Benzoyl chloride

Base Information

• Chemical Name: Benzoyl chloride
• CAS No.: 98-88-4
• Deprecated CAS: 1258517-80-4,1640987-68-3,2231811-43-9
• Molecular Formula: C7H5ClO
• Molecular Weight: 140.569
• Hs Code.: 2916.32
• European Community (EC) Number: 202-710-8
• ICSC Number: 1015
• UN Number: 1736
• UNII: VTY8706W36
• DSSTox Substance ID: DTXSID9026631
• Nikkaji Number: J3.987J
• Wikipedia: Benzoyl chloride
• Wikidata: Q412825
• ChEMBL ID: CHEMBL2260719
• Mol file: 98-88-4.mol

Synonyms:alpha-Chlorobenzaldehyde;Benzaldehyde, alpha-chloro-;Benzoyl chloride [UN1736] [Corrosive];Benzenecarbonyl chloride;4-09-00-00721 (Beilstein Handbook Reference);Benzoic acid, chloride;cyclohexanecarbonyl chloride;1,4-Dibromobutane;benzoyl chloride;alpha-chloroBenzaldehyde; benzenecarbonyl chloride;Benzoylchloride;

Chemical Property of Benzoyl chloride

Chemical Property:

• Appearance/Colour: Colorless liquid
• Vapor Pressure: 1 mm Hg ( 32 °C)
• Melting Point: -1 ºC
• Refractive Index: 1.553
• Boiling Point: 197.2 ºC at 760 mmHg
• Flash Point: 70.7 ºC
• PSA: 17.07000
• Density: 1.213 g/cm³
• LogP: 2.06560
• Storage Temp.: Store at 0-5°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: reacts
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 140.0028925
• Heavy Atom Count: 9
• Complexity: 106
• Transport DOT Label: Corrosive

Purity/Quality:

99% ^*data from raw suppliers

Benzoyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-43-20/21/22
• Safety Statements: 26-45-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Acid Halides
• Canonical SMILES: C1=CC=C(C=C1)C(=O)Cl
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly.
• Effects of Short Term Exposure: Lachrymation. The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion. Inhalation of the vapour or aerosol may cause lung oedema.
• Uses: Benzoyl Chloride is used in the manufacturing of dye intermediates. For acylation, i.e., introduction of the benzoyl group into alcohols, phenols, and amines (Schotten-Baumann reaction); in the manufacture of benzoyl peroxide and of dye intermediates. In organic analysis for making benzoyl derivatives for identification purposes. Benzoyl chloride is widely utilized for the synthesis of peroxides. It is employed in the production of dyes and perfumes. It also serves in the manufacturing of pharmaceuticals and resins.

Technology Process of Benzoyl chloride

There total 296 articles about Benzoyl chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

iodobenzene (591-50-4) + 4-nitro-benzoyl chloride (122-04-3) → p-nitrobenzene iodide (636-98-6) + benzoyl chloride (98-88-4)

Guidance literature:

With (Xantphos)Pd(4-C₆H₄NO₂)(I); In benzene; at 90 ℃; for 20h; Sealed tube; Inert atmosphere;

DOI:10.1021/jacs.8b06605

Reference yield: 83.0%

2,2,2',2'-Tetrachlor-1,1'-diphenyl-2,2'-trithiobis(ethanon) (74128-90-8) + acetophenone (98-86-2) → benzoyl chloride (98-88-4) + chlorothio-trichloro-methane (594-42-3)

Guidance literature:

acetophenone; With pyridine; thionyl chloride; at 75 ℃; for 6.5h;

2,2,2',2'-Tetrachlor-1,1'-diphenyl-2,2'-trithiobis(ethanon); In neat (no solvent); at 140 ℃; for 15h;

DOI:10.1021/acs.joc.5b01707

Reference yield:

4-methoxybenzoic acid (100-09-4) → benzoyl chloride (98-88-4) + 4-methoxy-benzoyl chloride (100-07-2)

Guidance literature:

With Benzotrichlorid; iron(III) chloride; In benzene; at 55 ℃; Product distribution; Rate constant; Thermodynamic data; ΔE(excit.), var. temp.;

upstream raw materials:

pyridine

p-toluenesulfonyl chloride

benzoic acid

benzoic acid methyl ester

Downstream raw materials:

N-benzoylpiperidine

N-(piperidylthiocarbonyl)benzamide

1,2-bisbenzoylpyrazolidine

1,3-dibenzoyl-imidazolidine

Refernces

• 1、 Chattopadhyay, Buddhadeb,Hassan, Mirja Md Mahamudul,Hoque, Md Emdadul. "Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates". supporting information. p. 5022 - 5037. Retrieved 2021/05/04.
• 2、 -. "Butyrylcholine esterase selective inhibitor as well as preparation method and application thereof". Paragraph 0035; 0039-0040. . Retrieved 2021/06/22.