2,5-Dichlorobenzoyl chloride

Base Information

• Chemical Name: 2,5-Dichlorobenzoyl chloride
• CAS No.: 2905-61-5
• Molecular Formula: C7H3Cl3O
• Molecular Weight: 209.459
• Hs Code.: 2916399090
• European Community (EC) Number: 220-812-0
• NSC Number: 41887
• UNII: F7C0V01SK6
• DSSTox Substance ID: DTXSID4062698
• Nikkaji Number: J152.929C
• Wikidata: Q27277761
• Mol file: 2905-61-5.mol

Synonyms:2,5-DICHLOROBENZOYL CHLORIDE;2905-61-5;Benzoyl chloride, 2,5-dichloro-;2,5-dichlorobenzoic acid chloride;UNII-F7C0V01SK6;F7C0V01SK6;HSDB 5902;EINECS 220-812-0;MFCD00035821;NSC 41887;NSC-41887;2,5-dichlorobenzoylchoride;2,5-dichlorobenzoic chloride;2,5-dichlorobenzoyl-chloride;Benzoyl chloride,5-dichloro-;SCHEMBL699001;DTXSID4062698;2,5-bis(chloranyl)benzoyl chloride;NSC41887;AKOS009218476;2,5-Dichlorobenzoyl chloride, AldrichCPR;SY051215;2,5-DICHLOROBENZOYL CHLORIDE [HSDB];D2953;FT-0601027;D90136;EN300-399450;A819743;Q-200194;Q27277761;F2146-0392

Chemical Property of 2,5-Dichlorobenzoyl chloride

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 0.0195mmHg at 25°C
• Melting Point: 30 °C
• Refractive Index: 1.576
• Boiling Point: 252.3 °C at 760 mmHg
• Flash Point: 103.6 °C
• PSA: 17.07000
• Density: 1.498 g/cm³
• LogP: 3.37240
• Solubility.: soluble in Toluene
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 207.924948
• Heavy Atom Count: 11
• Complexity: 160

Purity/Quality:

99% ^*data from raw suppliers

2,5-Dichlorobenzoyl Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C,Xn
• Statements: 34-22
• Safety Statements: 36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Plant Growth Regulators
• Canonical SMILES: C1=CC(=C(C=C1Cl)C(=O)Cl)Cl
• Description: 2,5-Dichlorobenzoyl chloride is a white-yellow chemical used as a pharmaceutical intermediate. Its molecular structure includes two chlorine atoms attached to a benzene ring, with a carbonyl chloride functional group. 2,5-Dichlorobenzoyl chloride has been synthesized and utilized in various applications, including pharmaceutical synthesis and plant growth regulation. Its use in the synthesis of MLN9708, a proteasome inhibitor, indicates its importance in pharmaceutical development.
• Uses and Mechanism of Action: Pharmaceutical Intermediate: ; 2,5-Dichlorobenzoyl Chloride serves as a pharmaceutical intermediate in the synthesis of drugs or active pharmaceutical ingredients (APIs).; ; Plant Growth Regulator: ; In gaseous or aqueous solution forms, it functions as a plant growth regulator, affecting the germination, growth, and morphology of plants.
• Production Methods: 2,5-Dichlorobenzoyl chloride can be synthesized through a Friedel–Crafts acylation reaction of benzene or aromatic compounds with 2,5-dichlorobenzoyl chloride. The latter can be prepared from 2,5-dichlorobenzoic acid and thionyl chloride.
• Analysis Method: 2,5-Dichlorobenzoyl chloride can be quantified using ultra-high-performance liquid chromatography coupled with high-resolution quantitation mass spectrometry (UHPLC/HRQMS). This method allows for the determination of 2,5-Dichlorobenzoyl chloride in drug substances at low levels, addressing regulatory requirements and ensuring product quality and safety.

Technology Process of 2,5-Dichlorobenzoyl chloride

There total 4 articles about 2,5-Dichlorobenzoyl 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: 93.0%

2,5-dichlorobenzoic acid (50-79-3) → 2,5-dichlorobenzoyl chloride (2905-61-5)

Guidance literature:

With thionyl chloride; for 3h; Reflux; Inert atmosphere;

DOI:10.1080/00397910903534056

Reference yield:

2,5-dichlorobenzonitrile (21663-61-6) → 2,5-dichlorobenzoyl chloride (2905-61-5)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hydroxide / ethylene glycol / 7 h / 170 °C

2: thionyl chloride / 3 h / Reflux

With thionyl chloride; potassium hydroxide; In ethylene glycol;

DOI:10.1016/j.tet.2016.02.035

Reference yield:

para-dichlorobenzene (106-46-7,84348-21-0) + Phthaloyl dichloride (88-95-9) → 2,5-dichlorobenzoyl chloride (2905-61-5)

Guidance literature:

With aluminum (III) chloride; phthalic anhydride; sodium chloride; at 115 ℃; for 6h;

DOI:10.3762/bjoc.9.48

upstream raw materials:

2,5-dichlorobenzoic acid

para-dichlorobenzene

Phthaloyl dichloride

2,5-dichlorobenzonitrile

Downstream raw materials:

2-(2,5-dichlorobenzamido)-5-nitrothiazole

C₁₁H₁₁Cl₂NO₃

5-(2'.5'-Dichlor-benzoyl)-2-indancarbonsaeure-methylester

C₂₂H₁₅Cl₄N₅O

Refernces

• 1、 -. "A substituted boric acid ester compound preparation method and its crystalline form (by machine translation)". Paragraph 0190; 0192; 0193; 0194; 0195. . Retrieved 2019/02/04.
• 2、 Lei, Peng,Xu, Yan,Du, Juan,Yang, Xin-Ling,Yuan, Hui-Zhu,Xu, Gao-Fei,Ling, Yun. "Design, synthesis and fungicidal activity of N-substituted benzoyl-1,2,3,4-tetrahydroquinolyl-1-carboxamide". supporting information. p. 2544 - 2546. Retrieved 2016/07/07.