Triclocarban

Base Information

• Chemical Name: Triclocarban
• CAS No.: 101-20-2
• Molecular Formula: C13H9 Cl3 N2 O
• Molecular Weight: 315.586
• Hs Code.: 38220090
• European Community (EC) Number: 202-924-1
• NSC Number: 72005
• UNII: BGG1Y1ED0Y
• DSSTox Substance ID: DTXSID4026214
• Nikkaji Number: J60.108J
• Wikipedia: Triclocarban
• Wikidata: Q416579
• NCI Thesaurus Code: C47770
• Pharos Ligand ID: DVWJJMKLZUPC
• Metabolomics Workbench ID: 56951
• ChEMBL ID: CHEMBL1076347
• Mol file: 101-20-2.mol

Synonyms:3,4,4'-trichlorocarbanilide;Cutisan;Septivon;Septivon-Lavril;Solubacter;trichlorcarban;trichlorocarbanilide;triclocarban

Chemical Property of Triclocarban

Chemical Property:

• Appearance/Colour: white crystals or powder
• Vapor Pressure: <0.1 mm Hg ( 25 °C)
• Melting Point: 254-256 °C(lit.)
• Refractive Index: 1.6300 (estimate)
• Boiling Point: 344.2 °C at 760 mmHg
• PKA: 12.77±0.70(Predicted)
• Flash Point: 162 °C
• PSA: 41.13000
• Density: 1.534 g/cm³
• LogP: 5.43680
• Storage Temp.: Refrigerator
• Solubility.: methanol: soluble
• Water Solubility.: <0.1 g/100 mL at 26 oC
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 313.978046
• Heavy Atom Count: 19
• Complexity: 308

Purity/Quality:

99% ^*data from raw suppliers

3,4,4` Trichlorocarbanilide (Triclocarban) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Biocides/Disinfectants
• Canonical SMILES: C1=CC(=CC=C1NC(=O)NC2=CC(=C(C=C2)Cl)Cl)Cl
• Description: Triclocarban (TCC) is a polychlorinated aromatic antimicrobial agent belonging to the class of diarylureas or bis-arylureas. It falls under the category of antimicrobial agents and antiseptics.
• Uses and Mechanism of Action: Triclocarban(TCC) is utilized for its broad-spectrum antimicrobial and antiseptic properties in personal care products and healthcare settings, including antibacterial soaps, body lotions, deodorants, detergents, medical disinfectants, aftershave soaps, hand sanitizers, toothpaste, mouthwash, air fresheners, fabric and leather finishing agents, and more. It acts as a fungicide and preservative in various consumer products. Its precise mechanism of action involves disrupting microbial membranes and interfering with cellular functions, leading to microbial death.
• History and Development: Discovery and Synthesis:; Triclocarban was discovered in the late 1930s and early 1940s during the exploration of antimicrobial compounds derived from chlorinated aromatic rings.; ; Regulatory Status:; In September 2016, the U.S. Food and Drug Administration (FDA) banned its use in over-the-counter hand and body washes due to concerns about its toxicity. However, triclocarban is still used in various countries, although banned in some regions like the EU for certain applications.; ; Triclocarban has been a widely used antimicrobial agent in personal care products for over 60 years, but concerns about its toxicity and environmental impact have led to regulatory restrictions in some regions. Research efforts are ongoing to develop alternative antimicrobial compounds to replace triclocarban in consumer products.
• References: [1] A simple and reliable electrochemical method employing an unmodified boron-doped diamond electrode for the determination of triclocarban; DOI 10.1016/j.electacta.2024.144093; [2] The pH-specific response of soil resistome to triclocarban and arsenic co-contamination; DOI 10.1016/j.jhazmat.2023.132952; [3] The Different Facets of Triclocarban: A Review; DOI 10.3390/molecules26092811

Technology Process of Triclocarban

There total 5 articles about Triclocarban 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: 94.0%

carbon monoxide (201230-82-2) + 4-chloro-aniline (106-47-8) + m,p-dichloroaniline (95-76-1) → 3,4,4'-trichlorocarbanilide (101-20-2)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate; triethylamine; sodium iodide; at 50 ℃; for 24h; under 760.051 Torr;

Reference yield: 29.0%

p-chlorphenylisocyanate (104-12-1) + m,p-dichloroaniline (95-76-1) → 3,4,4'-trichlorocarbanilide (101-20-2)

Guidance literature:

In acetone; at 100 ℃; for 6h;

DOI:10.3390/antibiotics10020204

Reference yield:

4-chloro-aniline (106-47-8) + 3,4-dichlorophenylisocyanate (102-36-3) → 3,4,4'-trichlorocarbanilide (101-20-2)

Guidance literature:

DOI:10.1021/ja01562a053

upstream raw materials:

p-chlorphenylisocyanate

m,p-dichloroaniline

4-chloro-aniline

3,4-dichlorophenylisocyanate

Downstream raw materials:

4-chloro-aniline

m,p-dichloroaniline

Refernces

• 1、 -. "Method for synthesizing asymmetric disubstituted urea through catalytic oxidation and carbonylation". Paragraph 0091; 0092. . Retrieved 2017/12/28.
• 2、 Minatchy, S.,Mathew, Nisha. "Synthesis and structure activity relationships in diphenylureas against Culex quinouefasciatus". . p. 1066 - 1068. Retrieved 2007/10/03.