Basic information
- Name:
Diisopropyl azodicarboxylate
- CAS No.:
2446-83-5
- Molecular Structure:

- 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:
Xn,
Xi,
N,
F- Risk Codes:
- 36/38-51/53-5-43-36/37/38-11-48/20/22-40
- Safety Description:
- 36-61-47A-36/37/39-29-26-16-60 Details
- Transport Information:
- UN 3082 9/PG 3
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Chemistry
IUPAC Name: propan-2-yl (NE)-N-propan-2-yloxycarbonyliminocarbamate
Empirical Formula: C8H14N2O4
Molecular Weight: 202.2078g/mol
EINECS: 219-502-8
Structure of Diisopropyl azodicarboxylate (CAS NO.2446-83-5):

Index of Refraction: 1.475
Molar Refractivity: 49.26 cm3
Molar Volume: 174.8 cm3
Polarizability: 19.52×10-24cm3
Surface Tension: 34 dyne/cm
Density: 1.15 g/cm3
Flash Point: 106.1 °C
Enthalpy of Vaporization: 51.56 kJ/mol
Melting Point: 3-5 °C
Boiling Point: 277 °C at 760 mmHg
Vapour Pressure: 0.00463 mmHg at 25°C
Water Solubility: insoluble
Sensitive: Light Sensitive
Product Categories: Aromatic Esters
Canonical SMILES: CC(C)OC(=O)N=NC(=O)OC(C)C
Isomeric SMILES: CC(C)OC(=O)/N=N/C(=O)OC(C)C
InChI: InChI=1S/C8H14N2O4/c1-5(2)13-7(11)9-10-8(12)14-6(3)4/h5-6H,1-4H3/b10-9+
InChIKey: VVWRJUBEIPHGQF-MDZDMXLPSA-N
Uses
Diisopropyl azodicarboxylate (CAS NO.2446-83-5) 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.
Safety Profile
Hazard Codes:
Xn,
Xi,
N,
F
Risk Statements:
36/38: Irritating to eyes and skin
51/53: Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
5: Heating may cause an explosion
43: May cause sensitization by skin contact
36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements:
36/37/39: Wear suitable protective clothing, gloves and eye/face protection
26: In case of contact with eyes, rinse immediately with plenty of WATER and seek medical advice
29: Do not empty into drains
RIDADR:UN 3082 9/PG 3
WGK Germany:1
Hazard Note:Harmful/Irritant
HazardClass:9
PackingGroup:III
Specification
Diisopropyl azodicarboxylate , its cas register number is 2446-83-5. 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 ; Azodicarboxylic Acid Diisopropyl Ester . Diisopropyl azodicarboxylate (CAS NO.2446-83-5) is a clear orange liquid.

