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Dichlorophen

CAS No.
97-23-4
Chemical Name:
Dichlorophen
Synonyms
Preventol;DICHLOROPHENE;2,2-METHYLENEBIS(4-CHLOROPHENOL);phenol,2,2’-methylenebis-[4-chloro-;bis-2-hydroxy-5-chlorfenylmethan(czech);4-Chloro-2-(5-chloro-2-hydroxybenzyl)phenol, Bis(5-chloro-2-hydroxyphenyl)methane;G 4;DDDM;Fungo;Gefir
CBNumber:
CB9111491
Molecular Formula:
C13H10Cl2O2
Molecular Weight:
269.12
MDL Number:
MFCD00002322
MOL File:
97-23-4.mol
MSDS File:
SDS
Last updated:2024-04-17 18:50:11

Dichlorophen 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
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)
Indirect Additives used in Food Contact Substances 2,2'-DIHYDROXY-5,5'-DICHLOROPHENYLMETHANE (DICHLOROPHENE)
FDA 21 CFR 176.170; 310.545
EWG's Food Scores 6-9
FDA UNII T1J0JOU64O
Proposition 65 List Dichlorophene
ATC code P02DX02
NIST Chemistry Reference Phenol], 2,2'-methylenebis[4-chloro-(97-23-4)
EPA Substance Registry System Dichlorophene (97-23-4)
Pesticides Freedom of Information Act (FOIA) Dichlorophene

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS09
Signal word  Warning
Hazard statements  H302-H319-H410
Precautionary statements  P273-P301+P312+P330-P305+P351+P338
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
Toxicity LD50 in adult male, female rats (mg/kg): 1506, 1683 orally (Gaines, Linder)
NFPA 704
1
2 0

Dichlorophen price More Price(25)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 133221 Bis(5-chloro-2-hydroxyphenyl)methane 95% 97-23-4 50g $91.8 2024-03-01 Buy
Sigma-Aldrich 35992 Dichlorophene PESTANAL 97-23-4 250mg $29.7 2022-05-15 Buy
TCI Chemical M0213 2,2'-Methylenebis(4-chlorophenol) 97-23-4 25g $46 2024-03-01 Buy
TCI Chemical M0213 2,2'-Methylenebis(4-chlorophenol) 97-23-4 500g $156 2024-03-01 Buy
Alfa Aesar A12640 2,2'-Methylenebis(4-chlorophenol), 95% 97-23-4 25g $33.65 2024-03-01 Buy
Product number Packaging Price Buy
133221 50g $91.8 Buy
35992 250mg $29.7 Buy
M0213 25g $46 Buy
M0213 500g $156 Buy
A12640 25g $33.65 Buy

Dichlorophen Chemical Properties,Uses,Production

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

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

Uses

anthelmintic

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.

50-00-0
106-48-9
97-23-4
Synthesis of Dichlorophen from Formaldehyde and 4-Chlorophenol
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View Lastest Price from Dichlorophen manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Dichlorophen pictures 2024-04-18 Dichlorophen
97-23-4
US $15.00 / kg 1kg 99.912% 10ton Ouhuang Engineering Materials (Hubei) Co., Ltd
Dichlorophen pictures 2023-06-26 Dichlorophen
97-23-4
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
Dichlorophen pictures 2023-03-06 Dichlorophen
97-23-4
US $8.70 / Kg/Bag 10g 99% 10000kg Hebei Guanlang Biotechnology Co,.LTD
  • Dichlorophen pictures
  • Dichlorophen
    97-23-4
  • US $15.00 / kg
  • 99.912%
  • Ouhuang Engineering Materials (Hubei) Co., Ltd
  • Dichlorophen pictures
  • Dichlorophen
    97-23-4
  • US $0.00 / KG
  • 99%
  • Hebei Mojin Biotechnology Co., Ltd
  • Dichlorophen pictures
  • Dichlorophen
    97-23-4
  • US $8.70 / Kg/Bag
  • 99%
  • Hebei Guanlang Biotechnology Co,.LTD
Compound g4 Cordocel Cuniphen DDDM biocide-algaecide NL-4 Dichloorfeen Dichlorofen Dichlorofen (Czech) dichlorofen(czech) Dichlorophen B dichlorophenb Dichlorophene 10 dichlorophene10 Dichlorphen Didroxan Didroxane Difentan Diphentane 70 diphentane70 Diphenthane 70 diphenthane70 Ecco MP 2004 Embephen Fungicide fx Fungicide GM Fungicide M Plath-Lyse Prevental Preventol GD Preventol GDC preventolgd preventolgdc sindarg4 Super moss killer & lawn fungicide Taeniatol Teniathane Teniatol Teniotol Trivex Vermithana Wespuril Westpuril HYOSAN(R) G-4(R) DICHLOROPHEN 3,7-Dihydro-8-[(β-hydroxy-α-methylphenethyl)amino]-1,3,7-trimethyl-1H-purine-2,6-dione 4-chloro-2-[(5-chloro-2-hydroxyphenyl)methyl]phenol 4-chloro-2-[(5-chloro-2-hydroxy-phenyl)methyl]phenol Diclorofen Bis(5-chloro-2-hydroxyphenyl)methane 5,5'-Dichloro-2,2'-dihydroxydiphenylmethane Dichlorophen Dichlorophen 1g [97-23-4] 4-chloro-2-(5-chloro-2-hydroxybenzyl)phenol, tech 2,2zzhlxy-Methylenebis(4-chlorophenol) Dichlorophenol(DDM) SUPER MOSSTOX TENIATOL(R) TENIATHANE(R) PARABIS(R)