Triclosan

Base Information

• Chemical Name: Triclosan
• CAS No.: 3380-34-5
• Deprecated CAS: 112099-35-1,88032-08-0,164325-69-3,261921-78-2,1155174-27-8,1155174-27-8,164325-69-3,261921-78-2,88032-08-0
• Molecular Formula: C12H7Cl3O2
• Molecular Weight: 289.545
• Hs Code.: 2909.50
• European Community (EC) Number: 222-182-2
• NSC Number: 759151
• UNII: 4NM5039Y5X
• DSSTox Substance ID: DTXSID5032498
• Nikkaji Number: J7.727E
• Wikipedia: Triclosan
• Wikidata: Q408646
• NCI Thesaurus Code: C61986
• RXCUI: 10795
• Pharos Ligand ID: GK49HFJ5SFU1
• Metabolomics Workbench ID: 52732
• ChEMBL ID: CHEMBL849
• Mol file: 3380-34-5.mol

Synonyms:2,4,4'-trichloro-2'-hydroxydiphenyl ether;2-Hydroxy-2',4,4'-trichlorodiphenyl Ether;Aquasept;Clearasil Daily Face Wash;Cliniclean;DP300, Irgasan;Irgasan DP 300;Irgasan DP300;Irgasan-DP300;Manusept;Microshield T;Oxy Skin Wash;pHisoHex;Sapoderm;Ster Zac Bath Concentrate;Ster-Zac Bath Concentrate;SterZac Bath Concentrate;Tersaseptic;Triclosan;Trisan

Chemical Property of Triclosan

Chemical Property:

• Appearance/Colour: powder
• Vapor Pressure: 9.31E-15mmHg at 25°C
• Melting Point: 56-60 °C(lit.)
• Refractive Index: 1.4521 (estimate)
• Boiling Point: 344.6 °C at 760 mmHg
• PKA: 7.9(at 25℃)
• Flash Point: 162.2 °C
• PSA: 29.46000
• Density: 1.49 g/cm³
• LogP: 5.14470
• Storage Temp.: Refrigerator
• Solubility.: H2O: soluble12g/L at 20°C
• Water Solubility.: Soluble in ethanol, methanol, diethyl ether and sodium hydroxide solution (1M). Slightly soluble in water.
• XLogP3: 5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 287.951163
• Heavy Atom Count: 17
• Complexity: 252

Purity/Quality:

≥99%, ^*data from raw suppliers

Triclosan ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, N
• Hazard Codes: Xi,N
• Statements: 36/38-50/53-36/37/38
• Safety Statements: 26-39-46-60-61-24/25-22-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Biocides/Disinfectants
• Canonical SMILES: C1=CC(=C(C=C1Cl)O)OC2=C(C=C(C=C2)Cl)Cl
• Recent ClinicalTrials: Pre-surgical Antisepsis of Hands After Washing With Triclosan 0.5% Compared to Propan-1-ol 60%
• Recent EU Clinical Trials: Multicentric, randomized, double-blinded, vehicle-controlled, phase III-bilateral comparative study for treatment of staphylococcus superinfection in atopic dermatitis with hydrophobic Triclosan-cream 2% (InfectoDermaSept)
• Uses: 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 Used as bacteriostat and preservative for cosmetic and detergent compositions. Antiseptic, disinfectant. anticonvulsant Bacteriostat and preservative for cosmetic and detergent preparations. triclosan is a preservative considered to have a low sensitizing potential in leave-on preparations.
• 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.
• Description: Triclosan is a broad-spectrum antibacterial agent that inhibits bacterial fatty acid synthesis. It is effective against Gram-negative and Gram-positive bacteria, as well as against Mycobacteria. Triclosan is used in a variety of products, including antiseptic soaps, deodorants, and hand washes.
• Physical properties: Triclosan is a slightly aromatic high-purity white crystalline powder; Solubility: slightly soluble in water, moderately soluble in dilute alkali, has high solubility in many organic solvents, in water-soluble solvents or surfactants After dissolving, it can be made into a transparent concentrated liquid product.
• Indications: Triclosan is a broad-spectrum antimicrobial compound. It was originally used in soaps, antiperspirants, and cosmetic toiletries as a germicide. Today, triclosan is incorporated into toothpaste because of its wide spectrum of antimicrobial activities and low toxicity.
• Therapeutic Function: Antiseptic
• Clinical Use: Triclosan plus copolymer is available in toothpaste. Commercially available dentifrice concentrations contain 0.3% triclosan and 2.0% PVM/MA copolymer.

Technology Process of Triclosan

There total 25 articles about Triclosan which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.2%

TBDMS-TCS → triclosan (3380-34-5,88032-08-0)

Guidance literature:

With copper dichloride; In tetrahydrofuran; water; at 50 ℃;

Reference yield: 97.0%

2,4,4'-trichloro-2'-trimethylsilyloxy diphenyl ether → triclosan (3380-34-5,88032-08-0)

Guidance literature:

With copper(II) choride dihydrate; In 1,4-dioxane; water; at 20 ℃;

Reference yield: 96.0%

C28H25Cl3O2Si → triclosan (3380-34-5,88032-08-0)

Guidance literature:

With copper(ll) sulfate pentahydrate; In water; acetone; at 35 ℃;

upstream raw materials:

7-(2-thienylacetylamino)-3-[5-chloro-2-(2,4-dichlorophenoxy)phenoxymethyl]-3-cephem-4-carboxylic acid

1-ethenyl-2-pyrrolidinone

5-chloro-2-(2,4-dichlorophenoxy)phenyl acrylate

propan-1-ol

Downstream raw materials:

Dithiocarbonic acid O-[5-chloro-2-(2,4-dichloro-phenoxy)-phenyl] ester S-phenyl ester

Thiocarbonic acid O-biphenyl-2-yl ester O-[5-chloro-2-(2,4-dichloro-phenoxy)-phenyl] ester

C₁₃H₆Cl₄O₂S

Thiocarbonic acid O,O-bis-[5-chloro-2-(2,4-dichloro-phenoxy)-phenyl] ester

Refernces

• 1、 -. "Synthesis method of triclosan". . . Retrieved 2021/01/15.
• 2、 -. "CYCLIC PEROXIDE OXIDATION OF AROMATIC COMPOUND PRODUCTION AND USE THEREOF". Page/Page column 10. . Retrieved 2014/10/15.