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101-20-2,MFCD00013254
Catalog No.:AA0003CW

101-20-2 | 3-(4-chlorophenyl)-1-(3,4-dichlorophenyl)urea

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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA0003CW
Chemical Name:
3-(4-chlorophenyl)-1-(3,4-dichlorophenyl)urea
CAS Number:
101-20-2
Molecular Formula:
C13H9Cl3N2O
Molecular Weight:
315.5824
MDL Number:
MFCD00013254
SMILES:
O=C(Nc1ccc(c(c1)Cl)Cl)Nc1ccc(cc1)Cl
NSC Number:
72005
Properties
Properties
 
Form:
Solid  
MP:
254-256 °C(lit.)  
Refractive Index:
1.6300 (estimate)  
Solubility:
methanol: soluble  
Storage:
Keep in dry area;Room Temperature;  

Computed Properties
 
Complexity:
308  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
1  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
2  
XLogP3:
5.3  

Downstream Synthesis Route

[1]Catalano,Alessia;Iacopetta,Domenico;Rosato,Antonio;Salvagno,Lara;Ceramella,Jessica;Longo,Francesca;Sinicropi,MariaStefania;Franchini,Carlo[Antibiotics,2021,vol.10,#2,p.1-13]

[2]CurrentPatentAssignee:PFIZERINC-US2818390,1954,ACurrentPatentAssignee:PFIZERINC-US2846398,1955,A

[1]Audu,AramaniA.[ActaChimicaHungarica,1987,vol.124,#4,p.603-608]

[2]Kumar,Amit;Luk,James[EuropeanJournalofOrganicChemistry,2021,vol.2021,#32,p.4546-4550]

[1]Minatchy,S.;Mathew,Nisha[IndianJournalofChemistry-SectionBOrganicandMedicinalChemistry,1998,vol.37,#10,p.1066-1068]

Literature

Title: Development of a screening approach to detect thyroid disrupting chemicals that inhibit the human sodium iodide symporter (NIS).

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20170401

Title: Effect of triclosan, triclocarban, 2,2',4,4'-tetrabromodiphenyl ether, and bisphenol A on the iodide uptake, thyroid peroxidase activity, and expression of genes involved in thyroid hormone synthesis.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20160401

Title: The in vitro estrogenic activities of triclosan and triclocarban.

Journal: Journal of applied toxicology : JAT 20140901

Title: Effects of triclocarban on the transcription of estrogen, androgen and aryl hydrocarbon receptor responsive genes in human breast cancer cells.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20130801

Title: Transfer of wastewater associated pharmaceuticals and personal care products to crop plants from biosolids treated soil.

Journal: Ecotoxicology and environmental safety 20121101

Title: Metabolization of the bacteriostatic agent triclosan in edible plants and its consequences for plant uptake assessment.

Journal: Environmental science & technology 20121002

Title: High-performance liquid chromatographic determination of triclosan and triclocarban in cosmetic products.

Journal: International journal of cosmetic science 20121001

Title: Simultaneous determination of triclosan, triclocarban, and transformation products of triclocarban in aqueous samples using solid-phase micro-extraction-HPLC-MS/MS.

Journal: Journal of separation science 20121001

Title: Occurrence of triclosan, triclocarban, and its lesser chlorinated congeners in Minnesota freshwater sediments collected near wastewater treatment plants.

Journal: Journal of hazardous materials 20120830

Title: Effects of triclosan and triclocarban, two ubiquitous environmental contaminants, on anatomy, physiology, and behavior of the fathead minnow (Pimephales promelas).

Journal: Archives of environmental contamination and toxicology 20120701

Title: Bioconcentration of triclosan, methyl-triclosan, and triclocarban in the plants and sediments of a constructed wetland.

Journal: Chemosphere 20120701

Title: [Triclocarban antibacterial activity on resistant staphylococci, streptococci, and enterococci].

Journal: Medecine et maladies infectieuses 20120601

Title: Metabolism of the antibacterial triclocarban by human epidermal keratinocytes to yield protein adducts.

Journal: Journal of biochemical and molecular toxicology 20120601

Title: Combined sewer overflows: an environmental source of hormones and wastewater micropollutants.

Journal: Environmental science & technology 20120515

Title: Whole blood is the sample matrix of choice for monitoring systemic triclocarban levels.

Journal: Chemosphere 20120501

Title: Removal of selected endocrine disrupting chemicals (EDCs) and pharmaceuticals and personal care products (PPCPs) during ferrate(VI) treatment of secondary wastewater effluents.

Journal: Water research 20120501

Title: Pharmaceutical and personal care products in groundwater, subsurface drainage, soil, and wheat grain, following a high single application of municipal biosolids to a field.

Journal: Chemosphere 20120401

Title: Fate of triclosan and triclocarban in soil columns with and without biosolids surface application.

Journal: Environmental toxicology and chemistry 20120201

Title: Automated on-line column-switching HPLC-MS/MS method for the quantification of triclocarban and its oxidative metabolites in human urine and serum.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20120115

Title: An immunoassay to evaluate human/environmental exposure to the antimicrobial triclocarban.

Journal: Environmental science & technology 20120103

Title: In vitro glucuronidation of the antibacterial triclocarban and its oxidative metabolites.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20120101

Title: Influence of Nitrate and Nitrite on Thyroid Hormone Responsive and Stress-Associated Gene Expression in Cultured Rana catesbeiana Tadpole Tail Fin Tissue.

Journal: Frontiers in genetics 20120101

Title: Impairment of the bacterial biofilm stability by triclosan.

Journal: PloS one 20120101

Title: Triclocarban mediates induction of xenobiotic metabolism through activation of the constitutive androstane receptor and the estrogen receptor alpha.

Journal: PloS one 20120101

Title: Comment on 'Effects of triclocarban, triclosan, and methyl triclosan on thyroid hormone action and stress in frog and mammalian culture systems'.

Journal: Environmental science & technology 20111201

Title: Phytoaccumulation of antimicrobials from biosolids: impacts on environmental fate and relevance to human exposure.

Journal: Water research 20111101

Title: Effects of bisphenol A and triclocarban on brain-specific expression of aromatase in early zebrafish embryos.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20111025

Title: Mobilization of endocrine-disrupting chemicals and estrogenic activity in simulated rainfall runoff from land-applied biosolids.

Journal: Environmental toxicology and chemistry 20111001

Title: Bioconcentration, metabolism and excretion of triclocarban in larval Qurt medaka (Oryzias latipes).

Journal: Aquatic toxicology (Amsterdam, Netherlands) 20111001

Title: Determination of preservative and antimicrobial compounds in fish from Manila Bay, Philippines using ultra high performance liquid chromatography tandem mass spectrometry, and assessment of human dietary exposure.

Journal: Journal of hazardous materials 20110915

Title: Competitive selection from single domain antibody libraries allows isolation of high-affinity antihapten antibodies that are not favored in the llama immune response.

Journal: Analytical chemistry 20110915

Title: The structure-activity relationship of urea derivatives as anti-tuberculosis agents.

Journal: Bioorganic & medicinal chemistry 20110915

Title: Inhibition of soluble epoxide hydrolase contributes to the anti-inflammatory effect of antimicrobial triclocarban in a murine model.

Journal: Toxicology and applied pharmacology 20110901

Title: Comment on 'Effects of triclocarban, triclosan, and methyl triclosan on thyroid hormone action and stress in frog and mammalian culture systems'.

Journal: Environmental science & technology 20110901

Title: Biomarkers of exposure to triclocarban in urine and serum.

Journal: Toxicology 20110815

Title: Multi-residue screening of prioritised human pharmaceuticals, illicit drugs and bactericides in sediments and sludge.

Journal: Journal of environmental monitoring : JEM 20110801

Title: Effects of triclocarban, triclosan, and methyl triclosan on thyroid hormone action and stress in frog and mammalian culture systems.

Journal: Environmental science & technology 20110615

Title: Dual-resolution molecular dynamics simulation of antimicrobials in biomembranes.

Journal: Journal of the Royal Society, Interface 20110606

Title: Multiresidue analytical method for the determination of antimicrobials, preservatives, benzotriazole UV stabilizers, flame retardants and plasticizers in fish using ultra high performance liquid chromatography coupled with tandem mass spectrometry.

Journal: Journal of chromatography. A 20110603

Title: Distribution and accumulation of endocrine-disrupting chemicals and pharmaceuticals in wastewater irrigated soils in Hebei, China.

Journal: Environmental pollution (Barking, Essex : 1987) 20110601

Title: Sorption of biocides, triazine and phenylurea herbicides, and UV-filters onto secondary sludge.

Journal: Water research 20110601

Title: Para- and ortho-substitutions are key determinants of polybrominated diphenyl ether activity toward ryanodine receptors and neurotoxicity.

Journal: Environmental health perspectives 20110401

Title: Investigation of human exposure to triclocarban after showering and preliminary evaluation of its biological effects.

Journal: Environmental science & technology 20110401

Title: Occurrence and behavior of pharmaceuticals, steroid hormones, and endocrine-disrupting personal care products in wastewater and the recipient river water of the Pearl River Delta, South China.

Journal: Journal of environmental monitoring : JEM 20110401

Title: Persistence of triclocarban and triclosan in soils after land application of biosolids and bioaccumulation in Eisenia foetida.

Journal: Environmental toxicology and chemistry 20110301

Title: A review of personal care products in the aquatic environment: environmental concentrations and toxicity.

Journal: Chemosphere 20110301

Title: High throughput analysis of solid-bound endocrine disruptors by LDTD-APCI-MS/MS.

Journal: Journal of environmental monitoring : JEM 20110301

Title: Effects of triclocarban on intact immature male rat: augmentation of androgen action.

Journal: Reproductive sciences (Thousand Oaks, Calif.) 20110201

Title: Review of 'emerging' organic contaminants in biosolids and assessment of international research priorities for the agricultural use of biosolids.

Journal: Environment international 20110101

Title: Toxicity and bioaccumulation of biosolids-borne triclocarban (TCC) in terrestrial organisms.

Journal: Chemosphere 20110101

Title: Determination of pharmaceuticals, steroid hormones, and endocrine-disrupting personal care products in sewage sludge by ultra-high-performance liquid chromatography-tandem mass spectrometry.

Journal: Analytical and bioanalytical chemistry 20110101

Title: Toward identifying the next generation of superfund and hazardous waste site contaminants.

Journal: Environmental health perspectives 20110101

Title: Cleansers and their role in various dermatological disorders.

Journal: Indian journal of dermatology 20110101

Title: The Matthew effect in environmental science publication: a bibliometric analysis of chemical substances in journal articles.

Journal: Environmental health : a global access science source 20110101

Title: Occurrence and loss over three years of 72 pharmaceuticals and personal care products from biosolids-soil mixtures in outdoor mesocosms.

Journal: Water research 20101201

Title: Electrochemistry-mass spectrometry unveils the formation of reactive triclocarban metabolites.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20101201

Title: Identification of wastewater bacteria involved in the degradation of triclocarban and its non-chlorinated congener.

Journal: Journal of hazardous materials 20101115

Title: Personal care products and endocrine disruption: A critical review of the literature.

Journal: Critical reviews in toxicology 20101101

Title: Some flame retardants and the antimicrobials triclosan and triclocarban enhance the androgenic activity in vitro.

Journal: Chemosphere 20101101

Title: Rapid resolution liquid chromatography-tandem mass spectrometry method for the determination of endocrine disrupting chemicals (EDCs), pharmaceuticals and personal care products (PPCPs) in wastewater irrigated soils.

Journal: Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes 20101001

Title: Aquatic hazard assessment for pharmaceuticals, personal care products, and endocrine-disrupting compounds from biosolids-amended land.

Journal: Integrated environmental assessment and management 20101001

Title: Computational thermochemistry of six ureas, imidazolidin-2-one, N,N'-trimethyleneurea, benzimidazolinone, parabanic acid, barbital (5,5'-diethylbarbituric acid), and 3,4,4'-trichlorocarbanilide, with an extension to related compounds.

Journal: The journal of physical chemistry. A 20100902

Title: Use of chemical mixtures to differentiate mechanisms of endocrine action in a small fish model.

Journal: Aquatic toxicology (Amsterdam, Netherlands) 20100901

Title: Triclocarban and triclosan biodegradation at field concentrations and the resulting leaching potentials in three agricultural soils.

Journal: Chemosphere 20100901

Title: Retention-release characteristics of triclocarban and triclosan in biosolids, soils, and biosolids-amended soils.

Journal: Environmental toxicology and chemistry 20100901

Title: Uptake of pharmaceutical and personal care products by soybean plants from soils applied with biosolids and irrigated with contaminated water.

Journal: Environmental science & technology 20100815

Title: Stir-bar-sorptive extraction and ultra-high-performance liquid chromatography-tandem mass spectrometry for simultaneous analysis of UV filters and antimicrobial agents in water samples.

Journal: Analytical and bioanalytical chemistry 20100801

Title: Occurrence and risks of triclosan and triclocarban in the Pearl River system, South China: from source to the receiving environment.

Journal: Journal of hazardous materials 20100715

Title: Fate of 14C-triclocarban in biosolids-amended soils.

Journal: The Science of the total environment 20100601

Title: Trace determination of triclosan and triclocarban in environmental water samples with ionic liquid dispersive liquid-phase microextraction prior to HPLC-ESI-MS-MS.

Journal: Analytical and bioanalytical chemistry 20100601

Title: Measured physicochemical characteristics and biosolids-borne concentrations of the antimicrobial Triclocarban (TCC).

Journal: The Science of the total environment 20100601

Title: Quantitative gene monitoring of microbial tetracycline resistance using magnetic luminescent nanoparticles.

Journal: Journal of environmental monitoring : JEM 20100601

Title: Temperature-controlled ionic liquid dispersive liquid-phase microextraction for the sensitive determination of triclosan and triclocarban in environmental water samples prior to HPLC-ESI-MS/MS.

Journal: Journal of separation science 20100601

Title: Characterization of the androgen-sensitive MDA-kb2 cell line for assessing complex environmental mixtures.

Journal: Environmental toxicology and chemistry 20100601

Title: The antimicrobial triclocarban stimulates embryo production in the freshwater mudsnail Potamopyrgus antipodarum.

Journal: Environmental toxicology and chemistry 20100401

Title: Quantitative determination of triclocarban in wastewater effluent by stir bar sorptive extraction and liquid desorption-liquid chromatography-tandem mass spectrometry.

Journal: Journal of chromatography. A 20100312

Title: Triclocarban, triclosan, polybrominated diphenyl ethers, and 4-nonylphenol in biosolids and in soil receiving 33-year biosolids application.

Journal: Environmental toxicology and chemistry 20100301

Title: Mass loadings of triclosan and triclocarbon from four wastewater treatment plants to three rivers and landfill in Savannah, Georgia, USA.

Journal: Archives of environmental contamination and toxicology 20100201

Title: Pharmaceuticals and personal care products in archived U.S. biosolids from the 2001 EPA National Sewage Sludge Survey.

Journal: Water research 20100101

Title: Fate of triclocarban during soil aquifer treatment: soil column studies.

Journal: Water science and technology : a journal of the International Association on Water Pollution Research 20100101

Title: Self-reported chemicals exposure, beliefs about disease causation, and risk of breast cancer in the Cape Cod Breast Cancer and Environment Study: a case-control study.

Journal: Environmental health : a global access science source 20100101

Title: Transformation of triclosan and triclocarban in soils and biosolids-applied soils.

Journal: Journal of environmental quality 20100101

Title: Analysis of triclosan and triclocarban in soil and biosolids using molecularly imprinted solid phase extraction coupled with HPLC-UV.

Journal: Journal of AOAC International 20100101

Title: Bioaccumulation of triclocarban in Lumbriculus variegatus.

Journal: Environmental toxicology and chemistry 20091201

Title: Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20091201

Title: Fate of organohalogens in US wastewater treatment plants and estimated chemical releases to soils nationwide from biosolids recycling.

Journal: Journal of environmental monitoring : JEM 20091201

Title: Toxicology in the fast lane: application of high-throughput bioassays to detect modulation of key enzymes and receptors.

Journal: Environmental health perspectives 20091201

Title: On-line solid-phase extraction of large-volume injections coupled to liquid chromatography-tandem mass spectrometry for the quantitation and confirmation of 14 selected trace organic contaminants in drinking and surface water.

Journal: Journal of chromatography. A 20091127

Title: Impact of biosolids on the persistence and dissipation pathways of triclosan and triclocarban in an agricultural soil.

Journal: The Science of the total environment 20091115

Title: Effect of triclosan and triclocarban biocides on biodegradation of estrogens in soils.

Journal: Chemosphere 20091101

Title: Ultra-high-performance liquid chromatography-tandem mass spectrometry for determining the presence of eleven personal care products in surface and wastewaters.

Journal: Journal of chromatography. A 20091016

Title: Runoff of pharmaceuticals and personal care products following application of dewatered municipal biosolids to an agricultural field.

Journal: The Science of the total environment 20090801

Title: Pharmaceutical and personal care products in tile drainage following surface spreading and injection of dewatered municipal biosolids to an agricultural field.

Journal: The Science of the total environment 20090701

Title: Adsorption and degradation of triclosan and triclocarban in soils and biosolids-amended soils.

Journal: Journal of agricultural and food chemistry 20090610

Title: Simultaneous determination of parabens, triclosan and triclocarban in water by liquid chromatography/electrospray ionisation tandem mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20090601

Title: Comparative microscale analysis of the effects of triclosan and triclocarban on the structure and function of river biofilm communities.

Journal: The Science of the total environment 20090501

Title: Detection of the antimicrobials triclocarban and triclosan in agricultural soils following land application of municipal biosolids.

Journal: Water research 20090501

Title: Determination of triclosan, triclocarban and methyl-triclosan in aqueous samples by dispersive liquid-liquid microextraction combined with rapid liquid chromatography.

Journal: Journal of chromatography. A 20090410

Title: Simultaneous determination of 21 preservatives in cosmetics by ultra performance liquid chromatography.

Journal: International journal of cosmetic science 20081001

Title: In vitro biologic activities of the antimicrobials triclocarban, its analogs, and triclosan in bioassay screens: receptor-based bioassay screens.

Journal: Environmental health perspectives 20080901

Title: Meta-analysis of mass balances examining chemical fate during wastewater treatment.

Journal: Environmental science & technology 20080901

Title: Snail bioaccumulation of triclocarban, triclosan, and methyltriclosan in a North Texas, USA, stream affected by wastewater treatment plant runoff.

Journal: Environmental toxicology and chemistry 20080801

Title: Fate of triclosan and evidence for reductive dechlorination of triclocarban in estuarine sediments.

Journal: Environmental science & technology 20080615

Title: Determination of household chemicals using gas chromatography and liquid chromatography with tandem mass spectrometry.

Journal: Journal of chromatography. A 20080509

Title: Growth-inhibiting effects of 12 antibacterial agents and their mixtures on the freshwater microalga Pseudokirchneriella subcapitata.

Journal: Environmental toxicology and chemistry 20080501

Title: Ab initio and in situ comparison of caffeine, triclosan, and triclocarban as indicators of sewage-derived microbes in surface waters.

Journal: Environmental science & technology 20080501

Title: Detection of trace triclocarban in water sample using solid-phase extraction-liquid chromatography with stochastic resonance algorithm.

Journal: Environmental science & technology 20080415

Title: Triclocarban enhances testosterone action: a new type of endocrine disruptor?

Journal: Endocrinology 20080301

Title: Urinary concentrations of triclosan in the U.S. population: 2003-2004.

Journal: Environmental health perspectives 20080301

Title: Biological degradation of triclocarban and triclosan in a soil under aerobic and anaerobic conditions and comparison with environmental fate modelling.

Journal: Environmental pollution (Barking, Essex : 1987) 20071201

Title: Simultaneous determination of triclocarban and triclosan in municipal biosolids by liquid chromatography tandem mass spectrometry.

Journal: Journal of chromatography. A 20070914

Title: Algal bioaccumulation of triclocarban, triclosan, and methyl-triclosan in a North Texas wastewater treatment plant receiving stream.

Journal: Chemosphere 20070501

Title: Detection of triclocarban and two co-contaminating chlorocarbanilides in US aquatic environments using isotope dilution liquid chromatography tandem mass spectrometry.

Journal: Environmental research 20070101

Title: Removal of E. coli from water using surface-modified activated carbon filter media and its performance over an extended use.

Journal: Environmental science & technology 20061001

Title: Media- and method-dependent variations in minimal inhibitory concentrations of antiplaque agents on oral bacteria.

Journal: Letters in applied microbiology 20060901

Title: Triclocarban seems to defy wastewater treatment.

Journal: Environmental science & technology 20060601

Title: Partitioning, persistence, and accumulation in digested sludge of the topical antiseptic triclocarban during wastewater treatment.

Journal: Environmental science & technology 20060601

Title: Measuring environmental phenols and chlorinated organic chemicals in breast milk using automated on-line column-switching-high performance liquid chromatography-isotope dilution tandem mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20060202

Title: [Contact allergy to antiseptics: 75 cases analyzed by the dermato-allergovigilance network (Revidal)].

Journal: Annales de dermatologie et de venereologie 20051201

Title: Comment on 'Co-occurrence of triclocarban and triclosan in U.S. water resources'.

Journal: Environmental science & technology 20050815

Title: Effect of handwashing on child health: a randomised controlled trial.

Journal: Lancet (London, England) 20050701

Title: Cyclodextrin solubilization of the antibacterial agents triclosan and triclocarban: formation of aggregates and higher-order complexes.

Journal: International journal of pharmaceutics 20050613

Title: Co-occurrence of triclocarban and triclosan in U.S. water resources.

Journal: Environmental science & technology 20050315

Title: Simultaneous determination of chlorinated bacteriostats in cosmetic and pharmaceutical products.

Journal: Journal of cosmetic science 20050101

Title: Analysis of triclocarban in aquatic samples by liquid chromatography electrospray ionization mass spectrometry.

Journal: Environmental science & technology 20040915

Title: Optimization by experimental design and artificial neural networks of the ion-interaction reversed-phase liquid chromatographic separation of twenty cosmetic preservatives.

Journal: Journal of chromatography. A 20040312

Title: Activity and mechanisms of action of selected biocidal agents on Gram-positive and -negative bacteria.

Journal: Journal of applied microbiology 20030101

Title: The effect of antibacterial soap on impetigo incidence, Karachi, Pakistan.

Journal: The American journal of tropical medicine and hygiene 20021001

Title: National and regional assessment of the antibacterial soap market: a step toward determining the impact of prevalent antibacterial soaps.

Journal: American journal of infection control 20011001

Title: Kanbara Y, et al. Nanomolar concentration of triclocarban increases the vulnerability of rat thymocytes to oxidative stress. J Toxicol Sci. 2013 Feb;38(1):49-55.

Title: Huang H, et al. The in vitro estrogenic activities of triclosan and triclocarban. J Appl Toxicol. 2014 Sep;34(9):1060-7.

Title: Kennedy RC, et al. Early life triclocarban exposure during lactation affects neonate rat survival. Reprod Sci. 2015 Jan;22(1):75-89.

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Tags:101-20-2 Molecular Formula|101-20-2 MDL|101-20-2 SMILES|101-20-2 3-(4-chlorophenyl)-1-(3,4-dichlorophenyl)urea |Organic_Building_Blocks