Diisopropyl azodicarboxylate
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=N/C(=O)OC(C)C |
| InChIKey | VVWRJUBEIPHGQF-MDZDMXLPSA-N |
| PubChem CID | 5363146 |
| EC No. | 219-502-8 |
| DTXSID | DTXSID50894754 |
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 |
| Physical Description | Orange liquid[Merck Index] Pungent odor[Alfa Aesar MSDS] |
| 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
| GHS classification | This chemical does not meet GHS hazard criteria for 35.9% (52 of 145) of reports.WarningH315 (62.8%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (62.8%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (61.4%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]H373 (54.5%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]H411 (61.4%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]P260, P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 145 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 52 of 145 reports by companies.There are 20 notifications provided by 93 of 145 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatory information | Status: Active Update: 02-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/23916Diisopropylazodicarboxylate: Does not have an individual approval but may be used under an appropriate group standard |
| Hazards summary | A skin, respiratory tract, and strong eye irritant[Alfa Aesar MSDS] See Diethyl azodicarboxylate. |
| Hazard Classes and Categories | Skin Irrit. 2 (62.8%)Eye Irrit. 2 (62.8%)STOT SE 3 (61.4%)STOT RE 2 (54.5%)Aquatic Chronic 2 (61.4%) |
| 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.