Tris(formylamino)methane

[4774-33-8] C4H7N3O3 (MW 145.14) InChI = 1S/C4H7N3O3/c8-1-5-4(6-2-9)7-3-10/h1-4H,(H,5,8)(H,6,9)(H,7,10) InChIKey = HNPCDFJZADHNHD-UHFFFAOYSA-N (a source for formamide; for 'N-formylformamidine (H2NCHNCHO)'; for the 'N-formylformimidoyl group (HCNHCHO)' as a building block in heterocyclic synthesis) Alternate Names: TRIFO; N,N′N″-methylidynetrisformamide; triformamidomethane. Physical Data: mp 162–164 °C (dec). Solubility: sol formamide; sol aprotic dipolar solvents such as DMF or DMA on heating. Form Supplied in: white crystals; commercially available. Analysis of Reagent Purity: melting point. Preparative Methods: Triethyl Orthoformate reacts with formamide under catalysis of mineral acids to give TRIFO (eq 1).2, 3 The reaction of excess formamide with inorganic and organic acyl chlorides such as PCl3, POCl3, SOCl2, acetyl chloride, benzoyl chloride, and ethyl chloroformate proceeds via iminium salts to afford TRIFO.2, 4, 5 Analogously, alkylating reagents such as dialkyl sulfates, alkyl sulfonates or triethyloxonium tetrafluoroborate transform formamide to TRIFO. Alkoxymethyleneiminium salts and formamidinium salts are intermediates in these reactions.2 Pure salts of this type are also converted to the reagent by formamide.2 Reaction of Dimethyl Sulfate with formamide is the easiest way to prepare TRIFO.2 (1) Handling, Storage, and Precautions: store at rt in closed bottles. Use in a fume hood.