N-{[(2,2,2-trichloroethoxy)carbonyl]imino}(2,2,2-trichloroethoxy)formamide

• ChemBase ID: 146767
• Molecular Formular: C6H4Cl6N2O4
• Molecular Mass: 380.82496
• Monoisotopic Mass: 377.8302227
• SMILES: C(C(Cl)(Cl)Cl)OC(=O)/N=N/C(=O)OCC(Cl)(Cl)Cl
• Canonical SMILES: O=C(/N=N/C(=O)OCC(Cl)(Cl)Cl)OCC(Cl)(Cl)Cl
• InChI: InChI=1S/C6H4Cl6N2O4/c7-5(8,9)1-17-3(15)13-14-4(16)18-2-6(10,11)12/h1-2H2
• InChIKey: LIEOEYTUTSDYKB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{[(2,2,2-trichloroethoxy)carbonyl]imino}(2,2,2-trichloroethoxy)formamide
• IUPAC Traditional name: N-{[(2,2,2-trichloroethoxy)carbonyl]imino}(2,2,2-trichloroethoxy)formamide
• Synonyms: Azodicarboxylic acid bis(2,2,2-trichloroethyl ester); Bis(2,2,2-trichloroethyl) azodicarboxylate; 偶氮二甲酸二(2,2,2-三氯乙基)酯; 偶氮基二羧酸双(2,2,2-三氯乙酯)

Database IDs

• CAS Number: 38857-88-4
• MDL Number: MFCD00010607
• Beilstein Number: 2141527
• PubChem SID: 162240959; 24857539; 24847273
• PubChem CID: 6183558

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 3.2099955
• LogD (pH = 7.4): 3.2099955
• Log P: 3.2099955
• Molar Refractivity: 68.888 cm^3
• Polarizability: 27.041348 Å^3
• Polar Surface Area: 77.32 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 109-111 °C; 109-111 °C(lit.)

Safety Information

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

Product Information

• Purity: ≥97%; ≥97.0% (H-NMR)
• Grade: purum
• Linear Formula: CCl3CH2OCON=NCOOCH2CCl3

DETAILS

Sigma Aldrich - 291536

Packaging
5 g in glass bottle
Application
Used in the synthesis of acid- and base-sensitive azo compounds and in Diels-Alder cycloadditions.1

Sigma Aldrich - 11623

Other Notes
Stable, crystalline ester of azodicarboxylate with many advantages over other esters of this diacid: the trichloroethyl esters in reaction products can be removed under neutral conditions, the reagent is more reactive in cycloaddition reactions1,2,3; electrophilic aromatic substitution to give hydrazines or amines4