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Ammonium formate is widely used in various organic reactions like Leuckart reaction which involves the reductive amination of aldehydes and ketones. It serves as a buffer in high performance liquid chromatography (HPLC) and liquid chromatography-mass spectrometry (LC/MS). It finds application in palladium on carbon (Pd/C) reduction of functional groups. For example, reduction of alkenes to alkanes and formaldehyde to methanol. It is also used to prepare formic acid insitu as well as used to store formic acid by making it as an ammonium salt.
Reagent for N-formylation of secondary amines and anilines: Tetrahedron Lett., 41, 9149 (2000).
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).
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).
Sridhar, M.; Ferri, D.; Elsener, M.; Bokhoven, J. A. V.; Krocher, O. Promotion of Ammonium Formate and Formic Acid Decomposition over Au/TiO2by Support Basicity under SCR-Relevant Conditions ACS. Catal 2015, 5 (8), 4772-4782.
Su, J.; Lu, M.; Lin, H.. High yield production of formate by hydrogenating CO2 derived ammonium carbamate/carbonate at room temperature. Green Chem. 2015, 17 (5), 2769-2773.
Hazard Statements: H315-H319-H335-H500
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. May form combustible dust concentrations in air
Precautionary Statements: P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P362-P501c
Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant