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3380-34-5 Structure

3380-34-5 Structure



2,4,4'-Trichloro-2-2' Hydroxy Diphenyl Ether
2,4,4'-Trichloro-2'-hydroxydiphenyl ether (Triclosan)
Phenol, 5-chloro-2-(2,4-dichlorophenoxy)-

[Molecular Formula]

[MDL Number]

[Molecular Weight]

[MOL File]

Chemical PropertiesBack Directory

[mp ]

56-60 °C(lit.)

Stable. Incompatible with strong oxidizing agents.
[Merck ]

[BRN ]

[CAS DataBase Reference]

3380-34-5(CAS DataBase Reference)
[NIST Chemistry Reference]

[EPA Substance Registry System]

3380-34-5(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

[Risk Statements ]

R36/38:Irritating to eyes and skin .
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S39:Wear eye/face protection .
S46:If swallowed, seek medical advice immediately and show this container or label .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S24/25:Avoid contact with skin and eyes .
S22:Do not breathe dust .
S36:Wear suitable protective clothing .

UN 3077 9/PG 3
[WGK Germany ]


[HazardClass ]

[PackingGroup ]

[HS Code ]

[Hazardous Substances Data]

3380-34-5(Hazardous Substances Data)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Potassium hydroxide -->Iron-->Copper-->Bromobenzene-->Diphenyl oxide-->2,4-Dichlorophenol-->Guaiacol-->2,6-Dichlorophenol-->2-Phenoxyaniline
Questions And AnswerBack Directory

Triclosan is an efficient broad-spectrum topical antimicrobial disinfectant which is normally white or off-white crystalline powder. It has a slightly phenolic odor. It is insoluble in water but easily soluble in organic solvents and alkali. It has a relative stable chemical property and is heating-resistant and also resistant to acid and alkali hydrolysis without generating any symptoms of the toxicity and environmental pollution. It is internationally recognized as a fungicide variety with specific efficacy. It can kill bacteria such as Staphylococcus aureus, Escherichia coli and fungi such as Candida albicans. It also has an inhibitory effect on the virus (e.g., hepatitis B virus, etc.) while being able to protect the beneficial bacteria. The mechanism of action of triclosan is as below: it is first adsorbed on the bacterial cell wall and then further penetrates through the cell wall and has reaction with the lipid and protein in the cytoplasm, and thus resulting in protein denaturation which further kill the bacteria. Currently it has been widely applied to highly-efficient medicated soap (health soap, health lotion), removing underarm odor (foot aerosol), hand sanitizer, wound disinfectant sprays, medical equipment disinfectants, hygiene cleanser (cream), and air fresheners and refrigerator deodorants and some other daily chemicals. It is also used for the cleaning of the health fabric and the anti-corrosion treatment of plastics. Its high purity version can be added to the toothpaste and mouthwash for treatment of gingivitis, periodontitis and oral ulcers. The State content must not exceed 0.3%.

In 2004, a teacher (Dr. Peter Vikesland) from the Virginia Tech University (US) had found from the experiments that the reaction between the triclosan-containing product and the chlorine-containing tap water containing can generate a substance known as "chloroform aryl", that is, chloroform (chemical name: trichloromethane) which is a colorless, volatile liquid with a special sweetness. Upon exposure to light, it will be oxidized to generate hydrogen chloride and phosgene. It had been once used as an anesthetic. Animal experiments have found that this substance will do harm to the heart and liver with mild teratogenicity and can induce the liver cancer of mice. However, so far no studies on the human carcinogenicity have been reported. For insurance purposes, both the International Cancer Research Centre and the United States have already has the chloroform be listed as suspected carcinogens to the human body.
[Toothpaste Standard]

The national standard of the toothpaste used in China is the new national standard of toothpaste (GB8372-2008) implemented on February 1, 2009. Compared with the 2001 version of toothpaste standard, the new national standard has been supplemented and adjusted in various aspects. In the new national standard of toothpaste, the prohibited or restricted ingredients include nearly 1,500 kinds, including diethylene glycol and triclosan. The provision of diethylene glycol is that it is not allowed to artificially add it to the raw materials, such as being introduced as impurities. Its content in the toothpaste should not exceed 0.1%. Triclosan were listed as being allowable preservatives but with the usage amount not exceeding 0.3%. The new national standard has ruled that the fluorine content of the fluoride-containing toothpaste should be within the range of 0.04%-0.15%, and the fluoride content should be within the range of 0.05% to 011% for children fluoride-containing toothpaste.
The above information is edited by the chemicalbook of Dai Xiongfeng.
[Chemical Properties]

It is colorless and long needle-like crystals with a melting point being around 54-57.3 ℃ (60-61 ℃). It is slightly soluble in water and soluble in ethanol, acetone, ethyl ether and alkali solution. It has a chloro-phenol odor.

1. It can be used as antiseptic and fungicide and applied to cosmetics, emulsions and resins; also can be used for the manufacture of disinfection medicated soap. The LD50 of mice subject to oral administration of this product is 4g/kg.
2. It can be used for the production of top-grade daily chemical product, the disinfectants of medical instrument as well as diet instrument as well as the preparation of the anti-bacterial, deodorant finishing agent of fabric.
3. It can also be applied to biochemical studies. It is a kind of broad-spectrum antimicrobial agents which inhibit the type II fatty acid synthase (FAS-II) of bacteria and parasites, and also inhibits the mammalian fatty acid synthase (FASN), and may also have anticancer activity
[Production method]

1. Take 2, 4-dichloro-phenol as the raw material; use 2,4-dichloro-phenol to react with potassium hydroxide to generate dichlorophenol potassium which further reacts with 2,5-dichloro-nitrobenzene in the catalysis of copper for generation of 2,4,4-trichloro-2'-nitro diphenyl ether. It is further reduced by iron powder to generate 2, 4, 4-trichloro-2'-amino diphenyl ether, and then further went through diazotization hydrolysis to obtain the product.
2. Take o-methoxyphenol as the raw material: have potassium hydroxide powder reacted with guaiacol to generate guaiacol potassium. Apply reaction between bromobenzene and methoxy ether, together with chlorine for chlorination to obtain 2, 4, 4’-trichloro-2'-methoxydiphenyl ether. Take AICI3 as hydrolysis catalyst to generate 2,4,4'-trichloro-2'-hydroxydiphenyl ether.
Spectrum DetailBack Directory
[Spectrum Detail]

Well-known Reagent Company Product InformationBack Directory
[Alfa Aesar]

5-Chloro-2-(2,4-dichlorophenoxy)phenol, 99%(3380-34-5)
[Sigma Aldrich]


2,4,4'-Trichloro-2'-hydroxydiphenyl Ether,>96.0%(GC)(3380-34-5)
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