Dimethyl phenylpropanol - ≥95% , CAS No.13351-61-6

CAS: 13351-61-6 Cat. No.: D1067098 Formula: C₁₁H₁₆O Peso molecolare: 164.240 Numero EC: 236-400-9

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

Sorrisi canonici

CC(C)(CC1=CC=CC=C1)CO

IUPAC Name

2,2-dimethyl-3-phenylpropan-1-ol

InChIKey

VNGAHMPMLRTSLF-UHFFFAOYSA-N

INCHI

1S/C11H16O/c1-11(2,9-12)8-10-6-4-3-5-7-10/h3-7,12H,8-9H2,1-2H3

Peso molecolare

164.240

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: Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Phenylpropane - Organic oxygen compound - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Alcohol - Aromatic homomonocyclic compound
• Descrizione: 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

Proprietà chimiche e fisiche

• Peso molecolare: 164.240 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 164.12 Da
• Monoisotopic Mass: 164.12 Da
• Topological Polar Surface Area: 20.200 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 123.000
• 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 tested bioassay formats (e.g., WB, IHC, IF, FC) or analytical application protocols are provided in the Product Data for this small organic compound.

General lab use notes (literature/general):

• For use as a reaction substrate, standard organic synthesis workflows apply (weighing under ambient conditions, dissolution in suitable solvent, inert atmosphere if required by the transformation).
• For enzymatic screens, prepare stock solutions in DMSO or EtOH, filter if needed (PTFE syringe filter, 0.45 μm), and dilute into assay buffer keeping organic content low.

Biological Roles

This product is a small synthetic organic alcohol intended for research and chemical synthesis. No biological function, pathway involvement, or endogenous role is provided in the Product Data.

General notes (literature/general):

• Aryl aliphatic alcohols of this class are not typical biological buffers or cofactors. They may be used as model substrates for studying oxidation, dehydrogenation, or biocatalytic esterification in enzyme screening platforms.
• Hydrophobicity and aromaticity can make such compounds useful as probe substrates to assess enzyme active-site tolerance for bulky/benzylic alcohols (e.g., alcohol dehydrogenases, lipases for kinetic resolution).

Important: No claims are made regarding bioactivity, pharmacology, or clinical use. For research use only.

Buffer Applications

Not typically applicable. Dimethyl phenylpropanol is a hydrophobic organic alcohol and is not used as a buffering agent or pH control component.

Practical note: If employed in biochemical assays, it is usually as a substrate or additive dissolved in an organic co-solvent (e.g., DMSO, EtOH) and then diluted into buffer. Keep organic co-solvent content low (commonly ≤1–2% v/v) to avoid perturbing protein activity; optimize empirically for the specific assay.

Green Alternatives

Where this alcohol is used as a substrate or intermediate, greener choices pertain mainly to solvent and reagent selection rather than the substrate itself.

Greener solvent options (literature/general):

• Replace DCM with ethyl acetate or 2‑MeTHF when feasible.
• Replace THF with 2‑MeTHF or CPME to reduce peroxide concerns and improve process safety.
• Favor alcoholic solvents (EtOH/iPrOH) for some esterifications and oxidations when compatible.

Comparison (general guidance)

• DCM vs. EtOAc: EtOAc is biodegradable and has a better EHS profile; DCM offers higher solvency power for very hydrophobic substrates.
• THF vs. 2‑MeTHF: 2‑MeTHF often allows simpler aqueous workups and can be sourced from biomass; THF has broader historical data and lower viscosity.
• Traditional oxidants (PCC/CrVI) vs. TEMPO/O2 or bleach: catalytic protocols reduce hazardous waste but may require careful phase management and buffering.

Process intensification ideas:

• Use Dean–Stark in toluene/xylenes or azeotropic EtOAc for water removal instead of strong dehydrating agents.
• Explore biocatalytic acylation/oxidation if stereoselectivity or milder conditions are desired.

Always confirm that greener swaps maintain required yield, selectivity, and impurity profiles for your specific isomer.

Pharmaceutical Uses

No pharmacopeial status, excipient role, or formulation use is specified for this item in the Product Data.

General context (literature/general):

• Aryl aliphatic alcohols can serve as intermediates in the synthesis of APIs or fine chemicals (e.g., converted to esters, halides, or carbonyls). They are not typically used directly as excipients due to hydrophobicity and lack of established safety dossiers.

Compliance note: This product is supplied for research use only and is not intended for human or veterinary use, API manufacture, or clinical applications. For regulated development, obtain full specifications, impurity profiles, and regulatory documentation from appropriate sources.

Physical Properties

Item-specific specifications are not provided in the Product Data and must be confirmed on the CoA/Spec Sheet.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not specified for this item; refer to CoA/Spec Sheet. (Varies by isomer; do not assume.)
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.
• LogP, pKa: Not specified for this item; refer to CoA/Spec Sheet.

General literature guidance for aryl aliphatic alcohols of this type (non‑specific):

• Typically low water solubility and good solubility in aprotic organics (e.g., DCM, THF, EtOAc) and alcoholic solvents.
• Physical state is often liquid or low‑melting solid depending on isomer and purity.
• The benzylic/branched nature (if present) tends to increase hydrophobicity and boiling point relative to unbranched analogs.

Note: Because the precise isomer and specifications are not listed in the Product Data, do not rely on generalized values for critical process design. Verify against the specific batch CoA.

Quality and Grades

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

How to interpret grade (general guidance):

• If supplied as analytical reagent (AR) or >95–98% organic intermediate, expect suitability for synthetic use with routine trace impurity levels; confirm by GC/HPLC assay on CoA.
• If designated HPLC/GC grade, that indicates tight control of UV absorbance/background and particulates for chromatography; confirm UV cutoffs and residue specs on CoA.
• If a stabilizer is present (not indicated here), it will be listed on the label/CoA. Stabilizers can affect downstream reactions (e.g., acid-catalyzed transformations); remove by washing or distillation if necessary.

Batch-specific quality controls to expect (typical for this class; verify on CoA):

• Identity by 1H/13C NMR and/or GC–MS.
• Purity/assay by GC or HPLC.
• Water by Karl Fischer if relevant; residual solvents by GC.

Note: Do not assume trace-metal limits, peroxide content, or exact UV characteristics without the CoA. For regulated applications, request full specification and methods.

Reaction and Applications

Manufacturer Applications: Not provided in Product Data.

General synthetic applications for aryl aliphatic alcohols of this type (literature/general):

• Esterification to benzylic/alkyl esters via acid chloride/anhydride or Fischer protocols; catalytic DMAP or pyridine base often beneficial.
• Oxidation to the corresponding carbonyl (ketone or aldehyde, depending on substitution) using Dess–Martin periodinane, PCC, TEMPO/bleach, or Swern. Benzylic positions typically oxidize cleanly.
• Activation as leaving group: conversion to tosylates/mesylates enables SN2/SN1 substitutions (reaction pathway depends on whether the center is primary/secondary/tertiary; isomer not specified here).
• Protection of the alcohol as silyl ethers (TBDMS, TIPS) or benzyl/allyl ethers for multistep sequences.
• Dehydration (acid-catalyzed) to alkenes; benzylic/tertiary alcohols dehydrate readily under mild conditions.
• Mitsunobu reaction (for secondary alcohols) to invert configuration and install various nucleophiles; applicability depends on isomer/stereochemistry.

Practical tips:

• Dry glassware/solvents for moisture-sensitive transformations (acylations, silylations, Swern, etc.).
• Monitor by TLC/GC; benzylic substrates often show strong UV response.
• Workup: neutralize acids/bases thoroughly; avoid prolonged exposure to strong acids if dehydration is undesired.

Note: Selectivity and mechanism (SN1 vs. SN2; E1 vs. E2) depend on the specific isomer and substitution pattern, which are not specified for this item.

Reaction Conditions

Typical conditions for common transformations of aryl aliphatic alcohols (literature/general; adjust to your substrate/isomer):

• Esterification: Acyl chloride (1.1–1.5 eq), Et3N or pyridine, DCM, 0–25°C, 1–4 h; or DCC/DMAP, CH2Cl2, 0–25°C. Fischer esterification: ROH/acid catalyst (p‑TsOH), toluene, Dean–Stark, reflux.
• Oxidation: Dess–Martin periodinane (1.3 eq), CH2Cl2, 0–25°C, 0.5–2 h; or TEMPO (2–5 mol%), NaOCl (1.5 eq active), pH ~9, 0–10°C for primary alcohols. Avoid overoxidation as needed.
• Activation to sulfonate: TsCl (1.1–1.5 eq), pyridine or Et3N, catalytic DMAP, 0–25°C, 1–6 h. Appel halogenation: PPh3/CX4 (CCl4/CBr4), CH2Cl2, 0–25°C.
• Dehydration: H2SO4 or p‑TsOH (cat.), toluene or neat, 60–110°C; monitor for rearrangements with tertiary/benzylic substrates.
• Mitsunobu (secondary alcohols): DEAD or DIAD (1.1–1.5 eq), PPh3 (1.1–1.5 eq), THF or toluene, 0–25°C, with nucleophile (e.g., carboxylic acid, phenol).

Notes:

• Reaction pathway (SN1 vs. SN2; E1/E2) and stereochemical outcomes depend on whether the center is primary, secondary, or tertiary—information not specified in this product’s data.
• Conduct small‑scale trials to establish solvent, base/acid loading, and temperature windows compatible with your exact isomer and impurity tolerances.

Safety and Handling

Authoritative safety information must be taken from the product SDS.

Item-specific hazard data (from Product 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 handling guidance for aryl aliphatic alcohols (literature/general):

• Use in a chemical fume hood. Avoid inhalation of vapors/aerosols and contact with skin/eyes.
• Recommended PPE: lab coat, safety glasses/goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Consider face shield for scale-up or transfer operations.
• Avoid strong oxidizers and strong acids/bases that may induce undesired reactions (e.g., dehydration under acid, oxidation to carbonyls).
• Spill response: contain with inert absorbent, transfer to waste in accordance with institutional and local regulations. Ventilate area.
• First aid (overview; consult SDS):
  • Inhalation: move to fresh air; seek medical attention if symptoms occur.
  • Skin: wash with soap and water; remove contaminated clothing.
  • Eyes: rinse cautiously with water for several minutes; remove contacts if present and easy to do; seek medical attention if irritation persists.
  • Ingestion: rinse mouth; do not induce vomiting unless directed by medical personnel.
• Fire safety: Many benzylic alcohols are combustible; keep away from ignition sources. Use CO2, dry chemical, or foam for small fires (per SDS guidance).

For definitive hazard classification and exposure limits, consult the SDS for this exact SKU/batch.

Solvent Selection

This item is a small, hydrophobic aryl aliphatic alcohol. No item-specific solubility data are provided; verify with a small-scale test.

General solvent behavior (literature/general):

• Likely miscible or highly soluble in common organic solvents: dichloromethane, ethyl acetate, THF, diethyl ether, toluene, and lower alcohols (MeOH/EtOH/IPA). Limited solubility in water is typical for phenylalkyl alcohols.
• Polarity class: low-to-moderate polarity protic substrate; hydrogen-bond donor/acceptor.

Selection tips by application:

• For nucleophilic substitutions/esterifications: use aprotic solvents (DCM, MeCN, THF) or toluene for azeotropic water removal.
• For oxidations (e.g., Dess–Martin, TEMPO): DCM, EtOAc, MeCN commonly used.
• For protection (silylation/acylation): DCM or pyridine/DMAP co-solvent.
• For metal-catalyzed dehydrations/isomerizations: toluene or xylene at reflux.

Comparison (general):

• DCM vs. EtOAc: DCM dissolves more hydrophobic substrates and is easily removed; EtOAc is a greener alternative with higher polarity.
• THF vs. 2-MeTHF: Similar performance; 2‑MeTHF offers greener credentials and better partitioning in workups.

Always confirm solubility and stability experimentally for your exact isomer and batch.

Storage and Reconstitution

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

General storage guidance (literature/general):

• Store in a tightly closed container in a cool, dry, well-ventilated place away from strong oxidizers and strong acids/bases.
• Protect from prolonged light and heat exposure. If volatility or oxidation is a concern for your application, consider storage under inert gas and use of desiccant.
• If a stabilizer is present, it will be indicated on the label/CoA; do not remove unless your process requires it.

Reconstitution/use:

• If solid or viscous at room temperature, gently warm to facilitate transfer. Prepare solutions in a compatible solvent (e.g., DCM, EtOAc, THF, alcohols) based on your application; verify solubility first on a small scale.
• For analytical or biochemical assays, prepare fresh stock solutions, label with concentration and date, and avoid repeated freeze–thaw or prolonged bench exposure. Filter through PTFE if particulates are present.

Always follow the SDS for handling and storage precautions specific to this SKU.

Structure and Identity

• Product name: Dimethyl phenylpropanol (common descriptor; exact isomer not specified)
• CAS: 13351-61-6
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data shows an incomplete placeholder.)
• 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, based on the name; literature/generic):

• Contains a phenyl (C6H5–) ring bonded to a propanol backbone (–CH2–CH(OH)–CH3 or isomeric) that bears two methyl substituents (dimethyl-). Exact substitution pattern (e.g., 2,2-dimethyl-3-phenylpropan-1-ol vs. 1,1-dimethyl-2-phenylpropan-1-ol, etc.) is not specified in the item data.
• Functional groups: aromatic ring, aliphatic alcohol (–OH); may be primary, secondary, or tertiary depending on isomer (not specified for this item).
• 2D description in words: a benzene ring attached to a short, branched three‑carbon chain that terminates (or bears) a hydroxyl group; two methyl groups create a branched (dimethyl) center on the propyl fragment. Stereochemical information is not provided in the product data.

Synthetic Utility

From a retrosynthetic standpoint, Dimethyl phenylpropanol represents a benzylic/branched aliphatic alcohol synthon. While the precise isomer is unspecified, the following general utilities apply (literature/general):

• As an electrophile (after activation): Convert the alcohol to tosylate/mesylate or halide (Appel, PBr3) to access benzylic substitution products. Benzylic positions favor substitution; tertiary centers may undergo SN1.
• As a nucleophile equivalent: Oxidize to the corresponding carbonyl, then perform nucleophilic additions (e.g., Grignard, organolithium) to elaborate side chains; re-reduce if needed.
• Elimination chemistry: Acid-catalyzed dehydration to form styrenyl/isopropenyl aromatics (depending on connectivity), a gateway to further hydroboration–oxidation, epoxidation, or cross-metathesis.
• Protection/derivatization: Install silyl or carbonate protecting groups for orthogonal manipulation in multistep routes.
• Cross-coupling adjacency: If converted to a benzylic halide, it can participate in C(sp3)–C(sp2) couplings (e.g., Ni-catalyzed Kumada/Negishi variants), enabling late-stage diversification.

These strategies make such alcohols valuable branch points in routes targeting substituted aromatics, fragrances, and advanced intermediates. Selectivity depends on the isomer (primary/secondary/tertiary) and should be confirmed experimentally.

Target Specificity

Not applicable. This product is a small-molecule alcohol and not a biological targeting reagent (e.g., antibody, ligand with defined receptor selectivity) in this catalog entry. No target, epitope, or species specificity is provided or implied.