This compound belongs to the class of organic compounds known as n-phenylureas. These are compounds containing a N-phenylurea moiety, which is structurally characterized by a phenyl group linked to one nitrogen atom of a urea group.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
252.740 g/mol
XLogP3
3.500
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
2
Exact Mass
252.103 Da
Monoisotopic Mass
252.103 Da
Topological Polar Surface Area
41.100 Ų
Heavy Atom Count
17
Formal Charge
0
Complexity
254.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
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Recensioni
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Application Protocols
Item-specific tested applications and recommended conditions: Not specified for this item; refer to CoA/Spec Sheet.
General laboratory use examples (informational):
Preparation of DMSO stock: Weigh appropriate amount under a hood, dissolve in anhydrous DMSO to 10–100 mM, vortex and gently heat if necessary, then sterile-filter (0.22 µm PTFE) for cell-free assays.
Use as H-bonding additive: Add 5–10 mol% to a dried reaction flask containing electrophile and nucleophile in CH2Cl2 or toluene; stir at rt and monitor by TLC/HPLC. Compare with control lacking additive to quantify rate/selectivity effects.
For validated, application-specific protocols, please consult primary literature or develop in-house methods aligned to your system.
Biological Roles
Item-specific biological/clinical roles: None specified; this product is offered strictly for research use only.
General context (literature; not claims about this specific item):
Urea motifs are prevalent in medicinal chemistry as peptide bond isosteres and robust hydrogen-bonding elements. They can engage enzyme active sites and receptors via dual H-bond donation and carbonyl acceptance.
Aryl/alkyl substitution patterns tune acidity (pKa of N–H) and lipophilicity, impacting membrane permeability and protein binding.
The 3-chloro substituent on the phenyl ring modestly withdraws electron density and increases lipophilicity, typically strengthening H-bond donor character of the adjacent urea N–H.
Practical implications for researchers:
In biochemical assays, compounds of this class are usually prepared as DMSO stocks and screened for binding or functional modulation; adsorption to plastics/glass can occur due to hydrophobicity.
Non-specific aggregation is possible at high micromolar concentrations; include detergent controls and perform orthogonal assays to confirm specific effects.
No medical or therapeutic claims are made for this product.
Buffer Applications
This compound is a neutral organic urea and is not used as a pH buffer component. It does not provide defined acid/base conjugate pairs suitable for buffering. For aqueous work involving this compound, prepare DMSO stocks and dilute into assay media buffered by standard systems (e.g., PBS, HEPES), ensuring final DMSO content is compatible with your assay.
Green Alternatives
Because this product is a solid reagent rather than a volatile solvent, green chemistry considerations focus on solvent choice and reaction design rather than replacing the substance itself.
Greener solvent selection (literature guidance):
Prefer ethyl acetate, 2-methyltetrahydrofuran (2-MeTHF), CPME, dimethyl carbonate, or MeOH over chlorinated solvents when compatible with solubility and reaction performance.
For polar media, consider propylene carbonate or Cyrene where feasible instead of DMF/DMSO; evaluate stability and workup complexity.
Typical tradeoffs:
Chlorinated solvents (e.g., CH2Cl2) often maximize urea-catalyzed rate enhancements but have higher environmental/health impacts.
Biobased ethers (2-MeTHF) improve sustainability and facilitate phase separations but may slightly reduce rates or change selectivity.
2-MeTHF: renewable, hydrophobic; good for extractions and many organocatalytic reactions; modest peroxide risk over time (manage with inhibitor/testing).
EtOAc: greener, readily biodegradable; moderate polarity; often suitable for workup and recrystallization.
Implement solvent switches with small-scale scouting to confirm solubility, rate, and selectivity before scale-up.
Pharmaceutical Uses
Item-specific pharmacopeial status/uses: Not specified for this item; refer to CoA/Spec Sheet.
General formulation/manufacturing context (not specific to this item):
Urea derivatives may be employed as intermediates in API synthesis, as crystallization modifiers, or as co-formers in pharmaceutical co-crystals to modulate solubility and stability.
Due to strong, directional hydrogen bonding, ureas can influence solid-state forms and may be leveraged in salt/co-crystal screening campaigns.
No therapeutic or clinical claims are made for this product. Any use in drug development should be confined to research and process development settings with appropriate qualification.
Physical Properties
Item-specific specifications:
Melting point, boiling point, density, refractive index, water content, metal content, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Literature/expectation (non-spec; for context only):
Physical state: Many mono-aryl/alkyl ureas are crystalline solids at ambient conditions due to strong intermolecular H-bonding; this compound is expected to be a low-volatility solid.
Solubility profile: Poorly soluble in water; typically soluble in polar aprotic organics (DMSO, DMF, NMP) and moderately soluble in chlorinated or aromatic solvents (CH2Cl2, chloroform, toluene). Limited solubility in alkanes or highly nonpolar solvents.
Lipophilicity: Moderate-to-high, owing to cyclohexyl and chlorophenyl groups; this generally correlates with low aqueous solubility and good partitioning into organic phases.
Practical handling implications:
Dissolution for assays commonly uses DMSO to prepare concentrated stock solutions (e.g., 10–100 mM), followed by dilution into assay medium or reaction solvent.
Robust hydrogen-bonding can lead to higher melting points and potentially polymorphism; gentle heating and stirring aid dissolution.
Note: For authoritative numerical property data specific to this item (e.g., mp, purity, residual solvents), consult the lot-specific CoA/Specification Sheet.
Quality and Grades
Item-specific quality information:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting typical grades (general guidance):
Research grade: Suitable for most synthetic, screening, and materials research applications. Purity typically verified by HPLC/GC and NMR.
Screening/library grade: Emphasis on identity confirmation and sufficient purity for HTS or SAR work; may specify LC-MS purity and salt/solvate form.
If HPLC/LC-MS grade purity is indicated on CoA, expect low UV background and well-defined impurity profile to support analytical and biological screening assays.
Stabilizers and additives:
This compound class generally does not require stabilizers. If any additive or special drying is used, it will be disclosed on the CoA/Spec Sheet.
What to check on receipt:
Identity confirmation (NMR/LC-MS), purity (% area by HPLC), residual solvents, water content (if relevant), and polymorph/solid form if your application is sensitive to form.
Refer to the lot-specific CoA for authoritative purity, residual solvent, and appearance details for SKU C668489.
Reaction and Applications
Research use note: For research use only (per Product Data).
Application themes for aryl/alkyl ureas (literature/general):
Hydrogen-bond donor (HBD) organocatalyst/additive: Ureas and thioureas can accelerate and steer polar reactions (e.g., Michael additions, nitroolefin activations, glycosylations) by dual H-bonding to electrophiles. The cyclohexyl/aryl balance tunes solubility and HBD strength.
Supramolecular recognition: Urea motifs bind anions (e.g., halides, carboxylates) via bidentate H-bonding; the meta-chloro aryl ring adjusts acidity of the N–H donors.
Materials/crystal engineering: Strong directional H-bonds enable co-crystal formation with acids/bases and guest molecules; useful for solid-form screening.
Intermediate for derivatization: Can be converted to thiourea (Lawesson’s reagent or P4S10) or further acylated at nitrogen under controlled conditions to modulate properties.
Practical tips:
Drying: If needed, dry under high vacuum at ambient or mild heat (<40–50 °C) to remove residual solvents without risking decomposition.
Use as additive: Typical organocatalysis loadings are 5–20 mol% in CH2Cl2, toluene, or THF at 0–25 °C (literature guidance). Screen solvent/polarity to maximize H-bonding effects.
Analytical tracking: Monitor by TLC (UV-active aryl ring) and/or HPLC; urea N–H stretches appear in IR near 3300–3400 cm−1 and C=O around 1620–1680 cm−1.
Limitations:
Urea nitrogens are relatively non-nucleophilic; direct N-alkylation is challenging and may require strong bases or activating strategies. Hydrolysis typically requires strong acid/base and heat.
Reaction Conditions
The following are general literature-style guidelines for working with aryl/alkyl ureas like 1-(3-chlorophenyl)-3-cyclohexylurea; they are not item-specific specifications.
As organocatalyst/additive (H-bond donor):
Loading: 5–20 mol% relative to substrate.
Solvents: CH2Cl2, toluene, THF, or EtOAc; choose less basic media to preserve urea H-bonding.
Temperature: 0–25 °C commonly; lower temperatures can enhance enantio-/regioselectivity in sensitive systems.
Atmosphere: Typically ambient; keep dry if moisture-sensitive substrates are involved.
Time: 1–24 h depending on substrate/electrophile activation (e.g., nitroolefins respond rapidly).
For derivatization (examples):
Thionation to thiourea: Lawesson’s reagent (0.6–1.2 equiv) in toluene or THF, 60–110 °C, 2–16 h; monitor for completion (IR shift of C=S ~1200–1400 cm−1).
Cross-coupling on aryl chloride: Pd-catalyzed Suzuki–Miyaura (if aryl chloride retained) may require bulky ligands (e.g., tBu3P, SPhos) at 80–110 °C in toluene/dioxane with base (K3PO4, Cs2CO3); ensure urea compatibility (consider N-protection or base choice).
Workup/purification:
Quench with water/brine; extract into appropriate organic solvent. Purify by silica gel chromatography using gradients from hexane/EtOAc to DCM/MeOH as needed. Recrystallization from EtOAc/hexane or toluene can afford high purity solids.
Adjust and optimize conditions empirically for your specific substrate set.
Safety and Handling
Item-specific hazard information:
GHS Classification, Signal Word, H-Statements, Pictograms: Not specified for this item; refer to SDS.
General safety guidance for aryl/alkyl ureas (informational; defer to SDS):
Likely hazards: May cause skin/eye irritation; dust may cause respiratory irritation. Low volatility reduces inhalation risk from vapors but avoid generating dust/aerosols.
PPE: Use lab coat, safety glasses or splash goggles, and suitable gloves (e.g., nitrile). Employ a fume hood during weighing, transfers, and any operations that could generate dust or involve reactive reagents.
Storage incompatibilities: Keep away from strong acids/bases (can hydrolyze/decompose ureas under forcing conditions), strong oxidizers, and acylating or chlorinating agents without proper controls.
First aid overview: If on skin/eyes, rinse with water for several minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth. Seek medical attention as needed. Always follow the SDS instructions.
Fire safety: Likely combustible organic solid. Use CO2, dry chemical, or foam extinguishers. Combustion may produce CO/CO2, HCl, and nitrogen oxides.
Always consult the product’s SDS for definitive hazard classification, exposure limits, and emergency measures.
Solvent Selection
Polarity and interactions (general):
Functional groups: One carbonyl (H-bond acceptor) and two urea nitrogens (H-bond donors if N–H present). The aryl chloride and cyclohexyl confer hydrophobic character.
Expected behavior: Poor aqueous solubility; good solubility in polar aprotics (DMSO, DMF, NMP). Variable solubility in medium-polarity organics (EtOAc, CH2Cl2) and aromatics (toluene). Minimal solubility in alkanes.
Typical solvent choices by task:
Stock solutions for screening: DMSO (anhydrous) at 10–100 mM; filter if needed.
Synthetic operations/additive use: CH2Cl2, THF, EtOAc, MeCN, or toluene depending on reaction. For high concentrations, DMF/NMP may be preferred.
Crystallization/recrystallization: Binary solvent systems such as EtOAc/hexane, toluene/hexane, or MeOH/water can tune solubility; screen for polymorphs.
Comparison (general guidance):
DMSO vs DMF: DMSO offers superior solvating power for aromatic ureas and is convenient for bioassay stocks; DMF provides lower viscosity and easier removal under vacuum.
CH2Cl2 vs toluene: CH2Cl2 enhances solubility and fast kinetics in organocatalysis; toluene favors less polar environments and can influence H-bonding outcomes.
Note: Verify solvent purity and water content for moisture-sensitive transformations involving this compound (e.g., when used alongside isocyanates or acid chlorides).
Storage and Reconstitution
Item-specific storage conditions:
Storage: Room temperature (per Product Data). Protect from moisture and direct light. Keep container tightly closed.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Stability considerations (general):
Urea derivatives are typically stable solids under ambient, dry conditions. Avoid prolonged exposure to strong acids/bases, which can induce decomposition.
Reconstitution/dissolution:
For analytical or screening use, prepare DMSO stock solutions (e.g., 10–100 mM). Mix thoroughly; gentle warming (≤40 °C) and sonication can aid dissolution.
For synthetic use, dissolve in suitable organic solvents (DMSO, DMF, CH2Cl2, toluene) according to solubility needs. Filter if particulates remain.
Store solutions at 2–8 °C or −20 °C for extended periods; bring to room temperature before opening to minimize moisture ingress. Avoid repeated freeze–thaw by aliquoting.
Always refer to the lot-specific CoA/SDS for definitive guidance on storage limits and solution stability for SKU C668489.
Structure and Identity
1-(3-Chlorophenyl)-3-cyclohexylurea is an aryl–alkyl urea featuring a urea carbonyl flanked by a 3-chlorophenyl substituent and a cyclohexyl group.
2D structural description: A central urea carbonyl with two nitrogens; one N is bound to a meta-chlorinated phenyl ring, the other to a cyclohexyl ring. The urea motif provides two H-bond donors (if N–H retained) and one H-bond acceptor at the carbonyl oxygen. No defined stereocenters.
General notes:
The meta-chloro substituent modulates aryl electronics and lipophilicity.
The cyclohexyl group adds bulk and hydrophobic surface area.
Synthetic Utility
Functional group features:
Urea carbonyl (C=O) as H-bond acceptor; two nitrogens as donors (if N–H present). The 3-chlorophenyl group offers a handle for further aryl chemistry; the cyclohexyl group contributes steric bulk.
Transformations (literature/general):
Thionation: Conversion to corresponding thiourea using Lawesson’s reagent or P4S10 under refluxing toluene/xylenes or in CH2Cl2 with activation.
N-acylation or sulfonylation: Under appropriate base/activator, one urea nitrogen may be selectively acylated to tune acidity/H-bonding.
Transcarbamoylation: With strong nucleophiles or under catalytic conditions, exchange of the carbamoyl moiety can occur; useful for late-stage diversification.
Aryl diversification: The meta-chloro substituent can participate in cross-coupling (e.g., Buchwald–Hartwig amination, Suzuki–Miyaura after halogen retention) provided conditions tolerate the urea. Protecting/conditioning the urea N–H may be necessary to prevent side reactions.
Retrosynthetic context:
Typically assembled via coupling of 3-chloroaniline (or its derivative) with cyclohexyl isocyanate, or by carbamoyl chloride routes (phosgene equivalents, CDI, or triphosgene) followed by amine addition.
Practical notes:
The urea can coordinate via H-bonding; additives/bases should be chosen to avoid deactivation/complexation in transition-metal catalysis.
Monitor reactions by TLC/HPLC; LC-MS readily detects [M+H]+ around m/z 253 (based on calculated MW).
Target Specificity
Not applicable. This product is a small-molecule urea, not a biological targeting reagent or antibody. No antigen/epitope, species reactivity, clone, or isotype information applies.
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