Product Name

  • Name

    Diisopropyl azodicarboxylate

  • EINECS 219-502-8
  • CAS No. 2446-83-5
  • Article Data11
  • CAS DataBase
  • Density 1.15 g/cm3
  • Solubility insoluble in water
  • Melting Point 3-5 °C
  • Formula C8H14N2O4
  • Boiling Point 277 °C at 760 mmHg
  • Molecular Weight 202.21
  • Flash Point 106.1 °C
  • Transport Information UN 3082 9/PG 3
  • Appearance clear orange liquid
  • Safety 36-61-47A-36/37/39-29-26-16-60
  • Risk Codes 36/38-51/53-5-43-36/37/38-11-48/20/22-40
  • Molecular Structure Molecular Structure of 2446-83-5 (Diisopropyl azodicarboxylate)
  • Hazard Symbols HarmfulXn, IrritantXi, DangerousN, FlammableF
  • Synonyms DIAD;propan-2-yl N-propan-2-yloxycarbonyliminocarbamate;Diisopropyl azodicarboxylate [DIAD];Di-isopropyl Azodicarboxylate;Diisopropyl-azodicarboxylate;Azodicarboxylic Acid Diisopropyl Ester;Diazenedicarboxylic acid,bis(1-methylethyl) ester;propan-2-yl (NE)-N-propan-2-yloxycarbonyliminocarbamate;Diisopropyl Azodicarboxylate (DIAD);
  • PSA 77.32000
  • LogP 2.52860

Synthetic route

ethyl acetate n-hexane

ethyl acetate n-hexane

N-(tert-butoxycarbonyl)-3-hydroxypyrrolidine
103057-44-9

N-(tert-butoxycarbonyl)-3-hydroxypyrrolidine

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

thioacetic acid
507-09-5

thioacetic acid

tert-butyl 3-(acetylthio)pyrrolidine-1-carboxylate

tert-butyl 3-(acetylthio)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran100%
...Expand
1-(3,5-dimethylbenzyl)-3-isothiocyanatoindolin-2-one

1-(3,5-dimethylbenzyl)-3-isothiocyanatoindolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 1-(3,5-dimethylbenzyl)-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

diisopropyl 1-(3,5-dimethylbenzyl)-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In diethyl ether at 0℃; for 0.0833333h; Inert atmosphere; enantioselective reaction;99%
1-benzyl-4-bromo-3-isothiocyanatoindolin-2-one

1-benzyl-4-bromo-3-isothiocyanatoindolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 1-benzyl-5'-{[1,2-bis(isopropoxycarbonyl)hydrazinyl]thio}-4-bromo-2-oxospiro[indoline-3,3'-[1,2,4]triazole]-1',2'-dicarboxylate

diisopropyl 1-benzyl-5'-{[1,2-bis(isopropoxycarbonyl)hydrazinyl]thio}-4-bromo-2-oxospiro[indoline-3,3'-[1,2,4]triazole]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In toluene at 0℃; for 0.0833333h; Inert atmosphere; enantioselective reaction;99%
3-isothiocyanato-1-methylindolin-2-one
1287715-28-9

3-isothiocyanato-1-methylindolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 1-methyl-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

diisopropyl 1-methyl-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In diethyl ether at -20℃; for 0.0833333h; Inert atmosphere; enantioselective reaction;99%
3-isothiocyanato-1-propylindolin-2-one
1422555-11-0

3-isothiocyanato-1-propylindolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 2-oxo-1-propyl-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

diisopropyl 2-oxo-1-propyl-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In diethyl ether at -20℃; for 0.0833333h; Inert atmosphere; enantioselective reaction;99%
3-isothiocyanato-1-phenylindolin-2-one
1354636-91-1

3-isothiocyanato-1-phenylindolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 2-oxo-1-phenyl-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

diisopropyl 2-oxo-1-phenyl-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In diethyl ether at 0℃; for 0.0833333h; Inert atmosphere; enantioselective reaction;99%
1-benzyl-3-isothiocyanatoindolin-2-one
1287715-31-4

1-benzyl-3-isothiocyanatoindolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 1-benzyl-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

diisopropyl 1-benzyl-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In diethyl ether at 0℃; for 0.0833333h; Solvent; Temperature; Inert atmosphere; enantioselective reaction;99%
3-tolyl isocyanate
621-29-4

3-tolyl isocyanate

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

1-methylethyl 4,5-dihydro-3-(1-methylethoxy)-4-(3-methylphenyl)-5-oxo-1H-1,2,4-triazole-1-carboxylate

1-methylethyl 4,5-dihydro-3-(1-methylethoxy)-4-(3-methylphenyl)-5-oxo-1H-1,2,4-triazole-1-carboxylate

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane at 20℃; for 1h;98%
phenyl isocyanate
103-71-9

phenyl isocyanate

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

1-methylethyl 4,5-dihydro-3-(1-methylethoxy)-5-oxo-4-phenyl-1H-1,2,4-triazole-1-carboxylate

1-methylethyl 4,5-dihydro-3-(1-methylethoxy)-5-oxo-4-phenyl-1H-1,2,4-triazole-1-carboxylate

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane at 20℃; for 1h;98%
1-oxoindane-2-carboxylic acid ethyl ester
6742-25-2

1-oxoindane-2-carboxylic acid ethyl ester

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

C20H26N2O7

C20H26N2O7

Conditions
ConditionsYield
chiral palladium complex In methanol at 20℃; for 0.5h;98%
diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

2,8,13,19-Tetrakis(1,1-dimethylethyl)-11H,22H-4,6:6,10:15,17:17,21-tetramethanodibenzo<1,10>dioxacyclooctadecin-23,25-dione
145986-91-0

2,8,13,19-Tetrakis(1,1-dimethylethyl)-11H,22H-4,6:6,10:15,17:17,21-tetramethanodibenzo<1,10>dioxacyclooctadecin-23,25-dione

C60H80N4O12

C60H80N4O12

Conditions
ConditionsYield
In toluene at 110℃; for 6h;98%
C19H14ONCl

C19H14ONCl

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

C27H28ClN3O4
1004974-38-2

C27H28ClN3O4

Conditions
ConditionsYield
With triphenylphosphine In toluene for 2h; Heating;98%
C15H12O3N2

C15H12O3N2

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

C23H26N4O6
1004974-44-0

C23H26N4O6

Conditions
ConditionsYield
With triphenylphosphine In toluene for 2h; Heating;98%
phenyl (3-phenylaziridin-2-yl) methanone
51659-21-3

phenyl (3-phenylaziridin-2-yl) methanone

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

C23H27N3O4
1004974-16-6

C23H27N3O4

Conditions
ConditionsYield
With triphenylphosphine In toluene for 2h; Heating;98%
diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

(4-Methoxy-phenyl)-[3-(4-nitro-phenyl)-aziridin-2-yl]-methanone

(4-Methoxy-phenyl)-[3-(4-nitro-phenyl)-aziridin-2-yl]-methanone

C24H28N4O7
1004974-32-6

C24H28N4O7

Conditions
ConditionsYield
With triphenylphosphine In toluene for 2h; Heating;98%
3-isothiocyanato-1-(naphthalen-2-ylmethyl)indolin-2-one

3-isothiocyanato-1-(naphthalen-2-ylmethyl)indolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 1-(naphthalen-2-ylmethyl)-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

diisopropyl 1-(naphthalen-2-ylmethyl)-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In diethyl ether at 0℃; for 0.0833333h; Inert atmosphere; enantioselective reaction;98%
3-isothiocyanato-1-(naphthalen-2-ylmethyl)indolin-2-one

3-isothiocyanato-1-(naphthalen-2-ylmethyl)indolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 5'-((1,2-bis(isopropoxycarbonyl)hydrazinyl)thio)-1-(naphthalen-2-ylmethyl)-2-oxospiro[indoline-3,3'-[1,2,4]triazole]-1',2'-dicarboxylate

diisopropyl 5'-((1,2-bis(isopropoxycarbonyl)hydrazinyl)thio)-1-(naphthalen-2-ylmethyl)-2-oxospiro[indoline-3,3'-[1,2,4]triazole]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In toluene at 0℃; for 0.0833333h; Inert atmosphere; enantioselective reaction;98%
1-benzyl-3-isothiocyanato-5-methoxyindolin-2-one

1-benzyl-3-isothiocyanato-5-methoxyindolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 1-benzyl-5'-{[1,2-bis(isopropoxycarbonyl)hydrazinyl]thio}-5-methoxy-2-oxospiro[indoline-3,3'-[1,2,4]triazole]-1',2'-dicarboxylate

diisopropyl 1-benzyl-5'-{[1,2-bis(isopropoxycarbonyl)hydrazinyl]thio}-5-methoxy-2-oxospiro[indoline-3,3'-[1,2,4]triazole]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In toluene at 0℃; for 0.0833333h; Inert atmosphere; enantioselective reaction;98%
propionaldehyde
123-38-6

propionaldehyde

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 1-propionylhydrazine-1,2-dicarboxylate

diisopropyl 1-propionylhydrazine-1,2-dicarboxylate

Conditions
ConditionsYield
dirhodium tetraacetate In ethyl acetate at 25℃; for 12h;97%
1-benzyl-3-isothiocyanato-5-methylindolin-2-one
1450988-91-6

1-benzyl-3-isothiocyanato-5-methylindolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 1-benzyl-5-methyl-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

diisopropyl 1-benzyl-5-methyl-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In diethyl ether at 0℃; for 0.0833333h; Inert atmosphere; enantioselective reaction;97%
1-benzyl-3-isothiocyanato-6-methylindolin-2-one

1-benzyl-3-isothiocyanato-6-methylindolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 1-benzyl-6-methyl-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

diisopropyl 1-benzyl-6-methyl-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In diethyl ether at 0℃; for 0.0833333h; Inert atmosphere; enantioselective reaction;97%
(E)-3-(anthracen-10-yl)-1-(4-chlorophenyl)prop-2-en-1-one
57076-91-2

(E)-3-(anthracen-10-yl)-1-(4-chlorophenyl)prop-2-en-1-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

C31H29ClN2O4

C31H29ClN2O4

Conditions
ConditionsYield
With triphenylphosphine In toluene for 3h; Heating;96%
3-[5-(2-Hydroxy-ethoxy)-indol-1-yl]-3-phenyl-propionic acid ethyl ester
445490-67-5

3-[5-(2-Hydroxy-ethoxy)-indol-1-yl]-3-phenyl-propionic acid ethyl ester

N-hydroxyphthalimide
524-38-9

N-hydroxyphthalimide

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

3-{5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-ethoxy]-indol-1-yl}-3-phenyl-propionic acid ethyl ester
445490-68-6

3-{5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-ethoxy]-indol-1-yl}-3-phenyl-propionic acid ethyl ester

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran96%
...Expand
N,N-di(tert-butoxycarbonyl)hydroxylamine
85006-25-3

N,N-di(tert-butoxycarbonyl)hydroxylamine

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

(E)-3-{3-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethoxy]-phenyl}-pent-2-en-1-ol
174258-43-6

(E)-3-{3-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethoxy]-phenyl}-pent-2-en-1-ol

(E)-N-tert-Butoxycarbonyloxy-(3-{3-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethoxy]-phenyl}-pent-2-enyl)-carbamic acid tert-butyl ester
174258-44-7

(E)-N-tert-Butoxycarbonyloxy-(3-{3-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethoxy]-phenyl}-pent-2-enyl)-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran96%
...Expand
C17H17ON

C17H17ON

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

C25H31N3O4
1004974-22-4

C25H31N3O4

Conditions
ConditionsYield
With triphenylphosphine In toluene for 2h; Heating;96%
diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

4,4'-Dichlorobenzophenone
90-98-2

4,4'-Dichlorobenzophenone

diisopropyl 2-[bis(4-chlorophenyl)methylene]hydrazine-1,1-dicarboxylate
1041432-63-6

diisopropyl 2-[bis(4-chlorophenyl)methylene]hydrazine-1,1-dicarboxylate

Conditions
ConditionsYield
With triphenylphosphine In toluene at 110℃; for 12h;96%
1-benzyl-6-chloro-3-isothiocyanatoindolin-2-one

1-benzyl-6-chloro-3-isothiocyanatoindolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 1-benzyl-5'-{[1,2-bis(isopropoxycarbonyl)hydrazinyl]thio}-6-chloro-2-oxospiro[indoline-3,3'-[1,2,4]triazole]-1',2'-dicarboxylate

diisopropyl 1-benzyl-5'-{[1,2-bis(isopropoxycarbonyl)hydrazinyl]thio}-6-chloro-2-oxospiro[indoline-3,3'-[1,2,4]triazole]-1',2'-dicarboxylate

Conditions
ConditionsYield
With (DHQD)2PHAL In toluene at 0℃; for 0.0833333h; Inert atmosphere; enantioselective reaction;96%
1-benzyl-3-isothiocyanatoindolin-2-one
1287715-31-4

1-benzyl-3-isothiocyanatoindolin-2-one

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

diisopropyl 1-benzyl-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

diisopropyl 1-benzyl-2-oxo-5'-thioxospiro[indoline-3,3'-[1,2,4]triazolidine]-1',2'-dicarboxylate

Conditions
ConditionsYield
With C31H32N2O2 In tetrahydrofuran at 20℃; for 0.0833333h; Reagent/catalyst; Solvent; Inert atmosphere;96%
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

1-methylethyl 4,5-dihydro-3-(1-methylethoxy)-4-phenyl-5-thioxo-1H-1,2,4-triazole-1-carboxylate

1-methylethyl 4,5-dihydro-3-(1-methylethoxy)-4-phenyl-5-thioxo-1H-1,2,4-triazole-1-carboxylate

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane at 20℃; for 1h;95%
diisopropyl (E)-azodicarboxylate
2446-83-5

diisopropyl (E)-azodicarboxylate

(E)-1-(4-chlorophenyl)-3-(naphthalen-2-yl)prop-2-en-1-one

(E)-1-(4-chlorophenyl)-3-(naphthalen-2-yl)prop-2-en-1-one

C27H27ClN2O4

C27H27ClN2O4

Conditions
ConditionsYield
With triphenylphosphine In toluene for 3h; Heating;95%

Diisopropyl azodicarboxylate Specification

Diisopropyl azodicarboxylate, with its cas register number 2446-83-5, is a kind of orange crystal or liquid. It also can be called 1,2-diazenedicarboxylic acid, bis(1-methylethyl) ester, (E)-; Diisopropyl (E)-1,2-diazenedicarboxylate; Diisopropyl (E)-diazene-1,2-dicarboxylate; Dipropan-2-yl-(E)-diazen-1,2-dicarboxylat and Azodicarboxylic Acid Diisopropyl Ester. Diisopropyl azodicarboxylate  should be stored in shady and cool warehouse and mainly used as pharmaceutical Intermediates.

Physical properties about Diisopropyl azodicarboxylate are: (1)ACD/LogP: 2.541; (2)ACD/LogD (pH 5.5): 2.54; (3)ACD/LogD (pH 7.4): 2.54; (4)ACD/BCF (pH 5.5): 50.29; (5)ACD/BCF (pH 7.4): 50.29; (6)ACD/KOC (pH 5.5): 574.83; (7)ACD/KOC (pH 7.4): 574.83; (8)#H bond acceptors:6; (9)#Freely Rotating Bonds: 6; (10)Index of Refraction: 1.475; (11)Molar Refractivity: 49.261 cm3; (12)Molar Volume: 174.886 cm3; (13)Polarizability: 19.529 10-24cm3; (14)Surface Tension: 34.0149993896484 dyne/cm; (15)Density: 1.156 g/cm3; (16)Flash Point: 106.111 °C; (17)Enthalpy of Vaporization: 51.558 kJ/mol; (18)Boiling Point: 277.038 °C at 760 mmHg; (19)Vapour Pressure: 0.00499999988824129 mmHg at 25°C

Uses of Diisopropyl azodicarboxylate: Diisopropyl azodicarboxylate is used as a reagent in the production of many organic compounds. It is often used is in the Mitsunobu reaction where it serves as an oxidant of Triphenylphosphine to Triphenylphosphine oxide. It has also be used to generate aza-Baylis-Hillman adducts with acrylates.It can also serve as a selective deprotectant of N-benzyl groups in the presence of other protecting groups.

When you are using this chemical, please be cautious about it as the following:
1. Wear suitable protective clothing;
2. Avoid release to the environment. Refer to special instructions safety data sheet;
3. Wear suitable protective clothing, gloves and eye/face protection;
4. Do not empty into drains;
5. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C8H14N2O4/c1-5(2)13-7(11)9-10-8(12)14-6(3)4/h5-6H,1-4H3/b10-9+;
(2)InChIKey=VVWRJUBEIPHGQF-MDZDMXLPSA-N;
(3)SmilesC(\N=N\C(=O)OC(C)C)(=O)OC(C)C;

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