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2446-83-5 molecular structure
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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 and InChIs

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

Cite this record

CBID:74363 http://www.chembase.cn/molecule-74363.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

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

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 1.6064495  LogD (pH = 7.4) 1.6064495 
Log P 1.6064495  Molar Refractivity 47.3138 cm3
Polarizability 18.836767 Å3 Polar Surface Area 77.32 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
insoluble in water expand Show data source
Melting Point
3-5 °C expand Show data source
3-5°C expand Show data source
3-5°C expand Show data source
Boiling Point
74-75°C/0.3mm expand Show data source
74-75°C/0.3mm expand Show data source
75 °C at 0.25 mmHg expand Show data source
75 °C/0.25 mmHg(lit.) expand Show data source
Flash Point
106 °C expand Show data source
106°C expand Show data source
106°C expand Show data source
160°C(320°F) expand Show data source
222.8 °F expand Show data source
223 °F expand Show data source
Density
1.027 expand Show data source
1.027 g/cm3 expand Show data source
1.027 g/mL at 25 °C(lit.) expand Show data source
Refractive Index
1.42 expand Show data source
1.4200 expand Show data source
n20/D 1.420 expand Show data source
n20/D 1.420(lit.) expand Show data source
Storage Warning
Harmful/Irritant/Keep Cold/Store under Argon expand Show data source
Light Sensitive expand Show data source
European Hazard Symbols
Env. Danger (N) expand Show data source
Flammable (F) expand Show data source
Irritant (Xi) expand Show data source
Nature polluting Nature polluting (N) expand Show data source
Irritant Irritant (Xi) expand Show data source
Harmful Harmful (Xn) expand Show data source
UN Number
3082 expand Show data source
UN3082 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
2 expand Show data source
Hazard Class
9 expand Show data source
Packing Group
3 expand Show data source
III expand Show data source
Risk Statements
36/37/38-40-48/20/22-51/53 expand Show data source
36/37/38-51/53 expand Show data source
36/38-51/53 expand Show data source
R5, R11, R36, R37, R38, R43, R51, R53 expand Show data source
Safety Statements
26-36/37-61 expand Show data source
26-37-61 expand Show data source
26-60 expand Show data source
S16, S26, S29, S36, S37, S39, S47, S61 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS09 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335-H351-H373-H411 expand Show data source
H315-H319-H335-H411-H401 expand Show data source
GHS Precautionary statements
P261-P273-P281-P305 + P351 + P338 expand Show data source
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
RID/ADR
UN 3082 9/PG 3 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥94% (GC) expand Show data source
94% expand Show data source
95+% expand Show data source
98% expand Show data source
Grade
technical expand Show data source
Impurities
≤2% dichloromethane expand Show data source
Linear Formula
(CH3)2CHOOCN=NCOOCH(CH3)2 expand Show data source

DETAILS

DETAILS

Apollo Scientific Apollo Scientific Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
Apollo Scientific Ltd - OR0923 external link
Alternative to DEAD
Sigma Aldrich - 225541 external link
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 external link
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

REFERENCES

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  • • 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).
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PATENTS

PATENTS

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INTERNET

INTERNET

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