Benzoyl chloride
| Names | |
|---|---|
| IUPAC name
Benzoyl chloride
| |
| Other names
Benzenecarbonyl chloride
Benzoylchloride α-Chlorobenzaldehyde | |
| Properties | |
| C7H5ClO C6H5COCl | |
| Molar mass | 140.57 g/mol |
| Appearance | Colorless fuming liquid |
| Odor | Pungent, aromatic, almond-like |
| Density | 1.211 g/cm3 (25 °C) |
| Melting point | −1 °C (30 °F; 272 K) |
| Boiling point | 197.2 °C (387.0 °F; 470.3 K) |
| Reacts | |
| Solubility | Reacts with alcohols, amines, bases Miscible with benzene, carbon disulfide, ethers, halocarbons |
| Vapor pressure | 0.4 mmHg (20 °C) |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | 72 °C (162 °F; 345 K) |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
1,900 mg/kg (rat, oral) |
| Related compounds | |
| Related compounds
|
Acetyl chloride |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C6H5COCl.
Contents
Properties
Chemical
Benzoyl chloride hydrolyzes in water or basic solutions.
Benzoyl chloride reacts with alcohols to give the corresponding esters. Similarly, it reacts with amines to give amides. Condensation with diethylamine for example, yields N,N-diethylbenzamide.
It undergoes the Friedel-Crafts acylation with aromatic compounds to give the corresponding benzophenones and related derivatives.[1]
Treating benzoyl chloride with hydrogen peroxide and sodium hydroxide yields benzoyl peroxide.[2]
Physical
Benzoyl chloride is a colorless fuming liquid, with a pungent aromatic odor. It reacts with water and other protic solvents.
Availability
Benzoyl chloride is sold by chemical suppliers.
Preparation
Benzoyl chloride is produced by reacting benzotrichloride with water or benzoic acid:[3]
- C6H5CCl3 + H2O → C6H5COCl + 2 HCl
- C6H5CCl3 + C6H5CO2H → 2 C6H5COCl + HCl
It can also be produced by the direct chlorination of benzaldehyde (Preparation of organic compounds, E. de. Barry Barnett, 52, 1912)[4]
As with other acyl chlorides, it can be generated from the parent acid and standard chlorinating agents such as phosphorus pentachloride, thionyl chloride or oxalyl chloride.[5][6]
Chlorination of benzyl alcohol is another possible route.[7]
Projects
- Preparation of benzoyl peroxide
- Make benzoate esters
- Make benzamides
- Preparation of more volatile acyl chlorides [8]
Handling
Safety
Benzoyl chloride is harmful, corrosive and lachrymator. Proper protection must be worn when handling the compound, such as thick gloves, gas mask, an apron and always keep a neutralizing agent nearby.
Storage
In closed bottles, away from bases and people.
Disposal
Can be neutralized by adding it in cold water or crushed ice. Sodium hydroxide may be added to fully hydrolyze the compound to sodium benzoate.
References
- ↑ http://orgsyn.org/demo.aspx?prep=CV2P0520
- ↑ https://www.fao.org/fileadmin/templates/agns/pdf/jecfa/cta/63/Benzoylperoxide.pdf
- ↑ https://onlinelibrary.wiley.com/doi/10.1002/14356007.a03_555
- ↑ https://www.prepchem.com/synthesis-of-benzoyl-chloride/
- ↑ https://www.prepchem.com/synthesis-of-benzoyl-chloride/
- ↑ https://babel.hathitrust.org/cgi/pt?id=hvd.hxdg3f&view=1up&seq=6
- ↑ https://patents.google.com/patent/US1851832
- ↑ https://pubs.acs.org/doi/10.1021/ja01273a014
