.3; Solvent; Temperature; Reagent/catalyst; pH-value; Large scale;98.4%
With citric acid; sodium hydroxide; sodium nitrite In o-xylene; para-xylene; ethylbenzene; water; m-xylene at 10℃; for 24h;94.4%
Stage #1: glycine ethyl ester hydrochloride With sodium nitrite In dichloromethane; water for 0.5h; Schlenk technique; Cooling with ice;
Stage #2: With sulfuric acid In dichloromethane; water at -10℃; for 0.333333h; Schlenk technique;
87%
(Z)-3-pyrrolidin-1-yl-but-2-enoic acid ethyl ester
70526-06-6

(Z)-3-pyrrolidin-1-yl-but-2-enoic acid ethyl ester

perfluorobutanesulfonyl azide
65245-26-3

perfluorobutanesulfonyl azide

A

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

B

N'-1,1,2,2-Tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)ethanesulfonyl-N,N-cyclo(ethyleneoxyethylene)acetamidine

N'-1,1,2,2-Tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)ethanesulfonyl-N,N-cyclo(ethyleneoxyethylene)acetamidine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.5h;A n/a
B 96%
(Z)-3-pyrrolidin-1-yl-but-2-enoic acid ethyl ester
70526-06-6

(Z)-3-pyrrolidin-1-yl-but-2-enoic acid ethyl ester

1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoro-2-iodoethoxy)-ethanesulfonyl azide
144951-87-1

1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoro-2-iodoethoxy)-ethanesulfonyl azide

A

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

B

N-perfluorobutanesulfonyl-1-(pyrrolidin-1-yl)ethylidenamine

N-perfluorobutanesulfonyl-1-(pyrrolidin-1-yl)ethylidenamine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.5h;A n/a
B 85%
β-morpholinoethylcrotonate
66003-96-1

β-morpholinoethylcrotonate

1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)-ethanesulfonyl azide
144951-88-2

1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)-ethanesulfonyl azide

A

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

B

N'-Perfluorobutanesulfonyl-N,N-cyclo(ethyleneoxyethylene)acetamidine

N'-Perfluorobutanesulfonyl-N,N-cyclo(ethyleneoxyethylene)acetamidine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.5h;A n/a
B 85%
1,2,3,4-tetrachloro-5,6-dinitrobenzene
781-15-7

1,2,3,4-tetrachloro-5,6-dinitrobenzene

GlyOEt*HCl
459-73-4

GlyOEt*HCl

A

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

B

N-(ethylacetoxy)-2,3,4,5-tetrachloro-6-nitroaniline
121904-46-9

N-(ethylacetoxy)-2,3,4,5-tetrachloro-6-nitroaniline

Conditions
ConditionsYield
In toluene for 1h; Heating;A 17%
B 83%
perfluorobutanesulfonyl azide
65245-26-3

perfluorobutanesulfonyl azide

β-morpholinoethylcrotonate
66003-96-1

β-morpholinoethylcrotonate

A

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

B

N'-1,1,2,2-Tetrafluoro-2-(1,1,2,2-tetrafluoro-2-iodoethoxy)ethanesulfonyl-N,N-cyclobutylacetamidine

N'-1,1,2,2-Tetrafluoro-2-(1,1,2,2-tetrafluoro-2-iodoethoxy)ethanesulfonyl-N,N-cyclobutylacetamidine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.5h;A n/a
B 81%
β-morpholinoethylcrotonate
66003-96-1

β-morpholinoethylcrotonate

1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoro-2-iodoethoxy)-ethanesulfonyl azide
144951-87-1

1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoro-2-iodoethoxy)-ethanesulfonyl azide

A

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

B

N'-1,1,2,2-Tetrafluoro-2-(1,1,2,2-tetrafluoro-2-iodoethoxy)ethanesulfonyl-N,N-cyclo(ethyleneoxyethylene)acetamidine

N'-1,1,2,2-Tetrafluoro-2-(1,1,2,2-tetrafluoro-2-iodoethoxy)ethanesulfonyl-N,N-cyclo(ethyleneoxyethylene)acetamidine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.5h;A n/a
B 81%
(Z)-3-pyrrolidin-1-yl-but-2-enoic acid ethyl ester
70526-06-6

(Z)-3-pyrrolidin-1-yl-but-2-enoic acid ethyl ester

1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)-ethanesulfonyl azide
144951-88-2

1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)-ethanesulfonyl azide

A

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

B

N'-1,1,2,2-Tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)ethanesulfonyl-N,N-cyclobutylacetamidine

N'-1,1,2,2-Tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)ethanesulfonyl-N,N-cyclobutylacetamidine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.5h;A n/a
B 80%
1-(p-nitrophenyl)-3-(ethoxycarbonylmethyl)triazene
10271-27-9

1-(p-nitrophenyl)-3-(ethoxycarbonylmethyl)triazene

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

Conditions
ConditionsYield
With acetic acid In dichloromethane; water66%
In chloroform Ambient temperature;
2-aminoacetimidate ethyl ester

2-aminoacetimidate ethyl ester

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

Conditions
ConditionsYield
With cis-nitrous acid
With cis-nitrous acid
ethyl 2-hydrazinylacetate
637-80-9

ethyl 2-hydrazinylacetate

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

Conditions
ConditionsYield
With cis-nitrous acid
With cis-nitrous acid
(N-nitroso-hydrazino)-acetic acid ethyl ester
861570-78-7

(N-nitroso-hydrazino)-acetic acid ethyl ester

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

Conditions
ConditionsYield
With cis-nitrous acid
5-phenyl-[1,2,3]oxadiazole-4-carboxylic acid ethyl ester
60474-28-4

5-phenyl-[1,2,3]oxadiazole-4-carboxylic acid ethyl ester

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

A

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

B

benzoic acid
65-85-0

benzoic acid

ethyl 2-diazo-3-oxo-3-phenylpropanoate
28383-65-5

ethyl 2-diazo-3-oxo-3-phenylpropanoate

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

A

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

B

benzoic acid
65-85-0

benzoic acid

(triphenylphosphoranylidene-hydrazono)-acetic acid ethyl ester
22610-15-7

(triphenylphosphoranylidene-hydrazono)-acetic acid ethyl ester

A

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

B

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
at 140 - 160℃;
GlyOEt*HCl
459-73-4

GlyOEt*HCl

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

Conditions
ConditionsYield
With cis-nitrous acid
With cis-nitrous acid
With isopentyl nitrite var. reag.: NaNO2;
pyrrolidine
123-75-1

pyrrolidine

mononitrosated DL-benzoylphenylalanylglycine ethyl ester
95205-17-7

mononitrosated DL-benzoylphenylalanylglycine ethyl ester

A

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

B

N-(1-oxo-3-phenyl-1-(pyrrolidin-1-yl)propan-2-yl)benzamide
95205-15-5

N-(1-oxo-3-phenyl-1-(pyrrolidin-1-yl)propan-2-yl)benzamide

Conditions
ConditionsYield
In dichloromethane for 0.0833333h;
pyrrolidine
123-75-1

pyrrolidine

dinitrosated DL-benzoylphenylalanylglycylglycine ethyl ester
95205-22-4

dinitrosated DL-benzoylphenylalanylglycylglycine ethyl ester

A

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

B

α-diazo-N,N-tetramethyleneacetamide
95205-14-4

α-diazo-N,N-tetramethyleneacetamide

C

N-(1-oxo-3-phenyl-1-(pyrrolidin-1-yl)propan-2-yl)benzamide
95205-15-5

N-(1-oxo-3-phenyl-1-(pyrrolidin-1-yl)propan-2-yl)benzamide

Conditions
ConditionsYield
In dichloromethane for 0.0833333h;
ethyl (E,Z)-6-azido-3-butylhexa-2,4-dienoate
80288-29-5

ethyl (E,Z)-6-azido-3-butylhexa-2,4-dienoate

A

2-butyl-1H-pyrrole
1551-10-6

2-butyl-1H-pyrrole

B

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

Conditions
ConditionsYield
In benzene at 70℃; for 1.5h;
ethyl (E,Z)-6-azido-3-butylhexa-2,4-dienoate
80288-29-5

ethyl (E,Z)-6-azido-3-butylhexa-2,4-dienoate

A

2-butyl-1H-pyrrole
1551-10-6

2-butyl-1H-pyrrole

B

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

(3R,3aS)-3a-Butyl-3a,6-dihydro-3H-pyrrolo[1,2-c][1,2,3]triazole-3-carboxylic acid ethyl ester

(3R,3aS)-3a-Butyl-3a,6-dihydro-3H-pyrrolo[1,2-c][1,2,3]triazole-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
In benzene at 78℃; for 0.666667h; Title compound not separated from byproducts;
ethyl N-methoxycarbonyl-N-nitrosoglycinate
95204-47-0

ethyl N-methoxycarbonyl-N-nitrosoglycinate

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

Conditions
ConditionsYield
With pyrrolidine In dichloromethane for 0.0833333h; Ambient temperature;
mononitrosated DL-benzoylphenylalanylglycine ethyl ester
95205-17-7

mononitrosated DL-benzoylphenylalanylglycine ethyl ester

A

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

B

N-(1-oxo-3-phenyl-1-(pyrrolidin-1-yl)propan-2-yl)benzamide
95205-15-5

N-(1-oxo-3-phenyl-1-(pyrrolidin-1-yl)propan-2-yl)benzamide

Conditions
ConditionsYield
With pyrrolidine In dichloromethane for 0.0833333h;
dinitrosated DL-benzoylphenylalanylglycylglycine ethyl ester
95205-22-4

dinitrosated DL-benzoylphenylalanylglycylglycine ethyl ester

A

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

B

α-diazo-N,N-tetramethyleneacetamide
95205-14-4

α-diazo-N,N-tetramethyleneacetamide

C

N-(1-oxo-3-phenyl-1-(pyrrolidin-1-yl)propan-2-yl)benzamide
95205-15-5

N-(1-oxo-3-phenyl-1-(pyrrolidin-1-yl)propan-2-yl)benzamide

Conditions
ConditionsYield
With pyrrolidine In dichloromethane for 0.0833333h;
2,2-Diethoxy-1-ethendiazonium-hexachloroantimonat

2,2-Diethoxy-1-ethendiazonium-hexachloroantimonat

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

Conditions
ConditionsYield
With water In acetonitrile at 0℃;
C10H17N2O5P

C10H17N2O5P

A

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

B

ethriol phosphite
824-11-3

ethriol phosphite

Conditions
ConditionsYield
at 45℃; Rate constant;
sodium 3-ethoxy-3-oxoprop-1-en-1-olate

sodium 3-ethoxy-3-oxoprop-1-en-1-olate

A

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

B

ethyl 2-diazo-3-oxo-propanoate
14762-48-2

ethyl 2-diazo-3-oxo-propanoate

Conditions
ConditionsYield
With 2-azido-1-ethylpyridin-1-ium tetrafluoroborate; acetic acid In methanol; water for 2.5h; Ambient temperature; Yield given. Yields of byproduct given;
3-oxo-propionic acid ethyl ester
34780-29-5

3-oxo-propionic acid ethyl ester

aniline
62-53-3

aniline

A

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

B

ethyl 2-diazo-3-oxo-propanoate
14762-48-2

ethyl 2-diazo-3-oxo-propanoate

Conditions
ConditionsYield
With 2-azido-1-ethylpyridinium fluoroborate; sodium acetate Yield given. Yields of byproduct given;
glycocoll ester hydrochloride

glycocoll ester hydrochloride

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

Conditions
ConditionsYield
With sodium nitrite Reaktion ueber mehrere Stufen;
With sulfuric acid; sodium nitrite
With water; sodium acetate; sodium nitrite
N-nitroso-N-acetyl-glycine ethyl ester

N-nitroso-N-acetyl-glycine ethyl ester

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

Conditions
ConditionsYield
With barium dihydroxide; diethyl ether; barium(II) oxide at -10℃;
Conditions
ConditionsYield
With (5,10,15,20-tetra-p-tolylporpyrinato)iron(II); benzaldehyde In toluene at 20℃;100%
2 In toluene at 100℃;96%
dirhodium tetraacetate Ambient temperature;95%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

1,1-Diphenylethylene
530-48-3

1,1-Diphenylethylene

ethyl 2,2-diphenylcyclopropane-1-carboxylate
67428-04-0, 105561-41-9, 37555-46-7

ethyl 2,2-diphenylcyclopropane-1-carboxylate

Conditions
ConditionsYield
With μ-carbido-bis[2,3,9,10,16,17,23,24-octa-n-butoxyphthalocyaninatoruthenium(IV)] In dichloromethane; toluene at 90℃; for 6h; Inert atmosphere;100%
With μ-oxo-diiron octapropylporphyrazine In toluene at 70℃; for 2h; Inert atmosphere;100%
cobalt(II) 5,10,15,20-tetraphenylporphyrin In dichloromethane for 7h; Heating;99%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

ethanol
64-17-5

ethanol

ethyl 2-ethoxyethanoate
817-95-8

ethyl 2-ethoxyethanoate

Conditions
ConditionsYield
dirhodium tetraacetate In dichloromethane at 20℃; for 0.0833333h;100%
With polystyrene-linked tris(triazolyl)methane copper(I)(NCMe)][PF6] In neat (no solvent) for 3h; Inert atmosphere;98%
copper(II) bis(trifluoromethanesulfonate) at 22℃;97%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

ethyl-3-hydroxy-2-diazo-3-(4-methoxyphenyl)-propanoate
39910-24-2

ethyl-3-hydroxy-2-diazo-3-(4-methoxyphenyl)-propanoate

Conditions
ConditionsYield
With n-butyllithium; diisopropylamine; lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; Inert atmosphere;100%
With magnesium iodide etherate; triethylamine In dichloromethane at 20℃; for 0.25h;92%
With magnesium iodide etherate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.5h; Aldol Addition;92%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

benzene
71-43-2

benzene

ethyl cyclohepta-2,4,6-trienecarboxylate
27332-37-2

ethyl cyclohepta-2,4,6-trienecarboxylate

Conditions
ConditionsYield
With Ag3(μ2-(3,5-(CF3)2PyrPy))3 In dichloromethane; benzene at 25℃; for 2h; Catalytic behavior; Time; Solvent; Buchner Ring Enlargement; Darkness;100%
rhodium(II) trifluoroacetate dimer at 22℃; for 2h;98%
With C28H6Au2Cu2F24N2 In cyclohexane for 12h; Inert atmosphere;98%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

iodo-diazoacetic acid ethyl ester
14790-53-5

iodo-diazoacetic acid ethyl ester

Conditions
ConditionsYield
With N-iodo-succinimide; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.0833333h;100%
(i) Ag2O, Et2O, (ii) I2; Multistep reaction;
Stage #1: diazoacetic acid ethyl ester In dichloromethane at 0℃;
Stage #2: With N-iodo-succinimide; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.0833333h;
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

2-dimethylaminomalonic acid diethyl ester
89222-12-8

2-dimethylaminomalonic acid diethyl ester

diethyl 2-(ethoxycarbonylmethylene)malonate
13049-86-0

diethyl 2-(ethoxycarbonylmethylene)malonate

Conditions
ConditionsYield
With copper In toluene Heating;100%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

N-tert-butyloxycarbonylpiperidin-4-one
79099-07-3

N-tert-butyloxycarbonylpiperidin-4-one

5-oxo-azepane-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester
141642-82-2

5-oxo-azepane-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester

Conditions
ConditionsYield
Stage #1: N-tert-butyloxycarbonylpiperidin-4-one With boron trifluoride diethyl etherate In diethyl ether at -30 - -25℃; for 0.333333h;
Stage #2: diazoacetic acid ethyl ester In diethyl ether at -30 - 20℃;
100%
With boron trifluoride diethyl etherate In diethyl ether at -25℃; for 1h; Inert atmosphere;99%
Stage #1: diazoacetic acid ethyl ester; N-tert-butyloxycarbonylpiperidin-4-one With boron trifluoride diethyl etherate In diethyl ether at 0℃; for 2h;
Stage #2: With sodium carbonate In diethyl ether; water at 0℃;
98%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

acrylonitrile
107-13-1

acrylonitrile

5-cyano-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester
67872-78-0

5-cyano-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
In pyridine at 60℃; for 3h;100%
With 1,4-diaza-bicyclo[2.2.2]octane at 20℃; for 6h; neat (no solvent);52%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

ethyl acrylate
140-88-5

ethyl acrylate

diethyl Δ2-pyrazoline-3,5-dicarboxylate
82706-83-0

diethyl Δ2-pyrazoline-3,5-dicarboxylate

Conditions
ConditionsYield
at 22℃; for 5h;100%
In pyridine at 60℃; for 3h;99%
With water at 20℃; for 3h; Green chemistry;99%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

ethyl α-deuteriodiazoacetate
26697-95-0

ethyl α-deuteriodiazoacetate

Conditions
ConditionsYield
With deuteriated sodium hydroxide; cetyldimethylbenzylammonium chloride In dichloromethane; water-d2 for 24h;100%
With water-d2; potassium carbonate In diethyl ether for 12h;65%
With deuteriated sodium hydroxide; water-d2; cetyltrimethylammonim bromide In dichloromethane for 48h; Ambient temperature;
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

ethyl glyoxalate hydrate
64805-08-9

ethyl glyoxalate hydrate

Conditions
ConditionsYield
With 3,3-dimethyldioxirane In acetone Ambient temperature;100%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

4-O-acetyl-2,3:5,6-di-O-isopropylidene-aldehydo-D-mannose
159423-91-3

4-O-acetyl-2,3:5,6-di-O-isopropylidene-aldehydo-D-mannose

(R)-3-{(4R,5R)-5-[(R)-Acetoxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-diazo-3-hydroxy-propionic acid ethyl ester
159423-92-4

(R)-3-{(4R,5R)-5-[(R)-Acetoxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-diazo-3-hydroxy-propionic acid ethyl ester

Conditions
ConditionsYield
for 8h; Ambient temperature; in the dark;100%
With diethylzinc for 8h;98%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

diisopropylcyanamide
3085-76-5

diisopropylcyanamide

2-(diisopropylamino)-5-ethyloxazole

2-(diisopropylamino)-5-ethyloxazole

Conditions
ConditionsYield
With dirhodium tetraacetate at 80℃; for 1h; Mechanism; other cyanamides;100%
With dirhodium tetraacetate at 80℃; for 1h;100%
With dirhodium tetraacetate In benzene at 80℃; for 1h;
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

1-(trifluoromethyl)ethenyl phenyl sulfide
73194-33-9

1-(trifluoromethyl)ethenyl phenyl sulfide

ethyl 5-trifluoromethyl-pyrazole-3-carboxylate

ethyl 5-trifluoromethyl-pyrazole-3-carboxylate

Conditions
ConditionsYield
In benzene a) 20 deg C, 15 min, b) 50 deg C, 45 min, c) reflux, 16 h;100%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

1-chloro-3-hydroxypropane
627-30-5

1-chloro-3-hydroxypropane

ethyl 2-(3-chloropropoxy)acetate
143165-48-4

ethyl 2-(3-chloropropoxy)acetate

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 0 - 37℃;100%
With boron trifluoride diethyl etherate In dichloromethane for 3h;75%
boron trifluoride diethyl etherate In dichloromethane at 37℃; cooling with ice-methanol;65%
boron trifluoride diethyl etherate In chloroform for 3h; Condensation;
With trifluoroborane diethyl ether In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

N-acetyl dehydrophenylalanine methyl ester
52386-78-4

N-acetyl dehydrophenylalanine methyl ester

4-Methyl 5-ethyl 4-acetylamino-3-phenyl-Δ2-pyrazoline-4,5-dicarboxylate
141035-00-9

4-Methyl 5-ethyl 4-acetylamino-3-phenyl-Δ2-pyrazoline-4,5-dicarboxylate

Conditions
ConditionsYield
dirhodium tetraacetate In chloroform for 6h; Heating;100%
rhodium(II) acetate Cycloaddition;40%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

α-(diethoxyphosphoryl)vinyl p-tolyl sulfoxide

α-(diethoxyphosphoryl)vinyl p-tolyl sulfoxide

diethyl 5-ethoxycarbonyl-3(1H)pyrazolylphosphonate

diethyl 5-ethoxycarbonyl-3(1H)pyrazolylphosphonate

Conditions
ConditionsYield
In benzene at 20℃; for 12h; Cycloaddition; elimination;100%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

ethyl 2-acetamido-2-(ethoxycarbonyl)-4-pentenoate
14109-62-7

ethyl 2-acetamido-2-(ethoxycarbonyl)-4-pentenoate

diethyl 2-acetylamino-2-ethoxycarbonyl-4-heptenedioate

diethyl 2-acetylamino-2-ethoxycarbonyl-4-heptenedioate

Conditions
ConditionsYield
dirhodium tetraacetate In dichloromethane at 22℃;100%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

2-acetylamino-2-allyl-malonic acid dimethyl ester

2-acetylamino-2-allyl-malonic acid dimethyl ester

1-O-methyl 7-O-ethyl 2-acetylamino-2-methoxycarbonyl-4-heptenedioate

1-O-methyl 7-O-ethyl 2-acetylamino-2-methoxycarbonyl-4-heptenedioate

Conditions
ConditionsYield
dirhodium tetraacetate In dichloromethane at 22℃;100%
pyridine
110-86-1

pyridine

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

bis(N-pyridinium)-terminated poly(ethoxycarbonylmethylene) dichloride, Mn = 700, Mw/Mn = 1.81; Monomer(s): ethyl diazoacetate; pyridine

bis(N-pyridinium)-terminated poly(ethoxycarbonylmethylene) dichloride, Mn = 700, Mw/Mn = 1.81; Monomer(s): ethyl diazoacetate; pyridine

Conditions
ConditionsYield
With palladium dichloride In dichloromethane; toluene at 55℃;100%
pyridine
110-86-1

pyridine

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

bis(N-pyridinium)-terminated poly(ethoxycarbonylmethylene) dichloride, Mn = 730, Mw/Mn = 1.80; Monomer(s): ethyl diazoacetate; pyridine

bis(N-pyridinium)-terminated poly(ethoxycarbonylmethylene) dichloride, Mn = 730, Mw/Mn = 1.80; Monomer(s): ethyl diazoacetate; pyridine

Conditions
ConditionsYield
With palladium dichloride In dichloromethane; toluene at 55℃;100%
pyridine
110-86-1

pyridine

diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

bis(N-pyridinium)-terminated poly(ethoxycarbonylmethylene) dichloride; Monomer(s): ethyl diazoacetate; pyridine

bis(N-pyridinium)-terminated poly(ethoxycarbonylmethylene) dichloride; Monomer(s): ethyl diazoacetate; pyridine

Conditions
ConditionsYield
With palladium dichloride In dichloromethane; toluene at 55℃; for 18h;100%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

[(1S,3aS,4S,6S,8aS)-4-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-7-oxo-decahydro-azulen-6-yl]-acetaldehyde

[(1S,3aS,4S,6S,8aS)-4-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-7-oxo-decahydro-azulen-6-yl]-acetaldehyde

4-[(1S,3aS,4S,6S,8aS)-4-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-7-oxo-decahydro-azulen-6-yl]-3-oxo-butyric acid ethyl ester

4-[(1S,3aS,4S,6S,8aS)-4-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-7-oxo-decahydro-azulen-6-yl]-3-oxo-butyric acid ethyl ester

Conditions
ConditionsYield
tin(ll) chloride In dichloromethane Heating;100%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

acrolein
107-02-8

acrolein

Conditions
ConditionsYield
With tetrafluoroboric acid diethyl ether In dichloromethane at -78℃; for 24h;100%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

2-Hydroxy-3-naphthaldehyde
581-71-5

2-Hydroxy-3-naphthaldehyde

2-hydroxy-2,3-dihydro-naphtho[2,3-b]furan-3-carboxylic acid ethyl ester

2-hydroxy-2,3-dihydro-naphtho[2,3-b]furan-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
With tetrafluoroboric acid diethyl ether In diethyl ether; dichloromethane at 23 - 38℃; Inert atmosphere;100%
With tetrafluoroboric acid diethyl ether In dichloromethane
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

3,5-dichlorosalicyclaldehyde
90-60-8

3,5-dichlorosalicyclaldehyde

5,7-dichloro-2-hydroxy-2,3-dihydro-benzofuran-3-carboxylic acid ethyl ester

5,7-dichloro-2-hydroxy-2,3-dihydro-benzofuran-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
With tetrafluoroboric acid diethyl ether In diethyl ether; dichloromethane at 23 - 38℃; Inert atmosphere;100%
With tetrafluoroboric acid diethyl ether In dichloromethane
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

benzyl 4-oxo-1-piperidinecarboxylate
19099-93-5

benzyl 4-oxo-1-piperidinecarboxylate

1-benzyl 4-ethyl 5-oxoazepane-1,4-dicarboxylate
31696-09-0

1-benzyl 4-ethyl 5-oxoazepane-1,4-dicarboxylate

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In diethyl ether100%
With boron trifluoride diethyl etherate In diethyl ether at -78℃; for 1h;100%
With boron trifluoride diethyl etherate In diethyl ether at -40℃; for 1h;99%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

1-benzyl-1H-pyrrole-2,5-dione
1631-26-1

1-benzyl-1H-pyrrole-2,5-dione

ethyl 5-benzyl-4,6-dioxo-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrazole-3-carboxylate
134575-05-6

ethyl 5-benzyl-4,6-dioxo-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrazole-3-carboxylate

Conditions
ConditionsYield
In diethyl ether100%
In diethyl ether at 20℃; for 36h; Diels-Alder Reaction;89%
In diethyl ether for 36h;89%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

(dimethylamino)trimethyltin
993-50-0

(dimethylamino)trimethyltin

ethyl (trimethylstannyl)diazoacetate

ethyl (trimethylstannyl)diazoacetate

Conditions
ConditionsYield
In diethyl ether at room temp.;;100%
In diethyl ether at room temp.;;100%
In diethyl ether; dichloromethane at 20℃; for 6h; Schlenk technique; Inert atmosphere;99%

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