Ethyl diazoacetate supplier

Name
Ethyl diazoacetate
EINECS 210-810-8
CAS No. 623-73-4
Article Data110
CAS DataBase
Density 1.085 g/cm³
Solubility insoluble in water, soluble in organic solvents such as dichloroethane
Melting Point -22 °C
Formula C₄H₆N₂O₂
Boiling Point 140-141 °C (720 mmHg)
Molecular Weight 114.104
Flash Point 46 °C
Transport Information UN 1993
Appearance colourless liquid
Safety 36/37
Risk Codes 5-10-22-40
Molecular Structure
Hazard Symbols Xn
Synonyms Aceticacid, diazo-, ethyl ester (6CI,8CI,9CI);DAAE;Diazoacetic acid ethyl ester;Diazoacetic ester;Ethoxycarbonyldiazomethane;Ethyl 2-diazoacetate;Ethyl2-diazoethanoate;Ethyl diazoacetate;NSC 79147;
PSA 63.69000
LogP -0.06884

Synthetic route

: 623-33-6
glycine ethyl ester hydrochloride

: 623-73-4
diazoacetic acid ethyl ester

Conditions

Conditions	Yield
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%

: 70526-06-6
(Z)-3-pyrrolidin-1-yl-but-2-enoic acid ethyl ester

: 65245-26-3
perfluorobutanesulfonyl azide

A: 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

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.5h;	A n/a B 96%

...Expand

: 70526-06-6
(Z)-3-pyrrolidin-1-yl-but-2-enoic acid ethyl ester

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

A: 623-73-4
diazoacetic acid ethyl ester

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

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.5h;	A n/a B 85%

...Expand

: 66003-96-1
β-morpholinoethylcrotonate

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

A: 623-73-4
diazoacetic acid ethyl ester

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

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.5h;	A n/a B 85%

...Expand

: 781-15-7
1,2,3,4-tetrachloro-5,6-dinitrobenzene

: 459-73-4
GlyOEt*HCl

A: 623-73-4
diazoacetic acid ethyl ester

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

Conditions

Conditions	Yield
In toluene for 1h; Heating;	A 17% B 83%

...Expand

: 65245-26-3
perfluorobutanesulfonyl azide

: 66003-96-1
β-morpholinoethylcrotonate

A: 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

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.5h;	A n/a B 81%

...Expand

: 66003-96-1
β-morpholinoethylcrotonate

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

A: 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

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.5h;	A n/a B 81%

...Expand

: 70526-06-6
(Z)-3-pyrrolidin-1-yl-but-2-enoic acid ethyl ester

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

A: 623-73-4
diazoacetic acid ethyl ester

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

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.5h;	A n/a B 80%

...Expand

: 10271-27-9
1-(p-nitrophenyl)-3-(ethoxycarbonylmethyl)triazene

: 623-73-4
diazoacetic acid ethyl ester

Conditions

Conditions	Yield
With acetic acid In dichloromethane; water	66%
In chloroform Ambient temperature;

: 2-aminoacetimidate ethyl ester

: 623-73-4
diazoacetic acid ethyl ester

Conditions

Conditions	Yield
With cis-nitrous acid
With cis-nitrous acid

: 637-80-9
ethyl 2-hydrazinylacetate

: 623-73-4
diazoacetic acid ethyl ester

Conditions

Conditions	Yield
With cis-nitrous acid
With cis-nitrous acid

: 861570-78-7
(N-nitroso-hydrazino)-acetic acid ethyl ester

: 623-73-4
diazoacetic acid ethyl ester

Conditions

Conditions	Yield
With cis-nitrous acid

: 60474-28-4
5-phenyl-[1,2,3]oxadiazole-4-carboxylic acid ethyl ester

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

A: 623-73-4
diazoacetic acid ethyl ester

B: 65-85-0
benzoic acid

...Expand

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

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

A: 623-73-4
diazoacetic acid ethyl ester

B: 65-85-0
benzoic acid

...Expand

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

A: 623-73-4
diazoacetic acid ethyl ester

B: 603-35-0
triphenylphosphine

Conditions

Conditions	Yield
at 140 - 160℃;

: 459-73-4
GlyOEt*HCl

: 623-73-4
diazoacetic acid ethyl ester

Conditions

Conditions	Yield
With cis-nitrous acid
With cis-nitrous acid
With isopentyl nitrite var. reag.: NaNO2;

: 123-75-1
pyrrolidine

: 95205-17-7
mononitrosated DL-benzoylphenylalanylglycine ethyl ester

A: 623-73-4
diazoacetic acid ethyl ester

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

Conditions

Conditions	Yield
In dichloromethane for 0.0833333h;

...Expand

: 123-75-1
pyrrolidine

: 95205-22-4
dinitrosated DL-benzoylphenylalanylglycylglycine ethyl ester

A: 623-73-4
diazoacetic acid ethyl ester

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

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

Conditions

Conditions	Yield
In dichloromethane for 0.0833333h;

...Expand

: 80288-29-5
ethyl (E,Z)-6-azido-3-butylhexa-2,4-dienoate

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

B: 623-73-4
diazoacetic acid ethyl ester

Conditions

Conditions	Yield
In benzene at 70℃; for 1.5h;

: 80288-29-5
ethyl (E,Z)-6-azido-3-butylhexa-2,4-dienoate

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

B: 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

Conditions

Conditions	Yield
In benzene at 78℃; for 0.666667h; Title compound not separated from byproducts;

...Expand

: 95204-47-0
ethyl N-methoxycarbonyl-N-nitrosoglycinate

: 623-73-4
diazoacetic acid ethyl ester

Conditions

Conditions	Yield
With pyrrolidine In dichloromethane for 0.0833333h; Ambient temperature;

: 95205-17-7
mononitrosated DL-benzoylphenylalanylglycine ethyl ester

A: 623-73-4
diazoacetic acid ethyl ester

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

Conditions

Conditions	Yield
With pyrrolidine In dichloromethane for 0.0833333h;

: 95205-22-4
dinitrosated DL-benzoylphenylalanylglycylglycine ethyl ester

A: 623-73-4
diazoacetic acid ethyl ester

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

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

Conditions

Conditions	Yield
With pyrrolidine In dichloromethane for 0.0833333h;

...Expand

: 2,2-Diethoxy-1-ethendiazonium-hexachloroantimonat

: 623-73-4
diazoacetic acid ethyl ester

Conditions

Conditions	Yield
With water In acetonitrile at 0℃;

: C10H17N2O5P

A: 623-73-4
diazoacetic acid ethyl ester

B: 824-11-3
ethriol phosphite

Conditions

Conditions	Yield
at 45℃; Rate constant;

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

A: 623-73-4
diazoacetic acid ethyl ester

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

Conditions

Conditions	Yield
With 2-azido-1-ethylpyridin-1-ium tetrafluoroborate; acetic acid In methanol; water for 2.5h; Ambient temperature; Yield given. Yields of byproduct given;

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

: 62-53-3
aniline

A: 623-73-4
diazoacetic acid ethyl ester

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

Conditions

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

...Expand

glycocoll ester hydrochloride: glycocoll ester hydrochloride

: 623-73-4
diazoacetic acid ethyl ester

Conditions

Conditions	Yield
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

: 623-73-4
diazoacetic acid ethyl ester

Conditions

Conditions	Yield
With barium dihydroxide; diethyl ether; barium(II) oxide at -10℃;

: 292638-84-7
styrene

: 623-73-4
diazoacetic acid ethyl ester

: 946-38-3, 946-39-4, 34702-96-0, 34702-97-1, 34703-00-9, 34716-60-4, 63038-62-0, 63038-63-1, 97-71-2
ethyl 2-phenylcyclopropylcarboxylate

Conditions

Conditions	Yield
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%

: 623-73-4
diazoacetic acid ethyl ester

: 530-48-3
1,1-Diphenylethylene

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

Conditions

Conditions	Yield
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%

: 623-73-4
diazoacetic acid ethyl ester

: 64-17-5
ethanol

: 817-95-8
ethyl 2-ethoxyethanoate

Conditions

Conditions	Yield
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%

: 623-73-4
diazoacetic acid ethyl ester

: 123-11-5
4-methoxy-benzaldehyde

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

Conditions

Conditions	Yield
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%

: 623-73-4
diazoacetic acid ethyl ester

: 71-43-2
benzene

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

Conditions

Conditions	Yield
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%

: 623-73-4
diazoacetic acid ethyl ester

: 14790-53-5
iodo-diazoacetic acid ethyl ester

Conditions

Conditions	Yield
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;

: 623-73-4
diazoacetic acid ethyl ester

: 89222-12-8
2-dimethylaminomalonic acid diethyl ester

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

Conditions

Conditions	Yield
With copper In toluene Heating;	100%

: 623-73-4
diazoacetic acid ethyl ester

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

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

Conditions

Conditions	Yield
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%

: 623-73-4
diazoacetic acid ethyl ester

: 107-13-1
acrylonitrile

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

Conditions

Conditions	Yield
In pyridine at 60℃; for 3h;	100%
With 1,4-diaza-bicyclo[2.2.2]octane at 20℃; for 6h; neat (no solvent);	52%

: 623-73-4
diazoacetic acid ethyl ester

: 140-88-5
ethyl acrylate

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

Conditions

Conditions	Yield
at 22℃; for 5h;	100%
In pyridine at 60℃; for 3h;	99%
With water at 20℃; for 3h; Green chemistry;	99%

: 623-73-4
diazoacetic acid ethyl ester

: 26697-95-0
ethyl α-deuteriodiazoacetate

Conditions

Conditions	Yield
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;

: 623-73-4
diazoacetic acid ethyl ester

: 64805-08-9
ethyl glyoxalate hydrate

Conditions

Conditions	Yield
With 3,3-dimethyldioxirane In acetone Ambient temperature;	100%

: 623-73-4
diazoacetic acid ethyl ester

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

: 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

Conditions	Yield
for 8h; Ambient temperature; in the dark;	100%
With diethylzinc for 8h;	98%

: 623-73-4
diazoacetic acid ethyl ester

: 3085-76-5
diisopropylcyanamide

: 2-(diisopropylamino)-5-ethyloxazole

Conditions

Conditions	Yield
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;

: 623-73-4
diazoacetic acid ethyl ester

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

: ethyl 5-trifluoromethyl-pyrazole-3-carboxylate

Conditions

Conditions	Yield
In benzene a) 20 deg C, 15 min, b) 50 deg C, 45 min, c) reflux, 16 h;	100%

: 623-73-4
diazoacetic acid ethyl ester

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

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

Conditions

Conditions	Yield
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

: 623-73-4
diazoacetic acid ethyl ester

: 52386-78-4
N-acetyl dehydrophenylalanine methyl ester

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

Conditions

Conditions	Yield
dirhodium tetraacetate In chloroform for 6h; Heating;	100%
rhodium(II) acetate Cycloaddition;	40%

: 623-73-4
diazoacetic acid ethyl ester

: α-(diethoxyphosphoryl)vinyl p-tolyl sulfoxide

: diethyl 5-ethoxycarbonyl-3(1H)pyrazolylphosphonate

Conditions

Conditions	Yield
In benzene at 20℃; for 12h; Cycloaddition; elimination;	100%

: 623-73-4
diazoacetic acid ethyl ester

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

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

Conditions

Conditions	Yield
dirhodium tetraacetate In dichloromethane at 22℃;	100%

: 623-73-4
diazoacetic acid ethyl ester

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

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

Conditions

Conditions	Yield
dirhodium tetraacetate In dichloromethane at 22℃;	100%

: 110-86-1
pyridine

: 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

Conditions	Yield
With palladium dichloride In dichloromethane; toluene at 55℃;	100%

: 110-86-1
pyridine

: 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

Conditions	Yield
With palladium dichloride In dichloromethane; toluene at 55℃;	100%

: 110-86-1
pyridine

: 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

Conditions	Yield
With palladium dichloride In dichloromethane; toluene at 55℃; for 18h;	100%

: 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

: 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

Conditions	Yield
tin(ll) chloride In dichloromethane Heating;	100%

: 623-73-4
diazoacetic acid ethyl ester

: 107-02-8
acrolein

: 13949-93-4, 13950-12-4, 77183-91-6, 77183-92-7, 109716-50-9, 109716-61-2, 20417-61-2
ethyl-2-formyl-1-cyclopropane carboxylate

Conditions

Conditions	Yield
With tetrafluoroboric acid diethyl ether In dichloromethane at -78℃; for 24h;	100%

: 623-73-4
diazoacetic acid ethyl ester

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

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

Conditions

Conditions	Yield
With tetrafluoroboric acid diethyl ether In diethyl ether; dichloromethane at 23 - 38℃; Inert atmosphere;	100%
With tetrafluoroboric acid diethyl ether In dichloromethane

: 623-73-4
diazoacetic acid ethyl ester

: 90-60-8
3,5-dichlorosalicyclaldehyde

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

Conditions

Conditions	Yield
With tetrafluoroboric acid diethyl ether In diethyl ether; dichloromethane at 23 - 38℃; Inert atmosphere;	100%
With tetrafluoroboric acid diethyl ether In dichloromethane

: 623-73-4
diazoacetic acid ethyl ester

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

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

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In diethyl ether	100%
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%

: 623-73-4
diazoacetic acid ethyl ester

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

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

Conditions

Conditions	Yield
In diethyl ether	100%
In diethyl ether at 20℃; for 36h; Diels-Alder Reaction;	89%
In diethyl ether for 36h;	89%

: 623-73-4
diazoacetic acid ethyl ester

: 993-50-0
(dimethylamino)trimethyltin

: ethyl (trimethylstannyl)diazoacetate

Conditions

Conditions	Yield
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%

Ethyl diazoacetate Specification

The systematic name of Diazoacetic ester is 2-diazonio-1-ethoxyethenolate. With the CAS registry number 623-73-4 and EINECS 210-810-8, it is also named as Diazoacetic acid, ethyl ester. The product's categories are Carboxylic; Azo / Diazo Compounds; Nitrogen Compounds; Organic Building Blocks. It is colourless liquid which is insoluble in water, soluble in organic solvents such as dichloroethane. When heated to decomposition it emits toxic fumes of NO_x. Additionally, the storage environment should be well-ventilated, low-temperature and dry.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.67; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.673; (4)ACD/LogD (pH 7.4): 0.673; (5)ACD/BCF (pH 5.5): 1.912; (6)ACD/BCF (pH 7.4): 1.912; (7)ACD/KOC (pH 5.5): 55.352; (8)ACD/KOC (pH 7.4): 55.352; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 26.3 Å².

Preparation of Diazoacetic ester: It can be obtained by Glycine ethyl ester hydrochloride and sodium nitrite. HCl•NH₂CH₂CO₂C₂H₅+NaNO₂→N₂CHCOOC₂H₅+NaCl+2H₂O

Uses of Diazoacetic ester: It is an important intermediate of chrysanthemic acid and DCVA. It also can be used in organic synthesis. For example: it can react with benzo[1,3]dioxole-5-carbaldehyde to get 3-benzo[1,3]dioxol-5-yl-3-oxo-propionic acid ethyl ester. This reaction needs solvent 1,2-dichloro-ethane by heating. The reaction time is 8 hours. The yield is 68%.

Diazoacetic ester can react with benzo[1,3]dioxole-5-carbaldehyde to get 3-benzo[1,3]dioxol-5-yl-3-oxo-propionic acid ethyl ester

When you are using this chemical, please be cautious about it as the following:
It is flammable. When heating it may cause an explosion. It is also harmful if swallowed. What's more, it has limited evidence of a carcinogenic effect. If you want to contact this product, you must wear suitable protective clothing and gloves.

People can use the following data to convert to the molecule structure.
1. SMILES:CCOC(=O)C=[N+]=[N-]
2. InChI:InChI=1/C4H6N2O2/c1-2-8-4(7)3-6-5/h3H,2H2,1H3
3. InChIKey:YVPJCJLMRRTDMQ-UHFFFAOYAC

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD50	intravenous	280mg/kg (280mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA LUNGS, THORAX, OR RESPIRATION: CYANOSIS	Proceedings of the Society for Experimental Biology and Medicine. Vol. 135, Pg. 219, 1970.
rat	LD50	oral	400mg/kg (400mg/kg)		Xenobiotica. Vol. 3, Pg. 271, 1973.

Product Name

Ethyl diazoacetate

Synthetic route

Ethyl diazoacetate Specification

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