腈

概览

Cyanide-derived intermediates that add one carbon to the chain.

The carbon in a nitrile group is part of the molecular carbon skeleton. Replacing a haloalkane leaving group with cyanide therefore adds one carbon; subsequent hydrolysis or reduction preserves that enlarged skeleton. Hydrolysis passes through an amide, while reduction gives a primary amine.

Identifiers

官能团

C≡N

性质

连接方式

有机腈的结构为 R-C≡N，与异腈 R-N≡C 不同。

水解产物

酸性水解得到羧酸；碱性水解先得到羧酸盐，经酸性后处理才得到羧酸。

Related compounds

• 丙烯腈

  制造 ABS 的三种单体之一。

• 乙腈

  一种极性非质子溶剂，其腈基也可作为反应位点。

• 丙腈

  一种三碳腈，在水解和还原中均保留腈基碳。

• 苯甲腈

  苯甲腈是一种有机化合物，分子式为 C7H5N。

• 丁腈

  含四个碳原子的腈，链长计入末端的腈基碳。

• 2-羟基丙腈

  乙醛形成的氰醇，羟基和腈基连接在同一碳上。

• 2-羟基-2-甲基丙腈

  丙酮形成的氰醇，保留两个等价的甲基。

Connected reactions

• Cyanation: Chloroalkanes → Nitriles

  氰根取代生成腈，使碳链增加一个碳原子。

• Cyanation: Bromoalkanes → Nitriles

  氰根取代生成腈，使碳链增加一个碳原子。

• Cyanation: Iodoalkanes → Nitriles

  氰根取代生成腈，使碳链增加一个碳原子。

• Hydrolysis: Nitriles → Carboxylic acids

  腈可水解为羧酸；此处将原先合并的腈到酰胺路线拆分为单步官能团转化。

• Reduction: Nitriles → Amines

  腈可还原为伯胺，将胺的制备与后续酰胺或材料化学分开呈现。

参考文献

1. Organic Chemistry: Chemistry of NitrilesJohn McMurry · OpenStax Organic Chemistry · 2023

   Supports nitrile reduction by two hydride additions to imine-anion and aluminium-stabilised dianion intermediates, followed by aqueous work-up to a primary amine; also documents nitrile hydrolysis through amide intermediates.

2. ABS: monomers and manufacturing routesINEOS
3. PubChem Compound Summary: Acetonitrile (CID 6342)National Center for Biotechnology Information · PubChem

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

4. 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.

5. PubChem Compound Summary: Benzonitrile (CID 7505)National Center for Biotechnology Information · PubChem

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

6. PubChem Compound Summary: Butanenitrile (CID 8008)National Center for Biotechnology Information · PubChem

   Identity, molecular formula, molecular weight and selected English aliases retrieved via PUG REST on 2026-09-16. Chinese search names are curated nomenclature translations. Unspecified stereochemistry remains unspecified.

7. PubChem Compound Summary: 2-Hydroxypropanenitrile (CID 6572)National Center for Biotechnology Information · PubChem

   Identity, molecular formula, molecular weight and selected English aliases retrieved via PUG REST on 2026-09-16. Chinese search names are curated nomenclature translations. Unspecified stereochemistry remains unspecified.

8. PubChem Compound Summary: 2-Hydroxy-2-methylpropanenitrile (CID 6406)National Center for Biotechnology Information · PubChem

   Identity, molecular formula, molecular weight and selected English aliases retrieved via PUG REST on 2026-09-16. Chinese search names are curated nomenclature translations. Unspecified stereochemistry remains unspecified.