酰氯
酰氯通过酰化，将羧酸化学与酯、酰胺和 N-取代酰胺相连。
- 官能团
- COCl
- Also known as
- acid chloride, acyl chloride
概览
Reactive carboxylic acid derivatives containing C(O)-Cl.
Acyl chlorides contain R-C(=O)-Cl. The electrophilic carbonyl carbon is attacked by water, alcohols or nitrogen nucleophiles, followed by chloride departure. Their readiness to hydrolyse explains why dry conditions matter when water is not the intended reactant.
Identifiers
- 官能团
- COCl
- Also known as
- acid chloride, acyl chloride
化学标识符
- SMILES
- CC(=O)Cl
性质
- 酰氯或卤代烷
- 羰基 C=O 处的酰基取代，与 R-CH2-Cl 中饱和碳上的取代不同。
- 酸性副产物
- 必须考虑生成的 HCl；氨或胺既可作亲核试剂，也可作中和酸的碱。
Related compounds
Connected reactions
- Chlorination: Carboxylic acids → Acyl chlorides
PCl5 将羧酸转化为酰氯。
- Chlorination with thionyl chloride: Carboxylic acids → Acyl chlorides
氯化亚砜将羧酸转化为酰氯，同时生成二氧化硫和氯化氢。
- Hydrolysis: Acyl chlorides → Carboxylic acids
水使酰氯水解为羧酸，同时释放氯化氢。
- Acylation: Acyl chlorides → Esters
醇发生酰化，将酰氯转化为酯。
- Acylation: Acyl chlorides → Amides
氨发生酰化，将酰氯转化为酰胺。
- Acylation: Acyl chlorides → N-substituted amides
胺发生酰化，将酰氯转化为 N-取代酰胺。
参考文献
- Organic Chemistry: Chemistry of Acid HalidesJohn McMurry · OpenStax Organic Chemistry · 2023
Supports acid-halide preparation with thionyl chloride and nucleophilic acyl substitution chemistry, including tetrahedral intermediates, hydrolysis, alcoholysis and amine acylation at acid chlorides.
- PubChem Compound Summary: Acetyl chloride (CID 6367)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: Benzoyl chloride (CID 7412)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.