N-{[(propan-2-yloxy)carbonyl]imino}(propan-2-yloxy)formamide

• ChemBase ID: 74363
• Molecular Formular: C8H14N2O4
• Molecular Mass: 202.20776
• Monoisotopic Mass: 202.09535694
• SMILES: N(=N\C(=O)OC(C)C)/C(=O)OC(C)C
• Canonical SMILES: CC(OC(=O)/N=N/C(=O)OC(C)C)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{[(propan-2-yloxy)carbonyl]imino}(propan-2-yloxy)formamide; (E)-N-{[(propan-2-yloxy)carbonyl]imino}(propan-2-yloxy)formamide
• IUPAC Traditional name: diisopropyl azodicarboxylate; N-[(isopropoxycarbonyl)imino]isopropoxyformamide
• Synonyms: Azodicarboxylic acid diisopropyl ester; Diisopropyl azodicarboxylate; Diisopropyl azodiformate; Diisopropyl azodicarboxylate; DIAD; Diprop-2-yl diazene-1,2-dicarboxylate; Bis(isopropyl) azodicarboxylate 96%; Diisopropyl diazene-1,2-dicarboxylate; 偶氮二甲酸二异丙酯

Database IDs

• CAS Number: 2446-83-5
• EC Number: 219-502-8
• MDL Number: MFCD00008875
• Beilstein Number: 1912326
• PubChem SID: 24847276; 24853505; 162039282
• PubChem CID: 5363146
• Chemspider ID: 4515532
• Wikipedia Title: Diisopropyl_azodicarboxylate

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.6064495
• LogD (pH = 7.4): 1.6064495
• Log P: 1.6064495
• Molar Refractivity: 47.3138 cm^3
• Polarizability: 18.836767 Å^3
• Polar Surface Area: 77.32 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: insoluble in water
• Melting Point: 3-5 °C; 3-5°C; 3-5°C
• Boiling Point: 74-75°C/0.3mm; 74-75°C/0.3mm; 75 °C at 0.25 mmHg; 75 °C/0.25 mmHg(lit.)
• Flash Point: 106 °C; 106°C; 106°C; 160°C(320°F); 222.8 °F; 223 °F
• Density: 1.027; 1.027 g/cm^3; 1.027 g/mL at 25 °C(lit.)
• Refractive Index: 1.42; 1.4200; n20/D 1.420; n20/D 1.420(lit.)

Safety Information

• Storage Warning: Harmful/Irritant/Keep Cold/Store under Argon; Light Sensitive
• European Hazard Symbols: Env. Danger (N); Flammable (F); Irritant (Xi); Nature polluting (N); Irritant (Xi); Harmful (Xn)
• UN Number: 3082; UN3082
• German water hazard class: 1; 2
• Hazard Class: 9
• Packing Group: 3; III
• Risk Statements: 36/37/38-40-48/20/22-51/53; 36/37/38-51/53; 36/38-51/53; R5, R11, R36, R37, R38, R43, R51, R53
• Safety Statements: 26-36/37-61; 26-37-61; 26-60; S16, S26, S29, S36, S37, S39, S47, S61
• TSCA Listed: 否
• GHS Pictograms: GHS07; GHS08; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335-H351-H373-H411; H315-H319-H335-H411-H401
• GHS Precautionary statements: P261-P273-P281-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3082 9/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥94% (GC); 94%; 95+%; 98%
• Grade: technical
• Impurities: ≤2% dichloromethane
• Linear Formula: (CH3)2CHOOCN=NCOOCH(CH3)2

DETAILS

Apollo Scientific Ltd - OR0923

Alternative to DEAD

Sigma Aldrich - 225541

General description
Reacted with dioxaphosphorinanes and iron catalyst to generate rearranged phosphonium ylide products.8
Packaging
25, 100 g in poly bottle
5 g in glass bottle
Application
Reactant for preparation of:
• Chromenes resembling classical cannabinoids1
• MK-3281 inhibitor of the hepatitis C virus NS5B polymerase2
• Norbornene-based guanidine-rich polymers as mimcs of cell-penetrating peptides (CPP)3
• Analogues of the Pseudomonas aeruginosa quorum-sensing molecule N-(3-Oxododecanoyl)-l-homoserine lactone with immunosuppressive but non-LasR-inducing properties4
• Acceptor-donor-acceptor organic dyes for dye-sensitized solar cells5
• 1,3-dioxane-2-carboxylic acid derivatives as PPARα/γ dual agonists6
• Hydrazinophosphonates and hydrazinobisphosphonates via Mitsunobu and Arbuzov-type multicomponent application of the Morrison-Brunn-Huisgen betaine7

Sigma Aldrich - 11626

Other Notes
Reagent used in the Mitsunobu reaction, reviews8,9
Application
Reactant for preparation of:
• Chromenes resembling classical cannabinoids1
• MK-3281 inhibitor of the hepatitis C virus NS5B polymerase2
• Norbornene-based guanidine-rich polymers as mimcs of cell-penetrating peptides (CPP)3
• Analogues of the Pseudomonas aeruginosa quorum-sensing molecule N-(3-Oxododecanoyl)-l-homoserine lactone with immunosuppressive but non-LasR-inducing properties4
• Acceptor-donor-acceptor organic dyes for dye-sensitized solar cells5
• 1,3-dioxane-2-carboxylic acid derivatives as PPARα/γ dual agonists6
• Hydrazinophosphonates and hydrazinobisphosphonates via Mitsunobu and Arbuzov-type multicomponent application of the Morrison-Brunn-Huisgen betaine7

REFERENCES

• Alternative to 'DEAD' (Diethyl azodicarboxylate, L19348), more stable at elevated temperatures. DIAD has been used in combination with Triphenylphosphine, L02502, in Mitsunobu-type reactions of alcohols with acids, amides, etc. In the Mitsunobu esterification reaction yields improve with increasing acid strength. For a discussion, see: J. Org. Chem., 61, 2967 (1996).
• For use in the regioselective, stereospecific Mitsunobu azidation of 1,2- and 1,3-diols with Trimethylsilyl azide, L00173, see: J. Org. Chem., 64, 6049 (1999).
• An extremely mild route to isocyanates involves treatment of an aliphtic primary amine with CO₂ to form the carbamate salt which reacts at low temperature with the Mitsunobu reagent from DIAD and PPh₃, giving the isocyanate in high yield. 2,6-Dialkylanilines also undergo the reaction if Bu₃P is used; the reaction failed with other anilines: Tetrahedron Lett., 40, 363 (1999).
• For reviews of the Mitsunobu reaction, see: Synthesis, 1 (1981); Org. React., 42, 335 (1992); Org. Prep. Proced. Int., 28, 127 (1996). For a brief feature on synthetic uses of Mitsunobu reagents, see: Synlett, 1221 (2003).