苯甲酰氯
一种芳香族酰氯，可连接多种苯甲酸衍生物的反应。
- 化学式
- C7H5ClO
- 官能团
- 酰氯
- 摩尔质量
- 140.56 g/mol
- Also known as
- Benzenecarbonyl chloride, Benzoic acid, chloride, alpha-Chlorobenzaldehyde, benzoic acid chloride, Benzaldehyde, alpha-chloro-
概览
Chlorine is attached to the carbonyl carbon, not directly to the aromatic ring. Nucleophilic acyl substitution can give benzoic acid, a benzoate ester or benzamide. These transformations retain the benzoyl carbonyl and produce an HCl equivalent that affects work-up.
Identifiers
- 化学式
- C7H5ClO
- 官能团
- 酰氯
- 摩尔质量
- 140.56 g/mol
- Also known as
- Benzenecarbonyl chloride, Benzoic acid, chloride, alpha-Chlorobenzaldehyde, benzoic acid chloride, Benzaldehyde, alpha-chloro-
化学标识符
- SMILES
- C1=CC=C(C=C1)C(=O)Cl
- InChI
- InChI=1S/C7H5ClO/c8-7(9)6-4-2-1-3-5-6/h1-5H
- PubChem CID
- 7412
性质
- 熔点
- -0.5 °C
- 沸点
- BP: 197.2 °C at 760 mm Hg
- 相对密度（水 = 1）
- Relative density (water = 1): 1.21
- 水中溶解度
- Solubility in water: reaction
Related compounds
Connected reactions
- Acyl chloride preparation: Benzoic acid → Benzoyl chloride
与五氯化磷反应，以氯替代羧基中的 OH，保留酰基碳和芳环。新生成的酰氯更易发生亲核取代；其余原子进入 POCl3 和 HCl。
- Amide formation: Benzoyl chloride → Benzamide
氨向酰基羰基加成，形成四面体中间体。羰基重新形成时排出氯离子，质子转移后生成苯甲酰胺；额外的氨捕获酸，形成氯化铵。
- Ester formation: Benzoyl chloride → Ethyl benzoate
乙醇的氧进攻酰基羰基碳。氯离去和质子转移恢复 C=O 并生成酯；乙醇提供乙氧基，总反应同时生成 HCl。
参考文献
- 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.
- OpenStax Organic Chemistry: Chemistry of acid halidesJohn McMurry · OpenStax · 2023
Supports the qualitative structural interpretation of the recorded molecular structure; no new physical measurement or verified preparative yield is claimed.
- Hazardous Substances Data Bank (HSDB): Benzoyl chloride — melting pointHazardous Substances Data Bank (HSDB)
Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/7412#section=Melting-Point. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred. Original reference: Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 95th Edition. CRC Press LLC, Boca Raton: FL 2014-2015, p. 3-42
- Hazardous Substances Data Bank (HSDB): Benzoyl chloride — boiling pointHazardous Substances Data Bank (HSDB)
Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/7412#section=Boiling-Point. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred. Original reference: O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 196
- ILO-WHO International Chemical Safety Cards (ICSCs): Benzoyl chloride — densityILO-WHO International Chemical Safety Cards (ICSCs)
Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/7412#section=Density. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred.
- ILO-WHO International Chemical Safety Cards (ICSCs): Benzoyl chloride — solubilityILO-WHO International Chemical Safety Cards (ICSCs)
Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/7412#section=Solubility. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred.