N,N',N''-METHYLIDYNETRISFORMAMIDE Chemical Properties

Melting point:

170-172 °C (dec.)(lit.)

Boiling point:

720.5±55.0 °C(Predicted)

Density 

1.280±0.06 g/cm3(Predicted)

solubility 

water: soluble25mg/mL, clear, colorless

pka

12.69±0.23(Predicted)

form 

solid

Water Solubility 

water: soluble 25mg/mL, clear, colorless

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

N,N',N''-METHYLIDYNETRISFORMAMIDE Usage And Synthesis

Uses

N,N′N′′-methylidynetrisformamide (TRIFO) is a source for formamide; used for N-formylformamidine (H2N-CH=N-CHO); for the N-formylformimidoyl group (H-C=NHCHO) as a building block in heterocyclic synthesis).

Preparation

Triethyl Orthoformate reacts with formamide under catalysis of mineral acids to give TRIFO (eq 1). 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. 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. Pure salts of this type are also converted to the reagent by formamide. Reaction of Dimethyl Sulfate with formamide is the easiest way to prepare TRIFO.

General Description

N,N′,N′′-Methylidynetrisformamide is also referred as tris(formamido)methane.

Solubility in organics

N,N′N′′-methylidynetrisformamide is soluble in formamide; soluble in aprotic dipolar solvents such as DMF or DMA on heating.

storage

N,N′N′′-methylidynetrisformamide is stored at rt in closed bottles. Use in a fume hood.

N,N',N''-METHYLIDYNETRISFORMAMIDE(4774-33-8)Related Product Information

• TRIS(DIFORMYLAMINO)METHANE
• METHYLENEDIFORMAMIDE
• N,N',N''-METHYLIDYNETRISFORMAMIDE