3-(2-Hydroxypropan-2-yl)phenol - ≥96% , CAS No.7765-97-1

CAS: 7765-97-1 Cat. No.: H195026 분자식: C₉H₁₂O₂ 분자량: 152.19 EC 번호: 192-282-8

GRADE & PURITY ≥96%

Synonyms

3-(1-hydroxy-1-methyl-ethyl)phenol | m-Hydroxy-.gamma.,.gamma.-dimethylbenzyl alcohol | 3-hydroxyphenyldimethylcarbinol | Benzenemethanol,3-hydroxy-a,a-dimethyl- | AKOS006285365 | SB84081 | MFCD07437957 | SY111553 | DS-2800 | 3-(2-HYDROXY-2-PROPYL)PHENOL

Storage

Room temperature

Shipped In

Normal

Specifications

동의어

3-(1-hydroxy-1-methyl-ethyl)phenol | m-Hydroxy-.gamma.,.gamma.-dimethylbenzyl alcohol | 3-hydroxyphenyldimethylcarbinol | Benzenemethanol,3-hydroxy-a,a-dimethyl- | AKOS006285365 | SB84081 | MFCD07437957 | SY111553 | DS-2800 | 3-(2-HYDROXY-2-PROPYL)PHENOL

사양 및 순도

≥96%

보관 조건

Room temperature

배송

Normal

순수함

≥96%

이름과 식별자

Pubchem Sid

488189879

정식 스마일

CC(C)(C1=CC(=CC=C1)O)O

IUPAC Name

3-(2-hydroxypropan-2-yl)phenol

InChIKey

KNCICOZTHWGRMY-UHFFFAOYSA-N

INCHI

1S/C9H12O2/c1-9(2,11)7-4-3-5-8(10)6-7/h3-6,10-11H,1-2H3

이성체 SMILES

CC(C)(C1=CC(=CC=C1)O)O

분자량

152.19

Reaxy-Rn

2244911

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2244911&ln=

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Benzenoids
• 분류: Benzene and substituted derivatives
• Subclass: Phenylpropanes
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylpropanes
• Alternative Parents: 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Tertiary alcohols Hydrocarbon derivatives Aromatic alcohols
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Phenylpropane - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Tertiary alcohol - Organic oxygen compound - Hydrocarbon derivative - Aromatic alcohol - Organooxygen compound - Alcohol - Aromatic homomonocyclic compound
• 설명: 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

화학 및 물리적 특성

• 분자량: 152.190 g/mol
• XLogP3: 1.800
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 152.084 Da
• Monoisotopic Mass: 152.084 Da
• Topological Polar Surface Area: 40.500 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 132.000
• 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 validated bioassay or immunoassay protocols are provided for this small-molecule building block.

• General laboratory handling

  • Prepare concentrated stock solutions in DMSO, ethanol, or acetone; filter if needed (PTFE, 0.2 µm) for analytical use.
  • For reactions, dry solvents and maintain anhydrous conditions when required (e.g., base-promoted O-alkylations, triflation).

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

Biological Roles

No specific biological role is assigned to this compound in the Product Data. The information below provides general chemical-biology context for phenolic benzylic alcohols; it is not a statement of biological activity for this item.

• General context (literature)

  • Phenolic groups are abundant in natural products (e.g., lignin-derived phenols, flavonoids) and can participate in hydrogen bonding and redox chemistry. They often display antioxidant behavior in radical-scavenging assays due to phenoxyl radical stabilization, though activity is highly structure-dependent.
  • Benzylic tertiary alcohols are common in synthetic intermediates and can influence membrane affinity and metabolic stability in medicinal chemistry campaigns (as fragments or scaffolds), but specific ADME/tox profiles are molecule- and context-dependent.

• Laboratory use

  • As a research building block, 3-(2-hydroxypropan-2-yl)phenol may be incorporated into libraries to probe effects of phenolic acidity and benzylic sterics on binding in biochemical screening. Any such use requires appropriate controls and does not imply intrinsic bioactivity.

• Cautions

  • Avoid extrapolating from general phenol behavior to this specific compound without data. For any biological assay, prepare fresh solutions, control pH (phenol deprotonation above pH ~9–10), and check compound stability under assay conditions.

Item-specific biological data are not provided; consult primary literature if biological evaluation is intended.

Buffer Applications

This compound is not a buffering reagent. It lacks a conjugate acid–base pair in the physiological pH window with suitable capacity for buffer preparation.

• Practical note
  • If dissolved in buffered solutions for assays, account for phenolic deprotonation above pH ~9–10 (literature). Use co-solvents (e.g., DMSO, ethanol) for stock solutions and dilute into buffer to avoid precipitation.

No item-specific buffer recipes or uses are applicable.

Green Alternatives

This product is a solid organic building block rather than a process solvent. Green chemistry considerations therefore focus on choice of reagents and media used with it.

• Greener media (general guidance)

  • Replace chlorinated solvents (DCM, CHCl3) with ethyl acetate, 2-MeTHF, CPME, or Me-THF when compatible.
  • Favor ethanol/water or acetone where solubility and reactivity allow.

• Greener coupling/activation choices

  • Phenolic esterifications: prefer carbodiimide-free protocols (e.g., CDI in greener solvents) or enzymatic acylations in solvent-free or 2-MeTHF systems (literature) to avoid urea waste.
  • Etherifications: phase-transfer catalysis (aqueous K2CO3, toluene/2-MeTHF) can reduce polar aprotic solvent usage.

• Energy and protection economy

  • Conduct O-functionalizations at ambient temperature using catalytic DMAP or PTC to reduce heating.
  • Avoid unnecessary protecting groups; when needed, select removable groups under mild, waste-minimizing conditions (e.g., hydrogenolysis of benzyl ethers using flow hydrogenation).

• Illustrative comparison (general)

  • Conventional: O-alkylation in DMF with NaH → wasteful, safety concerns.
  • Greener: O-alkylation in acetone or 2-MeTHF with K2CO3 or aqueous biphasic PTC → safer base, easier workup, reduced EHS footprint.

Note: These are general recommendations; optimize to your reaction’s kinetics and selectivity. Item-specific environmental data are not specified for this product.

Pharmaceutical Uses

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

• General context (not item-specific)

  • Phenolic small molecules can serve as synthetic intermediates toward APIs or performance additives (antioxidants, UV absorbers) but are not typically used directly as excipients without significant safety and regulatory evaluation.
  • The tertiary benzylic alcohol motif can be leveraged to access isopropenyl phenols, aryl carbonates/carbamates, or to introduce steric bulk in medicinal chemistry scaffolds.

• Compliance note

  • No claims are made regarding therapeutic use, safety, or efficacy. For any GMP-related application, obtain full specifications, impurities profile, and validation data — none are specified for this catalog item.

Physical Properties

Item-specific physicochemical specifications are not provided in the Product Data; consult the CoA/Spec Sheet for definitive values.

• Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Melting/boiling points (literature, for reference only): Phenolic benzylic tertiary alcohols of this size are typically low-melting solids or high-boiling viscous liquids; reported values vary by isomer and purity. Check primary literature or PubChem CID 458142 for specific ranges.
• Density/refractive index (literature): Not widely standardized for this exact isomer; refer to primary sources. Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (general chemistry)
  • Water: expected low-to-moderate solubility due to two hydroxyls countered by an aromatic ring and tert-alkyl group.
  • Organic solvents: readily soluble in polar organics (ethanol, methanol, acetone, acetonitrile, DMSO) and miscible with many ethers and chlorinated solvents.
• Acid–base properties (literature/general)
  • Phenolic OH pKa typically ~9–10 (aqueous); deprotonates in basic media to phenoxide, increasing nucleophilicity and water solubility.
  • Tertiary benzylic alcohol is essentially neutral under physiological pH; not appreciably deprotonated (alcohol pKa ≳16–18 in water/MeOH).
• Partitioning (general): Expect moderate hydrophobicity with enhanced polarity versus nonphenolic cumyl alcohol; exact logP not consolidated. Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

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

• General notes on grades (context for selection)

  • Research grade: Suitable for most synthetic and analytical workflows; typical assay reported on CoA.
  • ≥98–99% purified organics (common for building blocks): Lower levels of aromatic/benzylic impurities facilitate reproducible reactivity in O-alkylation/acylation and minimize colored byproducts on storage.
  • Water/peroxide/metal content: Not specified for this item; refer to CoA/Spec Sheet. For phenolic substrates, low metal content is typically non-critical unless used in metal-catalyzed cross-couplings after further derivatization.

• Stabilizers

  • No stabilizer information provided for this item. Phenolic compounds generally do not require polymerization inhibitors; however, minimize prolonged exposure to air and light to reduce gradual discoloration/oxidation.

• What to check on receipt

  • Verify appearance versus CoA, assay (GC/HCNMR/HPLC), and identity (1H/13C NMR consistent with phenolic OH and tert-benzylic OH; characteristic benzylic tertiary carbon ~70–75 ppm in 13C NMR, literature).
  • Water by Karl Fischer may be relevant if using in moisture-sensitive couplings (e.g., acid chloride acylations).

Reaction and Applications

As a dual-functional building block (phenol + tertiary benzylic alcohol), 3-(2-hydroxypropan-2-yl)phenol participates in diverse transformations.

• Phenolic functionalization (literature/general)

  • Ether formation (Williamson): phenoxide generated with K2CO3/Cs2CO3 or NaH; alkylation with primary alkyl halides/sulfonates. Useful for installing protecting groups (Bn, PMB) or synthetic handles (allyl, propargyl).
  • Ester formation: acyl chlorides/anhydrides with base or Steglich esterification (DCC/EDC + DMAP). Enables carbonate and carbamate derivatives for protecting-group strategy or activation.
  • Aryl C–O cross-coupling after conversion to aryl pseudohalides (e.g., triflate) allows Suzuki/Negishi couplings to diversify the ring (two-step sequence).

• Benzylic tertiary alcohol chemistry

  • Dehydration under acid to isopropenyl phenol (m-isopropenylphenol), offering an alkene handle for hydroboration–oxidation, epoxidation, or Heck-type functionalization.
  • Electrophilic substitutions on the ring are influenced by the strongly activating phenolic OH (ortho/para directing) and the benzylic tertiary alcohol (also activating). Regioselectivity considerations are key.
  • Oxidative transformations: tertiary benzylic alcohols resist simple dehydrogenation to ketones; however, oxidative cleavage to acetone + phenolic species can occur under harsh conditions (literature precedent with cumyl systems).

• Protective strategies

  • Protect phenol as silyl ethers (TBS/TBDPS; imidazole/DMF) or benzyl ethers (BnBr/K2CO3/acetone) when manipulating the benzylic OH.
  • Convert the benzylic OH to an ether or carbonate to modulate stability under acidic conditions.

• Applications

  • Intermediate for tailored phenolic antioxidants, resins, UV-absorbing motifs, and as a model substrate for studying acid-catalyzed dehydration of benzylic tertiary alcohols (literature).

Reaction Conditions

Guidance below summarizes typical literature conditions for functional group interconversions involving phenolic substrates and benzylic tertiary alcohols. Adapt to your substrate and scale.

• Williamson ether synthesis (phenol → ether)

  • Base: K2CO3 (2–3 equiv) or Cs2CO3; solvent: acetone, acetonitrile, DMF; 40–80 °C; 2–24 h. Primary alkyl halides/tosylates preferred for SN2.
  • Alternative: NaH (60% in mineral oil, 1.1–1.5 equiv) in THF at 0–25 °C, then add electrophile; shorter times, more exotherm control required.

• Steglich esterification (phenol → ester)

  • DCC or EDC·HCl (1.1–1.5 equiv), catalytic DMAP (5–10 mol%), DCM or DMF, 0–25 °C, 2–18 h. Filter dicyclohexylurea (if DCC).

• Acid-catalyzed dehydration (tertiary alcohol → isopropenyl phenol)

  • Catalyst: p-TsOH (5–10 mol%) or H2SO4 (cat.); solvent: toluene or DCM; 0–80 °C; 0.5–6 h. Remove water (Dean–Stark) if using higher-boiling media to drive equilibrium.

• Protection of phenol (silylation)

  • TBSCl (1.2–1.5 equiv), imidazole (3 equiv), DMF or DCM, 0–25 °C, 1–4 h. Deprotect with TBAF or mild acid.

• Triflation (for cross-coupling via aryl triflate)

  • Tf2O (1.1–1.3 equiv), pyridine or 2,6-lutidine, DCM at −78 to 0 °C; then Pd-catalyzed coupling in dioxane/THF with base (K3PO4, Cs2CO3) at 50–90 °C.

• Notes

  • Control acid/base: strong acids risk dehydration; strong bases deprotonate phenol and may induce SN1 at benzylic center under certain conditions.
  • Monitor by TLC/GC/LC–MS; benzylic tertiary centers can form carbocations — avoid prolonged heating in strongly acidic media unless dehydration is desired.

Safety and Handling

• Regulatory/SDS

  • GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to the product SDS for authoritative information.
  • Research use only; not for human or animal diagnostic or therapeutic use.

• General hazards of phenolic/benzylic alcohols (general chemistry guidance)

  • May cause skin and eye irritation; phenols can be harmful if swallowed or absorbed through skin. Avoid inhalation of dust/vapors and contact with skin/eyes.
  • Combustible organic compound. Keep away from ignition sources.

• PPE and engineering controls

  • Use in a fume hood. Wear lab coat, safety glasses/goggles, and nitrile gloves. For large-scale handling, consider splash protection.

• Incompatibilities (general)

  • Strong oxidizers (risk of exothermic reaction/oxidation).
  • Strong bases will form the phenoxide; handle pressure/heat evolution when neutralizing.
  • Strong dehydrating acids can dehydrate the tertiary alcohol to an isopropenyl phenol (olefin formation) — avoid unintended acid exposure.

• First-aid (overview; defer to SDS)

  • Skin/eye contact: Rinse with water for ≥15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; seek medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

• Storage guidance

  • Store tightly closed at room temperature (per Product Data). Protect from light and moisture as good practice. Segregate from oxidizers and strong acids/bases.

Solvent Selection

This product is a multifunctional aromatic building block rather than a chromatography solvent. Solvent choice pertains to its dissolution and reaction medium.

• Polarity & dissolution (general)

  • Readily dissolves in polar organics: ethanol, methanol, acetone, acetonitrile, ethyl acetate, dioxane, THF, DMSO, DMF, and chlorinated solvents.
  • Limited water solubility is expected; aqueous workups benefit from pH control (phenoxide formation in base enhances aqueous solubility; reprotonation in acid facilitates extraction to organics).

• Typical medium by transformation (literature/general)

  • O-alkylation (Williamson): polar aprotic (DMF, DMSO, acetone, acetonitrile) with K2CO3/Cs2CO3/NaH.
  • O-acylation: anhydrous DCM, toluene, or THF with acyl chloride/anhydride and a base (pyridine, triethylamine) or carbodiimide/DMAP protocols in DCM/DMF.
  • Mitsunobu etherification/esterification: THF/THF–toluene with DIAD/DEAD and PPh3.
  • Acid-catalyzed dehydration to isopropenyl phenol: non-nucleophilic solvents (toluene, DCM) under strong Brønsted/Lewis acids.

• Selection tips

  • Choose polar aprotic solvents when maximizing phenoxide nucleophilicity.
  • For scale-up, prefer greener media (EtOAc, 2-MeTHF, CPME, Me-THF/H2O biphasic) where compatible.
  • For analytical dissolution, DMSO stocks (e.g., 10–100 mM) are commonly stable; dilute into assay buffer/organic as needed.

Storage and Reconstitution

• Storage (item-specific): Store at room temperature (per Product Data). Keep container tightly closed. Store in a dry place.

• Shipping: Shipped under normal conditions (per Product Data).

• General best practices for phenolic/benzylic alcohols

  • Protect from excessive heat, light, and moisture to minimize slow oxidation/discoloration. Consider using amber glass and desiccant for long-term storage.
  • After opening, purge headspace with inert gas if prolonged storage is expected.

• Reconstitution/solution preparation

  • Solvents: Readily soluble in DMSO, ethanol, methanol, acetone, acetonitrile, THF, and most chlorinated solvents (general chemistry). Begin with 10–100 mg/mL stocks depending on application.
  • Aqueous use: Prepare organic co-solvent stocks (e.g., DMSO 100 mM) and dilute into buffer with vigorous mixing; final organic content typically kept ≤1–2% v/v in biochemical assays (general guidance).

• Stability in solution

  • Item-specific stability data are not provided. For best results, prepare fresh working solutions and store concentrated stocks at 2–8 °C or −20 °C if extended storage is required; avoid repeated freeze–thaw by aliquoting.

Item-specific specifications (water content, impurities, exact solubility, etc.): Not specified for this item; refer to CoA/Spec Sheet.

Structure and Identity

3-(2-Hydroxypropan-2-yl)phenol is a phenolic aromatic bearing a tertiary benzylic alcohol substituent meta to the phenolic OH.

• Item identifiers (from Product Data)

  • SKU: H195026
  • CAS: 7765-97-1
  • PubChem CID: 458142
  • InChIKey: 184458 (as provided; format appears truncated — full InChIKey not specified for this item)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Structure description (general chemistry)

  • Core ring: monosubstituted phenyl bearing two substituents in a meta relationship.
  • Functional groups: one phenolic hydroxyl (Ar–OH) and one tertiary benzylic alcohol [Ar–C(OH)(CH3)2]. The benzylic center is tertiary (quaternary carbon attached to two methyls, one aryl, and one hydroxyl).
  • Stereochemistry: none (tertiary carbinol center is not stereogenic due to two identical methyl groups).

• Molecular formula and formula mass

  • Literature/computed: C9H12O2; formula mass ~152.19 g/mol (literature). These values are provided for reference only and are not item-specific specifications.
  • Item-specific MF/MW: Not specified for this item; refer to CoA/Spec Sheet.

• Synonym examples (literature)

  • 3-Hydroxycumyl alcohol; 3-(1-hydroxy-1-methylethyl)phenol; m-hydroxy-α,α-dimethylbenzyl alcohol.

• 2D structure in words

  • A benzene ring with an OH at position 1 and a 2-hydroxypropan-2-yl group at position 3; the side chain is –C(OH)(CH3)2 directly bonded to the ring (benzylic tertiary alcohol).

Synthetic Utility

Key reactivity arises from the combination of an activated aromatic ring and a tertiary benzylic alcohol.

• Phenol handle

  • O-alkylation/arylation: generate phenoxide (K2CO3/DMF; Cs2CO3/MeCN; NaH/THF) to install alkyl groups (SN2) or, after conversion to aryl triflate, engage in Pd-catalyzed cross-couplings (Suzuki–Miyaura, Negishi) to elaborate the ring.
  • O-acylation/carbonate formation: acyl chlorides or CDI/DCC protocols give esters/carbonates; carbamates via chloroformates or isocyanates.
  • Mitsunobu: invertible etherification with pronucleophiles (ROH, RCO2H) under DIAD/DEAD–PPh3.

• Tertiary benzylic alcohol handle

  • Dehydration → isopropenyl phenol under acid catalysis (H2SO4, TsOH, or Lewis acids such as BF3·OEt2), providing a versatile alkene for subsequent hydrofunctionalizations.
  • Conversion to benzylic ethers or carbonates to tune leaving-group ability; subsequent solvolysis or rearrangements under SN1/E1 conditions are facilitated by benzylic stabilization.
  • Oxidative and radical chemistry: cumyl-type substrates undergo oxidative cleavage to acetone plus phenolic fragments under peroxyl/radical conditions (literature), enabling deprotective strategies.

• Retrosynthetic value

  • Accessible from m-isopropenylphenol via hydroboration–oxidation or from m-isopropyl-substituted phenols by oxidation/hydroxylation. Its dual reactivity supports convergent route design and late-stage diversification.

Target Specificity

Not applicable. This product is a small-molecule research chemical, not a biological macromolecule or affinity reagent.

• Item-specific target/epitope/clone/isotype: Not specified for this item; refer to CoA/Spec Sheet if applicable to any conjugates or derivatives.

자주 묻는 질문

What is the purity of this product?

This product is supplied at ≥96% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 7765-97-1, the molecular formula is C9H12O2, and the molecular weight is 152.19 g/mol. InChIKey KNCICOZTHWGRMY-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.