3-(2-Chlorophenoxy)propan-1-ol - ≥95% , CAS No.60222-56-2

CAS: 60222-56-2 Cat. No.: C1308158 Fórmula: C₉H₁₁ClO₂ Peso molecular: 186.63 Número EC: 160-640-2

GRADE & PURITY ≥95%

Storage

Room temperature

Shipped In

Normal

Specifications

Especificaciones y pureza

≥95%

Condiciones de almacenamiento de almacenamiento

Room temperature

Enviado en

Normal

Pureza

≥95%

Nombres e identificadores

• Sonrisas canónicas: C1=CC=C(C(=C1)OCCCO)Cl
• IUPAC Name: 3-(2-chlorophenoxy)propan-1-ol
• InChIKey: CSCKMYSAZZCGBM-UHFFFAOYSA-N
• INCHI: 1S/C9H11ClO2/c10-8-4-1-2-5-9(8)12-7-3-6-11/h1-2,4-5,11H,3,6-7H2
• Peso molecular: 186.63

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Clase Phenol ethers

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Clase: Phenol ethers
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenol ethers
• Alternative Parents: Phenoxy compounds Chlorobenzenes Alkyl aryl ethers Aryl chlorides Primary alcohols Organochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Phenoxy compound - Phenol ether - Alkyl aryl ether - Chlorobenzene - Halobenzene - Monocyclic benzene moiety - Aryl halide - Aryl chloride - Ether - Organooxygen compound - Organochloride - Organohalogen compound - Alcohol - Organic oxygen compound - Primary alcohol - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
• 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

Propiedades químicas y físicas

• Peso molecular: 186.630 g/mol
• XLogP3: 2.400
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 186.045 Da
• Monoisotopic Mass: 186.045 Da
• Topological Polar Surface Area: 29.500 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 119.000
• 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 (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic use, refer to the Reaction & Applications and Reaction Conditions sections for representative procedures and optimization tips.

Biological Roles

This product is intended for research and synthetic use; no intrinsic biological role is assigned to the reagent in vivo.

General notes (biochemistry context; not product-specific claims):

• Aryl ether alcohols of this type can serve as probes or linkers in the preparation of affinity ligands, fluorescent tags, or surface modifiers after derivatization of the primary alcohol (e.g., to carbamates/urethanes or carbonates) for bioconjugation workflows.
• The presence of a chloro substituent modulates lipophilicity and can influence membrane association of derived conjugates; however, the parent reagent itself is not a characterized metabolite.
• Metabolic considerations (literature): aryl–alkyl ethers may undergo O-dealkylation and oxidation in biological systems; primary alcohols can be oxidized to acids. Such pathways are general to the class and do not imply biological activity for this compound.

For any biological or biochemical experiments, ensure appropriate validation of purity and identity, and confirm compatibility of residual solvents/impurities with the biological system under study. Research use only.

Buffer Applications

This compound is not a buffering agent and is not typically used to prepare pH buffer systems. If used in aqueous assays (e.g., as a derivatized conjugate), select a buffer compatible with alcohol/ether stability (e.g., phosphate, HEPES) and avoid strong acids/bases that may promote hydrolysis or ether cleavage. For standard buffer recipes and pH ranges, refer to dedicated buffering reagents.

Green Alternatives

While 3-(2-chlorophenoxy)propan-1-ol itself is a functionalized building block (not easily substituted one-for-one), its preparation and downstream transformations can be made greener.

• Greener solvent choices (general guidance):

  • Replace DMF/DMSO/NMP with MeCN, 2-MeTHF, CPME, or propylene carbonate when compatible with the reaction kinetics and solubility.
  • Use ethyl acetate or MeTHF for acylations and extractions to reduce chlorinated solvent usage.

• Greener bases and reagents:

  • Williamson ether synthesis: favor K2CO3 or Cs2CO3 in acetone/MeTHF over NaH in DMF. Phase-transfer catalysis (e.g., TBAB) in aqueous–organic systems can reduce solvent load and temperature.
  • Alcohol activations: employ greener sulfonylating agents with minimized byproducts; consider enzymatic esterifications where feasible.
  • Oxidations: TEMPO/NaOCl (pH ~9, biphasic) or O2/Pd systems as alternatives to chromium(VI). For aldehyde formation, Oxone or electrochemical methods can avoid toxic reagents.

• Energy and workup:

  • Microwave or flow synthesis may reduce reaction times and improve space–time yields.
  • Solvent recycling and minimal silica usage (by crystallization or liquid–liquid partitioning) lessen waste.

• Safety/EHS tradeoffs:

  • 2-chloro functionality can trigger stricter waste handling; if your end use allows, non-halogenated phenoxy analogs may be considered, noting potential changes to reactivity and properties.

Comparison snapshot (illustrative):

• Traditional: Williamson in DMF/NaH, halogenated workup.
• Greener: K2CO3 in acetone or 2-MeTHF, catalytic PTC, aqueous bleach oxidations, and recyclable solvents.

Pharmaceutical Uses

No pharmacopeial monograph or excipient designation is provided for this item. It is supplied for research use only.

General formulation/manufacturing context (non-clinical, not product-specific claims):

• As a synthetic intermediate: the primary alcohol can be transformed into carbamates, esters, or carbonates to introduce the 2-chlorophenoxypropyl motif into small molecules or polymeric excipients.
• As a linker: the –O–(CH2)3–OH unit enables attachment of the aryl headgroup to drug delivery matrices (e.g., via isocyanate or chloroformate chemistry) to modulate hydrophobicity or binding.
• Process considerations:
  • Control of residual solvents and halogenated impurities is critical for GMP processes; consult CoA and perform ICH-compliant impurity profiling if scaling for preclinical route scouting.
  • The aryl chloride may participate in late-stage cross-coupling to install amine or aryl substituents; ligand/catalyst selection for C–Cl activation is essential for scalability and metal residual control.

Note: This product is not approved as an API, excipient, or for clinical use. Any pharmaceutical application would pertain only to its role as an intermediate in route development under appropriate regulatory oversight.

Physical Properties

Item-specific measured values: Not specified for this item; refer to CoA/Spec Sheet for definitive specifications (e.g., purity, water content, residual solvents, UV cutoff, metals).

Literature/general expectations for the neutral compound (for planning only; verify before use):

• Physical state: typically a colorless to pale liquid or low-melting solid depending on purity and temperature (literature, aryl ether primary alcohols of this size are often liquids near ambient).
• Polarity: amphiphilic; contains one aryl ether oxygen and one primary alcohol (capable of hydrogen bonding as donor and acceptor).
• Solubility (qualitative, literature):
  • Miscible or highly soluble in polar aprotic organics (e.g., DMSO, DMF, acetone) and moderately soluble in lower alcohols.
  • Limited solubility expected in water due to aryl core and chloro substituent; the primary alcohol provides some aqueous compatibility.
• Volatility: significantly less volatile than small ethers/alcohols; moderate vapor pressure at room temperature (literature trend for C9 aryl ethers).
• Partitioning: logP expected in the low-to-moderate range for chlorophenoxy alcohols (literature trend); exact value not provided for this item.
• Spectral handles: strong IR O–H stretch (broad, ~3200–3600 cm⁻1, literature), C–O stretches (ether/alcohol, ~1000–1300 cm⁻1), aromatic C–H and C=C bands; 1H/13C NMR show characteristic O–CH2 (≈3.9–4.2 ppm), CH2 adjacent to OH (≈3.3–3.6 ppm), and aromatic region (≈6.8–7.4 ppm) (literature).

Quality and Grades

• Grade/purity: Not specified for this item; refer to CoA/Spec Sheet for exact assay, impurity profile, and any stabilizers.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

Interpreting common grades for this class of building block (general guidance):

• Research grade/Analytical grade: Suitable for routine synthesis and analytical work. Typically provides assay ≥95–98% with low residual solvents (spec-dependent). Lower UV background is advantageous if used in photometric analyses.
• Synthesis grade vs. HPLC grade (context): While HPLC grade is typically used for solvents, some reagents are offered with low-UV/low-fluorescence profiles to minimize chromatographic background when used as derivatization agents or internal standards.
• Stabilizers: Phenoxy alcohols generally do not require stabilizers; if any antioxidant or acid scavenger is present, it will be noted on the CoA and may affect certain reactions (e.g., acid-catalyzed steps). Always verify and remove stabilizers if incompatible (e.g., by aqueous wash or distillation) before sensitive transformations.

What to check on receipt (best practice):

• Confirm identity by quick NMR/GC-MS if your application is purity-critical.
• Review CoA for water content, assay, and residual halogenated solvents if relevant to your process.
• If using in photochemistry or trace analysis, request a spectral profile (UV/Vis) to understand baseline absorbance.

Reaction and Applications

As a bifunctional aryl ether bearing a primary alcohol, 3-(2-chlorophenoxy)propan-1-ol is a versatile intermediate. Typical uses (general chemistry guidance):

• Functionalization of the primary alcohol:

  • Esterification to lipophilic esters (e.g., with acyl chlorides/anhydrides; DMAP or acid catalysis).
  • Oxidation to the corresponding aldehyde or acid (e.g., Swern, Dess–Martin to aldehyde; TEMPO/bleach or Jones to acid). Aldehyde enables subsequent reductive amination.
  • Activation as a sulfonate ester (tosylate/mesylate) followed by SN2 substitution with halides, azide, thiols, or amines to furnish 3-(2-chlorophenoxy)propyl derivatives.
  • Mitsunobu reactions to invert configuration at C1 (here achiral) and couple with acidic nucleophiles; often replaced by greener alternatives (e.g., PPh3/DIAD swapping for safer reagents).

• Retaining/modifying the aryl ether:

  • The 2-chloro substituent can participate in cross-coupling after halogen–metal exchange or via Pd-catalyzed C–Cl activation (Buchwald–Hartwig amination, Suzuki–Miyaura, Sonogashira with suitable ligands and elevated temperatures).
  • Electrophilic aromatic substitution is deactivated by the chloro group but the phenoxy oxygen is ortho/para-directing; conditions must be tuned to avoid cleaving the alkyl ether.

• Linker chemistry:

  • The –O–(CH2)3–OH segment serves as a spacer for attaching the chlorophenyl headgroup to polymers, resins, or surfaces (e.g., via carbonate/urethane formation with phosgene-equivalents or isocyanates).

• Synthesis of the title compound (for reference): often prepared by Williamson ether synthesis of 2-chlorophenol with 3-bromopropan-1-ol (or protected derivatives), under basic conditions (e.g., K2CO3 in acetone), followed by workup and purification.

Reaction Conditions

The following are general literature-style conditions for common transformations of aryl–alkyl primary alcohols bearing aryl chloride and ether functionalities. Always optimize for your system.

• Williamson ether synthesis (for reference preparation): 2-chlorophenol (1.0 eq), 3-bromopropan-1-ol (1.1–1.5 eq), K2CO3 (2.0–3.0 eq), acetone or 2-MeTHF (0.2–0.5 M), reflux 6–18 h. Typical isolated yields: 60–85% (literature range for similar substrates). Protect –OH if competing O-alkylation occurs.

• Alcohol activation/substitution:

  • Tosylation: TsCl (1.2–1.5 eq), pyridine (or Et3N) 0–25 C, 2–6 h; then SN2 with NaN3, KSeCN, or amines in DMF/MeCN at 50–90 C, 2–16 h.
  • Halogenation (Appel): PPh3 (1.2–1.5 eq), CCl4 or NBS/CBr4 (1.2–1.5 eq), DCM, 0–25 C; or SOCl2 with catalytic DMF to give chloride; quench carefully.

• Oxidation of –CH2OH:

  • TEMPO (0.02–0.1 eq), NaOCl (1.5–2.0 eq active), KBr (cat.), pH 8.6–9.5 (NaHCO3 buffer), MeCN/H2O (1:1), 0–25 C to aldehyde; further oxidation (NaClO2, Pinnick) to acid.
  • Dess–Martin (1.3 eq), DCM, 0–25 C, 0.5–2 h to aldehyde.

• Cross-coupling at aryl C–Cl (after alcohol protection if needed):

  • Buchwald–Hartwig amination: Pd2(dba)3 (1–2 mol%), BrettPhos (2–4 mol%), NaOtBu (2.0 eq), toluene or dioxane, 90–120 C, 6–20 h; amine (1.2–1.5 eq). Yields often 50–85% depending on amine and ligand.
  • Suzuki–Miyaura: Pd(PPh3)4 (2–5 mol%) or Pd-precatalyst with SPhos/XPhos, K3PO4 (2–3 eq), toluene/H2O or dioxane/H2O, 80–110 C, 6–16 h; boronic partner (1.2–1.5 eq).

Note: Conditions are provided as general literature guidance for analogous substrates; adjust stoichiometry and temperature to balance reactivity with functional group tolerance.

Safety and Handling

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 and pictograms: Not specified for this item; refer to SDS.

General safety considerations for aryl–alkyl ether primary alcohols (informational; always consult the product’s SDS):

• Expected hazards: May cause skin/eye irritation; harmful if swallowed or inhaled. Avoid aerosol generation and prolonged contact.
• PPE: Wear lab coat, safety glasses or chemical splash goggles, and suitable gloves (e.g., nitrile). Use in a chemical fume hood.
• Handling: Avoid heat, sparks, and open flames. Prevent contact with strong oxidizers (may cause exothermic reactions) and strong acids/bases (can lead to cleavage or side reactions over time).
• First aid (overview):
  • Skin: Wash with soap and water. Remove contaminated clothing.
  • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; continue rinsing. Seek medical attention.
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Storage incompatibilities: Keep away from strong oxidizers (e.g., peroxides, chromates), strong acids (risk of hydrolysis under harsh conditions), and strong bases (risk of ether cleavage under forcing conditions). Not known to form peroxides appreciably (unlike dialkyl ethers), but good practice is to store tightly sealed.
• Spill/cleanup: Absorb on inert material, collect in suitable container, and ventilate area.
• Waste: Dispose according to local regulations; halogen-containing organics may have specific disposal requirements.

Solvent Selection

This product is a reagent/building block rather than a bulk solvent. However, solvent choice is important for its handling and reactions.

• Solubility/miscibility considerations (general):

  • High solubility in polar aprotic media (DMF, DMSO, NMP, acetone, acetonitrile) facilitates substitution and coupling reactions on the primary alcohol.
  • Soluble in most chlorinated and aromatic solvents (DCM, chloroform, toluene) for protection/activation steps and for extractions.
  • Limited aqueous solubility; co-solvents (MeOH, EtOH, acetonitrile) aid in phase-transfer or bioconjugation-like chemistry.

• Selecting solvents by transformation:

  • Nucleophilic substitutions after converting –CH2OH to a sulfonate (e.g., tosylate): use dry acetonitrile, DMF, or DMSO with appropriate base/nucleophile.
  • Esterifications/Acylations: DCM, toluene, or EtOAc with coupling reagents or acid chlorides; use molecular sieves or Dean–Stark where applicable.
  • Oxidations (to aldehyde/acid): Acetonitrile, DCM, or EtOAc depending on the oxidant (e.g., TEMPO/bleach biphasic systems benefit from MeCN/H2O).

• Small comparison (general):

  • DMF/DMSO: maximize solubility and SN2 rates; harder workup and odor (DMSO) are tradeoffs.
  • Acetonitrile: good balance of polarity and volatility; often preferred for clean workups.
  • Toluene/DCM: useful for moisture-sensitive or acid chloride chemistry; non-polar to moderately polar environment can improve selectivity.

Always match solvent choice to downstream isolation and EHS constraints.

Storage and Reconstitution

• Storage conditions (from Product Data): Store at room temperature. Ship under normal conditions.
• Container: Keep tightly closed in a chemically compatible, airtight container. Prefer amber glass to minimize photodegradation of aryl chlorides.
• Atmosphere: Store under dry conditions; desiccant recommended if the container is frequently opened to limit moisture uptake and potential hydrolysis of reactive derivatives.
• Stability: Aryl–alkyl ethers with primary alcohols are generally stable at ambient conditions when protected from strong acids/bases and oxidants. Avoid prolonged exposure to elevated temperatures.
• Reconstitution/Usage: Supplied neat. If preparing stock solutions, use dry, oxygen-free solvents when performing moisture-sensitive transformations. Common stock solvents include acetonitrile, DMSO, DMF, or ethanol depending on the application; label concentration and date.
• Freeze–thaw: Not required for neat reagent. If dissolved, avoid repeated freeze–thaw cycles that can cause condensation or concentration drift; aliquot solutions as needed.
• Compatibility and segregation: Store away from strong oxidizers, strong acids/bases, and reactive metals. Segregate from foodstuffs and incompatible chemicals per institutional policy.
• Shelf-life: Refer to CoA/Spec Sheet for retest/expiry date. Inspect periodically for discoloration or precipitates; analyze by NMR/GC if critical to application.

Research use only.

Structure and Identity

Brief overview: 3-(2-Chlorophenoxy)propan-1-ol is an aryl–alkyl ether bearing a primary alcohol tail; the aryl ring is ortho-chloro substituted. This makes it a bifunctional building block combining a nucleophilic/alcohol handle with an electron-deficient chlorophenyl ether motif.

• Item-specific identifiers (from Product Data)

  • SKU: C1308158
  • Product name: 3-(2-Chlorophenoxy)propan-1-ol
  • CAS: 60222-56-2
  • PubChem CID: 12293187
  • InChIKey: 52215 (as provided)
  • 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.

• Literature/computed identifiers and features (for general reference; verify against the item’s CoA):

  • Typical molecular formula (literature): C9H11ClO2
  • Typical molecular weight (literature): ~186.63 g/mol
  • Representative SMILES (literature): OCCCOc1c(Cl)cccc1 (one of several equivalent representations; substituent indexing conveys the 2-chloro/ortho relationship)
  • 2D structure description: A benzene ring bearing adjacent substituents at the 1- and 2-positions: an ether oxygen at the 1-position linked to a –CH2–CH2–CH2–OH chain, and a chlorine at the 2-position. The side chain terminates in a primary alcohol (–CH2OH).

• Structural features and functional groups (general chemistry):

  • Aryl–alkyl ether (phenoxy) linkage
  • Ortho-chloro substituent on the aromatic ring (electron-withdrawing, ortho/para-directing in SEAr, influences lipophilicity)
  • Primary aliphatic alcohol (amenable to oxidation, esterification, tosylation/halogenation, Mitsunobu, etc.)
  • No stereogenic centers (achiral as named)

Synthetic Utility

Key reactivity stems from two orthogonal handles: a primary alcohol and an ortho-chloro aryl ether.

• Transformations at the alcohol:

  • Protection: convert to TBDMS/TMS, benzyl, or acyl protecting groups to mask the alcohol during aryl transformations.
  • Activation: tosylate/mesylate formation (pyridine/DMAP) allows SN2 substitution with N, O, S, or C nucleophiles to access 3-(2-chlorophenoxy)propyl derivatives (halides, azides, thioethers, amines). Appel/DPPA variants convert –OH to halides.
  • Oxidation: Dess–Martin, Swern, or TEMPO/bleach to aldehyde; Pinnick or further oxidation to acid; subsequent amide coupling broadens chemical space.
  • Carbonate/urethane formation: with chloroformates or isocyanates to introduce handles for polymer conjugation.

• Transformations on the aryl chloride/ether:

  • Pd-catalyzed cross-couplings (Buchwald–Hartwig, Suzuki–Miyaura, Sonogashira) using strong ligands (e.g., BrettPhos, XPhos) at elevated temperatures to activate aryl C–Cl.
  • Metal–halogen exchange (e.g., iPrMgCl·LiCl “Turbo Grignard”) on the aryl chloride under controlled conditions, followed by electrophile trapping; ensure the alcohol is protected to avoid side reactions.
  • Electrophilic substitutions are limited due to deactivation by Cl; however, directed lithiation adjacent to the ether oxygen can be leveraged with appropriate protection.

• Retrosynthetic value:

  • Disconnection to 2-chlorophenol and 3-bromopropan-1-ol (or protected analog) under Williamson ether conditions provides a robust, scalable entry.
  • Orthogonality enables stepwise diversification: derivatize the chain first (via –OH) or modify the aryl chloride via cross-coupling after alcohol protection.

Target Specificity

Not applicable. This product is a small-molecule reagent/building block and is not an antibody, enzyme, or affinity reagent. No antigen/epitope or species reactivity information applies.