ammonium formate

• ChemBase ID: 106161
• Molecular Formular: CH5NO2
• Molecular Mass: 63.0559
• Monoisotopic Mass: 63.03202841
• SMILES: [NH4+].[O-]C=O
• Canonical SMILES: [O-]C=O.[NH4+]
• InChI: InChI=1S/CH2O2.H3N/c2-1-3;/h1H,(H,2,3);1H3
• InChIKey: VZTDIZULWFCMLS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ammonium formate
• IUPAC Traditional name: ammonium formate; ammonium formira
• Synonyms: Ammonium formate; Formic acid ammonium salt; AMMONIUM FORMATE; 甲酸铵

Database IDs

• CAS Number: 540-69-2
• EC Number: 208-753-9
• MDL Number: MFCD00013103
• Beilstein Number: 3625095
• Merck Index: 14523
• PubChem SID: 162087298
• PubChem CID: 2723923

CALCULATED PROPERTIES

• Acid pKa: 4.269118
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -1.5255477
• LogD (pH = 7.4): -3.257304
• Log P: -0.27204442
• Molar Refractivity: 18.9903 cm^3
• Polarizability: 3.1383486 Å^3
• Polar Surface Area: 40.13 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Crystalline
• Melting Point: 116 °C (241 °F); 119-121°C; ca 116°C
• Boiling Point: Decomposes at 180 °C (356 °F)
• Density: 1.28; 1.28 (water = 1)
• Vapor Pressure: Not applicable

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Hygroscopic
• RTECS: BQ6650000
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335-H303
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

Product Information

• Purity: 97%, water <3%; 99%

REFERENCES

• Reagent for N-formylation of secondary amines and anilines: Tetrahedron Lett., 41, 9149 (2000).
• Examples include:
• A simple microwave-assisted method for catalytic transfer hydrogenation in ethylene glycol or 1,3-propanediol has been reported: J. Org. Chem., 64, 5746 (1999).
• Widely used as a hydrogen donor in catalytic hydrogen transfer reductions. Review: Synthesis, 91 (1988). See also Palladium, A12012, Cyclohexene, A11359, Hydrazine monohydrate, A14005, Formic acid, A13285 and Sodium hypophosphite monohydrate, A13385.
• Reduction of aryl nitro groups to amines: Tetrahedron Lett., 25, 3415 (1984). For reductive cyclization of an o-nitrobenzyl ketone to an indole, see: Org. Synth. Coll., 9, 601 (1998). Hydrogenolysis of N-benzyl groups: Synthesis, 53 (1987); Tetrahedron Lett., 28, 515 (1987). Reduction of aldehydes and ketones to methyl and methylene groups: Tetrahedron Lett., 29, 3741 (1988). The temperature- and solvent-dependencies of this type of reaction have been studied: Synth. Commun., 22, 2673, 2683 (1992). Selective reduction of the heterocyclic ring of quinolines and isoquinolines: Synth. Commun., 20, 2815 (1990). Reduction of pyridine N-oxides to piperidines: J. Org. Chem., 66, 5264 (2001). Regioselective reduction of epoxides: J. Org. Chem., 60, 4922 (1995). Ammonium formate was found to be a more active H donor than either sodium formate or formic acid in the catalytic hydrogenolysis of aryl chlorides. For a comparative mechanistic study of this reaction, see: J. Org. Chem., 60, 1347 (1995).