(2-(Dimethoxymethyl)phenyl)methanol - ≥95% , CAS No.87656-32-4

CAS: 87656-32-4 Cat. No.: D984097 Summenformel: C₁₀H₁₄O₃ Molekulargewicht: 182.220

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥95%

Storage

Room temperature

Reinheit

≥95%

Namen und Kennungen

• Kanonisches Lächeln: COC(C1=CC=CC=C1CO)OC
• IUPAC Name: [2-(dimethoxymethyl)phenyl]methanol
• InChIKey: WRXSEVIJQSMXDN-UHFFFAOYSA-N
• INCHI: 1S/C10H14O3/c1-12-10(13-2)9-6-4-3-5-8(9)7-11/h3-6,10-11H,7H2,1-2H3
• Molekulargewicht: 182.220

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Klasse Benzene and substituted derivatives
      • Subclass Benzylethers

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Klasse: Benzene and substituted derivatives
• Subclass: Benzylethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzylethers
• Alternative Parents: Benzyl alcohols Acetals Primary alcohols Hydrocarbon derivatives Aromatic alcohols
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzylether - Benzyl alcohol - Acetal - Organic oxygen compound - Hydrocarbon derivative - Aromatic alcohol - Primary alcohol - Organooxygen compound - Alcohol - Aromatic homomonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).
• External Descriptors: Not available

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Chemische und physikalische Eigenschaften

• Molekulargewicht: 182.220 g/mol
• XLogP3: 0.700
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 182.094 Da
• Monoisotopic Mass: 182.094 Da
• Topological Polar Surface Area: 38.700 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 134.000
• 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

Application Protocols

No antibody- or assay-specific protocols are associated with this small-molecule reagent.

General laboratory protocol examples (non-validated; literature guidance):

• Acetal deprotection screen:
  • Dissolve 100 mg substrate in 2 mL MeOH; add 0.2 mL H2O and 10 mg p-TsOH·H2O. Stir at RT and monitor by TLC/NMR every 15 min. On completion, neutralize with solid NaHCO3, filter, concentrate, and purify by silica gel chromatography (hexanes/EtOAc).
• Benzylic oxidation (TEMPO/NaOCl):
  • In a biphasic EtOAc/NaHCO3 buffer (pH 8.6), add 5 mol% TEMPO and 10 mol% KBr at 0–5 °C. Portionwise add bleach to maintain mild oxidizing conditions. Quench with Na2S2O3, separate layers, and purify. Protect the acetal by maintaining neutral-to-basic pH.

Users should validate and optimize conditions for their specific equipment, scale, and quality requirements.

Biological Roles

This compound is intended for synthetic and analytical laboratory use and is not a biomolecule.

General context (biochemistry-oriented, literature):

• Structural class: small aromatic alcohol bearing an acetal group. It lacks inherent biochemical function, enzyme cofactors, or known signaling roles.
• Metabolic analogy: Benzyl alcohols can be oxidized by alcohol dehydrogenases in biological systems; however, the acetal motif is uncommon in vivo and would be hydrolyzed under acidic enzymatic conditions to an aldehyde and methanol.
• Protein/DNA interactions: No specific binding or intercalation tendencies are established for this structure; interactions are expected to be nonspecific hydrophobic and hydrogen-bonding in nature.

Use guidance:

• For research use only (as specified by the manufacturer). Not intended for diagnostic, therapeutic, or in vivo use.
• If employed as a probe precursor or derivatization agent, ensure adequate purification to remove residual acidic impurities that could hydrolyze the acetal during biological sample handling.

If a biologically relevant derivative is desired, the acetal can serve as a protected handle to introduce an ortho-formyl group on an aryl system, enabling conjugation chemistry (e.g., formation of imines/oximes with amines/hydroxylamines) after deprotection. Such transformations should be performed ex vivo under controlled conditions.

Buffer Applications

Not typically applicable. (2-(Dimethoxymethyl)phenyl)methanol is not a buffering agent and does not participate in defined acid/base conjugate pairs within physiological pH ranges.

Practical note:

• If working in aqueous media, recognize that acidic buffers will hydrolyze the acetal to the corresponding ortho-aldehyde and methanol. Use neutral buffers (e.g., phosphate at pH 7) only when acetal integrity must be preserved and confirm stability by analytical follow-up.

Green Alternatives

While the product itself is a building block rather than a solvent, greener choices in reagents and media around its common transformations can reduce environmental burden.

Greener solvent choices (when feasible):

• Replace DCM/chloroform with ethyl acetate or 2-MeTHF for extractions and many reactions (ensure acetal stability; both can be dried effectively).
• Use MeTHF or CPME instead of THF in reactions/workups to improve safety and ease of phase separation, while maintaining solubility.

Greener reagents for typical steps (literature):

• Benzylic alcohol oxidation:
  • TEMPO/NaOCl (bleach) in aqueous/organic biphasic systems as a safer alternative to Dess–Martin or chromium(VI) oxidants.
  • Oxygen/air with catalytic TEMPO or Cu/N-oxyl systems under benign conditions.
• Acetal deprotection:
  • Use solid acids (Amberlyst-15, montmorillonite K10) in EtOH/H2O or MeOH at ambient temperature to minimize corrosive mineral acids.

Comparison snapshot (literature-informed; not product specs):

• DCM vs EtOAc: EtOAc is biodegradable, lower toxicity, renewable feedstocks possible; may require attention to water content for acetal integrity.
• THF vs 2-MeTHF: 2-MeTHF derived from hemicellulose, lower peroxide hazard growth rate, favorable partitioning; similar reaction performance in many cases.

Waste minimization:

• Plan telescoped sequences: deprotect → condensations without isolation of o-formyl intermediate where selectivity permits, reducing solvent usage and workups.
• Recover and reuse alcohol-rich mother liquors when compatible (monitor acetal content by NMR to confirm stability).

Pharmaceutical Uses

No pharmacopeial status or excipient role is specified for this item; it is sold for research use only.

General formulation/manufacturing context (literature):

• As a synthetic intermediate: The dimethoxymethyl group functions as an aldehyde protecting group, enabling preparation of ortho-formyl–substituted benzyl derivatives that can be advanced to heteroaromatic pharmacophore fragments (e.g., benzofurans) after deprotection/cyclization.
• Handling in process settings: Control acidity in solvents and reagents to maintain the acetal during storage and transfer. Perform in-process controls (IPC) by NMR/GC to track potential hydrolysis to the aldehyde (which may alter impurity profiles and color).
• Residual solvents/impurities: If used upstream in an API synthesis, define acceptable limits for methanol and aldehyde by ICH Q3A/Q3C frameworks. Solid acid catalysis and solvent swaps to greener media can be considered to reduce residual mineral acids.

Regulatory note:

• No medical, diagnostic, or therapeutic claims are made or implied for this product. Suitability for GMP or clinical manufacturing must be established independently by the user, including full specification, impurity profiling, and stability studies where applicable.

Physical Properties

Item-specific specifications (as sold by Aladdin Scientific):

• 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.

Literature/computed (reference values; not product specifications):

• Empirical formula: C10H14O3 (derived from name/structure)
• Formula weight: ~182.22 g/mol (calculated)
• Physical state: typically a colorless liquid or low-melting solid depending on purity and temperature (literature, analogous benzyl alcohol acetals)
• Polarity/functional groups: benzylic primary alcohol and acetal; capable of hydrogen bonding as donor (–OH) and acceptor (acetal oxygens)
• Solubility profile (qualitative, literature/experience):
  • Water: low to moderate (hydrogen bonding present but limited by aromatic core)
  • Organic solvents: expected to be miscible or highly soluble in ethers (THF, MTBE), esters (EtOAc), chlorinated solvents (DCM, chloroform), alcohols (MeOH, EtOH) and aromatics (toluene)
• Volatility: lower than benzyl alcohol analogs with fewer heteroatoms; acetal reduces hydrogen bonding compared to diol/aldehyde counterparts (qualitative)
• Boiling/melting points, density, refractive index, pKa/logP: Not reliably established in a single consensus source; consult primary literature or measure as needed for process design.

Notes for use:

• The acetal can slowly hydrolyze under strong aqueous acid, potentially altering apparent properties (e.g., increasing polarity upon deprotection to o-formylbenzyl alcohol). Handle under dry conditions when property-critical.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on grades and implications (general):

• Research-grade organics may be offered as “technical,” “AR/ACS reagent,” or “≥95–99%” assay. Higher assay materials reduce side-product formation (e.g., from pre-existing aldehyde after partial acetal hydrolysis) and improve reproducibility in multi-step syntheses.
• Water and peroxides: Not typically specified for this class unless sold as a solvent. However, trace water can catalyze slow acetal equilibration under acidic conditions; drying over molecular sieves or short-path distillation under reduced pressure may be beneficial when acid-sensitive steps follow.
• Stabilizers: None specified for this item. In general, acetals do not require stabilizers, but storage under neutral, dry conditions is recommended to preserve integrity.
• Documentation: For assay, residual solvents, and impurity profile (e.g., benzyl alcohol, o-formylbenzyl alcohol, methanol), consult the product CoA/Spec Sheet.

Fit-for-purpose selection:

• Analytical applications (e.g., quantitative kinetic studies) benefit from higher purity to minimize background reactions upon acid treatment.
• Process development: Define and control the water content and acidity of your medium if you require the acetal functionality to remain intact during workup and storage.

Testing suggestions (user-performed):

• Verify identity/purity by 1H/13C NMR (diagnostic benzylic CH2OH and acetal CH resonances), IR (broad OH ~3300 cm−1; C–O stretches), and GC/LC if volatility allows. Titrate acid/base impurities when acetal stability is critical.

Reaction and Applications

This molecule is a versatile bifunctional building block combining a benzylic alcohol and an acid-labile acetal that unmask an ortho-aldehyde.

Representative applications (literature/practice):

• Orthogonal protection strategy: The dimethoxymethyl unit serves as a protected o-formyl group. Controlled acid-catalyzed deacetalization reveals the aldehyde (o-formylbenzyl alcohol), enabling subsequent condensations (e.g., Schiff base formation, Wittig, Knoevenagel) while the benzylic alcohol remains available for independent manipulation.
• Benzylic alcohol transformations:
  • Oxidation to the corresponding acid/aldehyde (e.g., TEMPO/NaOCl, Dess–Martin, Swern), enabling further derivatization or intramolecular cyclizations.
  • Conversion to halides (PBr3, SOCl2; Appel with PPh3/CBr4) to access o-formylbenzyl halides after prior deprotection, useful for nucleophilic substitutions or benzylation steps.
• Intramolecular cyclizations and benzannulations: After unveiling the ortho-formyl, acetal-to-aldehyde followed by acid- or base-promoted cyclization with the benzylic functionality can furnish benzofuran/benzopyran scaffolds in tailored contexts (literature precedents with o-formyl–benzylic precursors).
• Electrophilic aromatic substitution (EAS): The benzylic alcohol and acetal are weakly activating/ortho–para directing; however, the ring is already 1,2-disubstituted. Directed lithiation adjacent to the acetal-bearing carbon (via metal–halogen exchange after prior halogenation) can introduce further substituents (advanced use).

Practical tips:

• Maintain neutrality and dryness to preserve the acetal. Include base-washed glassware for acid-sensitive sequences.
• During acidolysis, vent appropriately to account for methanol evolution and control temperature to avoid overreaction or polymerization in subsequent condensation steps.

Reaction Conditions

General conditions from literature/practice for transformations of this motif (guidance only; optimize per application):

• Acetal deprotection to the ortho-aldehyde:

  • Solvent: MeOH/H2O (9:1 to 1:1), acetone/H2O, or EtOH/H2O
  • Catalyst: HCl (0.1–1.0 M), p-TsOH (1–10 mol%), or solid acids (Amberlyst-15)
  • Temperature: 0–25 °C for sensitive substrates; 40–60 °C for faster rates
  • Time: 0.5–6 h depending on acidity and solvent
  • Workup: Neutralize, extract with EtOAc or DCM, dry, and minimize exposure to acid to prevent side reactions

• Benzylic alcohol oxidation (to aldehyde or acid):

  • TEMPO/NaOCl: Biphasic CH2Cl2/H2O or EtOAc/H2O with buffer (pH 8–9), 0–25 °C, 0.5–2 h (selective to aldehyde with careful control)
  • Dess–Martin periodinane: DCM or MeCN, 0–25 °C, 0.5–2 h; quench with aqueous NaHCO3/Na2S2O3
  • Swern: DMSO, oxalyl chloride, Et3N; −78 to 0 °C; suitable if water-sensitive conditions are needed

• Appel/PBr3 halogenation of benzylic alcohol:

  • Appel: PPh3/CBr4 (or CCl4) in DCM, 0–25 °C, 1–4 h; avoid strong acid generation that might cleave the acetal
  • PBr3: Etheral solvents at 0–25 °C; add base or use mild conditions to minimize acetal hydrolysis

• Electrophilic aromatic substitution on the ring (if pursued):

  • Mild nitration/halogenation conditions may be possible but must be screened carefully due to potential acetal sensitivity to acids.

Monitoring:

• NMR (disappearance of acetal CH and OMe singlets upon hydrolysis), IR (appearance of C=O ~1680–1720 cm−1 after deprotection), GC/LC for quantitative kinetics.

Safety and Handling

Item-specific hazard information:

• GHS Classification: Not specified for this item; refer to SDS.
• Signal Word / H-Statements / Pictograms: Not specified for this item; refer to SDS.

General safety guidance (literature/practice; not a substitute for the item’s SDS):

• Likely hazards: Organic aromatic alcohols and acetals commonly cause eye/skin irritation; ingestion/inhalation may be harmful. Avoid creating aerosols or inhaling vapors. Acetals can release methanol upon acid hydrolysis; methanol is toxic.
• PPE: Lab coat, safety glasses or chemical splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Work in a fume hood when heating, handling bulk quantities, or using acids for deprotection.
• Incompatibilities:
  • Strong acids catalyze acetal cleavage to the corresponding aldehyde, liberating methanol. Control exotherm and pressure if acid treatment is intentional.
  • Strong oxidants can oxidize the benzylic alcohol (and possibly the aromatic ring under forcing conditions).
  • Avoid moisture during storage to minimize slow hydrolysis in acidic environments.
• First aid (overview; follow SDS):
  • Eye/skin contact: Rinse with water for ≥15 minutes; remove contaminated clothing.
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Fire safety: Treat as a combustible organic liquid/solid. Use CO2, dry chemical, or foam. Combustion may produce CO/CO2 and formaldehyde/methanol traces.
• Spill response: Absorb with inert material, collect for disposal. Decontaminate surfaces with organic solvent then detergent. Prevent entry to drains.

Always consult the product’s SDS for authoritative, item-specific safety data.

Solvent Selection

Compound-centric solubility and polarity considerations (literature/experience):

• Polarity class: Moderately polar aromatic due to one hydrogen-bond donor (–OH) and two ether oxygens (acetal). Expected to dissolve well in polar aprotic solvents and alcohols, and in common organic media used for acetal chemistry.
• Expected miscibility/solubility:
  • High: THF, MeTHF, DCM, chloroform, ethyl acetate, acetone, methanol, ethanol, toluene
  • Moderate: Hexanes/alkanes (enhanced by small amounts of polar co-solvent)
  • Water: low to moderate; solubility increases with added alcohol or under basic conditions via H-bonding to –OH

Selection guidance by use-case:

• For acetal stability: Prefer neutral, anhydrous solvents (DCM, toluene, EtOAc, THF). Avoid protic acids or acidic impurities.
• For acetal deprotection to o-formylbenzyl alcohol: Use aqueous alcoholic media with catalytic mineral acids (MeOH/H2O + HCl) or acetone/water with H2SO4; choose solvent to balance rate and substrate solubility.
• For oxidations of the benzylic alcohol: Acetonitrile, DCM, or EtOAc often provide clean reactions with TEMPO/bleach, Dess–Martin, or Swern systems.
• For cyclizations/formylation cascades: Aromatic solvents (toluene) or chlorinated media (DCM) facilitate intramolecular processes after acetal cleavage.

Comparison snapshot (literature-informed):

• DCM vs EtOAc: DCM maximizes acetal integrity and extraction efficiency; EtOAc offers greener profile with similar solubility but can retain more water.
• THF vs MeTHF: MeTHF provides comparable solubility with improved sustainability and phase-split properties; both are suitable if dry.

Storage and Reconstitution

Item-specific storage and logistics:

• Storage Conditions: Room temperature (per Product Data).
• Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

Best practices (general guidance for this class of compounds):

• Keep container tightly closed under an inert headspace (e.g., nitrogen) if available, particularly for long-term storage, to minimize adventitious moisture/acid exposure.
• Store in a cool, dry, well-ventilated place away from acidic vapors and oxidizers. Use amber glass if long light exposure is expected, although the compound is not strongly photosensitive.
• If frequent access is required, consider aliquoting to reduce cumulative headspace humidity and handling-induced contamination.

Stability notes:

• The dimethoxymethyl acetal is stable under neutral, anhydrous conditions. Prolonged exposure to acid or moist acidic environments can lead to hydrolysis, yielding the ortho-aldehyde and methanol. Verify integrity periodically by 1H NMR (acetal methoxy singlets and acetal CH signal).

Reconstitution:

• Not applicable; the product is supplied neat. If preparing stock solutions, use dry solvents (e.g., anhydrous DCM, THF, toluene, or EtOAc). Label solutions with solvent, concentration, and date; store at RT or 2–8 °C as appropriate for solvent volatility and planned use.

For definitive stability, packaging, and shelf-life, consult the batch-specific CoA/Spec Sheet and SDS.

Structure and Identity

Brief description: (2-(Dimethoxymethyl)phenyl)methanol is an ortho-disubstituted benzene bearing a benzylic alcohol (–CH2OH) and an acetal handle (–CH(OMe)2), making it a dual-functional aromatic building block.

• Item-specific identifiers (from Product Data):

  • CAS: 87656-32-4
  • SKU: D984097
  • Category: Life Science reagents (research use only)
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed identity (for reference; not item specifications):

  • Preferred name: (2-(Dimethoxymethyl)phenyl)methanol
  • Synonyms (common): o-(Dimethoxymethyl)benzyl alcohol; 2-(Dimethoxymethyl)benzyl alcohol (literature)
  • Molecular formula (computed from structure): C10H14O3 (literature)
  • Molecular weight: ~182.22 g/mol (literature)
  • Structural features: aromatic phenyl ring substituted ortho to a benzylic position by:
    • a primary alcohol (benzyl alcohol, –CH2OH)
    • a dimethoxymethyl group (acetal, –CH(OMe)2), which is an acetal equivalent of an o-formyl group

• 2D structure in words (literature): A benzene ring with two adjacent substituents. At position-1: –CH2OH. At position-2 (ortho): –CH(–OCH3)2. No stereocenters on the ring; the acetal carbon is prochiral under substitution but not configurationally stable. Functional groups include a benzylic primary alcohol and a mixed acetal (diether), both attached directly to an aromatic ring.

• PubChem CID: 343232 (literature reference only)

Synthetic Utility

Functional group handles and their reactivity (literature/practice):

• Acetal (–CH(OMe)2): Acid-labile protecting group for an ortho-formyl substituent. Stable to many bases and nucleophiles at ambient temperature; cleaved by Brønsted or Lewis acids to generate the aromatic aldehyde.
• Benzylic primary alcohol (–CH2OH): Amenable to oxidation (TEMPO, DMP, Swern), conversion to halides/esters/ethers, or activation for C–C bond formation (e.g., Mitsunobu etherification/inversion on derived secondary alcohols in multistep sequences).

Retrosynthetic value:

• Precursors to o-formyl benzyl scaffolds: Strategic use where an aldehyde must be masked during steps incompatible with carbonyl chemistry (e.g., strong bases, nucleophiles), while retaining a free benzylic alcohol for orthogonal elaboration.
• Divergent synthesis: After deprotection to o-formylbenzyl alcohol, one can perform:
  • Intramolecular acetalizations or cyclizations to benzofuran/benzopyran motifs (if an appropriate nucleophile is installed)
  • Condensations (Wittig/KN) selectively at the aldehyde while protecting or transforming the benzylic position

Named/related reactions (applicability):

• Acetal hydrolysis (general acid catalysis); Parikh–Doering/Swern/DMP for benzylic alcohol oxidation; Appel/PBr3 halogenations; Oxime/imine formation from the unveiled aldehyde; Wittig/HWE olefinations on the aldehyde after deprotection.

Practical considerations:

• Control pH rigorously. Scavenging residual acid (e.g., with Et3N, NaHCO3, or basic resin) after workups preserves the acetal in subsequent steps.
• Track the acetal proton (typically ~4.5–5.5 ppm in 1H NMR for –CH(OMe)2; literature) and the benzylic methylene (~4.5–5.0 ppm region depending on solvent) as orthogonal markers of integrity.

Target Specificity

Not applicable. This product is a small-molecule organic reagent and does not possess biological target specificity parameters (e.g., antigen, epitope, clone, isotype).