Propanenitrile

Overview

A three-carbon nitrile that retains its nitrile carbon in hydrolysis and reduction.

Hydrolysis converts the nitrile carbon into the carboxyl carbon of propanoic acid. Reduction instead gives propylamine. Carbon counting includes the C≡N carbon, explaining why this nitrile has one more carbon than a two-carbon haloalkane precursor.

Identifiers

Formula

C3H5N

Functional group

Nitriles

Molar mass

55.08 g/mol

Also known as

PROPIONITRILE, Ethyl cyanide, Propiononitrile, Cyanoethane, Propionic nitrile, Propylnitrile

Properties

Melting Point

-91.8 °C

Boiling Point

97.2 °C @ 760 mm Hg

Relative density (water = 1)

Relative density (water = 1): 0.78

Water solubility

In water, 1.03X10+5 mg/l @ 25 °C.

Related compounds

• Nitriles

  A three-carbon nitrile that retains its nitrile carbon in hydrolysis and reduction.

Connected reactions

• Cyanide substitution: Bromoethane → Propanenitrile

  The carbon end of cyanide attacks the primary carbon of bromoethane as bromide leaves. The new C-C bond joins cyanide’s carbon to the original chain, giving a three-carbon nitrile rather than acetonitrile.

• Nitrile hydrolysis: Propanenitrile → Propanoic acid

  Acid-assisted water addition converts the nitrile through an amide before hydrolysis gives the acid. The nitrile carbon becomes the carboxyl carbon, while its nitrogen leaves the organic skeleton as ammonium.

• Nitrile reduction: Propanenitrile → Propylamine

  Hydride additions reduce the carbon-nitrogen triple bond; the separate aqueous work-up protonates the nitrogen-containing intermediates. The nitrile carbon becomes CH2NH2, preserving the enlarged three-carbon skeleton.

References

1. PubChem Compound Summary: Propanenitrile (CID 7854)National Center for Biotechnology Information · PubChem

   Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.

2. OpenStax Organic Chemistry: Chemistry of nitrilesJohn McMurry · OpenStax · 2023

   Supports the qualitative structure and reactivity context; identity and numerical measurements retain their original references.

3. Hazardous Substances Data Bank (HSDB): Propanenitrile — melting pointHazardous Substances Data Bank (HSDB)

   Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/7854#section=Melting-Point. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred. Original reference: Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1345

4. Hazardous Substances Data Bank (HSDB): Propanenitrile — boiling pointHazardous Substances Data Bank (HSDB)

   Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/7854#section=Boiling-Point. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred. Original reference: Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1345

5. ILO-WHO International Chemical Safety Cards (ICSCs): Propanenitrile — densityILO-WHO International Chemical Safety Cards (ICSCs)

   Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/7854#section=Density. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred.

6. Hazardous Substances Data Bank (HSDB): Propanenitrile — solubilityHazardous Substances Data Bank (HSDB)

   Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/7854#section=Solubility. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred. Original reference: Riddick, J.A., W.B. Bunger, Sakano T.K. Techniques of Chemistry 4th ed., Volume II. Organic Solvents. New York, NY: John Wiley and Sons., 1985., p. 584