97-23-4

Usage

Sources

https://www.sciencedirect.com/topics/agricultural-and-biological-sciences/dichlorophen https://en.wikipedia.org/wiki/Dichlorophen https://pubchem.ncbi.nlm.nih.gov/compound/Dichlorophen#section=Top https://www.tabletwise.com/medicine/dichlorophene/uses-benefits-working Andersson, B. "Analysis of plant growth regulating substances [incl. dichlorophene]." Annals of Applied Biology 43.2(1982):342-354.

Originator

Dichlorophen,Aquapharm

Manufacturing Process

2.520 g of sulfuric acid (93%) is stirred and cooled to 0°C. A solution of 552 g of p-chlorophenol in 305 g of methyl alcohol is run into the acid, the temperature being kept below 10°C. The mixture is cooled to -5°C and a solution of 170 g of aqueous formaldehyde solution (37% CH2O in water) in 332 g of methyl alcohol is introduced at a more or less uniform rate over a period of 4 hours. The temperature of the reaction mixture is not allowed to rise above 0°C. After all of the formaldehyde-containing solution has been added, the batch is stirred for 3 hours longer at a temperature of -5°-0°C.Enough ice is then added to the contents of the reaction chamber in order to reduce the sulfuric acid concentration to 70%. 2,2'-Dihydroxy-5,5'-dichlorodiphenyl methane is extracted from the resulting mixture with a mixture of 1.069 g of isopropyl ether and 1.575 g of toluene. Ice is added until the acid concentration is about 30%. The acid layer is removed and the solvent layer is washed acid-free. Most of the isopropyl ether is removed by atmospheric distillation with a fractionating column, the temperature of the escaping vapors not being permitted to exceed 90°C. From the residue, about 280 g of pure 2,2'-dihydroxy-5,5'-dichloro-diphenyl methane, MP: 177°-178°C, crystallize. The product is filtered, washed with toluene and dried at about 100°C. By concentrating the mother liquor remaining after the foregoing crystallization and filtration, another 225 grams of substantially pure 2,2'- dihydroxy-5,5'-dichloro-diphenyl methane are obtained. This latter crop may be crystallized from toluene in order to convert it into 2,2'-dihydroxy-5,5'- dichlorodiphenyl methane of melting point of 177°-178°C.

Therapeutic Function

Antiseptic, Anthelmintic, Antifungal

Air & Water Reactions

Slowly oxidized in air. Insoluble in water.

Reactivity Profile

Dichlorophen is incompatible with strong oxidizing agents and strong bases . Weakly acidic.

Fire Hazard

Flash point data for Dichlorophen are not available; however, Dichlorophen is probably combustible.

Trade name

ANTHIPHEN?; DIPHENTANE 70?; DICHLOROPHEN?; DICHLOROPHEN B?; DICHLOROPHENE 10?; DICHLORPHEN?; DIDROXANE?; DIPHENTHANE 70?; FUNGICIDE F?; FUNGICIDE GM?; FUNGICIDE M?; G 4?; GEFIR?; HYOSAN; KORIUM?; PLATH-LYSE?; PREVENTAL?; PREVENTOL?; PREVENTOL GD?; PREVENTOL GDC?; SUPER MOSSTOX?; TAENIATOL?; TENIATOL?; TENIATHANE?; TRIVEX?; VERMITHANA?; WESPURIL?

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion. A skin and severe eye irritant. Mutation data reported. Can cause cramps and diarrhea. Possibly similar to DDT. An FDA over-the counter drug. An anthelmintic. When heated to decomposition it emits toxic fumes of Cl-.

Metabolic pathway

Limited information is available to describe the degradation and metabolic fate of dichlorophen. A photodegradation study showed that dichlorophen undergoes hydroxydechlorination and dechlorination reactions as the major degradation pathways. Direct conjugation of one or both hydroxyl groups with sulfate and/or glucuronic acid was observed as the major metabolic pathway in the rat.

Purification Methods

Crystallise dichlorophen from toluene. [Beilstein 6 III 5406.]

Degradation

Dichlorophen (1) underwent hydroxydechlorination in acidic solution (pH 5.6) when irradiated under a xenon lamp (280 and 300 nm). 4-Chloro- 4'-hydroxy-2,2'-methylenediphenol(2) was the major product from reactions conducted in the absence of oxygen. A benzoquinone-like tautomer (3) was detected in oxygenated solution. A dechlorination product [4- chloro-2,2'-methylenediphenol(4)] was also observed as a minor product (Mansfield and Richard, 1996). These pathways are shown in Scheme 1.

Upstream product

• 75-11-6 diiodomethane 
• 106-48-9 4-chloro-phenol 
• 109-87-5 Dimethoxymethane 
• 5330-38-1 4-chloro-2-hydroxymethylphenol 
• 50-00-0 formaldehyd 
• 2467-02-9 Bis(2-hydroxyphenyl)methane 

Downstream Products

• 102886-32-8 bis-(5-chloro-2-hydroxy-3-pyrrolidinomethyl-phenyl)-methane 
• 114400-05-4 bis-(5-chloro-2-hydroxy-3-piperidinomethyl-phenyl)-methane 
• 102886-33-9 4,4'-dichloro-6,6'-bis-morpholinomethyl-2,2'-methanediyl-di-phenol 
• 101574-09-8 bis-(2-ethoxy-5-chloro-phenyl)-methane 
• 2467-02-9 Bis(2-hydroxyphenyl)methane 
• 13590-90-4 5,5'-dichloro-3,3'-dinitro-2,2'-dihydroxydiphenylmethane 
• 83817-55-4 5,5'-dichloro-2,2'-dihydroxy-3,3'-methanediyl-bis-benzenesulfonic acid 
• 83817-56-5 5-chloro-3-(5-chloro-2-hydroxy-benzyl)-2-hydroxy-benzenesulfonic acid 
• 15435-29-7 6,6'-dibromo-4,4'-dichloro-2,2'-methanediyl-di-phenol 
• 40542-32-3 5,5'-dichloro-2,2'-dihydroxy-3,3'-bis(hydroxymethyl)diphenylmethane 
• 102008-00-4 4,4'-dichloro-6,6'-bis-dimethylaminomethyl-2,2'-methanediyl-di-phenol 
• 7569-57-5 bis-(5-chloro-2-methoxy-phenyl)-methane 
• 78563-28-7 C₂₇H₂₀Cl₄O₄ 
• 138650-19-8 2,10-Dichloro-6-(4-chloro-3-methyl-phenoxy)-12H-5,7-dioxa-6-phospha-dibenzo[a,d]cyclooctene 6-oxide 

Relevant academic research and scientific papers

One-step novel synthesis of methylene bisphenols and methylene bisnaphthols using Lewis acid mediated rearrangement

Mono- and di-substituted isomeric methylene bisphenols and methylene bisnaphthols have been synthesized by rearrangement of the corresponding O-methoxyacetyl derivatives of phenols and naphthols, respectively, in presence of aluminium chloride under dry conditions. The chemistry observed is different from the usual Fries rearrangement reaction and involves an intermolecular rearrangement. The reactions reported here also reflect the influence of substituents present in the substrate as is supported by the substitution of the bridging methylene at a position meta to the phenolic hydroxyl in some of the minor products formed along-side the majorly formed ortho substituted products.

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

Novel ester derivatives of 2, 10-dichloro-12H-dibenzo [d,g] 1,3 dioxocin-6-carboxylic acid were synthesized and evaluated for their in vitro human cholesteryl ester transfer protein (CETP) inhibition. Three out of twelve synthesized compounds showed good inhibition of CETP (more than 50%). Compound 10 showed 81.32% inhibition of CETP at the dose of 0.5 nM whereas compound 11 showed 75.78% inhibition when tested at the same concentration. Compound 8 and 13 also showed modest activity with 57.44 and 38.02% inhibition. All other synthesized compounds were devoid of significant inhibitory activity against CETP. We also performed molecular docking to predict the mode of binding of all compounds at the active site of CETP. Compound 10 showed the dock score of -9.16 whereas the dock score of compound 11 was found to be -9.09.

Synthesis and antimicrobial activities of halogenated bis(hydroxyphenyl)methanes

A series of halophenols was prepared by the reaction of bis(hydroxyphenyl)methanes with effective halogenating agents such as bromine and sulfuryl chloride. One of these compounds, a biologically active halophenol-2,2′,3,3′-tetrabromo-4,4′,5,5′-tetrahydroxydiphenylmethane (1)-frequently isolated from red algae, was synthesized for the first time. Other halophenols included several novel compounds, together with known derivatives that were synthesized from the phenolic intermediates, bis(3,4-dihydroxyphenyl)methane (5) and bis(2-hydroxyphenyl)methane (14). All of the synthesized compounds were tested for antimicrobial activity against Gram-positive, Gram-negative bacteria and fungi. The preliminary structure-activity relationship was investigated in order to determine the essential structural requirements for their antimicrobial activity. Of all these halophenols, 2,2′,3,3′,6-pentabromo-4,4′,5,5′-tetrahydroxydiphenylmethane (8) was found to be the most active against Candida albicans, Aspergillus fumigatus, Trichophyton rubrum, and Trichophyton mentagrophytes while 3,3′,5,5′-tetrachloro-2,2′-dihydroxydiphenylmethane (18) exerted a powerful antibacterial effect against Staphylococcus aureus, Bacillus subtilis, Micrococcus luteus, Proteus vulgaris, and Salmonella typhimurium.

Synergistic biocide composition

A biocide composition is provided as an addition to substances that can be infected by harmful microorganisms, in which the biocide composition has at least two active biocidal substances, one of which is 2-methylisothiazolin-3-one. The composition is characterized in that it contains 1,2-benzisothiazolin-3-one, compositions containing 5-chloro-2-methylisothiazolin-3-one being excluded. In comparison with its individual components, the composition of the invention has a synergistic biocidal activity.

SLIME REMOVER AND SLIME PREVENTING/REMOVING AGENT

A drainage slime remover capable of spreading a solution of a solid over slime generated wall surface portions, comprising a solid containing a microorganism growth retarding substance and a container which has a shape for permitting the installation thereof at the inlet or upper portion of a drain outlet and stores the solid characterized in that the container has drain flow-in holes having an opening capable of controlling a drain flow-in amount and provided in the upper surface or the upper side portion of the container and solution flow-out holes having an opening capable of controlling a flow-out amount of a solid solution and provided in the bottom or the lower side portion of the container or additionally in the side surface thereof, and a slime preventing/removing agent which can remove slime from portions such as kitchen sinks and bathroom drain outlets where slime is grown by metabolites such as miscellaneous germs and mildews and which can prevent the occurrence of slime safely and for an extended period of time.

Clathrate composition including essential oils and method of using same

A composition for killing harmful organisms, which contains a clathrate compound composed of one or more natural essential oils and/or derivatives thereof selected from the group consisting of the following substances (1) to (22) and a polymolecular host compound capable of including the natural essential oils and/or derivatives thereof: (1) hinoki oil; (2) 1,8-cineole; (3) l-α-terpineole; l-carbone; (5) l-menthone; (6) d-pulegone; (7) citronellal; (8) linelool oxide; (9) d,l-citronellol; (10) 3,3,5-trimethylcyclohexanol; (11) l-perillaldehyde; (12) l-carveol; (13) myrtenal; (14) peppermint oil; (15) eucalyptus oil; (16) cinnamic aldehyde; (17) α-bromo-cinnamic aldehyde; (18) salicylaldehyde; (19) benzaldehyde; (20) paraphenyl-propionaldehyde; (21) paratolualdehyde; and (22) l-menthol.

Compositions

The problem of providing a storage stable anti-calculus toothpaste comprising a tripolyphosphate salt is remedied by incorporating more than 4% of the salt and having the pH from about 8 to about 10. A tripolyphosphate salt may also be combined with a noncationic anti-bacterial agent such as triclosan to provide a composition having anti-calculus and anti-plaque activity.

Antiplaque oral hygiene composition

An oral hygiene composition in the form of a dentifrice or a mouthwash, comprising: (a) from 0.01 to 2% by weight of the composition of an antibacterial compound of formula (I): STR1 in which R1 is oxygen, sulphur or an alkylene group of from 1 to 6 carbon atoms, each of R2 to R6 and R2 ' to R6 ' is hydrogen, hydroxyl or halogen; (b) from 0 to 90% by weight of a dentally acceptable abrasive, (c) from 0.1% to 15% by weight of a dialkali or tetra-alkali metal pyrophosphate salt or a mixture thereof and (d) water.

Dentifrice compositions

It is disclosed that a dentifrice which includes a surfactant and an anti-plaque agent comprising a substantially water-insoluble non-cationic antimicrobial agent or a zinc salt or a mixture thereof has enhanced activity when the dentifrice comprises at least 0.2% by weight of a lamellar liquid crystal surfactant phase having a lamellar spacing of less than 6.0 nm.

Vat dye and sulfur dye compositions

Specific vatting accelerators according to claims 1 and 2 are described. These can be added to a vat dye or sulfur dye composition, or to a dye bath or printing paste containing a vat dye or sulfur dye, by virtue of which an improvement of dye yield, particularly on cellulose materials, is obtained.