(E)-N-[(ethoxycarbonyl)imino]ethoxyformamide

• ChemBase ID: 70308
• Molecular Formular: C6H10N2O4
• Molecular Mass: 174.1546
• Monoisotopic Mass: 174.06405681
• SMILES: N(=N\C(=O)OCC)/C(=O)OCC
• Canonical SMILES: CCOC(=O)/N=N/C(=O)OCC
• InChI: InChI=1S/C6H10N2O4/c1-3-11-5(9)7-8-6(10)12-4-2/h3-4H2,1-2H3/b8-7+
• InChIKey: FAMRKDQNMBBFBR-BQYQJAHWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (E)-N-[(ethoxycarbonyl)imino]ethoxyformamide; N-[(ethoxycarbonyl)imino]ethoxyformamide
• IUPAC Traditional name: diethyl azodicarboxylate; N-[(ethoxycarbonyl)imino]ethoxyformamide
• Synonyms: Diethyl azodicarboxylate; 1,2-Ethoxycarbonyl diazene; Diethyl diazene-1,2-dicarboxylate, 40% solution in toluene; 1,2-Ethoxycarbonyl diazene solution; DEAD; Diethoxycarbonyldiazene solution; Diethyl azodiformate solution; NSC 3474; NSC 679015; Unifoam AZ-AE 200; Diethyl azodicarboxylate solution; Diethyl azidoformate; Diazenedicarboxylic acid; Diethyl azo diformate; (E)-diethyl diazene-1,2-dicarboxylate; 1,2-Bis(ethoxycarbonyl) diazene; Diethyl diazene-1,2-dicarboxylate 97%; Diethyl azodicarboxylate; 1,2-Diazenedicarboxylic Acid 1,2-Diethyl Ester; Azodicarboxylic Acid Diethyl Ester; Diethoxycarbonyldiazene; Diethyl Azodiformate; Diethyl Diazenedicarboxylate; Diethyl Diazodicarboxylate; 偶氮二甲酸二乙酯 溶液; 偶氮二甲酸二乙酯

Database IDs

• CAS Number: 1972-28-7
• EC Number: 217-821-7
• MDL Number: MFCD00009103
• Beilstein Number: 908662
• PubChem SID: 162036031; 24847277; 24880080
• PubChem CID: 5462977
• Chemspider ID: 4510444
• Wikipedia Title: Diethyl_azodicarboxylate

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 0.77329946
• LogD (pH = 7.4): 0.77329946
• Log P: 0.77329946
• Molar Refractivity: 38.4762 cm^3
• Polarizability: 15.216925 Å^3
• Polar Surface Area: 77.32 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Orange to red to orange liquid
• Melting Point: 6 °C
• Boiling Point: 104.5 °C at 12 mm Hg; 106 °C/13 mmHg(lit.); 106°C/13mm; 106°C/13mm; 116-117 °C
• Flash Point: 105.8 °F; 113 °C; 235 °F; 41 °C; 41°C; 85 °C; 85°C; 85°C(185°F)
• Density: 0.956 g/mL at 25 °C; 0.96; 1.106; 1.106 g/mL at 25 °C(lit.); 1.11 g/cm^3
• Refractive Index: 1.420 (20 °C); 1.421; 1.4210; n20/D 1.43(lit.); n20/D 1.4690; n20/D 1.47

Safety Information

• Storage Warning: Air Sensitive; Highly Flammable/Harmful/Irritant/Teratogenic/Keep Cold; IRRITANT; Toxic/Harmful/Irritant/Air Sensitive/Store under Argon/Keep Cold
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 3379; UN2810
• German water hazard class: 3
• Hazard Class: 3; 6.1
• Packing Group: 1; III
• Risk Statements: 5-20-36/37/38; 5-21/22-36/37/38; 63-10-20-36/37/38-48/20-65; 63-5-10-20-36/37/38-48/20-65; R20 R21 R22 R36 R37 R38 R40 R44
• Safety Statements: 26-36/37-60; 26-36/37-62; 26-47; S15 S23 S26 S36
• TSCA Listed: false; 否
• GHS Pictograms: GHS02; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H242-H304-H315-H319-H335 + H336-H361d-H373; H226-H304-H315-H319-H335-H336-H361d-H373; H302-H312-H315-H319-H335-H227
• GHS Precautionary statements: P210-P305+P351+P338-P302+P352-P321-P405-P501A; P261-P281-P301 + P310-P305 + P351 + P338-P331
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3379 3/PG 1; UN REST
• Storage Temperature: 2-8°C

Product Information

• Purity: 85%; 95+%; 97%
• Concentration: ~40% in toluene (H-NMR); 40 wt. % in toluene
• Grade: purum; technical grade
• Linear Formula: C2H5OCON=NCOOC2H5

DETAILS

Sigma Aldrich - 563110

Application
A commonly used activating reagent in Mitsunobo reactions.9
Reactant for preparation of:
• Immunostimulants α-Galactosylceramides1
• Cellotriose and cellotetraose analogues as transition state mimics for mechanistic studies of cellulases2
• Bisubstrate inhibitors with molecular recognition at the active site of catechol-O-methyltransferase3
• Derivatives of F200 and S383 with cannabinoid CB1 receptor binding activities4
• Aza-β-lactams via NHC-catalyzed [2 + 2] cycloaddition with ketenes5Reagent for:
• Annulation of N-protected imines6
• α-thiocyanation of enolizable ketones with ammonium thiocyanate7
• Diels-Alder reactions8
General description
DOT Special Approval Submission is Under Review. Availability is Estimated as March 2012.
Packaging
100g unit contains ca. 40g DEAD solute
25g unit contains ca. 10g DEAD solute
25, 100 g in glass bottle
Warning
Toxic, Irritant, Flammable

Sigma Aldrich - 11627

Other Notes
Reagent used in the Mitsunobu reaction, reviews9,10,11
Application
Reactant for preparation of:
• Immunostimulants α-Galactosylceramides1
• Cellotriose and cellotetraose analogues as transition state mimics for mechanistic studies of cellulases2
• Bisubstrate inhibitors with molecular recognition at the active site of catechol-O-methyltransferase3
• Derivatives of F200 and S383 with cannabinoid CB1 receptor binding activities4
• Aza-β-lactams via NHC-catalyzed [2 + 2] cycloaddition with ketenes5Reagent for:
• Annulation of N-protected imines6
• α-thiocyanation of enolizable ketones with ammonium thiocyanate7
• Diels-Alder reactions8

Toronto Research Chemicals - D443765

A fluorescent CDK inhibitor for treatment of cancer.

REFERENCES

• Wilton, D., et al.: Biochem. J., 266, 435 (1990)
• Suzuki, K., et al.: J. Biol. Chem., 266, 18498 (1990)
• Wilson, W., et al.: Curr. Med. Chem., 7, 73 (1990)
• Details for esterification of (-)-menthol with 4-nitrobenzoic acid with stereoinversion: Org. Synth. Coll., 9, 607 (1998). For an example of its use to convert a secondary alcohol to an amine by reaction with phthalimide followed by hydrazinolysis, see: Org. Synth. Coll., 7, 501 (1990). For dehydration of Boc-L-serine to the cyclic anhydride (2-oxetanone), see: Org. Synth. Coll., 9, 24 (1998).
• ɑ-Amination of aldehydes can be effected in the presence of L-proline as an enantioselective catalyst, affording chiral ɑ-amino alcohols and ɑ-amino acids with good ee: Angew. Chem. Int. Ed., 41, 1790 (2002); for a similar reaction with scheme, see Dibenzyl azodicarboxylate, L19347.
• See also Di-tert-butyl azodicarboxylate, L00294, and Diisopropyl azodicarboxylate, L10386.
• Dehydrogenating agent and aza-dienophile. Oxidizes alcohols to aldehydes, thiols to disulfides and hydrazo to azo groups: J. Am. Chem. Soc., 88, 2328 (1966). Arylhydroxylamines are converted in high yield to nitroso compounds: Chem. Commun., 199 (1967).
• Undergoes pericyclic reactions with alkenes and dienes via both ene and Diels-Alder processes. For further details and references, see: Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, Ed., Wiley, Chichester (1995), vol. 3, p. 1790.
• In combination with Triphenylphosphine, L02502, is widely used in the Mitsunobu reaction for activation of primary and secondary alcohols by formation of the alkoxyphosphonium salts, which behave as versatile alkylating agents under mild S_N2 conditions: reactions normally proceed with inversion of configuration. For reviews, see: Synthesis, 1 (1981); Org. React., 42, 335 (1992); Org. Prep. Proced. Int., 28, 127 (1996); Synlett, 1221 (2003); Eur. J. Org. Chem., 2763 (2004):
  
• For study of the mechanism, see: J. Org. Chem., 67, 1751 (2002).
• Explosion risk by heating undiluted material.
• Secondary and tertiary amines have been dealkylated by reaction with DEAD under mild conditions, followed by acid hydrolysis: J. Org. Chem., 38, 1652 (1973).