N-{[(benzyloxy)carbonyl]imino}(benzyloxy)formamide

• ChemBase ID: 145900
• Molecular Formular: C16H14N2O4
• Molecular Mass: 298.29336
• Monoisotopic Mass: 298.09535694
• SMILES: c1ccc(cc1)COC(=O)/N=N/C(=O)OCc1ccccc1
• Canonical SMILES: O=C(/N=N/C(=O)OCc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C16H14N2O4/c19-15(21-11-13-7-3-1-4-8-13)17-18-16(20)22-12-14-9-5-2-6-10-14/h1-10H,11-12H2
• InChIKey: IRJKSAIGIYODAN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{[(benzyloxy)carbonyl]imino}(benzyloxy)formamide; (E)-N-{[(benzyloxy)carbonyl]imino}(benzyloxy)formamide
• IUPAC Traditional name: N-{[(benzyloxy)carbonyl]imino}benzyloxyformamide; (E)-N-{[(benzyloxy)carbonyl]imino}benzyloxyformamide
• Synonyms: Dibenzyl azodicarboxylate; Azodicarboxylic acid dibenzyl ester; DBAD; N-{[(benzyloxy)carbonyl]imino}(benzyloxy)formamide; Dibenzyl diazene-1,2-dicarboxylate; 偶氮二甲酸二苄酯; 偶氮二羟酸二苄酯

Database IDs

• CAS Number: 2449-05-0
• EC Number: 219-508-0
• MDL Number: MFCD00016737
• Beilstein Number: 2298734
• PubChem SID: 24850186; 162240100
• PubChem CID: 5387121

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.5086298
• LogD (pH = 7.4): 3.5086298
• Log P: 3.5086298
• Molar Refractivity: 78.2042 cm^3
• Polarizability: 30.527233 Å^3
• Polar Surface Area: 77.32 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 43 - 47°C; 43-47 °C(lit.); 43-47°C
• Flash Point: >110°C(230°F)
• Hydrophobicity(logP): 4.694

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: 90%; 95%; 95+%; 96%
• Grade: technical grade
• Linear Formula: C6H5CH2OCON=NCOOCH2C6H5

DETAILS

Sigma Aldrich - 166804

Packaging
5, 25 g in glass bottle

REFERENCES

• For the formation of functionalized ?-amino alcohols by the three-component asymmetric assembly with an aldehyde and a ketone, see: Org. Lett, 5, 1685 (2003).
• Aza-dienophile; the cycloaddition products can be debenzylated by hydrogenolysis: J. Am. Chem. Soc., 109, 285 (1987); 110, 5229 (1988); 111, 2995 (1989). Compare Di-tert-butyl azodicarboxylate, L00294, Diethyl azodicarboxylate, L19348, and Diisopropyl azodicarboxylate, L10386. Effects enantioselective ɑ-amination of aldehydes, mediated by L-Proline, A10199: J. Am. Chem. Soc., 124, 5656 (2002):