Diisopropyl diazene-1,2-dicarboxylate (HCID 75555)

Names & identifiers

Preferred name: Diisopropyl diazene-1,2-dicarboxylate
IUPAC: propan-2-yl N-propan-2-yloxycarbonyliminocarbamate
English name: Diisopropyl azodicarboxylate
Molecular formula: C8H14N2O4
Molecular weight: 202.21

Names & synonyms

DIADDiisopropyl diazene-1,2-dicarboxylateAzodicarboxylic Acid Diisopropyl EsterDiisopropyl (E)-diazene-1,2-dicarboxylateDiisopropyl (E)-1,2-diazenedicarboxylate(E)-diisopropyl diazene-1,2-dicarboxylateisopropyl N-isopropoxycarbonyliminocarbamate1,2-Diazenedicarboxylic Acid 1,2-Bis(1-methylethyl) Ester; Azodiformic Acid Diisopropyl Ester; DIAD; Diisopropyl Azodiformate; Diisopropyl diazodicarboxylate;diisopropylazocarboxylateisopropyl (NE)-N-isopropoxycarbonyliminocarbamateisopropyl (NZ)-N-isopropoxycarbonyliminocarbamatediisopropyazodicarboxylate

Show more names

diisopropyl azodiformateDisopropyl AzodicarboxylateAZODICARBONIC ACID DIISOPROPYL ESTERDiisopropyl azodicarboxylate [DIAD]Propan-2-yl N-propan-2-yloxycarbonyliminocarbamateDIAD(Diisopropylazodicarboxylate)

diisopropylazodicaroxylatediisoproylazodicarboxylateDiisopyl azodicarboxylateDiisopropylazodicarboxlatediisopropyl azocarboxylatediisoproyl azodicaroxylatediisopropyl azodicaboxylatediisopropyl azodicaroxylate

Database identifiers

CAS: 2446-83-5
PubChem CID: 75555

Properties

Computed structural properties

XLogP: 2.6
Topological polar surface area: 77.3 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 4
Heavy atoms: 14
Formal charge: 0
Complexity: 211

Physicochemical properties

Melting point: 3 · 3-5 °C
Boiling point: 75 °C/0.25 · 75 °C/0.25 mmHg (lit.)
Density: 1.027 g/mL · 1.027 g/mL at 25 °C (lit.)
vapor pressure: 1.04 hPa · 1.04 hPa (20 °C)
refractive index: 20 · n20/D 1.420(lit.)
Flash point: 223 °F · 223 °F
storage temp.: 30 °C · Store below +30°C.
solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
form: Liquid
color: Clear to slightly turbid yellow-orange to red
Water Solubility: insoluble
Sensitive: Light Sensitive
BRN: 1912326 · 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 · 2446-83-5(CAS DataBase Reference)
FDA UNII: 7 W701BXX4K · 7W701BXX4K
UNSPSC Code: 12352302 · 12352302
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07,GHS08,GHS09
Signal word: Warning
Hazard statements: 315 · H315-H319-H335-H351-H411
Precautionary statements: 202 · P202-P261-P273-P302+P352-P305+P351+P338-P308+P313
target organs: Respiratory system
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: Xn,Xi,N,F
Risk Statements: 36 · 36/38-51/53-5-43-36/37/38-11-48/20/22-40
Safety Statements: 36 · 36-61-47A-36/37/39-29-26-16-60-36/37
RIDADR: 3082 · UN 3082 9/PG 3
WGK Germany: 1 · 1
F: 4.1 · 4.10-8
Hazard Note: Harmful/Irritant
HazardClass: 9 · 9
PackingGroup: III
HS Code: 29270000 · 29270000
Storage Class: 10 · 10 - Combustible liquids
Hazard Classifications: 2 Carc · Aquatic Chronic 2Carc. 2Eye Irrit. 2Skin Irrit. 2STOT RE 2STOT SE 3
REACH Registrations: Active

Safety & regulation

Safety data

F: 4.10-8
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 1
ridadr: UN 3082 9/PG 3
hs_code: 29270000
risk_code: 36/38-51/53-5-43-36/37/38-11-48/20/22-40
Signal word: Warning
Symbol(GHS): GHS07,GHS08,GHS09
hazard_code: Xn,Xi,N,F
hazard_note: Harmful/Irritant
safety_code: 36-61-47A-36/37/39-29-26-16-60-36/37
hazard_class: 9
Storage Class: 10 - Combustible liquids
packing_group: III
target organs: Respiratory system
Hazard statements: H315-H319-H335-H351-H411
REACH Registrations: Active
Hazard Classifications: Aquatic Chronic 2Carc. 2Eye Irrit. 2Skin Irrit. 2STOT RE 2STOT SE 3
Precautionary statements: P202-P261-P273-P302+P352-P305+P351+P338-P308+P313

Chemistry & industry

Applications · 4 items

UsesIt 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.

UsesDiisopropyl 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.

UsesDiisopropyl 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 DescriptionReacted with dioxaphosphorinanes and iron catalyst to generate rearranged phosphonium ylide products.