(2-Propylphenyl)methanol - ≥97% , CAS No.17475-43-3

CAS: 17475-43-3 Cat. No.: P1293474 Fórmula: C₁₀H₁₄O Peso molecular: 150.22 Número CE: 822-129-9

GRADE & PURITY ≥97%

Storage

Room temperature

Specifications

Especificações e pureza

≥97%

Condições de armazenamento de armazenamento

Room temperature

Pureza

≥97%

Nomes e identificadores

Sorrisos canónicos

CCCC1=CC=CC=C1CO

IUPAC Name

(2-propylphenyl)methanol

InChIKey

ZAMZCSIXTWIEDY-UHFFFAOYSA-N

INCHI

1S/C10H14O/c1-2-5-9-6-3-4-7-10(9)8-11/h3-4,6-7,11H,2,5,8H2,1H3

Peso molecular

150.22

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Phenylpropanes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Phenylpropanes
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylpropanes
• Alternative Parents: Benzyl alcohols Primary alcohols Hydrocarbon derivatives Aromatic alcohols
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Phenylpropane - Benzyl alcohol - Organic oxygen compound - Hydrocarbon derivative - Aromatic alcohol - Primary alcohol - Organooxygen compound - Alcohol - Aromatic homomonocyclic compound
• Descrição: This compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
• 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

Propriedades químicas e físicas

• Peso molecular: 150.220 g/mol
• XLogP3: 2.400
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 150.104 Da
• Monoisotopic Mass: 150.104 Da
• Topological Polar Surface Area: 20.200 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 101.000
• 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

Not applicable. No validated bioassay or immunoassay protocols are associated with this small-molecule reagent.

For synthetic use, see the Reaction Conditions, Reaction & Applications, and Synthetic Utility sections for practical guidance on common transformations.

Biological Roles

This compound is a synthetic aromatic alcohol used as a chemical building block. It is not a natural metabolite or cofactor, and no specific biological role is established.

General observations for benzylic alcohols (literature context; not product-specific claims):

• Benzylic alcohol scaffolds appear in a variety of synthetic intermediates for ligands, materials, and probe molecules. The ortho‑propyl group increases hydrophobicity and can influence membrane affinity in model systems, but no defined biochemical pathway utilizes this structure.
• Metabolic considerations (if encountered in ADME research): benzylic alcohols can undergo oxidation to aldehydes/acids via alcohol and aldehyde dehydrogenases in mammalian systems; aromatic ring alkyls can be oxidized at benzylic positions. Such information is general and should not be construed as guidance for any biological use of this product.

Research use only: per product data, this material is supplied strictly for research and laboratory use. It is not intended for diagnostics, therapeutic, or clinical applications.

Buffer Applications

Not typically applicable. (2‑Propylphenyl)methanol is a hydrophobic benzylic alcohol used as a synthetic intermediate, not as a buffering agent or pH control component.

Practical note: If used in biochemical assays (e.g., as a small‑molecule precursor), introduce it in a compatible co‑solvent (DMSO, ethanol) at low percentages to avoid precipitation; verify that the co‑solvent does not perturb your buffer system. Otherwise, see Reaction & Applications and Synthetic Utility for relevant guidance.

Green Alternatives

Because (2‑propylphenyl)methanol is a building block rather than a process solvent, “green alternatives” are best considered for the transformations performed on it and for its synthesis route.

Greener choices in typical transformations (literature guidance):

• Oxidation to aldehyde/acid:
  • Greener alternative: catalytic TEMPO/O2 or TEMPO/NaOCl in aqueous biphasic media vs. chromium(VI) reagents (PCC/PDC). Trade‑offs: avoid toxic Cr waste; manage halogenated solvent use and pH control; biphasic mass transfer may require surfactant/PTC.
• Esterification/coupling:
  • Use CDI or isobutyl chloroformate alternatives to DCC to reduce urea waste; or employ enzyme‑catalyzed esterifications in green solvents (2‑MeTHF, CPME) where appropriate.
• Protection/etherification:
  • Solvent swaps: 2‑MeTHF or CPME can often replace THF/Et2O with improved safety (higher bp, lower peroxide tendency than Et2O) and better sustainability metrics.
• Appel halogenation replacement:
  • Use PPh3/CBr4 alternatives or sulfonate + NaBr in greener solvents; or electrochemical benzylic functionalization to avoid stoichiometric halogenating agents.

Synthesis route considerations:

• Biobased feedstocks: explore catalytic transfer hydrogenation or hydrogenolysis strategies from o‑propylbenzaldehyde or o‑propylbenzoate using renewable H‑donors (iPrOH, formate).
• Energy efficiency: perform reactions at ambient temperature/flow with in‑line workup to reduce solvent and energy footprints.

Always balance EHS gains with selectivity, throughput, and regulatory constraints.

Pharmaceutical Uses

No pharmacopeial or excipient designation is specified for this item. It is supplied for research use only and is not intended for clinical or therapeutic applications.

Contextual (non-clinical) information for process chemists:

• Role as an intermediate: benzylic alcohols are commonly advanced to aldehydes/acids, halides, or ethers en route to more complex targets. The ortho‑propyl substituent can adjust lipophilicity (cLogP) and steric profile, which is sometimes explored in SAR campaigns.
• Formulation relevance: if used as a process intermediate, residual solvent limits and impurity profiles for the intermediate are controlled per internal specifications rather than pharmacopeial monographs. Confirm acceptance criteria for carryover (e.g., residual benzyl alcohols, aldehydes) in final API specifications.

For any work that might intersect with GMP, consult your QA group and obtain lot-specific CoA, impurity profile, and stability information.

Physical Properties

Item-specific physico-chemical specifications (bp, mp, density, refractive index, water/peroxides/metals, UV cutoff): Not specified for this item; refer to CoA/Spec Sheet.

General/literature expectations for similar o-alkylbenzyl alcohols (context, not product specifications):

• Physical state: typically colorless to pale liquid or low-melting solid depending on substitution; benzylic alcohols with additional alkyl on the ring often are low‑viscosity liquids at ambient conditions.
• Volatility: lower than benzyl alcohol due to increased hydrophobic surface and molecular weight; vapor pressure is generally modest, enabling convenient handling in open bench operations with standard ventilation.
• Solubility: miscible with many organic solvents (e.g., ethers, esters, chlorinated solvents, aromatics); limited solubility in water compared with benzyl alcohol due to the ortho‑propyl group (qualitative literature trend).
• Partitioning: logP expected to be higher than benzyl alcohol owing to the extra propyl substituent (literature trend for ring‑alkylated benzyl alcohols).
• Spectroscopic handles: benzylic –CH2OH gives characteristic 1H NMR signals (benzylic CH2 ~4.5–4.8 ppm, OH variable) and IR O–H stretch ~3200–3600 cm−1 (broad) (literature).

Note: For numerical, lot-specific data suitable for method development, QC, or regulatory files, consult the product’s CoA/Spec Sheet and SDS.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• UV/LC suitability: Not specified for this item; refer to CoA/Spec Sheet.

General guidance on grades (context for selection):

• Research grade vs. analytical grade: Analytical/AR grades emphasize low nonvolatile residue and controlled impurity profiles; research grade focuses on suitability for general synthesis. For alcohol building blocks, peroxides are typically not a concern (vs. ethers), but aldehyde/acid impurities from oxidation and residual solvents/water content can affect sensitive reactions.
• Stabilizers: Primary alcohols are usually supplied unstabilized. If stabilizers are present (not indicated here), verify compatibility with intended reactions (e.g., transition‑metal catalysis).
• Quality control considerations for benzylic alcohols:
  • Water content (Karl Fischer) can influence esterifications, Mitsunobu reactions, and isocyanate chemistry.
  • Aldehyde (corresponding o‑propylbenzaldehyde) and ether impurities may arise upon storage/handling; monitor by GC or 1H NMR.
  • Trace acids/bases alter reactivity; confirm acid value where relevant.

Recommendation: For moisture‑ or oxidation‑sensitive applications, request most recent CoA and, if needed, perform pre-use QC (KF, GC, 1H/13C NMR) on your lot.

Reaction and Applications

As a benzylic primary alcohol, (2‑propylphenyl)methanol is a versatile handle for elaboration into aldehydes, acids, ethers, esters, and benzylated derivatives. Typical research and process applications include:

• Oxidation to the corresponding aldehyde or acid:
  • Swern or Dess–Martin oxidation to the aldehyde under mild, chemoselective conditions (literature). TEMPO/NaOCl or PDC can also be applied. The ortho‑propyl group modulates sterics, sometimes improving chemoselectivity against overoxidation.
• Esterification/acylation:
  • Fischer esterification, Steglich (DCC/DMAP), or mixed anhydride routes to access o‑propylbenzyl esters (useful protecting groups or intermediates).
• Activation and substitution:
  • Convert to sulfonates (mesylate/tosylate) enabling SN2/SN1 substitutions to install heteroatoms (Cl, Br via Appel or SOCl2; azides; thiols) to reach o‑propylbenzyl derivatives.
• Ether formation and protection:
  • Williamson ether synthesis (RO–CH2–Ar) after deprotonation; benzyl protection of nucleophiles, later removable by hydrogenolysis or oxidative cleavage (depending on substrate stability).
• Oxidative coupling/functionalization:
  • Formation of o‑propylbenzaldehyde allows access to imines, oximes, and subsequent reductive amination to o‑propylbenzylamines.
• Polymer/ligand design:
  • Hydrophobic, ortho‑substituted benzyl motif can tune solubility and sterics in ligands, monomers, or small‑molecule libraries.

Practical notes:

• Drying: If water sensitive steps (Mitsunobu, acyl chloride formation) are planned, dry over molecular sieves or distill under reduced pressure if feasible (verify thermal stability and avoid prolonged heating).
• Avoid strong oxidants during storage to limit aldehyde formation.

Reaction Conditions

General literature conditions for common operations on benzylic primary alcohols (guidance; optimize for this substrate):

• Oxidation to aldehyde:
  • Swern: oxalyl chloride/DMSO, −78 to −40 °C; quench with Et3N. Typically fast (≤1 h at low temperature) with high chemoselectivity.
  • Dess–Martin periodinane: DCM at 0–25 °C, 0.5–2 h. Mild, tolerates many functionalities.
  • TEMPO/NaOCl: biphasic CH2Cl2 or EtOAc/aqueous buffer (pH ~9–10), 0–25 °C; catalytic TEMPO, co-catalyst KBr often used. Monitor to avoid overoxidation.
• Oxidation to acid: TEMPO/NaClO2 (Pinnick) or stepwise aldehyde then NaClO2; aqueous acetonitrile, 0–25 °C.
• Esterification:
  • Steglich: carboxylic acid (1.2 eq), DCC (1.2 eq), catalytic DMAP, DCM, 0–25 °C, 2–16 h. Remove DCU by filtration.
  • Fischer: acid catalyst (H2SO4, TsOH), ROH solvent, reflux; water removal drives equilibrium.
• Halide formation:
  • Appel (to chloride/bromide): PPh3/CX4 (1.1–1.5 eq), DCM, 0–25 °C, 1–3 h. Alternatively, SOCl2 (1.5–2 eq) with catalytic DMF in DCM, 0–25 °C.
• Tosylate/mesylate formation: TsCl or MsCl (1.1–1.5 eq), base (pyridine or Et3N), DCM, 0–25 °C; 1–4 h.
• Etherification (Williamson): NaH or KOtBu in THF/DMF, 0–25 °C; add alkyl halide electrophile; 1–6 h.

Notes:

• The ortho‑propyl group can marginally reduce rates in sterically demanding substitutions; modest temperature elevation or higher catalyst/base loadings may be beneficial.
• Choose solvents compatible with both substrate solubility and reagent stability; ensure anhydrous conditions for moisture‑sensitive reagents (DCC, SOCl2, Appel systems).

Safety and Handling

GHS information (signal word, hazard statements, pictograms, classification): Not specified for this item; refer to SDS.

General safety guidance for benzylic/aromatic primary alcohols (informational; defer to SDS for this product):

• Hazards: may cause skin/eye irritation; ingestion/inhalation may be harmful. Combustible liquid; keep away from ignition sources. Benzylic alcohols can form irritating vapors/mist upon heating.
• PPE: use appropriate lab PPE—lab coat, safety glasses or goggles, and suitable gloves (e.g., nitrile). Employ local exhaust ventilation or work in a fume hood to minimize vapor/aerosol exposure.
• Handling: avoid breathing vapors; avoid contact with skin/eyes. Do not smoke near the material. Ground/bond during transfer if handling liter quantities.
• Incompatibilities: strong oxidizers (risk of exotherm/oxidation), strong reducing agents (in presence of activators), acid chlorides/anhydrides (acylation), bases with dehydrating agents (can promote ether formation). Avoid reactive metals if water/alcoholysis is undesired.
• First aid (overview):
  • Inhalation: move to fresh air; seek medical advice if symptoms persist.
  • Skin: wash with soap/water; remove contaminated clothing.
  • Eyes: rinse cautiously with water for several minutes; remove contact lenses if present and easy; seek medical attention for persistent irritation.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
• Fire-fighting: use CO2, dry chemical, or alcohol-resistant foam. Combustion may produce CO/CO2. Cool containers with water spray.

Always consult the product’s SDS for authoritative hazard, exposure limit, and emergency guidance.

Solvent Selection

This product is a benzylic alcohol building block, not a solvent. Solvent selection should be driven by the transformation being performed on (2‑propylphenyl)methanol.

General solvent compatibility and selection tips (literature/generic guidance):

• Miscibility: benzylic alcohols are soluble in common organic solvents (Et2O, THF, toluene, DCM, MeCN, EtOAc). Water solubility is limited due to the hydrophobic ortho‑propyl group.
• Polar transformations (e.g., Mitsunobu, acylations, sulfonations): THF, DCM, DMF, or MeCN are frequently used; maintain anhydrous conditions if required.
• Oxidations to aldehyde/acid: DCM, MeCN, acetone, or EtOAc are common; choose solvent to match oxidant solubility (e.g., DCM for Swern/IBX variants; MeCN/DCM for TEMPO/bleach biphasic with phase-transfer).
• Reductions (to alkane or dihydrogenolysis of derived species): alcoholic or ether solvents under catalytic hydrogenation (EtOH, iPrOH, EtOAc) or neat if viscosity allows.
• Substitutions/etherifications: use polar aprotic media (DMF, DMSO) for SN1/SN2 on activated derivatives (e.g., mesylates/tosylates), or toluene for phase separation.

For chromatographic workup, toluene/hexanes/EtOAc systems usually separate o‑alkylbenzyl alcohols well; adjust polarity to minimize streaking from the –OH group (add 0.5–1% Et3N to eluents to suppress tailing).

Storage and Reconstitution

• Storage conditions (product data): Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution: Not applicable; supplied neat as an organic compound. If solidification occurs at low temperature, warm gently to room temperature and homogenize before use.

Good storage practices for benzylic alcohols:

• Keep container tightly closed under inert gas (nitrogen or argon) if long-term storage is anticipated to minimize aerial oxidation to the corresponding aldehyde/acid.
• Store away from heat, sparks, or open flames; protect from strong oxidizers.
• If moisture-sensitive transformations are planned, consider subdividing into aliquots and drying immediately before use (e.g., over 3 Å molecular sieves or by brief high-vacuum at ambient temperature). Avoid prolonged heating to prevent side reactions (ether formation/oxidation).
• Label date opened and monitor by 1H NMR or GC for aldehyde formation over time.

Disposal: Handle waste according to institutional and local regulations for organic alcohols; segregate from oxidizers and halogenated waste streams as appropriate.

Research use only (product data).

Structure and Identity

A benzylic primary alcohol bearing an ortho n‑propyl substituent on the aromatic ring; useful as a hydrophobic benzyl building block.

• Product name: (2-Propylphenyl)methanol (also describable as o‑propylbenzyl alcohol)
• CAS: 17475-43-3 (product data)
• CID: 12841288 (product data)
• InChIKey (as provided): 451791 (product data)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: C10H14O (literature, derived from name)
• Molecular weight: ~150.22 g/mol (literature/computed from formula)

Structural features (description):

• Core ring: benzene ring disubstituted at adjacent (ortho) positions.
• Substituents: one benzylic –CH2OH (primary alcohol) and one normal‑alkyl n‑propyl (–CH2–CH2–CH3) on the adjacent ring carbon.
• Functional groups: benzylic primary alcohol (oxidation/sulfonation/esterification competent), hydrophobic propyl chain (modulates lipophilicity and sterics).
• Stereochemistry: none (achiral as drawn; no stereogenic centers).
• 2D arrangement (verbal): starting from the benzyl carbon bearing –CH2OH as position 1, a propyl chain is attached to position 2 of the ring (ortho). The alcohol carbon is benzylic (one carbon away from the aromatic ring).

Synthetic Utility

Functional group profile and reactivity:

• Primary benzylic alcohol: readily undergoes oxidation (to aldehyde/acid), activation (as halide/sulfonate), esterification/carbonate formation, and etherification. The benzylic position enables SN1/SN2 pathways when suitably activated.
• Ortho‑propyl aryl substituent: increases steric bulk/hydrophobicity and can bias regioselectivity in electrophilic aromatic substitutions on derivatives (if further ring functionalization is attempted).

Transformations of high utility (literature):

• Oxidation to o‑propylbenzaldehyde (Swern, DMP, TEMPO systems) followed by Wittig/Grignard or reductive amination to access libraries of o‑propylbenzylamines and secondary alcohols.
• Conversion to halides: Appel (PPh3/CX4) or SOCl2/PBr3 after pre‑activation; provides o‑propylbenzyl halides useful for N-/O-/S‑alkylation.
• Protection chemistry: as benzylating agent (via halide) or as benzyl ether precursor; removable under hydrogenolysis (Pd/C, H2) or oxidative cleavage (DDQ) depending on substrate.
• Ester formation: Steglich or acid chloride methods furnish tuneable leaving groups or pro-moieties.
• C–C bond formation: oxidation to aldehyde followed by Grignard addition yields secondary alcohols with defined benzylic stereocenters.

Practical considerations:

• Ortho substitution may slightly slow some benzylic substitutions due to sterics; ensure sufficient activation and consider phase-transfer catalysis.
• Monitor for aldehyde formation during storage/processing; use antioxidants or inert atmosphere if prolonged heating is required.

Target Specificity

Not applicable. This product is a small-molecule building block, not a biological macromolecule or affinity reagent. No antigen/epitope/clone/isotype or species reactivity information applies.