N-formyl-N-sodioformamide

• ChemBase ID: 152067
• Molecular Formular: C2H2NNaO2
• Molecular Mass: 95.03255
• Monoisotopic Mass: 94.99832259
• SMILES: C(=O)N(C=O)[Na]
• Canonical SMILES: O=CN(C=O)[Na]
• InChI: InChI=1S/C2H3NO2.Na/c4-1-3-2-5;/h1-2H,(H,3,4,5);/q;+1/p-1
• InChIKey: QJXDSDLNUKLDBP-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: N-formyl-N-sodioformamide
• IUPAC Traditional name: N-formyl-N-sodioformamide
• Synonyms: Diformylimide sodium salt; Sodium diformylamide; 二甲酰亚氨基 钠盐; 二甲酰氨基钠

Database IDs

• CAS Number: 18197-26-7
• MDL Number: MFCD00145302
• Beilstein Number: 3567185
• PubChem SID: 24886201; 162246212
• PubChem CID: 10877056

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -2.4114
• LogD (pH = 7.4): -2.4114
• Log P: -2.4114
• Molar Refractivity: 14.2508 cm^3
• Polarizability: 7.507065 Å^3
• Polar Surface Area: 37.38 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

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

Product Information

• Purity: ≥97.0% (NT)
• Linear Formula: (HCO)2NNa

DETAILS

Sigma Aldrich - 71494

Other Notes
Modified Gabriel reagent for the synthesis of amines; mild hydrolysis to release the amine7,8,9
Packaging
25, 50 g in glass bottle
Application
Reactant for preparation of:
• Functionalized condensed benzazoles1
• α-ketoheterocycles as inhibitors of Leishmania mexicana cysteine protease CPB2
• INOS inhibitor PHA-399733 via Bucherer-Bergs hydantoin synthesis3
• Antibiotic resistance (C β-lactamase AmpC ) inhibitor analogues, with improved cell permeability properties4
• BINOL- and H8-BINOL-based aryl phosphites as ligands in palladium-catalyzed asymmetric allylation and amination reactions5
• Precursors of αVβ3 integrin antagonists6