Dichlorophen Chemical Properties

Melting point:

168-172 °C (lit.)

Boiling point:

418.7±40.0 °C(Predicted)

Density 

1.3239 (estimate)

vapor pressure 

1.3 x 10^-5 Pa (25 °C)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Soluble in methanol, ether

form 

Solid

pka

pK1:7.6;pK2:11.5 (25°C)

color 

White to Light yellow to Light orange

Water Solubility 

<0.1 g/100 mL at 22 ºC

Merck 

14,3071

BRN 

1884514

Stability:

Stable. Incompatible with strong bases, strong oxidizing agents.

LogP

4.260

CAS DataBase Reference

97-23-4(CAS DataBase Reference)

NIST Chemistry Reference

Phenol], 2,2'-methylenebis[4-chloro-(97-23-4)

EPA Substance Registry System

Dichlorophene (97-23-4)

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

22-36-50/53

Safety Statements 

26-60-61

RIDADR 

UN 3077 9/PG 3

WGK Germany 

3

RTECS 

SM0175000

TSCA 

Yes

HazardClass 

9

PackingGroup 

III

HS Code 

29081990

Hazardous Substances Data

97-23-4(Hazardous Substances Data)

Toxicity

LD50 in adult male, female rats (mg/kg): 1506, 1683 orally (Gaines, Linder)

MSDS

• Language:English Provider:2,2'-Methylene-bis(4-chlorophenol)
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Dichlorophen Usage And Synthesis

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

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.

Uses

anthelmintic

Uses

Agricultural fungicide; antimicrobial; germicide in soaps, shampoos, etc.

Definition

ChEBI: Dichlorophen is a diarylmethane and a bridged diphenyl fungicide.

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.

Dichlorophen(97-23-4)Related Product Information

• p-Cresol
• 4-Chlorophenol
• 3-Trifluoromethylphenol
• m-Cresol
• Xylenol
• Methylene Blue
• 4,4'-Diphenylmethane diisocyanate
• Solvent Red 43
• Baclofen
• 2,3,6-Trimethylphenol
• Epichlorohydrin
• DICLOFENAC ACID
• Difluorochloromethane
• Chloroacetic acid
• Pentachlorophenol
• Bis(2-hydroxy-3,5-dichlorophen
• Cefazedone
• Methylene Chloride