This compound belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
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
231.040 g/mol
XLogP3
2.400
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Exact Mass
229.958 Da
Monoisotopic Mass
229.958 Da
Topological Polar Surface Area
27.700 Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
164.000
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
Not applicable. No tested bioassay or immunoassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule building block. For practical use, refer to the Reaction & Applications and Reaction Conditions sections for synthetic protocols.
Biological Roles
This product is a synthetic aromatic building block and does not have an intrinsic biological role specified in the Product Data. The following notes are general background for related structural motifs (literature/general) and are provided for research context only.
Benzodioxane/benzodioxole scaffolds occur in natural products and agrochemical leads; they often serve as rigid, heteroatom-rich aromatics that modulate polarity and H-bonding pattern.
Aryl bromides and methoxyarenes are common handles in medicinal chemistry for diversification, SAR exploration, and tuning of metabolic stability.
The acetal (1,3-dioxa) ring is typically metabolically labile in vivo; however, no metabolic or biochemical data are provided for this specific compound. Any biotransformation discussion should be considered speculative until experimentally verified.
Research Use Note: For research use only. Not intended for human or animal therapeutic or diagnostic applications.
Buffer Applications
Not typically applicable. This compound is a neutral, hydrophobic organic building block and is not used to prepare aqueous buffer systems. For practical laboratory use, focus on the Solvent Selection, Reaction & Applications, and Synthetic Utility sections instead.
Green Alternatives
Greener choices center on solvent and reagent selection, as the substrate itself is a fixed building block.
Prefer greener solvents when feasible (literature/general):
Replace DCM/chloroform with EtOAc, MeTHF, CPME, or toluene where reactivity allows.
For Suzuki couplings, aqueous MeOH/EtOH, 2-MeTHF, or green amide alternatives (e.g., NEP) can be effective with suitable catalyst systems.
Bases: Favor inorganic bases with lower EHS impacts (K2CO3, K3PO4) over strong, hazardous bases where compatible.
Catalysts: Employ modern high-activity Pd precatalysts at low loading to minimize precious metal use; consider Ni catalysis for certain couplings as a Pd alternative.
Comparison (general guidance; not item-specific):
THF vs 2-MeTHF: 2-MeTHF is bio-based, higher boiling, and less miscible with water (facilitates workup); both form peroxides—test and manage accordingly.
DCM vs EtOAc: EtOAc reduces chlorinated solvent usage; may require different temperature or base to maintain rate/solubility.
DMF/NMP vs Cyrene/PC/GBL: Emerging dipolar aprotics can replace toxic amides for some cross-couplings, subject to catalyst compatibility.
Trade-offs:
Greener solvents can change solubility and reaction kinetics; catalyst/ligand and base may need re-optimization.
Workup and isolation can improve with phase-splitting solvents (MeTHF/CPME), offsetting potential rate penalties.
Pharmaceutical Uses
Item-specific pharmacopeial status, excipient role, or GMP suitability: Not specified for this item; refer to CoA/Spec Sheet.
General context (literature/general; no therapeutic claims):
Role in drug discovery: Aryl bromides such as this are frequently used as intermediates to access analog libraries via cross-coupling, enabling rapid scaffold diversification for SAR.
Formulation relevance: The compound itself is not a typical excipient. If incorporated into an API synthesis route, attention should be paid to purge of residual metal catalysts and organobromide impurities according to ICH guidelines.
Quality considerations for pharmaceutical R&D: When used in preclinical route scouting, higher purity grades and trace metal analytics facilitate smoother tech transfer and regulatory documentation later in development.
Physical Properties
Item-specific physico-chemical specifications are not provided in the Product Data.
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.
Melting/Boiling point, density, refractive index, UV cutoff, water content, residual solvents, metals: Not specified for this item; refer to CoA/Spec Sheet.
General expectations for this class (literature/general; informative, not item specifications):
State: Small aromatic acetals are typically low-melting solids or high-boiling liquids.
Solubility: Generally soluble in common organic solvents (e.g., dichloromethane, THF, ethyl acetate, toluene, acetone); poorly soluble in water.
Polarity: Moderately nonpolar aromatic with heteroatoms; amenable to normal-phase and reversed-phase chromatography.
Stability: Acetals are typically stable to base and mild nucleophiles, but hydrolyze under aqueous acidic conditions; aryl bromides are thermally stable yet sensitive to strong nucleophiles under SNAr only when activated (here deactivated by methoxy/benzodioxane ring).
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance for selection and implications (general for building-block reagents):
Research grade vs. high-purity: For cross-coupling chemistry, trace metal and halide content are typically less critical than for analytical solvents, but residual halides/water can affect sensitive steps (e.g., Grignard formation). Choose higher purity if performing metal-catalyzed reactions at low catalyst loading or doing medicinal chemistry that proceeds to bioassays.
HPLC assay/GC assay: If an assay value is provided on the CoA, it reflects bulk purity of the main component. Minor regioisomeric or deprotected impurities can influence downstream selectivity; review chromatograms when available.
Stabilizers: None are listed in Product Data. If present (per CoA), stabilizers can influence reactivity in Lewis-acid-mediated transformations or purification; remove by prewash or chromatography if needed.
UV-Vis background: Not specified for this item. For photochemistry or UV-detection analytics, assess background absorbance empirically.
Batch-to-batch considerations: For aryl bromides, variability can occur in residual inorganic bromide and palladium (from prior steps). CoA metal testing, if provided, indicates suitability for trace-sensitive applications.
Reaction and Applications
As a 6-brominated, 4-methoxy-substituted benzodioxane/benzodioxole-type building block, this compound serves as a versatile aryl bromide in C–C and C–N bond constructions.
Key application families (literature/general):
Cross-couplings (aryl bromide handle):
Suzuki–Miyaura: Coupling with boronic acids/esters to access diverse substitution at C-6; tolerant of methoxy and acetal functionalities under neutral/basic conditions.
Buchwald–Hartwig amination: Formation of aryl amines with appropriate Pd precatalysts and ligands (e.g., BrettPhos, XPhos) under mild base.
Kumada/Negishi/Stille: Formation of C–C bonds with Grignard, organozinc, or stannanes; choose conditions to preserve the acetal ring.
Electrophilic aromatic substitution (EAS): The 4-methoxy group is strongly activating and ortho/para-directing; however, acid-mediated EAS risks acetal cleavage—buffered Lewis acids or milder nitration/halogenation protocols are preferred.
Further functional group manipulations:
Demethylation (Ar–OMe to Ar–OH) with BBr3/BCl3 or strong Lewis acids (literature) affords phenols, enabling late-stage diversification.
Acetal deprotection under aqueous acid to unveil corresponding o-diol/phenolic motifs (context-dependent for benzodioxane/benzodioxole frameworks).
Late-stage diversification: Bromide enables rapid library expansion for SAR in discovery chemistry while retaining the heteroatom-rich ring.
Practical tips:
Maintain anhydrous, neutral/basic conditions to preserve the acetal during cross-couplings.
Use ligand/catalyst systems optimized for aryl bromides at moderate temperatures (80–110 °C) when sensitive groups are present.
Monitor for debromination as a side reaction; adjust hydrogen sources and base choice accordingly.
Reaction Conditions
General literature guidance for aryl bromide couplings and related manipulations (informative; not item-specific specifications):
Suzuki–Miyaura C–C coupling:
Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd-precatalyst with bulky dialkylbiaryl phosphine (0.5–2 mol%).
Notes: Maintain neutral to basic pH to preserve the acetal.
Buchwald–Hartwig amination:
Catalyst/ligand: Pd2(dba)3 (0.5–1 mol% Pd) with BrettPhos/XPhos/RuPhos; or precatalysts (0.5–2 mol%).
Base: NaOtBu, K3PO4, or Cs2CO3.
Solvent: Toluene, dioxane, or t-BuOH/PhMe mixtures.
Temperature: 80–110 °C.
Negishi/Kumada/Stille:
Negishi: THF, 0–80 °C; Kumada: THF/Et2O, −20 to rt (sensitive to functional groups); Stille: DMF/toluene, 80–110 °C with Pd(PPh3)4 or Pd(dppf)Cl2.
Demethylation (Ar–OMe to Ar–OH):
Reagent: BBr3 (1–3 equiv) in DCM, −78 to 0 °C, then quench; monitor to avoid acetal cleavage or consider stepwise protection strategies.
Acetal deprotection (if desired):
Conditions: Aqueous mineral acid (HCl/H2SO4), MeOH/H2O, 25–60 °C; avoid during couplings unless intended.
Expected outcomes: Aryl bromides typically couple in good to excellent yields with optimized catalysts; substrate electronics (OMe activating; acetal mildly deactivating) may influence rates—screen ligands accordingly.
Safety and Handling
Authoritative safety information should be taken from the product SDS. The following are general considerations for aryl-brominated aromatic acetals and methoxyarenes.
GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.
Likely hazards (general):
May cause skin/eye irritation; harmful if swallowed or inhaled (typical of many aromatic organobromides).
Combustible organic solid/liquid; vapors/mists may form explosive mixtures with air when heated.
Acetals can release aldehydes or diols upon strong acid hydrolysis.
PPE and engineering controls:
Use chemical-resistant gloves (e.g., nitrile), safety goggles/face shield, lab coat.
Handle in a fume hood to avoid inhalation of vapors/particles and to control solvent exposure during reactions/purifications.
Incompatibilities (general):
Strong acids (risk of acetal cleavage), strong Lewis acids (risk of demethylation/complexation), powerful oxidants, strong bases at high temperature.
First aid (summary; defer to SDS):
Skin/eye: Rinse with water for at least 15 minutes, remove contaminated clothing, seek medical attention if irritation persists.
Inhalation: Move to fresh air; if symptoms persist, seek medical attention.
Ingestion: Rinse mouth, do not induce vomiting, seek medical attention.
Storage: See Storage & Reconstitution tab; Product Data indicates room temperature storage.
Solvent Selection
This compound is a neutral, moderately nonpolar aromatic acetal with an aryl bromide and a methoxy substituent.
Solubility profile (general/literature):
Good solubility in chlorinated solvents (DCM, chloroform), ethers (THF, MTBE), esters (EtOAc), aromatics (toluene), and ketones (acetone/MEK).
Poor solubility in water and highly protic media; acidic aqueous conditions can cleave the acetal.
Polarity/dielectric considerations:
For cross-coupling catalysis, polar aprotic solvents (DMF, DMAc, NMP, dioxane, THF) support catalyst solubility and base compatibility.
For electrophilic substitution or Friedel–Crafts on the ring (if attempted), use non-coordinating solvents (DCE, nitromethane) with caution due to acetal sensitivity to acids.
When to choose alternatives:
If acetal stability is a concern, avoid protic/acidic media; consider neutral, dry solvents.
For greener processes, consider 2-MeTHF or CPME in place of THF/DCM (see Green Alternatives).
Small comparison (general):
THF/1,4-dioxane: Balance of polarity and catalyst solubility; peroxide formation risk with ethers requires inhibitor checks.
Toluene: Good for high-temperature couplings; lower polarity may reduce rates for some Pd systems.
EtOAc/MeTHF: Greener options; may require higher temperature or different bases to reach full conversion.
Container: Store in a tightly sealed container under an inert atmosphere (e.g., nitrogen/argon) if possible to minimize oxidative or acidic moisture exposure.
Environmental controls: Keep dry and protect from prolonged exposure to strong light and acids; acetal functionality is acid-labile.
Stability: Long-term stability depends on moisture and acid exclusion. Periodically check integrity by NMR/LC if stored for extended periods.
Handling: Warm to ambient temperature before opening if stored cold; allow any condensed moisture to dissipate. Reseal promptly after use.
Reconstitution: Not applicable—this item is supplied neat (appearance not specified). If preparing stock solutions, use dry, neutral organic solvents (e.g., DCM, THF, toluene, EtOAc) and store solutions in amber vials at room temperature or 2–8 °C, away from acids. Validate solution stability empirically prior to scale-up.
Shipping: Not specified for this item; refer to CoA/Spec Sheet and shipment documents.
Research Use Note: For research use only.
Structure and Identity
A brominated, methoxy-substituted bicyclic acetal belonging to the benzodioxane/benzodioxole family (an aromatic ring fused to a 1,3-dioxa ring). The scaffold makes it a versatile aryl bromide building block.
Item-specific identifiers (Product Data):
SKU: B1052391
Product Name: 6-Bromo-4-methoxy-1,3-dioxaindane
CAS: 91511-83-0
CID: 10911396
InChIKey: 284322 (as provided; note: typical InChIKeys are 27-character strings)
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.
Structural features (general description from name; literature/general):
Core: A benzene ring annulated with a five- or six-membered 1,3-dioxa ring (a cyclic acetal). Often referred to as benzodioxole/benzodioxane-type frameworks.
Substituents: A bromine at the 6-position (aryl bromide handle) and a methoxy group at the 4-position (electron-donating, ortho/para-directing on the arene).
Functional groups: Aromatic ring, aryl bromide (for cross-coupling), acetal (acid-labile), aryl methoxy ether (generally stable to base; can be demethylated with strong Lewis acids or BBr3).
Stereochemistry: None expected at the ring system (achiral framework; no stereocenters implied by the name).
Synthetic Utility
Functional handles and their value (literature/general):
Aryl bromide (C–Br):
Cross-coupling platform for C(sp2)–C(sp2/sp3) formation (Suzuki, Negishi, Kumada, Stille) and C–N/C–O/C–S couplings (Buchwald–Hartwig/Chan–Lam variants).
Oxidative additions to Pd(0)/Ni(0) are generally fast for aryl bromides, enabling lower catalyst loadings.
Methoxy (Ar–OMe):
Electron-donating, activates ring toward EAS; serves as a synthetic placeholder for phenol (demethylation with BBr3/BCl3/AlCl3–thiols).
Directing group potential in metalation strategies (lithiation ortho to OMe under strong base/low temp; caution with acetal stability).
1,3-Dioxa ring (acetal):
Acid-labile protecting group; strategic unmasking can reveal diol/phenolic functionality for downstream diversification.
Contributes to polarity and three-dimensionality without adding ionizable groups.
Retrosynthetic perspectives:
The target can be traced back to a suitable bromo-methoxy-substituted catechol or phenol, then cyclized to the benzodioxane/benzodioxole, or vice versa—install bromide late to minimize incompatibility during acetal formation.
Purification/analysis tips:
Aromatic acetals often show distinctive 1H NMR acetal methylene signals (dioxane/dioxole CH2) and a deshielded aryl pattern from OMe/Br substituents.
For LC, moderate retention on C18 with MeCN/H2O (with 0.1% base) is typical; avoid acidic mobile phases if hydrolysis is a concern.
Target Specificity
Not applicable. This product is a small-molecule chemical building block and is not an antibody, biological, or affinity reagent. No antigen/epitope/clonal specificity information is associated with this item.
Domande frequenti
What is the purity of this product?
This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at room temperature.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 91511-83-0, the molecular formula is C8H7BrO3, and the molecular weight is 231.04 g/mol. InChIKey PQIWDZBUHXVOKA-UHFFFAOYSA-N.
What documentation is provided?
Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.
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