This compound belongs to the class of organic compounds known as sulfanilides. These are organic aromatic compounds containing a sulfanilide moiety, with the general structure RS(=O)(=O)NC1=CC=CC=C1.
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
251.100 g/mol
XLogP3
1.100
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
2
Exact Mass
249.941 Da
Monoisotopic Mass
249.941 Da
Topological Polar Surface Area
80.600 Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
228.000
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
No item-specific validated biological application protocols (e.g., WB, IHC, IF, FC) are provided for this small-molecule reagent. Typical laboratory use involves synthetic transformations as described in Reaction & Applications and Synthetic Utility. For assay work, prepare DMSO stock solutions (e.g., 10–50 mM), filter through 0.2 µm PTFE if particulate is observed, and dilute into assay buffer keeping final DMSO ≤1–2% v/v unless the assay tolerates higher co-solvent.
Biological Roles
Item-specific biological roles are not provided and this product is intended strictly for research use (not for human or animal administration).
General context (literature):
Sulfonamide functionality is prevalent in bioactive small molecules as a hydrogen-bonding motif and conformational modulator. The sulfamide variant (–SO2–NH–NH–) can act as a di-donor/di-acceptor system, engaging in specific H‑bond networks in protein binding sites.
The para-bromophenyl group modulates lipophilicity and can serve as a synthetic handle for late-stage diversification, enabling structure–activity relationship (SAR) exploration without altering the sulfamide core.
In fragment-based design, sulfamides can serve as isosteres of ureas/carbamates with altered acidity and metabolic stability profiles (general medicinal chemistry knowledge). The remaining sulfonamide N–H permits tuning of physicochemical properties via N‑substitution.
No target binding, mechanism-of-action, ADME, or efficacy claims are made for this specific compound. For any biological assays, prepare fresh DMSO stock solutions, filter if necessary (0.2 µm), and control final solvent percentages to avoid assay artifacts.
Buffer Applications
This compound is not a buffering reagent and is not typically used to prepare biological buffers or electrophoresis systems. If used in biochemical assays, it is generally dissolved in an organic co-solvent (e.g., DMSO) and diluted into an appropriate buffer selected for the biological system under study (HEPES, PBS, TRIS, etc.). Refer to the Solvent Selection and Storage & Reconstitution sections for practical handling guidance.
Green Alternatives
Greener process design for transformations involving N-(4-bromophenyl)sulfamide focuses on solvent/catalyst choices and waste minimization, since the substrate itself (an aryl bromide sulfonamide) is fixed.
Solvent substitution (literature/general):
Replace DMF/DMAc/NMP with 2‑MeTHF, CPME, acetone, or EtOAc where feasible (e.g., Suzuki in 2‑MeTHF/H2O; amide couplings in EtOAc with green coupling agents).
Employ aqueous micellar catalysis (e.g., TPGS‑750‑M or Savie) for Pd cross-couplings, minimizing organic solvent usage.
Catalysis and loading:
Use modern Pd precatalysts enabling low ppm–level catalyst loadings; consider Ni catalysis for certain couplings to reduce precious metal usage.
Base selection with benign profiles (K3PO4, K2CO3) and avoidance of strong organic amines where unnecessary.
Workup improvements:
Favor crystallization or phase-split workups over silica chromatography to reduce solvent consumption.
Recycle solvents (2‑MeTHF, EtOAc) using in-lab distillation where allowed.
Comparative snapshot (general guidance):
Conventional vs. greener choices:
Polar aprotic (DMF) vs. 2‑MeTHF/H2O: similar coupling performance; greener profile and easier removal for 2‑MeTHF.
Toluene vs. CPME: CPME offers broader liquid range and lower peroxide tendency than ethers like THF.
High Pd loading vs. low‑ppm Pd/Ni: reduces cost and metal residue.
Tradeoffs: greener solvents may reduce solubility of this sulfonamide; co-solvents or slight heating may be needed. Validate substitution on small scale prior to scale-up.
Pharmaceutical Uses
No pharmacopeial status or excipient role is specified for this item; it is supplied for research use only.
General formulation/manufacturing context (literature/general):
As a small-molecule intermediate, N-(4-bromophenyl)sulfamide can serve as a building block during route scouting in drug discovery and early process development, enabling diversification via aryl bromide cross-coupling and sulfonamide N‑functionalization.
Salt formation is uncommon for neutral sulfamides, but prodrug or masking strategies (e.g., carbamates/ureas) may be explored to modulate solubility in discovery settings.
If incorporated into candidate molecules, residual reagent control, metal residues from cross-couplings, and solvent limits should be managed per ICH Q3A/B, Q3C, and Q3D guidelines in later development. These considerations are general and not specific to this catalog item.
No therapeutic, diagnostic, or clinical claims are made for this material.
Physical Properties
Item-specific specifications are not provided in the Product Data; values below are literature/computed guidance for planning only (not product specifications).
Phase/appearance: Not specified for this item; refer to CoA/Spec Sheet. (Aromatic sulfonamides are typically crystalline solids.)
Molecular formula (literature): C6H7BrN2O2S
Molecular weight (literature): ~251.10 g/mol
Acid–base behavior (general): sulfonamide N–H is weakly acidic; pKa for analogous arylsulfonamides commonly ~9–11 (literature, compound-specific pKa not verified).
Solubility (general expectations):
Water: low to moderate due to H‑bonding but overall aromatic character; often improved by basification (to form the conjugate base) or by using co-solvents.
Organic solvents: good in polar aprotics (DMSO, DMF, NMP); moderate in alcohols; limited in nonpolar solvents (hexanes, toluene) unless heated.
Partitioning: aryl bromide increases lipophilicity; expect modest logP (literature trend for p‑bromophenyl sulfonamides ~1–2), exact value not verified for this structure.
Thermal properties: melting point and boiling point Not specified for this item; refer to CoA/Spec Sheet. (Aromatic sulfonamides generally have MP in the 120–220 °C range, literature.)
Refractive index, density, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/additives: None indicated in Product Data. If applicable to your method (e.g., trace-metal-sensitive catalysis), confirm absence/presence on the CoA.
Guidance on typical grades (general information):
Research grade: suitable for routine synthesis and screening; typical control of organic purity by NMR/GC/HPLC. Trace inorganic content may be unqualified.
High-purity/low-metals grade: advantageous for Pd-catalyzed cross-couplings where ppm-level metal contaminants can inhibit catalysis. Look for ICP-MS trace metal data if your process is catalyst-sensitive.
Chromatography grade (if offered): low UV background and residual solvents controlled—useful when relying on photometric detection.
Verification and documentation:
For this specific SKU, defer to the CoA/Spec Sheet for assay, residual solvent profile, water content, and trace metals. If specifications are critical (e.g., water ≤0.05%, residual halides, UV cutoff), request batch documentation prior to use.
Fitness for purpose:
If planning Pd-catalyzed Suzuki/Negishi couplings on the aryl bromide, consider pre-screening for halide content and verifying moisture level, as basic aqueous media can hydrolyze sensitive functionalities in certain substrates. Although sulfonamides are robust, catalyst poisons (sulfur-containing impurities) should be monitored in pharm. process development.
Reaction and Applications
N-(4-bromophenyl)sulfamide is a versatile bifunctional synthon combining an aryl bromide (for arene diversification) with a nucleophilic/weakly acidic sulfonamide N–H.
Aryl bromide manifold (literature examples):
Suzuki–Miyaura coupling to install (hetero)aryl groups; boronic acids/esters under Pd(0/II) catalysis with bases such as K2CO3, K3PO4, or Cs2CO3 in dioxane/H2O or MeCN/H2O.
Buchwald–Hartwig amination converting Ar–Br into Ar–NR2, leaving the sulfonamide largely intact; ligand choice (e.g., XPhos/BrettPhos) tunes reactivity.
Carbonylative couplings (Pd/COPd with CO) to access benzamides or ketones.
Lithiation/trapping is generally avoided on aryl bromides in presence of sulfonamide due to base sensitivity, but directed metalation strategies may be engineered with protecting groups.
Sulfonamide N–H manifold:
N‑Acylation or N‑carbamoylation to give ureas/carbamates (e.g., triphosgene or carbonyldiimidazole-mediated couplings).
Sulfonylation/alkylation (with care to avoid over-alkylation); base choice (NaH, K2CO3, DBU) controls chemoselectivity.
Formation of N‑protected derivatives to modulate acidity/nucleophilicity for sequential cross-couplings on the aryl bromide.
Orthogonality and sequencing:
Strategy A: First conduct Pd-catalyzed cross-coupling on Ar–Br under conditions benign to sulfonamides (aqueous carbonate base), then derivatize the sulfonamide N–H.
Strategy B: Protect/modify the sulfonamide (e.g., N‑Boc on sulfonamide nitrogens is less common; carbamate/urea masking more typical), then engage the aryl bromide in robust couplings.
Application domains (general): fragment growth in medicinal chemistry, preparation of sulfonamide-rich libraries, and as an intermediate toward bifunctional linkers.
Always confirm selectivity with a small-scale screen, as ligand/base choices can affect sulfonamide compatibility.
Reaction Conditions
The following are typical literature conditions for substrates closely related to N-(4-bromophenyl)sulfamide; adjust to your system and substrate. These are general guidelines, not product specifications.
Notes: If the sulfonamide interferes, temporarily protect/derivatize or switch to milder base (NaOMe) with more active ligand.
Sonogashira coupling (Ar–Br → Ar–C≡C–R):
Catalyst: Pd(PPh3)2Cl2 (1–2 mol%), CuI (5 mol%), Et3N or DIPEA, THF or MeCN, 25–60 °C, 2–12 h.
Notes: Amines as base may engage with sulfonamide; ensure adequate base equivalents.
N‑Acylation of sulfonamide N–H:
Reagents: acid chloride (1.1–1.5 equiv), base (DIPEA or pyridine, 2–3 equiv), solvent (DCM or MeCN), 0–25 °C, 1–4 h.
Alternative: CDI (1.2–1.5 equiv) mediated coupling with carboxylic acids in DMF, 25–60 °C.
Deprotonation/alkylation:
Base: NaH (1.1–1.5 equiv) in DMF or THF at 0–25 °C; then add alkyl halide (1.2–2 equiv). Monitor to avoid bis‑alkylation.
Expected isolated yields for well-optimized couplings commonly 70–95% (literature); verify on small scale.
Safety and Handling
Item-specific hazard information (from Product Data):
Signal Word: Not specified for this item; refer to SDS.
H‑Statements: Not specified for this item; refer to SDS.
GHS Classification and Pictograms: Not specified for this item; refer to SDS.
General safety considerations for aryl sulfonamides (literature/general):
Hazard profile: typically low to moderate acute toxicity; dust may cause mechanical irritation to eyes/respiratory tract. Avoid inhalation of powders and contact with skin/eyes.
PPE: lab coat, safety glasses, and suitable gloves (e.g., nitrile). Use a dust mask/respirator if handling large quantities of fine powders or if aerosolization is possible.
Engineering controls: handle solids in a fume hood; minimize dust formation; use closed transfer where possible.
First aid (general):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin contact: wash with soap and water; remove contaminated clothing.
Eye contact: rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; continue rinsing; obtain medical attention if irritation persists.
Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
Incompatibilities: strong oxidizers (may affect organic substrate); strong bases can deprotonate the sulfonamide N–H; strong dehydrating agents may lead to side reactions.
Thermal stability: avoid excessive heat; decomposes at elevated temperatures.
Always consult the product’s SDS for authoritative, item-specific safety and regulatory information.
Solvent Selection
As a neutral aromatic sulfonamide bearing an aryl bromide, N-(4-bromophenyl)sulfamide exhibits amphiphilic behavior: capable of strong H‑bonding yet overall moderately lipophilic due to the p‑bromophenyl ring.
Poorly soluble: alkanes, toluene, MTBE (unless warmed or with co-solvent)
Aqueous solubility: generally low at neutral pH; improved in basic media (deprotonation) or with co-solvents/surfactants.
Selection guidance by use-case:
Stock solutions for screening/biology: DMSO (10–100 mM) with subsequent dilution into assay buffer containing a small percentage of co-solvent or surfactant.
Cross-coupling on the aryl bromide: mixed aqueous organic systems (e.g., dioxane/H2O, MeCN/H2O, toluene/H2O) or neat polar aprotics (DMAc, NMP) depending on catalyst system.
N‑acylation/urethane formation at the sulfonamide N–H: dichloromethane or acetonitrile with base (e.g., DIPEA) for electrophile control; or DMF for less volatile handling.
Practical notes:
Pre-drying polar aprotics (molecular sieves or distillation) can improve consistency in base-mediated transformations.
For workups, partitioning from polar aprotics may require salting-out and back-extraction into EtOAc or MTBE; charcoal treatment can clarify colored solutions.
Quick comparison (general):
DMSO: maximal solubilization; hard to remove.
DMF/DMAc: good balance of solvency and processability; consider residual solvent limits.
2-MeTHF/EtOAc: greener options but may require co-solvent to fully dissolve substrate.
Storage and Reconstitution
Storage (from Product Data): Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Container: Store in a well-closed, chemically compatible container, protected from moisture and excessive heat. Use desiccation if your application is moisture-sensitive.
Stability (general): Aromatic sulfonamides are typically stable solids under ambient conditions. Avoid prolonged exposure to strong light and humidity. If performing air- or moisture-sensitive reactions, handle under inert gas.
Reconstitution and solution handling (general guidance):
Stock solutions: Prepare in dry DMSO, DMF, or acetonitrile at 10–100 mM depending on solubility needs.
Filtration: If necessary, clarify solutions using 0.2 µm PTFE syringe filters.
Aliquoting: For biological screening, aliquot DMSO stocks into single-use portions to avoid repeated freeze–thaw. Store at 2–8 °C or −20 °C as appropriate for the solvent matrix (check solvent freezing points).
Shelf life of solutions: Non-aqueous stocks are commonly stable for weeks at 2–8 °C, but verify by LC/MS before critical experiments.
Research Use Note: For research use only.
Structure and Identity
N-(4-bromophenyl)sulfamide is a bifunctional aryl bromide–sulfonamide building block featuring one free sulfonamide N–H and a para-brominated phenyl ring.
Item-specific identifiers (from Product Data)
CAS: 556068-14-5
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Computed/literature identifiers (for reference; not product specifications)
Typical molecular formula (literature): C6H7BrN2O2S
Core functional group: sulfamide (–SO2–NH–NH–), with one nitrogen N‑aryl substituted by a 4‑bromophenyl group and the other nitrogen remaining as –NH2.
Aromatic system: para-bromophenyl (Br at the 4-position relative to the N-linkage) enabling cross-coupling chemistry.
Hydrogen-bonding: two H‑bond donors (one on each N, aryl‑N has one H; the other N typically –NH2) and two strong H‑bond acceptors (sulfonyl oxygens).
2D verbal depiction: a benzene ring bearing a bromine at the para position; the ring is connected at the para position to an anilide-type nitrogen that is bound to an SO2 group; the SO2 is further bound to a terminal –NH2 group.
Stereochemistry: none (achiral under normal conditions).
Synthetic Utility
N-(4-bromophenyl)sulfamide is a strategically orthogonal synthon:
Functional group reactivity:
Aryl bromide: engages in Pd/Ni-catalyzed couplings (Suzuki, Sonogashira, Heck, carbonylation), enabling rapid installation of (hetero)aryl, vinyl, or carbonyl fragments on the ring.
Sulfonamide N–H: mildly acidic (typically pKa ~9–11, literature), enabling selective N‑acylation, N‑carbamoylation, or N‑alkylation under basic conditions; formation of ureas and cyclic sulfamides is accessible.
Retrosynthetic value:
Serves as a masked diamide isostere; the sulfamide can be revealed/modified late in a sequence while using the aryl bromide as a diversification node.
Orthogonal protection/activation: temporary N‑derivatization (e.g., carbonate/urea) can tune nucleophilicity to avoid over-alkylation and control chemoselectivity in multi-step sequences.
Selectivity considerations:
Under strong base, deprotonation of the sulfonamide may occur, potentially impacting cross-coupling conditions; carbonate/phosphate bases are often sufficiently mild.
Ligand choice in Pd catalysis influences tolerance toward sulfonamides; bulky biaryl phosphines often provide high yields and minimize competitive binding of the sulfonamide to metal centers.
Downstream elaborations:
After aryl coupling, electrophilic substitution on the ring is limited; instead, further N‑functionalization of the sulfamide tailor-makes polarity and H‑bonding geometry for library synthesis.
This dual-reactivity profile makes the compound valuable in convergent routes and parallel synthesis.
Target Specificity
Not applicable. This product is a small-molecule reagent, not a biological targeting agent (e.g., antibody, probe). No antigen/epitope or species reactivity information applies. If used in target-based research, any specificity arises from the user’s derived molecules rather than this starting material.
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