Dichlorophen

Base Information

• Chemical Name: Dichlorophen
• CAS No.: 97-23-4
• Deprecated CAS: 8017-86-5,1135443-66-1,1135443-66-1
• Molecular Formula: C13H10Cl2O2
• Molecular Weight: 269.127
• Hs Code.: 2930.90 DERIVATION
• European Community (EC) Number: 202-567-1
• NSC Number: 757391,39467,38642
• UNII: T1J0JOU64O
• DSSTox Substance ID: DTXSID6021824
• Nikkaji Number: J4.946H
• Wikipedia: Dichlorophen
• Wikidata: Q377552
• NCI Thesaurus Code: C47485
• Metabolomics Workbench ID: 152601
• ChEMBL ID: CHEMBL33845
• Mol file: 97-23-4.mol

Synonyms:Dichlorophen;Panacide

Chemical Property of Dichlorophen

Chemical Property:

• Appearance/Colour: white or off-white powder
• Vapor Pressure: 1.3 x 10-5 Pa (25 °C)
• Melting Point: 168-172 °C(lit.)
• Boiling Point: 418.7 °C at 760 mmHg
• PKA: pK1:7.6;pK2:11.5 (25°C)
• Flash Point: 207 °C
• PSA: 40.46000
• Density: 1.419 g/cm³
• LogP: 3.99540
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Soluble in methanol, ether
• Water Solubility.: <0.1 g/100 mL at 22 oC
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 268.0057849
• Heavy Atom Count: 17
• Complexity: 226

Purity/Quality:

99% ^*data from raw suppliers

Dichlorophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 22-36-50/53
• Safety Statements: 26-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Biocides/Disinfectants
• Canonical SMILES: C1=CC(=C(C=C1Cl)CC2=C(C=CC(=C2)Cl)O)O
• Description: Dichlorophen is a nontoxic laxative vermicide of chlorinated phenol compound. It is an anticestodal agent, fungicide, germicide, anti-protozoan and antimicrobial agent. Its efficacy is restricted to Taenia spp, with poor to no activity against Echinococcus spp and Dipylidium caninum. Against these and other species, it may act against the strobilus, leaving the scolex to generate new proglottids. Its mechanism of action is thought to induce the uncoupling of oxidative phosphorylation. Therefore, it can be included as an ingredient in antimicrobial soaps and shampoos. It can be used in combination with toluene for the removal of parasites such as ascarids, hookworms, and tapeworms from dogs and cats. Dichlorophene can be used as a growth regulator in containerized seedlings of pine and spruce to regulate plant growth.
• Uses: Dichlorophen exhibits algicidal, bactericidal and fungicidal activities. It is a contact fungicide used to control dollar spots and rots in turf. It is also an anthelminthic used for the treatment of various tapeworms in human and domestic animals. Agricultural fungicide; antimicrobial; germicide in soaps, shampoos, etc.
• Therapeutic Function: Antiseptic, Anthelmintic, Antifungal

Technology Process of Dichlorophen

There total 10 articles about Dichlorophen 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: 37.0%

methoxy-acetic acid 4-chloro-phenyl ester → 2,2'-methylenebis(4-chlorophenol) (97-23-4) + 2,2′?methylenebis(4?chlorophenol)

Guidance literature:

With aluminum (III) chloride; In neat (no solvent); at 170 ℃; for 4h;

DOI:10.1016/j.jics.2021.100292

Reference yield: 20.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 4-chloro-phenol (106-48-9,82344-39-6) → 2,2'-methylenebis(4-chlorophenol) (97-23-4) + 4-chloro-2,6-bis(5-chloro-2-hydroxybenzyl)phenol (6642-07-5)

Guidance literature:

With sulfuric acid; In methanol; water; at -5 - 0 ℃; for 2h;

DOI:10.1002/hlca.19810640224

Reference yield: 9.0%

Bis(2-hydroxyphenyl)methane (2467-02-9) → 2,2'-methylenebis(4-chlorophenol) (97-23-4) + 2,2'-methylenebis(4,6-dichlorophenol) (1940-43-8)

Guidance literature:

With sulfuryl dichloride; acetic acid;

DOI:10.1016/j.bmcl.2008.11.089

upstream raw materials:

diiodomethane

4-chloro-phenol

Dimethoxymethane

4-chloro-2-hydroxymethylphenol

Downstream raw materials:

bis-(5-chloro-2-hydroxy-3-pyrrolidinomethyl-phenyl)-methane

bis-(5-chloro-2-hydroxy-3-piperidinomethyl-phenyl)-methane

bis-(2-ethoxy-5-chloro-phenyl)-methane

Bis(2-hydroxyphenyl)methane

Refernces

• 1、 Talluri, Sirishadevi,Kini, Suvarna G.,Kandale, Ajit,Kumar, Ganesh,Ohlyan, Renu. "Synthesis and in vitro cholesteryl ester transfer protein inhibitory activity of novel esters of 2, 10-dichloro-12H-dibenzo [d,g] 1,3-dioxocin-6-carboxylic acid". . p. 4491 - 4499. Retrieved 2015/04/22.
• 2、 -. "Synergistic biocide composition". . . Retrieved 2008/06/13.