Ammonium formate

Ammonium formate
Names
	IUPAC name Ammonium formate
Identifiers
CAS Number	540-69-2 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	10442 ;
PubChem CID	2723923;
RTECS number	BQ6650000;
UNII	3801F9644E ;
	InChI InChI=1S/CH2O2.H3N/c2-1-3;/h1H,(H,2,3);1H3 Key: VZTDIZULWFCMLS-UHFFFAOYSA-N ; InChI=1/CH2O2.H3N/c2-1-3;/h1H,(H,2,3);1H3 Key: VZTDIZULWFCMLS-UHFFFAOYAT;
	SMILES O=CO.N; C(=O)O.N;
Properties
Chemical formula	CH5NO2
Molar mass	63.056 g·mol−1
Appearance	White monoclinic crystals, deliquescent
Odor	Slightly ammoniac
Density	1.26 g/cm3
Melting point	116 °C (241 °F; 389 K)
Boiling point	180 °C (356 °F; 453 K) ; decomposes
Solubility in water	(grams per 100g of water)102g(0 °C); 142.7 g (20 °C); 202.4 g (40 °C); 516 g (80 °C)
Solubility in other solvents	Soluble in liquid ammonia, ethanol, diethyl ether
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	−556.18 kJ/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P305+P351+P338
NFPA 704 (fire diamond)	<imagemap> File:NFPA 704.svg\|80px\|alt=NFPA 704 four-colored diamond poly 150 150 300 300 150 450 0 300 Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform poly 300 0 450 150 300 300 150 150 Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil poly 450 150 600 300 450 450 300 300 Instability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calcium poly 300 300 450 450 300 600 150 450 Special hazards (white): no code desc none </imagemap> 2 1 1
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	410 mg/kg (mice, intravenous)
Safety data sheet (SDS)	JT Baker MSDS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Ammonium formate, NH₄HCO₂, is the ammonium salt of formic acid. It is a colorless, hygroscopic, crystalline solid.

Reductive amination

Acetone can be transformed into isopropylamine as follows:^{[citation needed]}

CH₃C(O)CH₃ + 2 HCO₂⁻ ⁺NH₄ → (CH₃)₂CHNHCHO + 2 H₂O + NH₃ + CO₂

(CH₃)₂CHNHCHO + H₂O → (CH₃)₂CHNH₂ + HCO₂H

Uses

Pure ammonium formate decomposes into formamide and water when heated, and this is its primary use in industry. Formic acid can also be obtained by reacting ammonium formate with a dilute acid, and since ammonium formate is also produced from formic acid, it can serve as a way of storing formic acid.

Ammonium formate can also be used in palladium on carbon (Pd/C) reduction of functional groups. In the presence of Pd/C, ammonium formate decomposes to hydrogen, carbon dioxide, and ammonia. This hydrogen gas is adsorbed onto the surface of the palladium metal, where it can react with various functional groups. For example, alkenes can be reduced to alkanes, formaldehyde to methanol, and nitro compounds to amines.^[3]^[4] Activated single bonds to heteroatoms can also be replaced by hydrogens (hydrogenolysis).

Ammonium formate can be used for reductive amination of aldehydes and ketones (Leuckart reaction), by the following reaction:^[5]

Ammonium formate can be used as a mobile phase additive in high performance liquid chromatography (HPLC), and is suitable for use with liquid chromatography-mass spectrometry (LC/MS). The pK_a values of formic acid and the ammonium ion are 3.8 and 9.2, respectively.

Reactions

When heated, ammonium formate eliminates water, forming formamide. Upon further heating, it forms hydrogen cyanide (HCN) and water. A side reaction of this is the decomposition of formamide to carbon monoxide (CO) and ammonia.

References

^ ^1.0 ^1.1 ^1.2 ^1.3 Sigma-Aldrich Co., Ammonium formate. Retrieved on 2014-06-10.
^ ^2.0 ^2.1 ^2.2 ^2.3 "Ammonium formate".
^ Ram, Siya; Ehrenkaufer, Richard E. (1984). "A general procedure for mild and rapid reduction of aliphatic and aromatic nitro compounds using ammonium formate as a catalytic hydrogen transfer agent". Tetrahedron Lett. 25 (32): 3415–3418. doi:10.1016/S0040-4039(01)91034-2. hdl:2027.42/25034.
^ Smith, Michael B.; March, Jerry (2007). March's Advanced Organic Chemistry (6th ed.). John Wiley & Sons. p. 1816. ISBN 978-0-471-72091-1.
^ Alexander, Elliot; Ruth Bowman Wildman (1948). "Studies on the Mechanism of the Leuckart Reaction". Journal of the American Chemical Society. 70 (3): 1187–1189. doi:10.1021/ja01183a091. PMID 18909189.

External links

Media related to Ammonium formate at Wikimedia Commons

[sigma-1] 1.0 ^1.1 ^1.2 ^1.3 Sigma-Aldrich Co., Ammonium formate. Retrieved on 2014-06-10.

[chemister-2] 2.0 ^2.1 ^2.2 ^2.3 "Ammonium formate".

[3] Ram, Siya; Ehrenkaufer, Richard E. (1984). "A general procedure for mild and rapid reduction of aliphatic and aromatic nitro compounds using ammonium formate as a catalytic hydrogen transfer agent". Tetrahedron Lett. 25 (32): 3415–3418. doi:10.1016/S0040-4039(01)91034-2. hdl:2027.42/25034.

[March-4] Smith, Michael B.; March, Jerry (2007). March's Advanced Organic Chemistry (6th ed.). John Wiley & Sons. p. 1816. ISBN 978-0-471-72091-1.

[Ref1-5] Alexander, Elliot; Ruth Bowman Wildman (1948). "Studies on the Mechanism of the Leuckart Reaction". Journal of the American Chemical Society. 70 (3): 1187–1189. doi:10.1021/ja01183a091. PMID 18909189.

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