This compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
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.
Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
Sensibilidad
Light sensitive
Peso molecular
237.090 g/mol
XLogP3
4.200
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
1
Exact Mass
235.984 Da
Monoisotopic Mass
235.984 Da
Topological Polar Surface Area
9.200 Ų
Heavy Atom Count
13
Formal Charge
0
Complexity
171.000
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
Calculadoras de soluciones
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Application Protocols
Not applicable. This product is not an antibody, enzyme, or assay reagent with defined bioanalytical protocols. For synthetic applications, see Reaction Conditions for general literature procedures (e.g., Suzuki–Miyaura, Buchwald–Hartwig, Miyaura borylation).
Biological Roles
This compound is a synthetic aromatic building block with no established intrinsic biological role.
Item-specific biological data: Not specified for this item; refer to CoA/Spec Sheet.
General context (literature)
Naphthalene derivatives are common in materials and synthetic chemistry; methoxy substitution alters electronic properties but does not confer a defined biochemical function.
Any bioactivity of derivatives arises from appended functionalities introduced after cross-coupling or functionalization of the aryl bromide. No claims are made here.
For research use only, as indicated in the Product Data.
Buffer Applications
Not typically applicable. 2-Bromo-7-methoxynaphthalene is a hydrophobic organic building block and is not used as a buffering agent or pH control component. For practical guidance, see Reaction & Applications, Synthetic Utility, and Solvent Selection for relevant usage contexts.
Green Alternatives
Focus on greener solvents, bases, and protocols when deploying this aryl bromide in synthesis. The substrate itself is not readily replaceable without altering target structures, but the process chemistry can be improved.
Greener solvent options (literature)
Replace THF/dioxane with 2-MeTHF or CPME for Suzuki/Buchwald couplings; both are bio-derived/low peroxide propensity (CPME) and offer higher boiling points.
Use toluene/anisole instead of chlorinated solvents when feasible.
Bases and reagents
Aqueous K3PO4 or K2CO3 over Cs2CO3; avoid excessive carbonate loading to reduce waste.
Employ boronic acids/esters over organostannanes to avoid tin waste (favor Suzuki over Stille).
Catalysis and loading
Modern Pd precatalysts (e.g., Pd-PEPPSI-type or Pd-precatalysts with biaryl phosphines) allow ppm-level Pd loading in flow or batch, lowering metal footprint.
Energy and mode of activation
Microwave heating or continuous-flow reactors can shorten reaction times and improve safety/energy efficiency.
Comparison (process-level; literature):
Traditional: dioxane/H2O, Cs2CO3, Pd(PPh3)4 (1–3 mol%), 80–100 °C.
Greener: 2-MeTHF/H2O, K3PO4, Pd/RuPhos (100–1000 ppm), 60–90 °C; or CPME as sole solvent with aqueous base addition.
Trade-offs: Greener solvents may change solubility and rate; minor re-optimization of base, temperature, and ligand is typically required.
Pharmaceutical Uses
No item-specific pharmacopeial status or excipient role is provided.
Item-specific status: Not specified for this item; refer to CoA/Spec Sheet.
General context (non-clinical)
Aromatic bromides like this are sometimes employed as synthetic intermediates en route to candidate APIs or fine chemicals. They are not excipients and are not intended for human or veterinary use.
Process chemists may utilize this substrate to introduce substituted naphthyl motifs via cross-couplings or nucleophilic substitutions during route development.
Research-use only. No therapeutic or clinical claims are made.
Physical Properties
Item-specific specs were not provided; values below are general literature/computed guidance and should not be used as release specifications.
Item-specific values
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: 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.
Physical state: typically a crystalline solid for comparable bromo‑methoxynaphthalenes (literature; specific MP not listed here)
Solubility: sparingly soluble in water; soluble in common organic solvents (e.g., dichloromethane, chloroform, toluene, THF, ether) (literature/trend for aryl bromide ethers)
LogP: expected high (nonpolar aromatic core with ether; literature trend)
UV absorption: strong π–π* bands typical of naphthalenes (literature); useful for UV tracking in chromatography.
Practical notes (general)
For precise MP/BP, density, and refractive index, consult the CoA/SDS or measure under your lab conditions.
Drying before moisture‑sensitive reactions (e.g., metallation) is recommended; brief vacuum at ambient or mild heat under inert gas is typical practice (general).
Quality and Grades
Item-specific grade/purity
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
What grade implies (general guidance)
Research-grade aryl halide building blocks are typically supplied with assay by NMR/GC/HPLC and identity confirmation (NMR, MS). When labeled “>98%,” impurities are generally regioisomers, residual starting materials, or inorganic halides; low water content is typical for non-hygroscopic solids. UV cutoffs and metal traces are usually not specified unless labeled HPLC grade or trace-metal screened.
Stabilizers and additives
No stabilizer indicated for this item. If a stabilizer were present, it would be declared on the CoA/label. For coupling chemistry, absence of amine/phenolic stabilizers is often preferred to avoid catalyst inhibition.
Recommended verification (practical)
Record 1H/13C NMR in CDCl3 or DMSO-d6 to verify substitution pattern (diagnostic OMe singlet; aromatic splitting consistent with 2-/7-substitution). Consider GC-MS/LC-MS for purity; HRMS for exact mass confirmation.
Trace metals/UV cutoff/water/peroxide
Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
As a 2-bromonaphthalene bearing a 7-methoxy substituent, this molecule is a versatile electrophile and building block in aromatic synthesis.
Cross-coupling electrophile (literature/general)
Suzuki–Miyaura: couples with aryl/heteroaryl/vinyl boron species to access 2-substituted-7-methoxynaphthalenes. Pd(PPh3)4 or Buchwald-type ligands (SPhos/XPhos/RuPhos) are common; bases include K3PO4, Cs2CO3.
Kumada/Negishi/Stille: feasible via Grignard, organozinc, or organostannane partners under Pd/Ni catalysis for C(sp2)–C(sp2/sp3) formations.
Buchwald–Hartwig amination: aryl C–N bond formation at the 2-position using amines; BrettPhos/RuPhos ligands often effective with aryl bromides.
Directed metalation and halogen–metal exchange (general)
nBuLi or tBuLi enables Br–Li exchange at low temperature (≤ −78 °C) to give a 2-lithiated intermediate for subsequent electrophile trapping (e.g., formylation, borylation).
Grignard formation (2-MgBr) is possible under activated conditions (e.g., i-PrMgCl•LiCl) for subsequent cross-couplings.
The methoxy group donates electron density, promoting EAS at positions ortho/para to OMe within the naphthalene framework; regioselectivity is influenced by existing 2-bromo substituent.
Applications
Synthesis of polyaromatic scaffolds, OLED/OPV intermediates, dyes, ligands, and advanced intermediates toward fine chemicals and materials (literature examples).
Reaction Conditions
Guidance below is literature-based and for planning purposes only; optimize for your system. No item-specific specifications are implied.
Solvent: 1,4-dioxane/H2O or 2-MeTHF/H2O (4:1). Temp: 70–95 °C. Time: 2–16 h. Typical isolated yields for similar naphthyl bromides: 70–95% (literature).
B2pin2 (1.2–1.5 equiv), Pd(dppf)Cl2 (1–3 mol%), KOAc (3 equiv), dioxane, 80–90 °C, 4–12 h → pinacol boronate ester.
Halogen–metal exchange (general)
nBuLi (1.1–1.3 equiv) in anhydrous THF at −78 °C, then electrophile quench (e.g., DMF for formylation). Strictly anhydrous, inert conditions.
Carbonylation (general)
Under CO (1–10 bar), Pd catalyst, alcohol/amine nucleophile, base; solvent: toluene/DMF; 80–100 °C.
Notes
The methoxy substituent can influence oxidative addition rates favorably; steric hindrance is moderate. Monitor for proto-dehalogenation and homocoupling; adjust ligand/basicity accordingly.
Safety and Handling
No item-specific GHS details were provided; consult the SDS for authoritative information. The following are general precautions for aryl bromides and polycyclic aromatic ethers.
Item-specific hazard data
Signal word: Not specified for this item; refer to SDS.
H-statements: Not specified for this item; refer to SDS.
GHS classification/pictograms: Not specified for this item; refer to SDS.
General hazards (literature/analogous substances)
May cause skin/eye irritation and respiratory tract irritation if dust is generated. Aromatic bromides can be harmful if ingested or inhaled.
Combustible solid; dust may form explosive mixtures with air. Avoid ignition sources.
Handling and PPE (best practice)
Use in a fume hood. Wear safety glasses, lab coat, and appropriate chemical-resistant gloves (e.g., nitrile). Avoid dust formation; handle with antistatic measures if necessary.
Avoid contact with strong oxidizers and strong bases during storage; incompatible with strong reducing agents in the presence of catalytic metals.
First-aid overview (general)
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/eyes: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Fire-fighting (general)
Use dry chemical, CO2, or foam. Combustion may produce HBr, CO/CO2; wear SCBA.
Spill/leak (general)
Avoid dust; collect mechanically or with inert absorbent. Dispose according to local regulations.
Always defer to the product’s SDS and your institutional EHS protocols.
Solvent Selection
This is an apolar-to-moderately polar aromatic solid. Choose solvents based on solubility and the downstream reaction.
Poor solubility: water; aliphatic hydrocarbons may require heating.
Polarity considerations
Aryl bromides favor non-protic, moderately polar solvents for cross-coupling (THF, dioxane, 2-MeTHF, CPME) or polar aprotics for amination/arylation (DMF/DMAc/NMP).
When to choose which solvent (practical)
Suzuki–Miyaura: 1,4-dioxane/H2O, THF/H2O, or 2-MeTHF/H2O with base (K3PO4, Cs2CO3).
Buchwald–Hartwig amination: toluene, dioxane, CPME, or tBuOH under Pd catalysis; DMF/DMAc for difficult substrates.
Lithiation/magnesiation: anhydrous THF or 2-MeTHF at low temperature.
Small comparison (general)
THF vs 2-MeTHF: similar solvating power; 2-MeTHF is greener and higher boiling, aiding higher-temperature couplings.
Toluene vs dioxane: toluene is less polar/greener; dioxane can enhance rates/solubility but has higher EH&S concerns.
Storage and Reconstitution
Item-specific storage and shipping (from Product Data)
Storage: Protected from light; Room temperature; Desiccated.
Shipped in: Normal conditions.
General handling/reconstitution (practical)
Keep tightly closed in a dry, light-resistant container. Open and handle under low humidity; reseal promptly or store in a desiccator.
For solution preparation, dissolve in dry organic solvents compatible with your application: DCM, toluene, THF, 2-MeTHF, CPME, acetone, or DMF. Filter if particulates are present.
For moisture/air-sensitive transformations (e.g., halogen–metal exchange), pre-dry the solid under vacuum and transfer under inert atmosphere.
Stability considerations (general)
Aryl bromides are typically stable at ambient conditions when dry and protected from light. Avoid prolonged exposure to strong UV and bases during storage.
Freeze–thaw guidance
Not typically required for solids. If storing as a solution, aliquot under inert gas and keep at low temperature appropriate for the solvent; minimize freeze–thaw cycles.
Always consult the product CoA and SDS for item-specific stability and handling guidance.
Structure and Identity
A halo- and methoxy-substituted naphthalene designed for use as an aryl bromide building block and cross‑coupling substrate.
Item-specific identifiers (from Product Data)
SKU: B727231
Product name: 2-Bromo-7-methoxynaphthalene
CAS: 200875-36-1
CID: 12992759
InChIKey: 165706 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identifiers and features (non-item-specific)
Typical molecular formula: C11H9BrO (literature/computed from name)
2D structural description: A fused bicyclic naphthalene core bearing a bromine at the 2-position and a methoxy (–OCH3) at the 7-position. The ring system is fully aromatic; no stereocenters are present. Functional groups include an aryl bromide (C–Br) and an aryl methyl ether (Ar–O–CH3).
Representative literature SMILES: Brc1ccc2cc(OC)ccc12 (for 2-bromo-7-methoxynaphthalene; literature)
Structural implications (general)
The aryl bromide activates the 2-position toward oxidative addition in Pd/Ni-catalyzed cross-couplings.
The para-/meta-directing methoxy group modulates electronic density across the naphthalene framework, influencing regioselectivity in further electrophilic substitutions (literature).
Synthetic Utility
The juxtaposition of an aryl bromide (C–Br) and an electron-donating methoxy group on a naphthalene core offers complementary reactivity for stepwise diversification.
Strategic roles (general)
Electrophilic node: Oxidative addition at C2–Br enables Pd/Ni-catalyzed couplings, forging C(sp2)–C(sp2/sp3) bonds with high reliability.
Umpolung via metalation: Br–Li exchange or directed ortho metalation adjacent to OMe generates nucleophilic aryl metal species for electrophile trapping (e.g., carbonylation, borylation, silylation).
Orthogonal handles: Methoxy is stable under many coupling conditions yet can be demethylated (e.g., BBr3) to reveal a phenol for further derivatization (ether/ester formation, SNAr anchoring).
Named transformations (literature)
Suzuki–Miyaura, Buchwald–Hartwig, Kumada, Negishi, Stille, Miyaura borylation (to pinacol boronate), and carbonylation (to aryl esters/amides under CO).
Retrosynthetic value
Serves as an advanced intermediate toward 2-substituted-7-methoxynaphthalenes, dye precursors, and rigid polyaromatic ligands. The OMe substituent tunes electronics and solubility of targets without adding steric bulk comparable to tert-alkyl ethers.
Target Specificity
Not applicable. This product is a small-molecule chemical building block and does not possess biological target specificity parameters (no antigen/epitope/clone/isotype). Refer to Reaction & Applications and Synthetic Utility for relevant technical details.
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