97-23-4 Usage
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.
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.
Chemical Properties
white or off-white powder
Originator
Dichlorophen,Aquapharm
Uses
Different sources of media describe the Uses of 97-23-4 differently. You can refer to the following data:
1. 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.
2. Agricultural fungicide; antimicrobial; germicide in soaps, shampoos, etc.
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
General Description
White slightly cream or light pink-colored powder. Melting point 177°C. Slight phenolic odor and a saline phenolic taste. Moderately toxic. Used as a fungicide and bactericide.
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.
Agricultural Uses
Fungicide, Herbicide, Bactericide, Veterinary
medicine: Not currently registered in the U.S. Dichlorophene
is a wide-spectrum, non-oxidizing biocide used against
all types of algae and bacteria. Widely used to treat fungi,
fleas and worm conditions in pet animals and livestock.
See U.S. Food and Drug Administration 20 CFR 520.580
and 20 CFR 520.581
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.
Check Digit Verification of cas no
The CAS Registry Mumber 97-23-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 7 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 97-23:
(4*9)+(3*7)+(2*2)+(1*3)=64
64 % 10 = 4
So 97-23-4 is a valid CAS Registry Number.
97-23-4Relevant articles and documents
One-step novel synthesis of methylene bisphenols and methylene bisnaphthols using Lewis acid mediated rearrangement
Kumar, Sandeep,Mehta, Shilpika Bali
, (2021/12/20)
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 antimicrobial activities of halogenated bis(hydroxyphenyl)methanes
Oh, Ki-Bong,Lee, Ji Hye,Lee, Jong Wook,Yoon, Kyung-Mi,Chung, Soon-Chun,Jeon, Heung Bae,Shin, Jongheon,Lee, Hyi-Seung
scheme or table, p. 945 - 948 (2009/09/06)
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.
SLIME REMOVER AND SLIME PREVENTING/REMOVING AGENT
-
, (2008/06/13)
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.
