This compound belongs to the class of organic compounds known as thiophenols. These are compounds containing a thiophenol ring, which a phenol derivative obtained by replacing the oxygen atom from the hydroxyl group (attached to the benzene) by a sulfur atom.
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
267.970 g/mol
XLogP3
3.500
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
0
Exact Mass
267.838 Da
Monoisotopic Mass
265.84 Da
Topological Polar Surface Area
1.000 Ų
Heavy Atom Count
9
Formal Charge
0
Complexity
97.100
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
Calcolatori di soluzioni
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Recensioni
Recensioni dei clienti
Application Protocols
No biological assay protocols (WB, IHC, IF, FC) are applicable to this small-molecule reagent.
Synthetic usage notes
For S-alkylation: Dissolve substrate in dry DMF, cool to 0 °C, add base (e.g., NaH, portionwise), then add alkyl electrophile; warm to rt and monitor.
For Pd-catalyzed C–S coupling: Charge dry solvent and base under N2, add catalyst/ligand, then thiol and electrophile; heat with efficient stirring and monitor by GC/LC.
For cross-coupling at aryl–Br: Protect –SH if necessary; use standard Suzuki conditions with degassing and water co-solvent.
These are general literature workflows and should be optimized per substrate and scale.
Biological Roles
This product is a small-molecule aryl thiol used for chemical synthesis and materials research. It is not intended for biological administration.
General chemistry/biochemistry context (literature; not product-specific use claims)
Thiols participate in redox chemistry and radical scavenging; aryl thiols are less nucleophilic and less reducing than alkanethiols but can still engage in disulfide formation/cleavage equilibria under appropriate conditions.
Aromatic thiols can chelate or interact with soft metal centers via sulfur, informing ligand design in coordination chemistry.
Substituent effects: Electron-withdrawing bromines reduce thiol basicity and nucleophilicity relative to benzenethiol, potentially modulating reactivity toward biomimetic electrophiles in model studies.
Applicability to biology workflows
While not typically used directly in biochemical buffers or cell systems, aryl thiols and their thioethers can serve as intermediates toward probes, linkers, or materials that interface with biological assays after further derivatization.
Compliance note
Research use only. No medical, diagnostic, or therapeutic applications are recommended or supported.
Buffer Applications
2,5-Dibromobenzenethiol is a hydrophobic aryl thiol and is not typically used as a buffering component.
Guidance
It has no established buffering range or pKa pairing suitable for aqueous buffer systems, and its water solubility is poor.
For aqueous work, prepare stock solutions in a miscible organic co-solvent (e.g., DMSO, MeCN, ethanol) if needed for assay development, keeping final organic content compatible with the system.
Green Alternatives
Solvent and process choices (literature guidance)
Prefer greener solvents where feasible: 2-MeTHF, CPME, EtOAc, propylene carbonate, or bioethanol can often replace THF, DCM, or DMF depending on transformation and solubility.
Water-assisted couplings (Suzuki) with micellar catalysis have been reported to lower solvent footprint when substrate solubility permits.
Odor/volatility management
Closed systems, efficient condensers, and activated carbon traps during evaporation mitigate thiol emissions and improve occupational exposure metrics.
Catalysis and energy
Use low-Pd loading Buchwald-type C–S coupling or ligand-accelerated Cu-catalysis to reduce precious metal use and temperatures.
Photoredox-enabled thiol–ene couplings may proceed under milder conditions and shorter times compared to thermal initiators.
Comparison snapshot (typical, not item-specific)
THF vs 2-MeTHF: 2-MeTHF offers partial water miscibility, higher bp (~80 vs 66 °C), renewable sourcing, and easier phase separations.
DCM vs EtOAc: EtOAc reduces halogenated solvent waste and has favorable biodegradability; check product solubility and selectivity.
DMF/DMSO vs Cyrene/PC: Cyrene (dihydrolevoglucosenone) or propylene carbonate can substitute in some SN2 and coupling contexts, though base compatibility and viscosity must be validated.
Waste minimization
Capture oxidized sulfur byproducts (disulfides) for potential recovery; apply on-demand thiolate generation to reduce excess base and reagent.
Pharmaceutical Uses
This compound is not an approved excipient and has no pharmacopeial monograph known to us. It is supplied strictly for research use.
Relevant roles in pharmaceutical R&D (general, non-clinical)
Synthetic intermediate: The aryl–SH and aryl–Br groups enable stepwise installation of sulfur-containing motifs and further ring substitution, supporting SAR exploration and late-stage functionalization in medicinal chemistry.
Materials/interfaces: Aryl thioethers or protected derivatives derived from this thiol may be used in linker chemistry or as components of analytical reagents after additional processing.
Notes
Any application in drug substance or product manufacturing would require internal qualification of impurity profile, residual solvents, and elemental impurities per ICH guidelines; consult the CoA for lot-specific data.
Physical Properties
Item-specific physical data
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Purity/assay: Not specified for this item; refer to CoA/Spec Sheet.
Water, metals, UV cutoff, stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
Expected physical state: Aromatic thiols of this substitution pattern are often low-melting solids or viscous oils; actual form depends on batch and storage (confirm on CoA).
Solubility: Poorly soluble in water; typically soluble in common organic solvents (DCM, chloroform, THF, toluene, EtOAc, acetone, alcohols); limited solubility in alkanes increases with temperature.
Acidity (pKa, aryl thiols): Benzenethiol pKa ~6.5; electron-withdrawing bromine substituents typically lower the pKa modestly (literature trend).
Volatility/odor: Thiols characteristically possess a strong odor; vapor pressure is reduced relative to unsubstituted benzenethiol due to dibromination (qualitative literature expectation).
Practical notes
Handle in a well-ventilated hood to manage thiol odor.
Confirm exact BP/MP, density, refractive index, and solubility for your lot on the CoA/Spec Sheet (not provided in Product Data).
Quality and Grades
Item-specific quality information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting common grades (general guidance)
Research/technical grade: Suitable for most synthetic applications; impurity profiles (e.g., residual disulfide, inorganic salts) vary by lot. Verify by NMR/GC/LC as needed for sensitive steps (e.g., cross-couplings).
High-purity or HPLC grade: Tighter control of UV-absorbing and peroxide-like impurities; beneficial when optical or trace-metal-sensitive processes are critical.
For aryl thiols
Typical impurity concerns: Oxidative dimerization to disulfide, residual halogenated byproducts or starting materials, trace acids/bases from workup.
Fit-for-use testing: Quick 1H NMR can quantify SH proton (often broad singlet ~3–5 ppm depending on solvent) and detect disulfide formation; iodometric or LC methods can quantify oxidized species.
Recommendation
Consult the CoA for assay, impurity profile, and residual solvent/metals for your lot. If performing catalysis or materials fabrication, consider pre-use purification (short plug, wash with base, or recrystallization) based on method needs.
Reaction and Applications
Functional profile
Aryl thiol (Ar–SH) serving as a soft nucleophile; readily forms thiolates (ArS–) under basic conditions.
Two aryl bromides (2,5-positions) provide orthogonal reactivity handles for cross-coupling, lithiation, or substitution—enabling late-stage diversification.
Representative applications (literature examples)
S-Alkylation (SN2) to thioethers using alkyl halides/mesylates in polar aprotic solvents with base (NaH, K2CO3, Cs2CO3).
C–S bond formation with aryl/vinyl electrophiles via Cu-catalyzed Ullmann-type coupling or Pd-catalyzed Buchwald-type protocols.
Disulfide assembly (air, I2, or mild oxidants) for materials or redox probes; reversible reduction regenerates thiol.
Cross-coupling at aryl–Br sites (Suzuki–Miyaura, Stille, Sonogashira, Negishi) to introduce diverse substituents while retaining or protecting the thiol.
Directed metalation/halogen–lithium exchange on an aryl–Br under controlled cryogenic conditions to access regioselective elaborations (protect SH as thioether or thioester if required).
Thiol–ene/thiol–yne additions in radical conditions to functional alkenes/alkynes (more common for alkanethiols; aryl thiols react more slowly but can be enabled with photoinitiators).
Use cases
Scaffold for conjugated small molecules, ligands, and sulfur-containing functional materials.
Precursor to aryl thioethers and thioesters that serve as directing groups, redox handles, or cross-coupling partners.
Practical considerations
Control oxidation state: exclude oxygen when free –SH is required; add antioxidant if compatible.
Sequence planning: exploit differential reactivity of the two C–Br sites (e.g., oxidative addition rates) and the –SH/thiolate to orchestrate selective transformations.
Reaction Conditions
General literature guidance (not item specifications; optimize for your substrate and setup):
Thiolate formation and S-alkylation (to thioethers)
Base: NaH (0.9–1.2 equiv), K2CO3/Cs2CO3 (1.5–2.5 equiv) or t-BuOK (1.0–1.5 equiv)
Solvent: DMF, MeCN, acetone, or DMSO
Temperature: 0–25 °C (NaH) or 20–60 °C (carbonates)
Catalyst/ligand: Pd2(dba)3 (0.5–2 mol%) with Xantphos/BrettPhos/SPhos (1–4 mol%)
Base: Cs2CO3, K3PO4, or NaOtBu (2–3 equiv)
Solvent: Toluene, dioxane, or CPME; dry, degassed
Temperature: 80–110 °C; 2–12 h
Cu-catalyzed Ullmann-type C–S coupling
CuI (5–20 mol%) with diamine or 1,10-phenanthroline ligand
Base: K2CO3/K3PO4 (2–3 equiv)
Solvent: DMSO, DMF, or NMP
Temperature: 80–120 °C; 6–24 h
Cross-coupling at aryl–Br positions (Suzuki example)
Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd-PEPPSI variants
Base: K2CO3, Cs2CO3, or Na2CO3 (2–3 equiv)
Solvent: 1,4-dioxane/H2O (4:1) or toluene/H2O; 70–100 °C
Notes: Consider temporary protection of –SH to prevent catalyst poisoning; thiols can coordinate to Pd.
Disulfide formation
Conditions: Air/O2 with catalytic base in EtOH or MeOH; or I2 (0.5 equiv) in CH2Cl2 at rt
Workup: Quench oxidant, wash with thiosulfate if iodine used.
Analytical control
Monitor for disulfide (mass +1 relative to dimerization loss of 2H) and residual starting thiol by LC-MS/NMR.
Safety and Handling
Item-specific hazard data
GHS classification: Not specified for this item; refer to SDS.
Signal word / H-statements / Pictograms: Not specified for this item; refer to SDS.
General safety guidance for aryl thiols and brominated aromatics (literature-driven; not a substitute for SDS)
Hazards: Thiols can cause skin/eye irritation and may provoke strong odors even at low concentrations. Brominated aromatics may be harmful if swallowed and can pose environmental hazards to aquatic life.
PPE: Wear lab coat, nitrile gloves, splash goggles; use in a chemical fume hood.
Incompatibilities: Strong oxidizers (may form disulfides or oxidized sulfur species); strong bases (form thiolate salts; exotherms possible upon neutralization); soft metals (corrosion/tarnishing). Avoid prolonged air/oxygen exposure if oxidative stability is a concern.
Handling: Minimize headspace and container opening time to reduce odor release and oxidative darkening. For moisture‑sensitive transformations, prepare thiolate in dry, oxygen-free solvent.
First aid (overview): Eye/skin contact—rinse with water for ≥15 min; remove contaminated clothing. Inhalation—move to fresh air. Ingestion—rinse mouth; seek medical attention. Always follow institutional protocols.
Always defer to the product’s SDS and institutional risk assessments for authoritative safety information and local regulatory requirements.
Solvent Selection
Polarity/miscibility (literature trends)
Water: Expected very low solubility.
Organic solvents: Typically soluble in chlorinated solvents (DCM, CHCl3), aromatics (toluene), ethers (THF, MTBE), esters (EtOAc), ketones (acetone/MEK), and alcohols; variable in alkanes.
Choosing solvents by application
S-alkylation/S-arylation: Polar aprotic solvents (DMF, DMSO, MeCN) favor thiolate formation and SN2 rate; nonpolar aromatics (toluene) often used for Pd- or Cu-catalyzed C–S couplings.
Disulfide formation/oxidations: Alcohols or mixed EtOH/H2O with base or catalytic iodine; control rate via solvent polarity and oxygen availability.
Cross-coupling on aryl–Br handles: Dioxane, toluene, THF, or DMAc are common; H2O cosolvent improves Suzuki couplings with boronic acids.
Comparison notes (literature)
THF vs 2-MeTHF: 2-MeTHF offers greener profile and higher boiling point for elevated-temperature couplings while maintaining thiolate solubility.
DCM vs EtOAc: EtOAc is a greener extraction/crystallization alternative when the substrate’s polarity allows.
Practical tips
Degas for air-sensitive catalytic couplings.
For odor control, perform manipulations in closed systems or in hood with cold traps if evaporating thiol-containing solutions.
Storage and Reconstitution
Item-specific storage
Storage conditions: Room temperature (per Product Data).
Shipped in: Normal (per Product Data).
General handling/storage best practices for aryl thiols
Store tightly closed in a cool, well-ventilated place away from oxidants and bases.
To minimize oxidation to disulfide and odor release, consider blanketing headspace with inert gas (N2/Ar) after use and using PTFE-lined caps.
Avoid prolonged exposure to air and light if oxidative stability is critical for your application.
Reconstitution/use
The product is supplied neat; no reconstitution is required. Prepare solutions in suitable dry solvents immediately before use for moisture/air-sensitive transformations.
If solids/oils have partially oxidized (color change or reduced SH signal by NMR), a quick purification (e.g., short silica plug with 0.5–2% Et3N or reducing workup) may restore performance.
Shelf-life
Not specified for this item; refer to CoA/Spec Sheet. Monitor by NMR/LC for thiol/disulfide ratio during long-term storage.
Research use note
For research use only (per Product Data).
Structure and Identity
Overview: 2,5-Dibromobenzenethiol is a brominated aryl thiol useful as a sulfur nucleophile and as a bifunctional building block via the two aryl–Br handles.
Item-specific (from Product Data)
CAS: 38441-47-3
CID: 12322762
InChIKey: 466461
Storage conditions: Room temperature
Shipped in: Normal
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Computed/Literature identity data (for reference; not item specifications)
Structural features: Benzene ring bearing a thiol (–SH) group and two bromine atoms at the 2- and 5-positions relative to –SH (one ortho and one meta). The thiol is the only heteroatom substituent; no stereocenters.
2D description: A planar phenyl core; –SH substituent para-flanked by two C–H sites with bromine substituents situated ortho (C2) and meta (C5) to –SH, yielding a deactivated, halogenated aryl thiol.
Representative literature SMILES: c1c(Br)ccc(Br)c1S
Notes
Values labeled “literature” are general chemical information and not the certified specifications for this catalog item.
Synthetic Utility
Bifunctional handle
Thiol (–SH): Convertible to thiolate for nucleophilic substitutions; oxidizable to disulfides; protectable as thioesters or S-alkyl thioethers; transformable to sulfenyl, sulfinyl, or sulfonyl derivatives.
Two aryl bromides: Amenable to oxidative addition for Pd-catalyzed couplings; suitable for halogen–lithium exchange or metal–halogen interconversion; participate in directed ortho-metalation sequences with appropriate protecting/activating groups.
Strategic sequences (literature)
Orthogonal C–S then C–C coupling: First convert –SH to thioether under mild base, then perform Suzuki coupling on one C–Br, leveraging differential reactivity of 2- vs 5-bromide via ligand/temperature choice.
Temporary protection of –SH: As S-acetyl or S-benzyl to tolerate strong bases or organolithiums for regioselective metalation; final deprotection restores the thiol.
Disulfide toggling: Air/I2 oxidation to disulfide for purification or masking; reduce back with DTT, NaBH4, or PPh3 when needed.
Retrosynthetic value
Serves as a sulfur-bearing synthon for aryl thioethers/thiolates while preserving two programmable aryl positions, streamlining exploration of 1,4-related substitution patterns (via 2,5 on the thiophenol skeleton).
Target Specificity
Not applicable. This product is a small-molecule chemical reagent and does not have biological target specificity, antigen/epitope information, or isotype/clone data.
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