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Diethyl azodicarboxylate

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Name

Diethyl azodicarboxylate

EINECS 217-821-7
CAS No. 1972-28-7 Density 1.2 g/cm3
PSA 77.32000 LogP 1.75160
Solubility N/A 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 Molecular Structure of 1972-28-7 (Diethyl azodicarboxylate) Hazard Symbols FlammableF,HarmfulXn,IrritantXi
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;

Article Data 40

Diethyl azodicarboxylate Synthetic route

622-08-2

2-Benzyloxyethanol

2042-14-0

4-methyl-5-nitrophenol

1972-28-7

diethylazodicarboxylate

Conditions
ConditionsYield
With triphenylphosphine95%
4114-28-7

diethyl hydrazodicarboxylate

1972-28-7

diethylazodicarboxylate

Conditions
ConditionsYield
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
ConditionsYield
In diethyl ether; acetone at -25 - -20℃; for 6h; Irradiation;A n/a
B 46%
C 7%
D n/a
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
ConditionsYield
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
5311-96-6

diethyl hydrazinedicarboxylate

1972-28-7

diethylazodicarboxylate

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

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

1972-28-7

diethylazodicarboxylate

Conditions
ConditionsYield
With bromine; benzene
4114-28-7

diethyl hydrazodicarboxylate

71-43-2

benzene

1972-28-7

diethylazodicarboxylate

Conditions
ConditionsYield
With water; chlorine
817-87-8

ethyl azidocarbonate

1972-28-7

diethylazodicarboxylate

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
at 26℃;
at 95℃; Geschwindigkeit;

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%.
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.

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