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2446-83-5

Basic Information
CAS No.: 2446-83-5
Name: Diisopropyl azodicarboxylate
Article Data: 11
Molecular Structure:
Molecular Structure of 2446-83-5 (Diisopropyl azodicarboxylate)
Formula: C8H14N2O4
Molecular Weight: 202.21
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);
EINECS: 219-502-8
Density: 1.15 g/cm3
Melting Point: 3-5 °C
Boiling Point: 277 °C at 760 mmHg
Flash Point: 106.1 °C
Solubility: insoluble in water
Appearance: clear orange liquid
Hazard Symbols: HarmfulXn, IrritantXi, DangerousN, FlammableF
Risk Codes: 36/38-51/53-5-43-36/37/38-11-48/20/22-40
Safety: 36-61-47A-36/37/39-29-26-16-60
Transport Information: UN 3082 9/PG 3
PSA: 77.32000
LogP: 2.52860
Synthetic route

ethyl acetate n-hexane

103057-44-9

N-(tert-butoxycarbonyl)-3-hydroxypyrrolidine

2446-83-5

diisopropyl (E)-azodicarboxylate

507-09-5

thioacetic acid

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

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran100%

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

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

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

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

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

3-isothiocyanato-1-methylindolin-2-one

2446-83-5

diisopropyl (E)-azodicarboxylate

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%
1422555-11-0

3-isothiocyanato-1-propylindolin-2-one

2446-83-5

diisopropyl (E)-azodicarboxylate

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%
1354636-91-1

3-isothiocyanato-1-phenylindolin-2-one

2446-83-5

diisopropyl (E)-azodicarboxylate

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%
1287715-31-4

1-benzyl-3-isothiocyanatoindolin-2-one

2446-83-5

diisopropyl (E)-azodicarboxylate

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%
621-29-4

3-tolyl isocyanate

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

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

phenyl isocyanate

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

Conditions
ConditionsYield
With triphenylphosphine In dichloromethane at 20℃; for 1h;98%
6742-25-2

1-oxoindane-2-carboxylic acid ethyl ester

2446-83-5

diisopropyl (E)-azodicarboxylate

C20H26N2O7

Conditions
ConditionsYield
chiral palladium complex In methanol at 20℃; for 0.5h;98%
Raw Materials
19740-72-8
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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;