This compound belongs to the class of organic compounds known as bromobenzenes. These are organic compounds containing a bromine atom attached to a benzene ring.
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
Not applicable. No validated bioassay or immunoassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent in the Product Data. For practical use, refer to the Reaction Conditions and Synthetic Utility sections for representative synthetic procedures.
Biological Roles
This compound is a synthetic aryl isocyanate and is not a known natural metabolite.
General biochemical considerations for isocyanates (literature; not product-specific):
Electrophilicity: The N=C=O group is strongly electrophilic and can react with nucleophilic residues in biomacromolecules (e.g., Lys, Cys, Ser), forming urea/carbamate/thiocarbamate adducts. This underlies their sensitization potential.
Haptenation: Covalent modification of proteins can provoke immune sensitization. Laboratory exposure should be minimized to avoid confounding biological assays.
Stability in aqueous media: Rapid hydrolysis in water to carbamic acids, which decompose to amines and CO2. Thus, free aryl isocyanates are short-lived under physiological conditions.
Use in chemical biology: Although isocyanates have been explored as reactive probes for labeling nucleophilic sites, their lack of selectivity and potential toxicity typically limit direct biological use. Protected derivatives (e.g., carbamates/ureas) are more common.
Research-use reminder: As stated in Product Data, For research use only. Not for diagnostic, therapeutic, or clinical use.
Buffer Applications
Not typically applicable. 2-Bromophenyl isocyanate is moisture-reactive and unstable in aqueous systems; it is not used to prepare or adjust laboratory buffer solutions. For experimental planning, focus on the anhydrous organic reaction media discussed under Solvent Selection and Reaction Conditions.
Green Alternatives
Considerations for greener practice with aryl isocyanates (general):
Solvent substitution: Replace chlorinated solvents and THF where possible.
Comparison (general guidance; literature-based):
DCM vs 2-MeTHF or CPME:
Greener option: 2-MeTHF, CPME (biorenewable/low peroxide propensity with proper controls)
Pros: lower environmental impact, good solubility for many substrates, higher boiling points facilitate urethane formation.
Cons: ensure anhydrous grade; CPME/2-MeTHF can form peroxides over time—monitor and manage.
THF vs EtOAc or MeCN:
Greener option: EtOAc (readily biodegradable) or MeCN (less ideal EHS profile than EtOAc but non-chlorinated).
Cons: EtOAc may participate in transcarbamoylation under strong conditions; MeCN demands careful waste management.
Process-intensification strategies:
Microliter-scale screening to reduce material use.
Flow addition of amine/alcohol to isocyanate to control exotherms and suppress over-reaction.
Catalysis: nucleophilic catalysts (DMAP) lower temperature/energy input for carbamate formation.
Alternatives to isocyanates (contextual):
For carbamate formation, dialkyl carbonates or CDI-based methods can avoid free isocyanates, albeit with different selectivity and byproducts. Trade-offs include higher temperatures or different activating agents.
Note: This product is for research use only. Green choices must remain compatible with strict moisture exclusion for NCO integrity.
Pharmaceutical Uses
This material is not an excipient and is not intended for clinical use. For research and process chemistry, 2-bromophenyl isocyanate can serve as a versatile intermediate (literature/general):
Medicinal chemistry building block: Rapid urea and carbamate formation enables SAR exploration. The ortho-bromide provides a handle for late-stage diversification via Pd-catalyzed cross-couplings.
Prodrug/linker construction: Carbamates derived from this isocyanate can function as protective or cleavable linkages in discovery chemistry, though free isocyanate is typically not carried into formulated products.
Process considerations: Handling at scale requires closed systems, rigorous drying, and engineering controls to mitigate exposure and moisture ingress. In many programs, the isocyanate is generated or immediately consumed in situ to minimize storage of free NCO materials.
No pharmacopeial monograph or excipient role is indicated for this item. Consult internal quality systems and regulatory guidance when deploying isocyanates in preclinical API intermediate syntheses.
Physical Properties
Item-specific specifications (this product):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general properties for 2-bromophenyl isocyanate (for reference only; not product specifications):
Physical state: typically a colorless to pale yellow liquid at ambient temperature; may darken upon air/moisture exposure due to polymerization or hydrolysis byproducts.
Molecular weight: ~198.01 g/mol (C7H4BrNO)
Density, refractive index, melting/boiling points, UV cutoff: Not reliably consolidated in open literature sources; consult primary references or measurement for your method development.
Solubility: miscible with many dry aprotic organic solvents (e.g., dichloromethane, toluene, THF, acetonitrile). Reacts with protic solvents (alcohols, water) to form carbamates or hydrolysis products.
Vapor pressure: expected to be moderate for an aryl isocyanate; minimize inhalation exposure (handle in fume hood).
Practical notes (general):
Moisture sensitivity: the N=C=O group reacts with water to form unstable carbamic acid that decomposes to amine/CO2; surface moisture leads to urea oligomers. Store and handle under inert gas in dry glassware.
Spectroscopy: strong IR band near ~2260–2275 cm⁻¹ characteristic of the isocyanate stretch (literature). Aryl–Br facilitates diagnostic signals in 13C NMR (ipso C–Br downfield).
Quality & Grades
Item-specific quality details:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades (general):
Research-grade aryl isocyanates are typically supplied with low hydrolytic impurities and minimized urea content. If HPLC or spectrophotometric applications are planned, request UV trace specifications and inhibitor/stabilizer disclosure on the CoA.
Stabilizers: Many aryl isocyanates are shipped without added stabilizers but under inert gas to minimize moisture-driven oligomerization. If a stabilizer is present, it should be listed on the CoA; stabilizers can affect certain catalytic couplings.
Verification on receipt:
IR: sharp NCO stretch near ~2260–2275 cm⁻¹ indicates integrity.
1H/13C NMR: check for absence of urea/carbanilate signals.
Titrimetric or GC purity can be used to quantify low-level hydrolysis.
Trace metal/UV-cutoff/water content: Not specified for this item; refer to CoA/Spec Sheet. For moisture-sensitive transformations, Karl Fischer analysis of a sample aliquot is recommended.
Practical QC tips:
If color has developed during transit, pass through a short plug of basic alumina (pre-dried) under inert atmosphere; avoid silica (may catalyze decomposition).
For exact acceptance criteria, consult the product-specific CoA/Spec Sheet accompanying SKU B153169.
Reaction & Applications
As a bifunctional building block, 2-bromophenyl isocyanate combines an electrophilic isocyanate with a cross-coupling-competent aryl bromide. Typical research applications (literature/general):
Urea synthesis (amines → ureas): Rapid addition of primary/secondary amines to the N=C=O gives mono- and bis-ureas in high yield, often at 0–25 °C. Ortho-bromo substitution enables subsequent diversification (e.g., Suzuki, Buchwald–Hartwig) of the aryl moiety.
Carbamate/urethane formation (alcohols → carbamates): Requires base or nucleophilic catalysis (e.g., DMAP, DBU) and mild heating (40–90 °C). Useful for installing protecting groups or pro-moieties on alcohol-bearing substrates.
Thioureas (thiols → thioureas): Proceed efficiently under basic or neutral anhydrous conditions; valuable for H-bonding motifs and ligand synthesis.
Sequential chemistry leveraging Ar–Br:
Suzuki–Miyaura, Negishi, or Stille coupling to elaborate the aryl core after formation or protection of the isocyanate functionality (or its urea/carbamate derivative for robustness).
Buchwald–Hartwig amination on the aryl bromide can be orthogonal to nucleophilic attack on NCO, enabling two-directional library synthesis.
Heterocycle construction: Intramolecular cyclizations from o-substituted ureas/carbamates to benzoxazolinone/benzimidazolinone scaffolds are reported (literature), exploiting the ortho relationship.
Practical tips:
Order of operations matters. Often, trap the isocyanate first (to a urea/carbamate) before Pd-catalyzed couplings to avoid NCO deactivation under basic, heated conditions.
Strictly exclude moisture; trace water rapidly consumes NCO and generates ureas or amines, complicating analyses.
Reaction Conditions
General literature guidance (not item-specific; verify for your substrates):
Urea formation (amine + isocyanate):
Solvent: dry DCM, THF, or MeCN.
Temperature: 0–25 °C; exothermic—add isocyanate to amine slowly.
Time: minutes to 2 h, depending on sterics.
Notes: Usually no catalyst required. For hindered amines, gentle warming (30–40 °C) can help. Monitor by IR (loss of ~2260–2275 cm⁻¹ band).
Carbamate (alcohol + isocyanate):
Solvent: toluene, CPME, 2-MeTHF, or THF (all anhydrous).
Catalyst: 5–10 mol% DMAP or DBU.
Temperature: 40–90 °C (higher bp solvents advantageous).
Time: 2–16 h. Remove catalyst thoroughly during workup.
Thiourea (thiol + isocyanate):
Solvent: MeCN or THF, anhydrous.
Base: triethylamine (0–1 equiv) can modulate rate.
Temperature: 0–25 °C; typically fast.
Cross-coupling on the aryl bromide (perform preferably after converting NCO to a stable urea/carbamate):
Suzuki–Miyaura: Ar–B(OH)2 (1.2 equiv), Pd(PPh3)4 (1–3 mol%), K2CO3 (2–3 equiv), toluene/EtOH/H2O or 1,4-dioxane/H2O, 70–90 °C, 4–12 h.
Buchwald–Hartwig amination: Pd2(dba)3 (1–2 mol% Pd), BINAP/XPhos (2–4 mol%), NaOtBu (2 equiv), toluene or dioxane, 80–100 °C, 6–16 h.
Workup considerations:
Quench unreacted isocyanate with a small amount of anhydrous alcohol under cooling before aqueous workup to avoid uncontrolled CO2 evolution and emulsions.
Maintain inert atmosphere until NCO is consumed.
These conditions are representative literature practices; optimize for your specific substrates and scale.
Safety & Handling
Item-specific hazard information provided: none. Always consult the SDS for authoritative, product-specific safety data.
General GHS guidance for aryl isocyanates (literature-based; not item-specific):
Likely classifications: Acute Tox (inh.) Category 4, Skin Irrit. 2, Eye Irrit. 2, Skin Sens. 1, Resp. Sens. 1. Typical H-statements may include H332, H315, H319, H317, H334. Pictograms commonly GHS07 and GHS08. Verify on the SDS for this SKU.
Key hazards and precautions (general):
Sensitization: isocyanates can cause respiratory and skin sensitization. Prevent inhalation and skin contact.
Reactivity: reacts with water, alcohols, and amines; exothermic. Avoid moisture; keep containers tightly closed under inert gas.
PPE: lab coat, nitrile gloves (change regularly), splash goggles; consider face shield for bulk transfers. Use in a certified fume hood.
Inhalation: move to fresh air, keep warm at rest; seek medical attention.
Skin contact: remove contaminated clothing; wash with soap and water for ≥15 min.
Eye contact: rinse cautiously with water for ≥15 min; seek medical advice.
Ingestion: rinse mouth; do not induce vomiting; get medical help.
Spill/containment: absorb with inert, non-reactive material in a fume hood; quench residues carefully with anhydrous alcohol only if appropriate and controlled; otherwise, contain and dispose as hazardous waste.
Storage from Product Data: Room temperature, Argon charged. Ship: Normal. Maintain dryness and exclude air/moisture.
Solvent Selection
Solvent behavior (general for aryl isocyanates):
Polarity class: moderately polar, aprotic; engages in dipole–dipole interactions via the N=C=O function.
Miscibility: soluble in common dry organics (DCM, toluene, THF, EtOAc, MeCN). Avoid protic solvents (MeOH, EtOH, water) during storage/handling unless intentional reaction.
Dielectric constants (literature examples of useful media):
Dichloromethane (ε ~8.9): good for rapid urea formation with amines at 0–25 °C.
Toluene (ε ~2.4): suitable for higher-temperature urethane formation with alcohols.
THF (ε ~7.6) or MeCN (ε ~37): useful when polarity aids solubility of nucleophiles.
When to choose each (general):
Fast urea assembly with secondary amines: DCM or THF at 0–25 °C.
Carbamate formation from alcohols: toluene, CPME, or 2-MeTHF at 50–90 °C (often with catalytic DBU/DMAP).
Thiourea synthesis from thiols: acetonitrile or THF with base suppression to control rate.
Comparison (general):
DCM vs toluene: DCM enables low-temperature control and easy workup; toluene favors elevated temperatures, minimizing side hydrolysis.
THF vs MeCN: THF offers broad solubility; MeCN is more polar and can suppress oligomerization but must be anhydrous.
Note: Select rigorously anhydrous solvents. Pre-dry glassware and maintain an inert atmosphere, consistent with the product’s “Argon charged” storage guidance.
Keep container tightly closed under inert gas (argon or nitrogen). Use septum-sealed bottles where possible.
Store in a dry place away from moisture, alcohols, and amines. A desiccant in the secondary container is recommended.
Minimize headspace oxygen and repeated air exchange; blanket with inert gas after each use.
If solidification or crystallization occurs (some batches may thicken at low temperature), warm gently to ambient and swirl under inert atmosphere until homogeneous.
Do not refrigerate in high-humidity environments where condensation can occur upon warming.
Reconstitution: Not applicable. This product is typically supplied neat. If dilution is needed for dosing/addition, prepare an anhydrous stock solution (e.g., in dry DCM, THF, toluene, or MeCN) immediately before use and store only short-term under inert gas at room temperature.
Note: For research use only. Always consult the product CoA/Spec Sheet and SDS for lot-specific stability limits and handling instructions.
Structure & Identity
Brief overview: 2-Bromophenyl isocyanate is an ortho-brominated aryl isocyanate featuring an electrophilic N=C=O group para- to neither but ortho to the bromo substituent on a benzene ring. This motif combines a cross-coupling handle (Ar–Br) with a highly reactive isocyanate for rapid urea/carbamate assembly.
Item-specific identifiers (from Product Data):
SKU: B153169
CAS: 1592-00-3
CID: 137097
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Ring system: monosubstituted benzene (ortho relationship between Br and isocyanate-bearing nitrogen)
2D description: A benzene ring bearing bromine at C2 and an isocyanate group bound via nitrogen at C1 (–N=C=O projecting from the ring). No stereogenic centers.
Notes:
All structure/numeric values in this section marked “literature” are provided for general reference and are not item-specific specifications. Consult the product CoA/Spec Sheet for definitive identifiers for this lot.
Synthetic Utility
Functional reactivity (literature/general):
Isocyanate electrophilicity: Reacts rapidly with nucleophiles (Nu–H) to form: ureas (Nu = amines), carbamates/urethanes (Nu = alcohols), thiocarbamates/thioureas (Nu = thiols), and can add to enolates or other soft nucleophiles under controlled conditions.
Orthogonal handle: The aryl bromide allows C–C or C–N bond formation by cross-coupling (Suzuki–Miyaura, Negishi, Stille, Kumada, Buchwald–Hartwig), enabling modular assembly of densely functionalized ureas/carbamates.
Strategic applications:
Two-step diversification: (1) Capture the NCO with a chosen amine/alcohol to lock in the urea/carbamate motif; (2) Diversify the aryl core via Pd-catalyzed coupling. This protects the NCO functionality from base/heat in step 2.
Intramolecular cyclizations: Ortho-substitution can predispose to cyclocondensations forming benzoxazolinone/benzimidazolinone scaffolds from appropriately substituted precursors.
Protecting-group logic: Urea/carbamate formation can mask nucleophilicity or tune physicochemical properties for subsequent steps, with potential deprotection under reductive or hydrolytic conditions (depending on substituents).
Selectivity and control:
Use stoichiometric control and slow addition to minimize bis-urea formation when reacting with diamines.
Additives such as DMAP (for alcohols) or mild bases can accelerate desired pathways and reduce side reactions.
For cross-coupling, ligands and bases should be chosen to avoid NCO interference; conducting couplings on the urea/carbamate derivative is often higher-yielding.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent, not a biological targeting agent (e.g., antibody, ligand with defined biomolecular specificity). No target/epitope specificity is provided in the Product Data.
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