Diethyl azodicarboxylate supplier

Name
Diethyl azodicarboxylate
EINECS 217-821-7
CAS No. 1972-28-7
Article Data40
CAS DataBase
Density 1.2 g/cm³
Solubility
Melting Point 6°C
Formula C₆H₁₀N₂O₄
Boiling Point 226.3 °C at 760 mmHg
Molecular Weight 174.156
Flash Point 106.9 °C
Transport Information UN 3233
Appearance Clear orange to orange-red liquid
Safety 26-36/37-62-47-36
Risk Codes 5-11-20-36/37/38-48/20-63-65-67-48/20/22-40-20/22-20/21/22
Molecular Structure
Hazard Symbols F,Xn,Xi
Synonyms Diazenedicarboxylicacid, diethyl ester (9CI);Formic acid, azodi-, diethyl ester (6CI,8CI);1,2-Ethoxycarbonyl diazene;Azodicarboxylic acid diethyl ester;DEAD;Diethoxycarbonyldiazene;Diethyl azodicarboxylate;Diethyl diazenedicarboxylate;Diethyl diazodicarboxylate;NSC 3474;NSC 679015;Unifoam AZ-AE 200;
PSA 77.32000
LogP 1.75160

Synthetic route

: 622-08-2
2-Benzyloxyethanol

: 2042-14-0
4-methyl-5-nitrophenol

: 1972-28-7
diethylazodicarboxylate

Conditions

Conditions	Yield
With triphenylphosphine	95%

: 4114-28-7
diethyl hydrazodicarboxylate

: 1972-28-7
diethylazodicarboxylate

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene In dichloromethane for 0.25h; Ambient temperature;	88%
With N-Bromosuccinimide In dichloromethane 1.) 0 deg C, 0.5 h, 2.) RT, 1h;	86.6%
Stage #1: diethyl hydrazodicarboxylate With chlorine In water; benzene Stage #2: With sodium carbonate	81%

: 73240-57-0, 77881-55-1
4,7-Dimethyl-15-oxo-5,6-diphenyl-11,12-diazapentacyclo<8.2.2.14,7.02,9.03,8>pentadeca-5,13-dien-11,12-dicarbonsaeure-diethylester

A: 4114-28-7
diethyl hydrazodicarboxylate

B: 13102-23-3
methyl 3',6'-dimethyl[1,1*:2',1"-terphenyl]-4'-carboxylate

C: 86814-76-8
4,9-Dimethyl-6,7-diphenyl-5,8-dioxa-13,14-diazahexacyclo<10.2.2.02,11.03,10.04,6.07,9>hexadec-15-en-13,14-dicarbonsaeure-diethylester

D: 1972-28-7
diethylazodicarboxylate

Conditions

Conditions	Yield
In diethyl ether; acetone at -25 - -20℃; for 6h; Irradiation;	A n/a B 46% C 7% D n/a

...Expand

: 73240-57-0, 77881-55-1
4,7-Dimethyl-15-oxo-5,6-diphenyl-11,12-diazapentacyclo<8.2.2.14,7.02,9.03,8>pentadeca-5,13-dien-11,12-dicarbonsaeure-diethylester

A: 4114-28-7
diethyl hydrazodicarboxylate

B: 13102-23-3
methyl 3',6'-dimethyl[1,1*:2',1"-terphenyl]-4'-carboxylate

C: 86814-76-8
4,9-Dimethyl-6,7-diphenyl-5,8-dioxa-13,14-diazahexacyclo<10.2.2.02,11.03,10.04,6.07,9>hexadec-15-en-13,14-dicarbonsaeure-diethylester

D: 1972-28-7
diethylazodicarboxylate

E: 71-43-2
benzene

Conditions

Conditions	Yield
In diethyl ether; acetone at -25 - -20℃; for 6h; Product distribution; Irradiation;	A n/a B 46% C 7% D n/a E n/a

...Expand

: 5311-96-6
diethyl hydrazinedicarboxylate

: 1972-28-7
diethylazodicarboxylate

Conditions

Conditions	Yield
With nitric acid
With water; nitric acid Reagens 4:Aether;

: bis-ethoxycarbonylmercurio-hydrazine-N,N'-dicarboxylic acid diethyl ester

: 1972-28-7
diethylazodicarboxylate

Conditions

Conditions	Yield
With bromine; benzene

: 4114-28-7
diethyl hydrazodicarboxylate

: 71-43-2
benzene

: 1972-28-7
diethylazodicarboxylate

Conditions

Conditions	Yield
With water; chlorine

: 817-87-8
ethyl azidocarbonate

: 1972-28-7
diethylazodicarboxylate

Conditions

Conditions	Yield
In tetrachloromethane at 25℃; for 100h; Rate constant; Irradiation; other solvents;

mercury salt of hydrazinedicarboxylic acid diethyl ester: mercury salt of hydrazinedicarboxylic acid diethyl ester

: 1972-28-7
diethylazodicarboxylate

Conditions

Conditions	Yield
With iodine

: 17696-93-4
diethyl 3-phenyltriazane-1,2-dicarboxylate

: 71-43-2
benzene

A: 108673-54-7
[1,4]benzoquinon-[4-(4-amino-anilino)-phenylimine]-phenylimine

B: 62-53-3
aniline

C: 1972-28-7
diethylazodicarboxylate

D hydrazodicarboxylic acid ester: hydrazodicarboxylic acid ester

Conditions

Conditions	Yield
at 26℃;
at 95℃; Geschwindigkeit;

...Expand

: 4114-28-7
diethyl hydrazodicarboxylate

: 7697-37-2
nitric acid

: 1972-28-7
diethylazodicarboxylate

: 4114-28-7
diethyl hydrazodicarboxylate

: 7732-18-5
water

: 7782-50-5
chlorine

: 71-43-2
benzene

: 1972-28-7
diethylazodicarboxylate

Conditions

Conditions	Yield
Explosionsgefahr !;

...Expand

: 4114-28-7
diethyl hydrazodicarboxylate

nitrogen oxides: nitrogen oxides

: 1972-28-7
diethylazodicarboxylate

: hydrazine-N,N'-dicarboxylic acid diethyl ester; mercury salt

etheric iodine: etheric iodine

: 1972-28-7
diethylazodicarboxylate

: 7726-95-6
bromine

: bis-ethoxycarbonylmercurio-hydrazine-N,N'-dicarboxylic acid diethyl ester

: 71-43-2
benzene

A: 17759-76-1
ethyl 1-bromoformate

B: 1972-28-7
diethylazodicarboxylate

C mercury (II)-bromide: mercury (II)-bromide

...Expand

: 24009-91-4, 73285-36-6
(1R,2R,5S,6S)-7,8-Diaza-tricyclo[4.2.2.02,5]deca-3,9-diene-7,8-dicarboxylic acid diethyl ester

: 1972-28-7
diethylazodicarboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / benzene / 48 h / Heating 2: diethyl ether; acetone / 6 h / -25 - -20 °C / Irradiation View Scheme

: 1316208-44-2
C11H18N3O6(1-)*C16H36N(1+)

A: proline, tetrabutylammonium carboxylate salt

B: 1972-28-7
diethylazodicarboxylate

Conditions

Conditions	Yield
In chloroform Equilibrium constant;

: 542-92-7
cyclopenta-1,3-diene

: 1972-28-7
diethylazodicarboxylate

: 14011-60-0
diethyl 2,3-diazanorbornene-2,3-dicarboxylate

Conditions

Conditions	Yield
In dichloromethane at 0℃;	100%
In diethyl ether at 0℃; for 12h;	100%
In diethyl ether; toluene at 20℃; for 21.5h; Reflux;	55%
With diethyl ether

: 110-83-8
cyclohexene

: 1972-28-7
diethylazodicarboxylate

: 17833-25-9
Diethyl 1-(2-cyclohexen-1-yl)-1,2-hydrazinedicarboxylate

Conditions

Conditions	Yield
With tin(IV) chloride In dichloromethane at -78℃;	100%
With tin(IV) chloride In dichloromethane at -60℃; for 0.0833333h;	77%

: 1972-28-7
diethylazodicarboxylate

: 4114-28-7
diethyl hydrazodicarboxylate

Conditions

Conditions	Yield
With hydrazine hydrate In toluene; acetonitrile at 20℃; for 0.166667h;	100%
With [bis(acetoxy)iodo]benzene; hydrazine hydrate In dichloromethane for 3.5h; Ambient temperature;	90%
With tert-Butyl iodide In acetonitrile for 0.166667h; Reflux;	90%

: 7114-39-8
[1,3,2]dioxaphospholan-2-yl-dimethyl-amine

: 1972-28-7
diethylazodicarboxylate

: 75386-16-2
dimethylamino-5 ethoxy-7 carboethoxy-9 trioxa-1,4,6diaza-8,9 phospha(V)-5 spiro(4,4)nonene-7,8

Conditions

Conditions	Yield
In dichloromethane 10 min, 5 deg C, then room t.,;	100%

: 14274-42-1
dimethyl-(4,4,5,5-tetramethyl-[1,3,2]dioxaphospholan-2-yl)-amine

: 1972-28-7
diethylazodicarboxylate

: 75386-17-3
tetramethyl-2,2,3,3-dimethylamino-5-ethoxy-7 carboethoxy-9 trioxa-1,4,6 diaza-8,9 phospha(V)-5 spiro(4,4)noneme-7,8

Conditions

Conditions	Yield
In dichloromethane Product distribution; 10 min, 5 deg C, then room t; reactions of phosphites and cyclis aminophosphites;	100%
In dichloromethane 10 min, 5 deg C, then room t.,;	100%

: 18389-60-1
2-dimethylamino-1,3,2-benzodioxaphosphole

: 1972-28-7
diethylazodicarboxylate

: O-phenylene-2,3 dimethylamino-5 ethoxy-7 carboethoxy-9 trioxa-1,4,6 diaza-8,9 phospha(V)-5 spiro(4,4)nonene-7,8

Conditions

Conditions	Yield
In dichloromethane 10 min, 5 deg C, then room t., 24 h;	100%

: 603-35-0
triphenylphosphine

: 1972-28-7
diethylazodicarboxylate

: 58477-00-2
diethylazodicarboxylate - triphenylphosphine (DEAD-Ph3P)

Conditions

Conditions	Yield
In tetrahydrofuran Mechanism; other phosphine;	100%
In chloroform-d1
In tetrahydrofuran at 0℃; for 1h;

: 64944-80-5
2-benzoylmethyleneimidazolidine

: 1972-28-7
diethylazodicarboxylate

: 112030-72-5
C17H22N4O5

Conditions

Conditions	Yield
In 1,4-dioxane for 48h; Ambient temperature;	100%

: 82100-30-9
1-phenyl-2-(tetrahydropyrimidin-2(1H)-ylidene)ethan-1-one

: 1972-28-7
diethylazodicarboxylate

: 112030-74-7
C18H24N4O5

Conditions

Conditions	Yield
In 1,4-dioxane for 48h; Ambient temperature;	100%

: 107165-82-2
2-(p-chlorobenzoylmethylene)imidazolidine

: 1972-28-7
diethylazodicarboxylate

: 112030-73-6
C17H21ClN4O5

Conditions

Conditions	Yield
In 1,4-dioxane for 48h; Ambient temperature;	100%

: 107165-83-3
1-(4-chlorophenyl)-2-(tetrahydropyrimidin-2(1H)-ylidene)ethan-1-one

: 1972-28-7
diethylazodicarboxylate

: 112030-75-8
C18H23ClN4O5

Conditions

Conditions	Yield
In 1,4-dioxane for 48h; Ambient temperature;	100%

: 107165-84-4
1-(4-methoxyphenyl)-2-(tetrahydropyrimidin-2(1H)-ylidene)ethan-1-one

: 1972-28-7
diethylazodicarboxylate

: 112030-76-9
C19H26N4O6

Conditions

Conditions	Yield
In 1,4-dioxane for 48h; Ambient temperature;	100%

: ((2S,4R,5S)-3,4-Dimethyl-5-phenyl-[1,3,2]oxazaphospholidin-2-yl)-dimethyl-amine

: 1972-28-7
diethylazodicarboxylate

: dimethyl-1,2-phenyl-3 dimethylamino-5 ethoxy-7 carboethoxy-9 dioxa-4,6-triaza-1,8,9 phospha(V)-5 spiro(4,4)nonene-7,8

Conditions

Conditions	Yield
In dichloromethane 10 min, 5 deg C, then room t., 24 h;	100%

: 59875-94-4
1,1-dibenzoylpropane

: 1972-28-7
diethylazodicarboxylate

: diethyl N-(dibenzoylpropyl)hydrazine-N,N-dicarboxylate

Conditions

Conditions	Yield
With triphenylphosphine In acetonitrile for 24h; Michael addition; Heating;	100%
triphenylphosphine In acetonitrile at 25℃; for 24h;	100%
tris(triphenylphosphine)ruthenium(II) chloride In acetonitrile for 24h; Product distribution; Further Variations:; Catalysts; Reaction partners; Temperatures; reflux, in dark;	83%

: 135-19-3
β-naphthol

: 1972-28-7
diethylazodicarboxylate

: (2-hydroxy-1-naphthyl)-hydrazine-N,N'-dicarboxylic acid diethyl ester

Conditions

Conditions	Yield
With lithium perchlorate; bis(tri-n-butyltin)oxide In diethyl ether at 24.85℃;	100%
With 1,3,4-triphenyl-1,2,4-triazolium hexafluorophosphate; potassium tert-butylate In chloroform at 20℃; for 4h; Inert atmosphere;	75%

: 90-15-3
α-naphthol

: 1972-28-7
diethylazodicarboxylate

: (1-hydroxy-4-naphthyl)-hydrazine-N,N'-dicarboxylic acid diethyl ester

Conditions

Conditions	Yield
With lithium perchlorate; bis(tri-n-butyltin)oxide In diethyl ether at 24.85℃;	100%

: 56826-61-0
(2-methylpyridin-3-yl)methanol

: 1972-28-7
diethylazodicarboxylate

: 362488-31-1
tert-butyl (3S,4S)-4-[(hydroxyamino)carbonyl]-3-({4-[(2-methyl-3-pyridinyl)methoxy]benzoyl}amino)-1-piperidinecarboxylate trifluoroacetate

Conditions

Conditions	Yield
With ammonium chloride; triphenylphosphine In tetrahydrofuran	100%

d5-ethanol: d5-ethanol

ethoxyphenylacetate: ethoxyphenylacetate

: 14199-15-6
Methyl 4-hydroxyphenylacetate

: 1972-28-7
diethylazodicarboxylate

: 22545-14-8
2-(2-ethoxyphenyl)ethanol

Conditions

Conditions	Yield
With triphenylphosphine In tetrahydrofuran; diethyl ether	100%

...Expand

: 35905-85-2
2-bromonicotinic acid

: 1972-28-7
diethylazodicarboxylate

: 52718-95-3
2-bromonicotinic acid methyl ester

Conditions

Conditions	Yield
With triphenylphosphine In methanol; diethyl ether	100%

: 1670-82-2
Indole-6-carboxylic acid

: 1972-28-7
diethylazodicarboxylate

: 1011-65-0
5-methoxycarbonylindole

Conditions

Conditions	Yield
With triphenylphosphine In tetrahydrofuran; methanol; dichloromethane	100%

: 123-56-8
Succinimide

: 429666-52-4
3-t-butyldiphenylsilyloxy-1-(4-hydroxymethyl-1,3-thiazol-2-yl)azetidine

: 1972-28-7
diethylazodicarboxylate

: 3-t-butyldiphenylsilyloxy-1-(4-succinimidomethyl-1,3-thiazol-2-yl)azetidine

Conditions

Conditions	Yield
With triphenylphosphine In tetrahydrofuran; toluene	100%

...Expand

: 542-92-7
cyclopenta-1,3-diene

: 1972-28-7
diethylazodicarboxylate

: diethyl 2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Conditions

Conditions	Yield
In dichloromethane at 0 - 20℃; Diels-Alder reaction;	100%
In dichloromethane at 20℃; Diels-Alder reaction;	100%
In diethyl ether at 0℃;	100%

: 51127-13-0, 71963-72-9, 87480-74-8, 13302-43-7
2-phenyl-4-methyl-4H-oxazolin-5-one

: 1972-28-7
diethylazodicarboxylate

: 1228801-83-9
1,2-bis(ethoxycarbonyl)-3-methyl-5-phenyl-2,3-dihydro-1H-1,2,4-triazole-3-carboxylic acid

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 11h;	100%

: 34713-70-7
2-Phenylpropanal

: 1972-28-7
diethylazodicarboxylate

: (R)-diethyl 1-(1-oxo-2-phenylpropan-2-yl)hydrazine-1,2-dicarboxylate

Conditions

Conditions	Yield
With (S)-4-(tert-butoxy)-2-methyl-4-oxobutanoic acid In tetrahydrofuran at 0℃; for 24h; enantioselective reaction;	100%
With (S)-N-((1R,2R)-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)cyclohexyl)pyrrolidine-2-carboxamide; salicylic acid In dichloromethane at 0℃; for 23h; optical yield given as %ee; enantioselective reaction;	96%
With trifluoroacetic acid; (1R,2R)-N-1',8'-naphthaloyl-1,2-diaminocyclohexane In 1,2-dichloro-ethane at 25℃; for 5h; enantioselective reaction;	96%

: 137235-13-3
1-(2,4-dichlorophenyl)-3-(dimethylamino)prop-2-en-1-one

: 1972-28-7
diethylazodicarboxylate

: diethyl 1-(1-(dimethylamino)-3-oxo-3-(2,4-dichlorophenyl)prop-1-en-2-yl)hydrazine-1,2-dicarboxylate

Conditions

Conditions	Yield
In toluene; acetonitrile at 20℃;	100%

: 124-38-9
carbon dioxide

: N,N-dimethyl-4-(3-methyl-3-(propylamino)but-1-yn-1-yl)aniline

: 1972-28-7
diethylazodicarboxylate

: diethyl (Z)-1-((4,4-dimethyl-2-oxo-3-propyloxazolidin-5-ylidene)(4-(dimethylamino)phenyl)methyl)hydrazine-1,2-dicarboxylate

Conditions

Conditions	Yield
With silver(I) acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at -40℃; for 12h; Schlenk technique; Molecular sieve; Inert atmosphere; stereoselective reaction;	100%

...Expand

: 124-38-9
carbon dioxide

: 2-methyl-4-phenyl-N-propylbut-3-yn-2-amine

: 1972-28-7
diethylazodicarboxylate

: diethyl (Z)-1-((4,4-dimethyl-2-oxo-3-propyloxazolidin-5-ylidene)(phenyl)methyl)hydrazine-1,2-dicarboxylate

Conditions

Conditions	Yield
With silver(I) acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at -40℃; for 12h; Schlenk technique; Molecular sieve; Inert atmosphere; stereoselective reaction;	100%

...Expand

: 124-38-9
carbon dioxide

: C15H21NO

: 1972-28-7
diethylazodicarboxylate

: diethyl (Z)-1-((4,4-dimethyl-2-oxo-3-propyloxazolidin-5-ylidene)(4-methoxyphenyl)methyl)hydrazine-1,2-dicarboxylate

Conditions

Conditions	Yield
With silver(I) acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at -40℃; for 12h; Schlenk technique; Molecular sieve; Inert atmosphere; stereoselective reaction;	100%

...Expand

: 124-38-9
carbon dioxide

: N-benzyl-2-methyl-4-phenylbut-3-yn-2-amine

: 1972-28-7
diethylazodicarboxylate

: diethyl (Z)-1-((3-benzyl-4,4-dimethyl-2-oxooxazolidin-5-ylidene)(phenyl)methyl)hydrazine-1,2-dicarboxylate

Conditions

Conditions	Yield
With silver(I) acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at -40℃; for 12h; Schlenk technique; Molecular sieve; Inert atmosphere; stereoselective reaction;	100%

...Expand

: 106-48-9
4-chloro-phenol

: 145881-74-9
2-<2-N-(benzyloxycarbonyl)aminoethoxy>ethanol

: 1972-28-7
diethylazodicarboxylate

: {2-[2-(4-chloro-phenoxy)-ethoxy]-ethyl}-carbamic acid benzyl ester

Conditions

Conditions	Yield
With triphenylphosphine In tetrahydrofuran; hexane; ethyl acetate	99.8%

...Expand

Diethyl azodicarboxylate Specification

The Diethyl azodicarboxylate with cas registry number of 1972-28-7 belongs to the class of aromatic esters. It is also known as Azodicarboxylic acid diethyl ester; DEAD. Its IUPAC name is called [(E)-acetyloxymethyldiazenyl]methyl acetate. It also has an EINECS registry number which is 217-821-7. Its appearance is clear orange to orange-red liquid. It is sensitive to air. This chemical is stable, but may explode if heated under confinement. It secomposes vigorously if heated above 100 C. It is also incompatible with strong acids, strong bases, strong oxidizing agents, strong reducing agents.

Physical properties about Diethyl azodicarboxylate are:
(1)ACD/LogP: 1.85; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.85; (4)ACD/LogD (pH 7.4): 1.85; (5)ACD/BCF (pH 5.5): 14.91; (6)ACD/BCF (pH 7.4): 14.91; (7)ACD/KOC (pH 5.5): 240.75; (8)ACD/KOC (pH 7.4): 240.75; (9)#H bond acceptors: 6; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 6; (12)Index of Refraction: 1.471; (13)Molar Refractivity: 40.41 cm³; (14)Molar Volume: 144.3 cm³; (15)Surface Tension: 38.7 dyne/cm; (16)Density: 1.2 g/cm³; (17)Flash Point: 106.9 °C; (18)Enthalpy of Vaporization: 46.28 kJ/mol; (19)Boiling Point: 226.3 °C at 760 mmHg; (20)Vapour Pressure: 0.0827 mmHg at 25°C.

Preparation of Diethyl azodicarboxylate:
It can be made by hydrazine-N,N'-dicarboxylic acid diethyl ester using reagent iodobenzene diacetate, solvent CH₂Cl₂ at ambient temperature. The reaction time is 15 min. The yield is about 88%.
It can be made by hydrazine-N,N'-dicarboxylic acid diethyl ester using reagent iodobenzene diacetate, solvent CH2Cl2 at ambient temperature. The reaction time is 15 min. The yield is about 88%.

Uses of Diethyl azodicarboxylate:
Diethyl azodicarboxylate can react with pyrrole to give 2,5-bis(N,N'-diethoxycarbonylhydrazinyl)pyrrole using solvent diethyl ether. It also needs heating. The reaction time is 24 hours. The yield is 56%.

When you are using Diethyl azodicarboxylate, please be cautious about it as the following:
This chemical is highly flammable. It is irritating to eyes, respiratory system and skin and harmful by inhalation, in contact with skin and if swallowed. It may cause lung damage if swallowed. If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label. Wear suitable protective clothing and gloves during using it. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Keep at temperature of 2-8°C.

You can still convert the following datas into molecular structure:
(1)SMILES:O=C(/N=N\C(=O)OCC)OCC;
(2)Std. InChI:InChI=1S/C6H10N2O4/c1-3-11-5(9)7-8-6(10)12-4-2/h3-4H2,1-2H3/b8-7-;
(3)Std. InChIKey:FAMRKDQNMBBFBR-FPLPWBNLSA-N.

Product Name

Diethyl azodicarboxylate

Synthetic route

Diethyl azodicarboxylate Specification

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