Ammonium formate

Names
IUPAC name Ammonium formate
Identifiers
CAS Number	540-69-2 Y
3D model (JSmol)	Interactive image Interactive image
ChemSpider	10442 Y
ECHA InfoCard	100.007.959
PubChemCID	2723923
RTECS number	BQ6650000
UNII	3801F9644E Y
CompTox Dashboard(EPA)	DTXSID6029624
InChI InChI=1S/CH2O2.H3N/c2-1-3;/h1H,(H,2,3);1H3 Y Key: VZTDIZULWFCMLS-UHFFFAOYSA-N Y 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[1]
Melting point	116 °C (241 °F; 389 K)
Boiling point	180 °C (356 °F; 453 K) decomposes[2]
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)[2]
Solubility in other solvents	Soluble in liquidammonia,ethanol,diethyl ether[2]
Thermochemistry
Std enthalpy of formation(ΔfH⦵298)	−556.18 kJ/mol
Hazards
GHS labelling:
Pictograms	[1]
Signal word	Warning
Hazard statements	H315,H319,H335[1]
Precautionary statements	P261,P305+P351+P338[1]
NFPA 704 (fire diamond)	2 1 1
Lethal dose or concentration (LD, LC):
LD50 (median dose)	410 mg/kg (mice, intravenous)[2]
Safety data sheet (SDS)	JT Baker MSDS
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Ammonium formate, NH₄HCO₂, is theammoniumsalt offormic acid. It is a colorless,hygroscopic,crystallinesolid.

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

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

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

Pure ammonium formate decomposes intoformamide andwater 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 inpalladium on carbon (Pd/C) reduction of functional groups. In the presence of Pd/C, ammonium formate decomposes tohydrogen,carbon dioxide, andammonia. This hydrogen gas is adsorbed onto the surface of thepalladium metal, where it can react with various functional groups. For example,alkenes can be reduced toalkanes,formaldehyde tomethanol, andnitro compounds toamines.^[3][4] Activated single bonds to heteroatoms can also be replaced by hydrogens (hydrogenolysis).

Ammonium formate can be used forreductive amination ofaldehydes andketones (Leuckart reaction), by the following reaction:^[5]

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

When heated, ammonium formate eliminates water, formingformamide. Upon further heating, it formshydrogen cyanide (HCN) and water. A side reaction of this is the decomposition of formamide tocarbon monoxide (CO) and ammonia.

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