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.
Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
Molekulargewicht
166.170 g/mol
XLogP3
1.800
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
0
Exact Mass
166.063 Da
Monoisotopic Mass
166.063 Da
Topological Polar Surface Area
38.700 Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
179.000
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
Lösungsrechner
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Application Protocols
No tested bioassay/immunoassay protocols are provided for this small molecule. Typical applications involve synthetic transformations and analytical chemistry.
Item-specific tested applications and recommended dilutions: Not specified for this item; refer to CoA/Spec Sheet.
General analytical protocol outlines (literature):
LC-MS/MS (negative ESI): Prepare stock in ACN or MeOH (e.g., 1–5 mg/mL), dilute into water/ACN with 0.1% formic acid or 5 mM ammonium acetate; inject onto C18, gradient 5–95% organic in 10–15 min; monitor phenolate [M–H]−.
GC-MS after silylation: Extract sample into EtOAc, evaporate, derivatize with BSTFA + 1% TMCS at 60 °C for 20 min, inject on low-bleed column with temperature program starting 70 °C → 300 °C.
General synthetic handling:
Dry solvents, exclude strong acids; maintain inert atmosphere for moisture-sensitive steps; assay purity by HPLC/GC before scale-up.
These are illustrative, non-validated procedures; adjust to your instrumentation and regulatory framework.
Biological Roles
Item-specific biological/biochemical function: Not specified for this item; refer to CoA/Spec Sheet. This product is provided for research use only.
General context (literature):
Phenolic benzodioxole motifs occur in several agrochemical scaffolds and natural products. The “bendiocarb phenol” is the de-carbamoylated phenolic core associated with bendiocarb; in environmental and metabolic studies, phenolic hydrolysis products are monitored as transformation products.
Phenolic groups participate in hydrogen bonding and can function as weak acids (phenolate formation near alkaline pH), influencing transport and partitioning in biological/environmental matrices.
Analytical toxicology/environmental chemistry:
The phenolic metabolite can serve as a marker analyte in studies of degradation pathways (hydrolysis and biotransformation) of carbamate insecticides. Researchers may track its formation kinetics, partitioning, and further conjugation (e.g., sulfate/glucuronide formation) in model systems. These are general research observations, not product-specific claims.
Note: No medical, diagnostic, or therapeutic use is intended or implied. Any in vivo or clinical applications are out of scope. Always follow institutional approvals for environmental or biochemical studies.
Buffer Applications
This compound is a small organic phenolic analyte/building block and is not typically used as a buffering agent.
Practical notes (general):
For aqueous work (e.g., LC-MS sample prep), compatibility with common buffers such as ammonium acetate/formate (2–20 mM) at pH 3–8 is usually acceptable; verify stability of the phenolic benzodioxole in your chosen pH range.
Phenolic deprotonation occurs at alkaline pH (typical phenol pKa ~9–10.5, literature). Strongly basic buffers may increase ionization but can risk base-promoted side reactions.
Item-specific buffer recommendations, pH range, and recipes: Not specified for this item; refer to CoA/Spec Sheet.
Green Alternatives
While the compound itself is a solid/solute rather than a process solvent, greener choices can be implemented in handling, synthesis, and analytical workflows.
Greener solvent choices (general guidance):
Prefer ethanol, isopropanol, ethyl acetate, and acetone over chlorinated solvents when feasible for dissolution, extractions, and crystallizations.
Replace DMF/DMAC/NMP with safer alternatives such as Cyrene, propylene carbonate, or 2-MeTHF (where reaction compatibility allows).
For extractions, MTBE or ethyl acetate can substitute for dichloromethane in many cases, reducing halogenated waste.
Greener derivatization/analyte handling:
Consider LC-MS workflows to avoid GC derivatization reagents where possible. If derivatization is required, choose lower-toxicity silylating reagents and minimize excess.
Energy and waste:
Use room-temperature or mild base-catalyzed O-acylation/O-carbamoylation protocols (e.g., CDI-mediated) to reduce heating and corrosive reagents.
Comparative snapshot (general):
2-MeTHF vs THF: similar polarity, lower peroxide hazard and bio-based sourcing for 2-MeTHF; check solubility of phenolic benzodioxoles.
Ethyl acetate vs DCM: EtOAc is biodegradable, lower toxicity, and suitable for SPE elution/extractions in many residue methods.
Note: No item-specific environmental certifications or green grade identifiers are provided. For this SKU, any “green” claims are Not specified for this item; refer to CoA/Spec Sheet.
Pharmaceutical Uses
No pharmacopeial or excipient status is provided for this item.
Item-specific status: Not specified for this item; refer to CoA/Spec Sheet.
General context (literature/industry):
Phenolic benzodioxoles are occasionally used as synthetic intermediates in the preparation of bioactive research compounds. In pharmaceutical R&D, such intermediates may be used to explore structure–activity relationships (SAR) in discovery chemistry.
They are not typically used as formulation buffers or classic excipients due to phenolic reactivity and limited water solubility.
Compliance note: This product is supplied strictly for research and laboratory use only. It is not intended for human or veterinary use, API manufacturing, or clinical applications.
Physical Properties
Item-specific specifications are not provided in the Product Data. The following notes separate item-specific information from literature guidance.
Item-specific data (from Product Data):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Physical constants (literature/general for phenolic benzodioxole cores; values vary by exact substitution pattern):
Melting point: often in the range of 60–130 °C for crystalline phenolic benzodioxoles (literature, compound-dependent).
Boiling point: typically >250 °C at 1 atm; many members decompose before boiling (literature).
Density: commonly ~1.1–1.3 g/mL for related solids/oils (literature, compound-dependent).
Solubility: low in water; good solubility in polar aprotic and moderately polar organic solvents (acetone, MeCN, EtOAc, DMSO, alcohols) (literature).
LogP: moderate lipophilicity expected for benzodioxole phenols (literature; exact value depends on substitution).
pKa (phenolic OH): typically 9–10.5 for substituted phenols; electron-withdrawing/–donating effects shift pKa (literature).
Refractive index: usually reported for liquids/oils; crystalline solids may be reported by melting point instead (literature).
Practical notes (general):
Phenolic benzodioxoles may show light/air sensitivity leading to gradual discoloration due to oxidation; store protected from strong light and air when possible.
Moisture has limited effect on the phenolic functionality but strong acids can open the dioxole ring.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret grades (general guidance for research chemicals):
Research/analytical grade typically indicates suitability for routine synthesis and method development. When used as an analytical reference (e.g., for residue analysis of bendiocarb), labs often require a certified reference material (CRM) or documentation of purity by HPLC/GC and identity by NMR/MS.
Low UV-absorbing (HPLC) grades are formulated to minimize background at 210–254 nm; if chromatographic baselines are critical, request UV cutoff data on the CoA. Not specified for this item; refer to CoA/Spec Sheet.
Metal content, residual solvents, water content, and stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/antioxidants:
Phenolic benzodioxoles can slowly oxidize in air/light; some vendors add trace stabilizers. For this SKU, stabilizer content is Not specified for this item; refer to CoA/Spec Sheet. If stabilizers are undesirable for your application (e.g., quantitative derivatization), request a stabilizer-free lot.
Fit-for-purpose recommendations:
For quantitative LC-MS/GC-MS work (e.g., environmental metabolite monitoring), request a lot with ≥98% assay by orthogonal techniques and known water/residual solvent profile.
For synthetic use, typical research grade is sufficient, but drying and a quick assay (TLC/HPLC) prior to scale-up are recommended.
Reaction and Applications
Analytical applications (research use):
Employed as an analytical reference/standard for the phenolic hydrolysis product of bendiocarb in environmental residue analysis (water, soil, and food matrices). Useful for method development/validation across GC-MS (after derivatization) and LC-MS/MS workflows.
Typical workflows include solid-phase extraction (SPE) or liquid–liquid extraction, followed by O-silylation (e.g., BSTFA) for GC-MS or direct RP-LC-MS in negative ESI when the phenolic functionality is deprotonated.
Synthetic applications (general for phenolic benzodioxoles):
Precursor to carbamate formation (reconstruction of bendiocarb-like structures) via O-carbamoylation using isocyanates, carbamoyl chlorides, or CDI/amine combinations.
O-alkylation to phenyl ethers under Williamson conditions (ArO– + R–X), phase-transfer catalysis, or Mitsunobu etherification with alcohol partners.
O-acylation to esters (e.g., acetyl, benzoyl) for protection or property tuning; deprotection by basic hydrolysis.
Electrophilic aromatic substitution (nitration, halogenation) can be directed by the phenolic OH and the benzodioxole ring; conditions must avoid ring opening of the acetal under strong acid.
Practical tips:
Keep moisture and strong acid minimal during reactions that must preserve the dioxole ring; use buffered or nonaqueous conditions.
For LC-MS quantitation, monitor possible in-source fragmentation of phenolic benzodioxoles; stable isotope internal standards improve accuracy.
Drying: brief vacuum desiccation over P2O5 or molecular sieves helps remove adventitious moisture prior to derivatization steps.
Manufacturer Applications: Not specified in Product Data; the above reflects common research/literature practices.
Reaction Conditions
Illustrative (literature/general) conditions frequently applied to phenolic benzodioxoles. These are guidance ranges, not item-specific specifications.
Reagents: acyl chloride/anhydride; base such as pyridine or Et3N; optional DMAP.
Solvent: DCM, toluene, or ACN; temperature 0–25 °C; 0.5–2 h; yields commonly 80–95% (literature).
O-Alkylation (Williamson ether):
Generate phenolate with K2CO3 or Cs2CO3 in acetone, ACN, or DMF; add alkyl halide (R–X).
Conditions: reflux in acetone (56 °C) 2–8 h or room temp in ACN with phase-transfer catalyst; 50–85% yields (literature).
Analytical derivatization (for GC-MS):
Silylation: BSTFA + 1% TMCS, 60–70 °C, 15–30 min; analyze promptly to avoid hydrolysis.
Stability cautions:
Avoid strong acids (H2SO4, HCl conc.) and prolonged heating in protic acids to prevent dioxole ring opening.
Under strong base and high temperature, competitive C-alkylation or rearrangements may occur; monitor by TLC/LC-MS.
Safety and Handling
GHS classification and hazard statements: Not specified for this item; refer to CoA/Spec Sheet and the product SDS for authoritative hazard and precautionary statements.
General laboratory precautions for phenolic benzodioxole compounds (literature/good practice):
Wear appropriate PPE: lab coat, nitrile gloves, safety glasses. Avoid inhalation of dust or aerosols; handle in a fume hood if dusting or heating.
Avoid contact with strong oxidizers and strong acids; the dioxole (acetal-like) ring can be acid-labile, and phenols can undergo oxidative darkening.
Incompatibilities: strong oxidants, strong mineral acids, bases strong enough to generate phenolate (handle with care), and reactive acylating/alkylating agents without proper controls.
Thermal stability: typical aromatic phenols are thermally stable under ambient handling; avoid excessive heating that may promote decomposition.
First-aid overview (general):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; seek medical advice if irritation develops.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Fire-fighting measures (general):
Use dry chemical, CO2, or foam. Combustion may produce CO/CO2 and phenolic/aryl-ether vapors. Firefighters should wear self-contained breathing apparatus.
Always consult the SDS specific to SKU B1062322 before use.
Solvent Selection
This product is a phenolic benzodioxole building block/analytical reference, not itself a solvent. The following guidance focuses on choosing solvents to dissolve and handle it effectively.
Polarity/miscibility considerations (general):
Expected to be sparingly soluble in water and readily soluble in moderately polar organics (acetone, acetonitrile, ethyl acetate) and polar aprotics (DMF, DMSO). Alcohols (MeOH, EtOH, i-PrOH) often provide good solubility while allowing easy workup.
For LC-MS sample prep, MeOH, ACN, or their water mixtures (with 0.1% formic acid or NH4OAc when appropriate) are common choices; ensure compound stability in the chosen modifier.
When to choose which solvent (general/literature):
DMSO: maximal solubilizing power; good for stock solutions; consider dilution into ACN/H2O before injection to avoid peak distortion.
ACN: excellent for LC-MS due to volatility and low viscosity; good for reversed-phase separations.
MeOH/EtOH: benign, versatile; may engage in H-bonding with phenols; useful for UV detection.
Ethyl acetate/MTBE: good for extraction from aqueous matrices during sample prep.
Small comparison (general):
ACN vs MeOH: ACN usually provides sharper peaks and stronger elution in RP-LC; MeOH may give better UV transparency below 205 nm.
DMSO vs DMF: DMSO preferred for lower toxicity profile and LC compatibility; DMF can be used for reactions but is less ideal for MS.
Note: Item-specific solubility parameters are Not specified for this item; refer to CoA/Spec Sheet.
Storage and Reconstitution
Storage (from Product Data):
Storage conditions: Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Practical storage guidance (general for phenolic benzodioxoles):
Keep tightly closed in a dry, inert atmosphere container. Protect from strong light to minimize slow oxidative discoloration.
If long-term storage is planned, consider desiccation (e.g., over silica gel or molecular sieves) and headspace purging with nitrogen/argon after each use.
Reconstitution and solution handling (general):
Prepare stock solutions in ACN, MeOH, or DMSO at 1–50 mg/mL depending on solubility and intended use. Filter (PTFE, 0.2 µm) if particulate forms.
For LC-MS, avoid prolonged storage of dilute aqueous solutions; prepare fresh daily. Store concentrated stocks at 2–8 °C or −20 °C in amber vials if required by your method, and allow to warm to room temperature before opening to avoid condensation.
Stability/shelf life:
Item-specific shelf life and assay specifications are Not specified for this item; refer to CoA/Spec Sheet.
Research use note: For research use only.
Structure and Identity
Brief overview: Bendiocarb phenol is the phenolic benzodioxole core associated with the carbamate insecticide bendiocarb; it is widely used as an analytical reference and synthetic intermediate in environmental residue chemistry.
Product Data (item-specific):
CAS: 22961-82-6
InChIKey: 52708 (as provided in Product Data; format appears truncated — verify on CoA/SDS)
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/literature description of the “bendiocarb phenol” scaffold):
Core ring system: a 1,3-benzodioxole (methylenedioxy/benzodioxole) or 1,3-benzodioxolane-type fused heteroaromatic ring, substituted with a phenolic OH.
Functional groups: phenol (acidic OH capable of H-bonding and O-acyl/O-alkyl derivatization); acetal/dioxole ring (acetal-like carbon sensitive to strong acid).
Typical substitution (literature): a dimethyl-substituted acetal carbon at the 2-position is characteristic of the bendiocarb phenyl moiety; the phenolic OH resides para to the dioxole bridge on the benzene ring.
Stereochemistry: none expected (all sp2/sp3 centers achiral in the common structure).
2D structure in words (general): a benzene ring bearing a fused 1,3-dioxole ring (–O–C(R)2–O– bridge) across adjacent ortho positions, with a phenolic hydroxyl approximately para to the bridge. This scaffold underlies the O-carbamoylated insecticide (bendiocarb), and the “phenol” refers to the de-carbamoylated hydrolysis product/precursor.
Synthetic Utility
The “bendiocarb phenol” scaffold is a versatile aryl phenol embedded in a benzodioxole ring, enabling multiple downstream transformations.
Key functional reactivity (general/literature):
Phenolic OH: readily undergoes O-acylation (acyl chlorides/anhydrides), O-carbamoylation (isocyanates, carbamoyl chlorides, CDI + amines), and O-alkylation (Williamson ether synthesis). Phenolate formation under base enhances nucleophilicity.
Aromatic ring: activated toward electrophilic substitution by the phenolic OH; regioselectivity influenced by the benzodioxole substituent pattern.
Dioxole ring: acetal-like; avoid strong acids to prevent ring opening. Under mild conditions, it is a stable, lipophilicity-imparting moiety.
Named/typical transformations:
Re-synthesis of bendiocarb analogs via O-carbamoylation with methyl isocyanate surrogates or carbamoyl chloride species in the presence of base (e.g., pyridine, DMAP) at 0–25 °C.
Mitsunobu ether formation with primary/secondary alcohols for SAR analogs; workup under non-acidic conditions to preserve the dioxole ring.
Protection–deprotection: convert to acetate/benzoate to modulate solubility and protect the phenol during multi-step routes; deprotect with Na2CO3/MeOH or catalytic transesterification.
Retrosynthetic value:
Serves as a convergent handle to attach diverse carbamate, carbonate, or ether functionalities while maintaining the benzodioxole pharmacophore for agrochemical or probe development studies.
Target Specificity
Not applicable. This product is a small-molecule phenolic benzodioxole, not a biologic or affinity reagent.
Item-specific antigen/epitope/clone/isotype data: Not specified for this item; refer to CoA/Spec Sheet.
For studies requiring target binding/selectivity, consider synthesizing or procuring conjugates (e.g., hapten–protein conjugates) or antibodies specific to bendiocarb-related structures; such reagents are outside the scope of this SKU.
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