丙腈

概览

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

化学式

C3H5N

官能团

腈

摩尔质量

55.08 g/mol

Also known as

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

性质

熔点

-91.8 °C

沸点

97.2 °C @ 760 mm Hg

相对密度（水 = 1）

Relative density (water = 1): 0.78

水中溶解度

In water, 1.03X10+5 mg/l @ 25 °C.

Related compounds

• 腈

Connected reactions

• Cyanide substitution: Bromoethane → Propanenitrile

  氰根的碳端进攻溴乙烷的伯碳，溴离去。新形成的 C-C 键使氰根中的碳接到原碳链上，得到三碳腈，而不是乙腈。

• Nitrile hydrolysis: Propanenitrile → Propanoic acid

  在酸促进下，水加成使腈先转化为酰胺，再经水解得到酸。腈基碳成为羧基碳，氮则以铵离子形式离开有机骨架。

• Nitrile reduction: Propanenitrile → Propylamine

  氢负离子加成还原碳氮三键；另行进行的水性后处理使含氮中间体质子化。腈基碳转化为 CH2NH2，保留扩展后的三碳骨架。

参考文献

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