Hydrazoic acid

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Chemical compound


Hydrazoic acid
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Chemical formula CHNO
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Hydrazoic acid, also known as hydrogen azide or azoimide, is a chemical compound with the formula HN₃. It is a volatile and explosive liquid at room temperature and is known for its pungent smell. Hydrazoic acid is a weak acid and is the simplest azide.

Structure and Properties[edit | edit source]

Hydrazoic acid is a linear molecule with a nitrogen-nitrogen-nitrogen bond sequence. The molecule can be represented as H-N=N=N. It is a colorless liquid with a density of 1.09 g/cm³ and a boiling point of 37 °C. The compound is highly soluble in water and forms hydronium and azide ions in solution.

Synthesis[edit | edit source]

Hydrazoic acid can be synthesized by the reaction of sodium azide with a strong acid, such as sulfuric acid:

NaN₃ + H₂SO₄ → HN₃ + NaHSO₄

This reaction must be carried out with caution due to the explosive nature of hydrazoic acid.

Reactions[edit | edit source]

Hydrazoic acid is known for its participation in the Schmidt reaction, which involves the conversion of carboxylic acids or ketones into amines or amides, respectively. The reaction proceeds via the formation of an acyl azide intermediate.

Schmidt reaction with carboxylic acids
Schmidt reaction with ketones

Applications[edit | edit source]

Hydrazoic acid is primarily used in the synthesis of other azide compounds, which are valuable in organic synthesis and materials science. Azides are used as precursors to amines, in click chemistry, and as propellants and explosives.

Safety[edit | edit source]

Hydrazoic acid is highly toxic and explosive. It can decompose violently when heated or subjected to shock. Proper safety precautions, including the use of fume hoods and protective equipment, are essential when handling this compound.

Also see[edit | edit source]


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