Diisopropyl diazene-1,2-dicarboxylate
DIAD · Diisopropyl diazene-1,2-dicarboxylate · diisopropyl (E)-diazene-1,2-dicarboxylate · diisopropyl azodiformate · Disopropyl Azodicarboxylate · AZODICARBONIC ACID DIISOPROPYL ESTER · (E)-diisopropyl diazene-1,2-dicarboxylate · Diisopropyl azodicarboxylate [DIAD]
Identifiers & Physical Properties
| CAS No. | 2446-83-5 |
|---|---|
| Molecular formula | C8H14N2O4 |
| Average molar mass | 202.21 g/mol |
| Monoisotopic mass | 202.09535693 g/mol |
| SMILES | CC(C)OC(=O)N=NC(=O)OC(C)C |
| InChIKey | VVWRJUBEIPHGQF-UHFFFAOYSA-N |
| PubChem CID | 75555 |
Chemical & Physical Properties
| XLogP | 2.6 |
|---|---|
| Topological polar surface area | 77.3 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 4 |
| Rotatable bonds | 4 |
| Heavy atoms | 14 |
| Formal charge | 0 |
| Complexity | 211 |
| Melting point | 3-5 °C |
| Boiling point | 75 °C/0.25 mmHg (lit.) |
| Density | 1.027 g/mL at 25 °C (lit.) |
| Vapor pressure | 1.04 hPa (20 °C) |
| Refractive index | n20/D 1.420(lit.) |
| Flash point | 223 °F |
| Storage conditions | Store below +30°C. |
| Solubility | Chloroform (Slightly), Ethyl Acetate (Slightly)insoluble |
| Physical state | Liquid |
| Color | Clear to slightly turbid yellow-orange to red |
| Sensitivity | Light Sensitive |
| BRN | 1912326 |
| InChI | InChI=1S/C8H14N2O4/c1-5(2)13-7(11)9-10-8(12)14-6(3)4/h5-6H,1-4H3 |
| InChIKey | VVWRJUBEIPHGQF-UHFFFAOYSA-N |
| SMILES | N(C(OC(C)C)=O)=NC(OC(C)C)=O |
| CAS DataBase Reference | 2446-83-5(CAS DataBase Reference) |
| FDA UNII | 7W701BXX4K |
| UNSPSC Code | 12352302 |
| NACRES | NA.22 |
| GHS pictogram | GHS07,GHS08,GHS09 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335-H351-H411 |
| GHS precautionary statements | P202-P261-P273-P302+P352-P305+P351+P338-P308+P313 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Hazard symbols | Xn,Xi,N,F |
| Risk statements (R) | 36/38-51/53-5-43-36/37/38-11-48/20/22-40 |
| Safety statements (S) | 36-61-47A-36/37/39-29-26-16-60-36/37 |
| UN transport number | UN 3082 9/PG 3 |
| Water hazard class (WGK) | 1 |
| F | 4.10-8 |
| Hazard Note | Harmful/Irritant |
| Hazard class | 9Aquatic Chronic 2Carc. 2Eye Irrit. 2Skin Irrit. 2STOT RE 2STOT SE 3 |
| Packing group | III |
| Customs code | 29270000 |
| Storage class | 10 - Combustible liquids |
| REACH registrations | Active |
Safety & Regulations
| F | 4.10-8 |
|---|---|
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 1 |
| UN transport number | UN 3082 9/PG 3 |
| Customs code | 29270000 |
| Risk statements (R) | 36/38-51/53-5-43-36/37/38-11-48/20/22-40 |
| Signal word | Warning |
| GHS pictogram | GHS07,GHS08,GHS09 |
| Hazard symbols | Xn,Xi,N,F |
| hazard_note | Harmful/Irritant |
| Safety statements (S) | 36-61-47A-36/37/39-29-26-16-60-36/37 |
| Hazard class | 9Aquatic Chronic 2Carc. 2Eye Irrit. 2Skin Irrit. 2STOT RE 2STOT SE 3 |
| Storage class | 10 - Combustible liquids |
| Packing group | III |
| Target organs | Respiratory system |
| GHS hazard statements | H315-H319-H335-H351-H411 |
| REACH registrations | Active |
| GHS precautionary statements | P202-P261-P273-P302+P352-P305+P351+P338-P308+P313 |
Applications & Uses
Uses
It can be used as dye intermediates, pharmaceutical intermediates, organic synthesis reagents, and the foaming agent of the rubber plastics liquid. Isopropyl azodicarboxylate can be used for the liquid foaming agent of vinyl resin. It can be used to make light-colored vinyl foam. It has a uniform pore structure with different formulations and processing conditions giving foam of either closed pore or open pore. It can also be used as pharmaceutical intermediates, and organic synthesis reagents.
Uses
Diisopropyl Azodicarboxylate is an azodicarboxylic acid derivative used as a reagent in the production of many organic compounds. Diisopropyl Azodicarboxylate is commonly used as an oxidizer in Mitsun obu reactions and can also serve as a selective deprotectant of N-benzyl groups in the presence of other protecting groups.
Uses
Diisopropyl azodicarboxylate is used as an important reagent in the production of many organic compounds. It is used in association with triphenyl phosphine in Mitsunobu reaction of alcohols, acids and amides. It acts as reactant in the preparation of chromenes resembling classical cannabinoids, norbornene-based guanidine-rich polymers and acceptor-donor-acceptor organic dyes.
General Description
Reacted with dioxaphosphorinanes and iron catalyst to generate rearranged phosphonium ylide products.