N-({[(4-chlorophenyl)methoxy]carbonyl}imino)[(4-chlorophenyl)methoxy]formamide

• ChemBase ID: 140617
• Molecular Formular: C16H12Cl2N2O4
• Molecular Mass: 367.18348
• Monoisotopic Mass: 366.01741223
• SMILES: c1cc(ccc1COC(=O)/N=N/C(=O)OCc1ccc(cc1)Cl)Cl
• Canonical SMILES: O=C(/N=N/C(=O)OCc1ccc(cc1)Cl)OCc1ccc(cc1)Cl
• InChI: InChI=1S/C16H12Cl2N2O4/c17-13-5-1-11(2-6-13)9-23-15(21)19-20-16(22)24-10-12-3-7-14(18)8-4-12/h1-8H,9-10H2
• InChIKey: UIFGGABIJBWRMG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-({[(4-chlorophenyl)methoxy]carbonyl}imino)[(4-chlorophenyl)methoxy]formamide
• IUPAC Traditional name: N-({[(4-chlorophenyl)methoxy]carbonyl}imino)[(4-chlorophenyl)methoxy]formamide
• Synonyms: DCAD; Bis(4-chlorobenzyl)azodicarboxylate; Di-(4-chlorobenzyl)azodicarboxylate; 偶氮二甲酸二(对氯苄基)酯; 双(4-氯苄基)偶氮二甲酸酯

Database IDs

• CAS Number: 916320-82-6
• PubChem SID: 24885598; 162234858
• PubChem CID: 11990352

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 4.716719
• LogD (pH = 7.4): 4.716719
• Log P: 4.716719
• Molar Refractivity: 87.8138 cm^3
• Polarizability: 34.362698 Å^3
• Polar Surface Area: 77.32 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 108-112 °C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 43
• Safety Statements: 36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317
• GHS Precautionary statements: P280

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C16H12Cl2N2O4

DETAILS

Sigma Aldrich - 680850

Application
Di-(4-chlorobenzyl)azodicarboxylate (DCAD) is a novel, stable, solid alternative to DEAD and DIAD for a variety of Mitsunobu couplings giving a readily separable hydrazine byproduct that can be recycled.4
Reactant for preparation of:
• Amino thioesters via guanidine-catalyzed biomimetic enantioselective decarboxylative Mannich and amination reactions of malonic acid half thioesters1
• Hydroacylation reaction of aldehydes in Ionic liquid (IL) medium2
• DCAD (di-p-chlorobenzyl azodicarboxylate) for Mitsunobu coupling reactions3,4
Packaging
1, 10 g in glass bottle