This compound belongs to the class of organic compounds known as n-phenylthioureas. These are compounds containing a N-phenylthiourea moiety, which is structurally characterized by a phenyl group linked to one nitrogen atom of a thiourea 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.
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Application Protocols
No item-specific, validated application protocols are provided for this small-molecule reagent. It is not an antibody or assay kit.
General laboratory usage suggestions (contextual)
Stock solutions: Prepare at 10–100 mM in dry DMSO or DMF; filter through 0.2 µm PTFE if particulate is present. Record exact concentration gravimetrically.
TLC/LC monitoring: Use UV at 254 nm for aryl chromophores; add sulfur-sensitive MS methods (ESI+/−) for confirmation.
Recrystallization: Trial EtOH, i-PrOH, or EtOAc/hexanes. Perform small-scale solubility scouting before scale-up.
Moisture control: For base- or metal-catalyzed reactions, pre-dry solids and solvents; run under inert atmosphere to minimize side reactions.
For any standardized method (e.g., heterocycle cyclization, coupling), refer to the Reaction Conditions tab and adapt to your substrate/catalyst system.
Biological Roles
Applicability note: This product is supplied for research use only. No medical or clinical claims are made.
General biochemical context (literature/class-based)
H-bond donor motif: The thiourea functional group is a strong, directional hydrogen-bond donor/acceptor pair often employed as a recognition element in supramolecular chemistry and in small-molecule probe design.
Heterocycle precursor: Conversion to 2-aminobenzothiazoles provides access to scaffolds frequently investigated in chemical biology for target binding studies. Any biological activity resides in downstream derivatives and must be determined case-by-case.
Metal binding: The soft sulfur and adjacent nitrogens can weakly coordinate to certain metal centers, informing design of sensor or catalyst systems rather than direct biological function.
Caveats
Parent thiourea (not this specific compound) has documented endocrine/thyroid effects in animal studies; handle all thioureas cautiously and avoid extrapolating biological roles without experimental confirmation.
If employing in biochemical assays (e.g., as a binding motif model), confirm purity, counterion content, and solvent vehicle compatibility (DMSO concentration, aqueous tolerance) to avoid assay artifacts.
Item-specific biological data (potency, targets, ADME) are not specified for this item; consult primary literature for derivatives of 2-bromophenyl thioureas.
Buffer Applications
Not typically applicable. 1-(2-Bromophenyl)-2-thiourea is a neutral organic building block, not a buffering agent. It does not provide a defined conjugate acid/base pair in the physiological pH range with sufficient capacity for buffer preparation.
Practical note
If dissolution in aqueous systems is required for assay work, prepare DMSO or ethanol stock solutions and dilute into the working buffer while keeping organic cosolvent levels low (e.g., ≤1–2% v/v), verifying solubility and absence of precipitation.
Choose buffers appropriate to your assay (e.g., phosphate, HEPES, MOPS). This product offers no buffer capacity; no item-specific buffer recipes apply.
Green Alternatives
Context: This material is a solid reagent/building block; “green” considerations focus on solvent and process choices rather than replacing the reagent itself.
Greener solvent options (literature/general)
Replace DMF/DMAc/NMP with safer alternatives when feasible:
Acetonitrile, MeOH/EtOH, ethyl acetate, 2-MeTHF, CPME can substitute depending on reaction class.
For Ullmann-type cyclizations:
Propylene carbonate or dimethyl sulfone have been explored as higher-boiling, lower-toxicity media; consider catalyst/ligand compatibility.
Workup and purification:
Favor solvent recycling and minimize chlorinated solvents; heptane/EtOAc systems over DCM/hexanes where chromatographic resolution permits.
Small comparison (qualitative)
2-MeTHF vs DCM: 2-MeTHF is renewable-based, higher boiling, and water-immiscible; may reduce VOC emissions but can change H-bonding landscapes relevant to thiourea organocatalysis.
Ethyl acetate vs DMF: EtOAc is biodegradable and easy to remove but offers lower polarity; solubility of aryl thioureas may be limited.
Operational improvements
Catalysis: Employ low-loading Cu or ligand-accelerated protocols to reduce metal waste in benzothiazole cyclizations.
Energy: Evaluate microwave or flow conditions to shorten reaction times and lower energy use.
Waste: Segregate sulfur- and halogen-containing residues for appropriate treatment; consider crystallization-based purifications to avoid large silica waste.
Note: No item-specific green certification is provided; tailor choices to your EHS and process metrics.
Pharmaceutical Uses
This product is intended for research use only.
Formulation/manufacturing context (general)
Role: As a synthetic intermediate or heterocycle precursor (e.g., to 2-aminobenzothiazoles), it may be used during discovery-phase route scouting, SAR library synthesis, or as a recognition motif in lead-like compounds. It is not an approved excipient or API.
Regulatory status: No pharmacopeial monograph is known for 1-(2-bromophenyl)-2-thiourea. Any use in GMP or clinical manufacturing would require full characterization, impurity profiling, and toxicological assessment.
Handling in discovery: Prepare small DMSO stocks for screening; filter through 0.2 µm PTFE to remove particulates prior to automated dispensing if used in high-throughput experimentation.
Caveats
Do not formulate for human or veterinary administration. Avoid claims of therapeutic function.
Downstream derivatives synthesized from this intermediate must be independently evaluated for quality, stability, and safety.
Physical Properties
Item-specific (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Storage conditions: Store at 2–8 °C (per Product Data)
Literature/typical values (for context only; not item specifications)
Physical state: Typically a crystalline solid for N-aryl thioureas.
Solubility profile: Generally sparingly soluble in water; soluble in polar aprotic solvents (DMSO, DMF, NMP) and moderately soluble in alcohols and chlorinated solvents. Solubility can increase upon gentle warming.
Acid–base: Thioureas are weak bases and weak acids; they exist predominantly in neutral form under ambient conditions, with strong hydrogen-bond donor ability from the two N–H groups and acceptor ability at sulfur.
UV–Vis: N→C=S and aromatic π→π* transitions typically give absorbance in the near-UV; exact cutoff depends on substituents (no item-specific UV data available).
Thermal behavior: Many aryl thioureas exhibit melting/decomposition in the ~150–220 °C range (literature ranges vary by substitution). Verify for this specific compound before thermal processing.
Practical notes
Drying: If needed, gentle vacuum drying at ambient temperature is usually sufficient; avoid prolonged heating to prevent decomposition.
Hygroscopicity: Generally low to moderate; store tightly closed to exclude moisture.
Provide exact numerical data (mp, solubility, density, refractive index) from the CoA when required by method validation.
Quality and Grades
Item-specific (from Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance
Without an explicit grade (e.g., “AR,” “ACS,” “>98%,” “HPLC grade”), method suitability should be established by the end user. Request the lot-specific CoA for assay, impurity profile, and residual solvents.
Typical expectations for building-block grade aryl thioureas:
Assay by HPLC or qNMR.
Identity by 1H NMR, 13C NMR, and HRMS.
Residual inorganic halides and water content may be reported on request. Where exact ppm limits are required, rely on the CoA; do not assume values.
Stabilizers: None are typically added to thioureas. If stabilizers or anti-caking agents are present, they will be disclosed on the CoA. For moisture-sensitive applications (e.g., strong-base-mediated couplings), pre-dry the material immediately prior to use.
Fit for purpose:
Synthesis and catalysis: Most procedures tolerate standard purity if the main impurities are inorganic salts or urea/thiourea homologs.
Analytical or mechanistic studies: Consider recrystallization or preparative HPLC if ultra-high purity is critical.
Documentation
For regulated workflows or reproducibility requirements, retain the CoA and SDS with lot and date codes, and record storage history (2–8 °C per Product Data).
Reaction and Applications
This aryl thiourea is valuable as both a functional building block and as a hydrogen-bond donor motif in synthesis.
Representative applications (literature/general)
Precursor to 2-aminobenzothiazoles: The ortho-bromine enables intramolecular C–S bond formation under Cu- or Pd-catalyzed conditions to afford 2-aminobenzothiazoles, key scaffolds in heterocycle libraries. Typical methods involve CuI or Cu(OAc)2 with bases (K2CO3, Cs2CO3) in DMSO/DMF at 80–130 °C.
Electrophile activation via H-bonding: Diaryl/aryl thioureas are used as organocatalysts to activate carbonyls, imines, and nitroolefins through dual H-bonding to facilitate Michael additions, Strecker-type reactions, and enantioselective transformations (with chiral variants). While 1-(2-bromophenyl)-2-thiourea is not a canonical Schreiner catalyst, it can serve as a tunable H-bond donor or a component in catalyst screening.
Isothiocyanate/thiocarbamoyl transfer: Under dehydrating or oxidative conditions, thioureas can participate in conversions to isothiocyanates or act as sulfur sources, enabling further derivatization (e.g., to thiocarbamates, thioamides).
Cross-coupling diversification: The aryl bromide enables metal-catalyzed C–C/C–N/C–S coupling to install additional functionality prior to or after thiourea transformations.
Practical tips
Keep material dry; trace water can impact base-mediated couplings or organocatalytic H-bonding equilibria.
In organocatalysis screens, use rigorously dried solvents and control temperature to avoid background pathways.
For intramolecular cyclization, monitor for competitive dehalogenation; ligand choice and base can be decisive.
Reaction Conditions
General guidance (literature; adjust per your system)
Intramolecular C–S cyclization to 2-aminobenzothiazoles
Catalyst: CuI (5–20 mol%) or Cu(OAc)2 (10–30 mol%)
Ligand: 1,10-Phenanthroline, TMEDA, or diamines (0–40 mol%)
Base: K2CO3, Cs2CO3, or K3PO4 (2–3 equiv)
Solvent: DMSO, DMF, or DMAc (0.1–0.3 M)
Temperature: 90–130 °C
Time: 4–24 h
Notes: Inert atmosphere preferred; water content reduces rates. Monitor by LC–MS; expected isolated yields commonly 60–90% depending on substitution.
Suzuki–Miyaura coupling on aryl bromide prior to cyclization
Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd-PEPPSI variants
Base: K2CO3, K3PO4, or Na2CO3 (2–3 equiv, aqueous or anhydrous)
Solvent: 1,4-Dioxane/H2O, toluene/H2O, or MeCN/H2O
Temperature: 60–90 °C
Time: 2–12 h
Notes: The thiourea may coordinate/potentially inhibit Pd; phosphine-rich or NHC catalysts often mitigate. Protecting one N–H can help if inhibition is significant.
Organocatalytic Michael addition (using the thiourea as H-bond donor)
Solvent: DCM, toluene, or EtOAc (dry)
Loading: 5–20 mol% if used as catalyst/additive
Temperature: 0–25 °C
Time: 2–48 h depending on substrates
Notes: Control moisture; high-polarity solvents can attenuate H-bonding efficacy.
These conditions are illustrative literature ranges; optimize for your substrates. No item-specific, validated conditions are provided.
Safety and Handling
Item-specific (from Product Data)
GHS signal word: Not specified for this item; refer to SDS.
H-statements/Pictograms/Classification: Not specified for this item; refer to SDS.
Shipping condition: Wet ice (per Product Data)
Storage: 2–8 °C (per Product Data)
General safety guidance for aryl thioureas (literature/class-based; consult SDS for this product)
Hazards: Thioureas may cause skin and eye irritation and can be harmful if swallowed or inhaled. Dust may irritate the respiratory tract. Some thioureas have shown thyroid and carcinogenic effects in animal studies; handle with caution and consult the specific SDS.
PPE: Wear lab coat, safety glasses/goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a well-ventilated fume hood to control dust and vapors from solvents used for dissolution.
Incompatibilities: Strong oxidizers (can oxidize sulfur to sulfoxide/sulfone species); strong acids or bases may promote decomposition or thiocarbamoyl transfer. Avoid prolonged exposure to heat and UV.
First aid overview: In case of skin contact, wash with soap and water. For eye exposure, rinse cautiously with water for several minutes; remove contact lenses if present. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting; seek medical attention. Always follow SDS-specific instructions.
Spill/Disposal: Avoid creating dust; sweep up with minimal agitation. Dispose of according to local regulations; classify waste as organic laboratory waste containing sulfur- and halogen-bearing compounds.
Fire safety: Use CO2, dry chemical, or foam. Combustion may release HBr, NOx, SOx.
Solvent Selection
Relevance: This product is a solid aryl thiourea used as a building block/organocatalyst component. Solvent choice primarily affects solubility, reactivity, and crystallization.
General solvent compatibility (literature/class-based)
Good solvents (dissolution, reactions): DMSO, DMF, NMP, acetonitrile, dichloromethane, ethyl acetate, methanol/ethanol (warming may be needed), THF (variable).
Limited solubility: Water and alkanes (hexane, heptane).
Crystallization: Often recrystallizes from alcohols (EtOH/i-PrOH) or binary systems (EtOAc/hexanes) depending on impurities.
Selection guidance
For organocatalysis or H-bonding studies: Use low-basicity, polar aprotic media (DCM, toluene, EtOAc) to preserve H-bonding interactions; avoid strongly basic solvents that disrupt thiourea binding.
For metal-catalyzed intramolecular C–S coupling to benzothiazoles: High-boiling polar aprotics such as DMSO, DMF, or DMAc support Ullmann/Chan–Lam-type conditions.
For purification: Choose solvents that differentiate polarity between product and urea/biaryl byproducts; normal-phase silica with DCM/MeOH or EtOAc/hexanes systems is common.
Small comparison (qualitative)
DMSO/DMF: Maximize solubility; may complicate workup due to strong solvation.
DCM/EtOAc: Favorable for H-bonding catalysis tests; easy removal.
Alcohols: Useful for crystallization; risk of transamidation is low but avoid strong acid/base.
Always confirm actual solubility for your lot and process temperature; no item-specific solubility is provided.
Storage and Reconstitution
Item-specific (from Product Data)
Storage: Store at 2–8 °C.
Shipping: Shipped on wet ice.
General guidance
Container: Keep tightly closed in the original container with desiccant if available. Protect from moisture and prolonged exposure to light.
Atmosphere: Store under ambient air unless your application is moisture-critical; purging with inert gas after opening can extend shelf life.
Stability: Aryl thioureas are generally stable solids at refrigerated temperatures. Avoid repeated heating; do not store solutions for extended periods unless validated.
Reconstitution/stock preparation:
Solvents: DMSO or DMF recommended for concentrated stocks; EtOH or MeCN for moderate concentrations.
Procedure: Warm solvent to room temperature, add weighed solid, and mix until fully dissolved. Filter through 0.2 µm PTFE if clarity is required.
Storage of solutions: Aliquot and store at 2–8 °C for short term (days) or at −20 °C for longer term (weeks). Minimize freeze–thaw cycles; discard upon precipitation, discoloration, or significant assay drift.
Documentation: Record lot number, date opened, and any repackaging. For regulated environments, attach CoA and SDS to inventory records.
Note: No item-specific stability-indicating data (e.g., impurity growth over time, water content limits) are provided; consult the CoA for lot-specific details.
Structure and Identity
Item-specific (from Product Data)
SKU: B185081
CAS: 5391-30-0
CID: 2735618
InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data lists: 297698)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed (reference only; not item-specific specs)
Common name: 1-(2-Bromophenyl)-2-thiourea (o-bromophenylthiourea)
Typical structural features: An anilide-type thiourea, with an ortho-bromine substituent on the phenyl ring; functional groups include a thiocarbonyl (C=S) and two exocyclic nitrogens (often presented as Ar–NH–C(=S)–NH–R, here R = H). The ortho-bromo substituent enables intramolecular C–S bond formations under metal catalysis.
2D description: A monosubstituted benzene ring bearing bromine at the ortho position relative to the thiourea-bearing nitrogen. The thiourea moiety presents two N–H donors flanking a central C=S acceptor (planar around the C=S), enabling bifurcated H-bonding.
Notes
Stereochemistry: None (achiral). Conformational preferences around the Ar–NH–C(=S) bond can lead to E/Z rotamers, but no permanent stereocenters.
Always confirm exact structure/identity against the product’s CoA/SDS before use in regulated workflows.
Synthetic Utility
Key functional elements
Aryl bromide: Enables Pd-, Ni-, or Cu-catalyzed cross-coupling (Suzuki–Miyaura, Buchwald–Hartwig, Ullmann-type) for diversification prior to or after thiourea transformation.
Thiourea core: Serves as a bidentate H-bond donor; convertible to thioamides, isothiocyanates, and heterocycles (benzothiazoles) under appropriate conditions.
Intramolecular C–S cyclization to 2-aminobenzothiazoles using CuI/base in polar aprotic solvents; ligands (e.g., 1,10-phenanthroline) can accelerate.
Conversion to isothiocyanate: Oxidative or dehydrative conditions (e.g., phosgene equivalents, thiophosgene alternatives, or safer reagents like CDI with sulfur reagents) may generate aryl isothiocyanates, which are versatile electrophiles for urea/thiourea/thiocarbamate synthesis.
Electrophile activation: As a noncovalent organocatalyst or cocatalyst, can promote Michael additions, Strecker reactions, and nitro-Mannich; chiral induction requires chiral variants.
Halogen–metal exchange at the aryl bromide (with care due to thiourea sensitivity) can enable directed lithiation/metalation followed by electrophile trapping.
Strategic value in retrosynthesis
Provides a convergent handle: The bromine allows late-stage diversification of the aromatic ring, while the thiourea can be a masked thiocarbonyl for subsequent heterocycle formation.
Notes
Protecting-group behavior: The thiourea N–H can be acylated or alkylated selectively, enabling N,N′-disubstitution patterns.
Sensitivities: Strong bases/nucleophiles can lead to thiocarbamoyl transfer; optimize conditions to preserve the C(=S)–NH framework.
Target Specificity
Not applicable. This product is a small-molecule building block, not a biological targeting reagent or antibody. No antigen, epitope, clone, isotype, or species reactivity information applies.
If used in chemical biology, any “target specificity” arises from the design of downstream derivatives or from noncovalent interactions studied in a particular assay, which must be determined experimentally.
Perguntas frequentes
How should this product be stored?
Store at 2–8 °C. Refrigerated storage is required to maintain the specified shelf life.
How is this product shipped?
This product ships chilled on wet ice. Unpack on arrival and transfer it to the storage condition stated above.
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