3-(Cyclopropyloxy)benzaldehyde - ≥98% , CAS No.1032527-40-4

CAS: 1032527-40-4 Cat. No.: C993374 Formula: C₁₀H₁₀O₂ Peso molecolare: 162.19 Numero EC: 834-470-0 PubChem CID: 57785476

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Specifiche e purezza

≥98%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥98%

Nomi e identificatori

• Sorrisi canonici: C1CC1OC2=CC=CC(=C2)C=O
• IUPAC Name: 3-cyclopropyloxybenzaldehyde
• InChIKey: QDIJKUXTBCBPNA-UHFFFAOYSA-N
• INCHI: 1S/C10H10O2/c11-7-8-2-1-3-10(6-8)12-9-4-5-9/h1-3,6-7,9H,4-5H2
• Isomeri SMILES: C1CC1OC2=CC=CC(=C2)C=O
• PubChem CID: 57785476
• Peso molecolare: 162.19

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Phenol ethers

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Phenol ethers
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenol ethers
• Alternative Parents: Phenoxy compounds Benzoyl derivatives Benzaldehydes Alkyl aryl ethers Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Phenoxy compound - Phenol ether - Benzoyl - Benzaldehyde - Aryl-aldehyde - Alkyl aryl ether - Monocyclic benzene moiety - Ether - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aldehyde - Aromatic homomonocyclic compound
• Descrizione: 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

Proprietà chimiche e fisiche

• Peso molecolare: 162.180 g/mol
• XLogP3: 2.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 162.068 Da
• Monoisotopic Mass: 162.068 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 163.000
• 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 antibody/assay protocols (WB, IHC, IF, FC) are associated with this small-molecule building block.

General laboratory usage notes (for chemists):

• Open under inert atmosphere if prolonged storage occurred; quickly assess by TLC or 1H NMR before use.
• For moisture-sensitive reactions, pre-dry with molecular sieves (3 Å) or distill under reduced pressure if practical.
• When scaling, perform calorimetric assessment for exothermic steps (e.g., Grignard additions, oxidations).

Biological Roles

This product is supplied for research use as a synthetic building block and is not intended for biological administration.

General/literature context (not product-specific and not implying suitability for biological use):

• Aryl aldehydes can serve as intermediates in the synthesis of ligands, enzyme probes, and small-molecule fragments. The cyclopropyl group is frequently used in medicinal chemistry to modulate lipophilicity, metabolic stability, and conformational preferences without adding heavy atoms.
• The aldehyde functional group can form reversible covalent adducts (e.g., imines with amines, hemiacetals with diols) relevant to bioconjugation research under controlled in vitro conditions. However, such reactivity also underlies potential irritation and is why handling requires care.

No endogenous biological role is associated with 3-(cyclopropyloxy)benzaldehyde. Any applications should remain in vitro/in silico and aligned with laboratory research protocols. Always ensure appropriate containment and do not use for clinical, diagnostic, or veterinary purposes.

Buffer Applications

Not typically applicable. 3-(Cyclopropyloxy)benzaldehyde is a hydrophobic aryl aldehyde, not a buffering agent. It does not form defined acid/base conjugate pairs suitable for maintaining pH in aqueous systems.

Practical notes:

• If reactions or assays require aqueous environments, employ co-solvents (e.g., MeCN, DMSO) and compatible buffers specific to the biological component (e.g., phosphate, HEPES), while verifying that the aldehyde remains stable (aldehydes may hydrate or react with amines in buffers).
• For biphasic oxidations (e.g., Pinnick), buffered systems such as phosphate (pH ~6.5–7) are commonly used to control selectivity, but the aldehyde itself is the substrate, not the buffer.

Green Alternatives

Sustainability perspectives focus on solvent choice, oxidation/reduction methods, and protecting-group strategies rather than on the aldehyde itself.

• Greener solvent options (vs common chlorinated or aprotic amide solvents):

  | Use case | Conventional | Greener alternative | Trade-offs | |---|---|---|---| | Reductive amination | DCM, DMF | Ethanol or 2-MeTHF | May impact solubility of amines; water produced—use molecular sieves. | | Wittig/HWE | THF, DCM | 2-MeTHF, CPME | Similar polarity; 2-MeTHF from renewable feedstocks; check base compatibility. | | Grignard additions | Diethyl ether | 2-MeTHF, CPME | Often better stability and higher bp; ensure reagent initiation. | | Oxidations (to acid) | Cr(VI), MnO2 | TEMPO/NaClO2 (Pinnick), O2/NOx-catalyzed | Reduced toxic waste; aqueous biphasic conditions possible. |

• Process-intensification ideas:

  • Use catalytic hydrogenation for reductions where feasible instead of stoichiometric hydrides.
  • Electrochemical oxidations or photoredox catalysis for selective functionalizations on the benzylic position can reduce reagent waste.
  • Avoid unnecessary protection by leveraging chemoselective methods (e.g., imine formation in alcohol solvents with azeotropic water removal).

• Waste minimization:

  • Employ solvent recycling for toluene/2-MeTHF.
  • Design workups that minimize brine and silica consumption (e.g., liquid–liquid extraction with greener solvents, crystallization-driven purifications when possible).

These suggestions are general/literature-based and should be validated for the specific substrate and route.

Pharmaceutical Uses

This product is offered strictly for research use only and is not intended for human or veterinary use.

General formulation/manufacturing context (literature-based; not product-specific):

• Role as an intermediate: Aryl aldehydes like 3-(cyclopropyloxy)benzaldehyde are frequently employed as intermediates in the synthesis of candidate APIs and advanced intermediates. The cyclopropyl motif is widely explored to fine-tune potency and ADME properties in discovery chemistry.
• Process considerations: When used in GMP settings as an intermediate, typical controls include aldehyde content (by qNMR), acid impurity (oxidation byproduct), residual solvents, and trace metals post-synthesis—defined by internal specifications.
• Pharmacopeial status: No monograph is known for this specific compound in major pharmacopeias (USP/EP/JP) as of typical literature surveys; any quality standards would be set per project-specific specifications.

No claims are made regarding therapeutic activity, safety, efficacy, or suitability for drug product use.

Physical Properties

Item-specific specifications (this product):

• Appearance, purity/grade, density, refractive index, UV cutoff, residual water/metals/peroxides: Not specified for this item; refer to CoA/Spec Sheet.

Literature/computed properties (for context only; not product specifications):

• Molecular formula: C10H10O2 (derived from structure)
• Molecular weight: ~162.19 g/mol (calculated)
• Physical state: Many aryl aldehydes of this size are colorless to pale-yellow liquids at ambient conditions; specific MP/BP for this exact compound were not located in standard references at the time of writing.
• Solubility profile (qualitative, literature expectations):
  • Low solubility in water; miscible with common organic solvents such as dichloromethane, ethyl acetate, toluene, THF, acetonitrile, and alcohols.
• Polarity/logP: Expected moderate hydrophobicity with polar functionality (aldehyde and ether); typical cLogP for analogous aryl aldehydes falls in the 1.5–2.5 range (no measured value located for this exact structure).
• Spectral characteristics: Aryl aldehydes typically show a strong IR C=O stretch near 1685–1705 cm⁻¹ (conjugated), and a diagnostic 1H NMR aldehydic singlet near δ 9.7–10.1 ppm; the cyclopropyl protons appear upfield (δ 0.2–1.2 ppm). These are general expectations pending item-specific data.

Note: For method development or QC acceptance criteria, rely on the product CoA/SDS for authoritative physical data.

Quality and Grades

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

General guidance on grades and quality considerations for building-block aldehydes:

• Typical research grades: “Reagent grade” materials are suitable for most synthesis. “High-purity” or “HPLC grade” (for solvents) indicates lower UV background and reduced trace impurities—useful if the aldehyde is a reagent in photochemical or analytical applications.
• Impurity profile concerns: Aldehydes can oxidize to the corresponding carboxylic acids or hydrate/polymerize under storage. For sensitive reactions (e.g., Wittig olefination, reductive amination with complex amines), pre-check by 1H NMR/GC and, if needed, purify by short-path distillation or column chromatography.
• Stabilizers: This listing does not indicate any stabilizer. If present in other aldehydes, stabilizers can slightly inhibit nucleophilic additions; confirm presence/absence on the CoA and, if necessary, remove by distillation before use.
• Trace metals/UV cutoff/water content: Not specified for this item; verify on CoA if relevant to your application (e.g., photoredox chemistry or water-sensitive transformations).

Fit-for-purpose selection:

• For route-scouting and library synthesis, standard reagent grade is generally adequate.
• For medicinal chemistry or structure–activity studies where analytical clarity is paramount, choose lots with tight specifications (low acid content, low residual solvents) and confirm by LC/MS and qNMR.

Reaction and Applications

As a meta-substituted aryl aldehyde bearing an electron-donating cyclopropyloxy group, 3-(Cyclopropyloxy)benzaldehyde is a versatile synthon for constructing functionalized aromatics and heterocycles.

• Core transformations (literature/general):
  • Imine formation and reductive amination to access benzylic amines; suitable with NaBH3CN, NaBH(OAc)3, or catalytic hydrogenation.
  • Wittig, Horner–Wadsworth–Emmons (HWE), and Julia–Kocienski olefinations to install styrenes and conjugated alkenes.
  • Nucleophilic 1,2-additions (Grignard/organolithium) to generate secondary/tertiary benzylic alcohols, followed by dehydration or further elaboration.
  • Oxidation to 3-(cyclopropyloxy)benzoic acid (e.g., Pinnick, TEMPO/NaClO2) or to the acid chloride for subsequent coupling.
  • Reductions of the aldehyde (NaBH4 or catalytic hydrogenation) to the corresponding benzyl alcohol; selective vs aryl ether typically feasible under mild conditions.
  • Acetal protection (e.g., ethylene glycol/acid catalyst) for orthogonal manipulation on the ring.
• Substituent/directing effects:
  • The –O–cyclopropyl is strongly donating by resonance, activating the ring toward electrophilic aromatic substitution (EAS) and directing ortho/para relative to itself. The formyl group is deactivating and meta-directing. Strategic use of protection and stepwise EAS can control regiochemistry.
• Cyclopropyl considerations:
  • The cyclopropyl ring is strain-rich and can undergo ring-opening under strong acidic or radical conditions; under most standard conditions it is robust and serves as a compact lipophilicity modulator.
• Use cases:
  • Library and medicinal chemistry as a probe of cyclopropyl-driven conformational and metabolic effects.
  • Synthesis of substituted benzylamines, cinnamaldehydes/cinnamates, and benzoic acid derivatives.

Note: Optimize water control and oxygen exclusion when high aldehyde integrity is critical (e.g., enantioselective additions).

Reaction Conditions

General guidance from literature for aryl aldehydes (optimize for this substrate):

• Reductive amination

  • Typical solvents: MeOH, EtOH, i-PrOH, or MeCN.
  • Reagents: NaBH3CN (pH 5–6, AcOH), NaBH(OAc)3 (AcOH or HOAc/MeCN), or H2/Pd-C.
  • Temperature/time: 0–25 °C, 1–16 h depending on amine nucleophilicity; monitor by TLC/LC–MS.

• Wittig/HWE olefination

  • Solvents: THF, toluene, DCM, or 2-MeTHF.
  • Bases: n-BuLi, NaHMDS for ylide generation (Wittig); NaH, K2CO3, or DBU for HWE.
  • Temperature: −78 to 25 °C (Wittig), 0 to 25 °C (HWE). E/Z control via ylide type (stabilized yields E-rich; non-stabilized Z-rich).

• Grignard/organolithium additions

  • Solvents: Dry THF or Et2O (stringently anhydrous).
  • Conditions: 0 °C to room temp; quench with saturated NH4Cl. Add aldehyde slowly to reagent to minimize over-reduction and side reactions.

• Oxidation to acid (Pinnick)

  • Solvent/buffer: t-BuOH/H2O with NaH2PO4 buffer (pH ~6.5–7), NaClO2 (1.5–2.0 eq), scavenger Na2SO3.
  • Temperature: 0–25 °C; typically complete in 1–3 h.

• Acetal formation (protection)

  • Reagents: Ethylene glycol (3–5 eq), catalytic p-TsOH or camphorsulfonic acid.
  • Solvent: Toluene or benzene with Dean–Stark; or MeOH under azeotropic removal of water.

• Workup/monitoring tips

  • Use sulfite/bisulfite washes to remove residual oxidants and to trap trace aldehyde if desired.
  • Monitor aldehyde integrity by 1H NMR (aldehydic proton near δ ~10 ppm) and by LC–MS (M+H+ ~163 for the parent, literature value).

All conditions are literature-style guidance and should be adapted and validated for this specific substrate.

Safety and Handling

Item-specific hazard information:

• GHS classification, signal word, hazard statements, and pictograms: Not specified for this item; refer to the SDS for authoritative safety data.

General safety information for aryl aldehydes (literature-based; not product-specific):

• Hazards: Aldehydes are irritants to skin, eyes, and respiratory tract; may cause sensitization in some individuals. Vapors can be irritating; handle in a fume hood.
• Incompatibilities: Strong bases (can induce aldol-type side reactions), strong oxidizers (risk of exothermic oxidation), strong reducing agents (can reduce the aldehyde). Avoid prolonged exposure to air and light that can promote oxidation to the acid.
• PPE: Lab coat, safety glasses/goggles, appropriate chemically resistant gloves (e.g., nitrile). Use fume hood and avoid inhalation of vapors or aerosols.
• First aid (general guidance):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin contact: Wash with soap and water; remove contaminated clothing.
  • Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; seek medical attention if irritation persists.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
• Fire safety: Likely combustible organic liquid; use CO2, dry chemical, or foam. Cool containers with water spray in case of fire.
• Waste: Collect organic waste in compatible, properly labeled containers; segregate halogenated from non-halogenated streams as applicable.

Always consult the SDS provided with the shipment for definitive hazard classifications and response measures.

Solvent Selection

Applicability: 3-(Cyclopropyloxy)benzaldehyde is a moderately lipophilic aryl aldehyde and dissolves readily in common organic solvents; aqueous systems are typically unsuitable except for biphasic conditions.

• Solubility/miscibility (literature expectations):
  • Good: DCM, chloroform, THF, EtOAc, toluene, acetonitrile, DMF/DMSO, alcohols (MeOH/EtOH).
  • Poor: Water (use surfactants, phase-transfer catalysts, or co-solvents if needed).
• Solvent choice by transformation:
  • Reductive amination: MeOH, EtOH, i-PrOH, or MeCN with hydrogenation or hydride reagents.
  • Wittig/HWE/Julia olefinations: THF, toluene, or DCM under anhydrous conditions.
  • Nucleophilic additions (Grignard/organolithium): Ether solvents (THF, diethyl ether); rigorous drying required.
  • Electrophilic aromatic substitution on the ring (if pursued): Polar aprotic (nitrobenzene, DCM) or Lewis acid media; note directing effects of –O– on regioselectivity.
• Comparison notes:
  • DCM vs toluene: DCM offers faster dissolution and lower viscosity; toluene provides higher boiling range for elevated-temperature operations.
  • THF vs MeCN: THF coordinates to metals and suits organometallics; MeCN gives higher polarity for imine formation and many catalytic reactions.
• Practical tips:
  • Dry, oxygen-limited environments help suppress aldehyde autoxidation.
  • For aqueous workups, saturated NaHCO3 or Na2SO3 can quench residual acids/oxidants while preserving the aldehyde.

For analytical assays (HPLC/LC–MS), MeCN/H2O with 0.1% formic acid or ammonium formate buffers typically gives good peak shape; confirm stability under acidic mobile phases.

Storage and Reconstitution

• Storage conditions (item-specific): Room temperature (per Product Data). Store tightly sealed in original container.
• Shipping: Not specified for this item; refer to the shipment documentation.

General handling to preserve aldehyde integrity:

• Protect from air and light to minimize gradual oxidation to the corresponding acid; if long-term storage is planned, consider an inert headspace (argon/nitrogen) and store in amber glass.
• If crystallization or precipitation occurs (compound-dependent), warm gently to ambient and mix thoroughly before sampling. No reconstitution is typically required; this compound is used as received or dissolved in a suitable anhydrous organic solvent prior to use.
• After opening: If sensitive applications are planned, assess purity by 1H NMR/LC–MS. If minor oxidation is detected, purify by short-path distillation or column chromatography under low-oxygen conditions.
• Freeze–thaw: Not generally necessary. Avoid repeated thermal cycling; maintain at a consistent room temperature. For long-term archiving, cool storage (e.g., 2–8 °C) under inert gas can further slow degradation, but follow laboratory SOPs.

Research Use Note: For research use only.

Structure and Identity

Brief description: 3-(Cyclopropyloxy)benzaldehyde is an aryl aldehyde bearing a para-directing cyclopropyloxy ether at the 3-position and a formyl group at the 1-position of the benzene ring. It functions as a versatile electrophilic building block.

• Item-specific identifiers (from Product Data)

  • SKU: C993374
  • Product name: 3-(Cyclopropyloxy)benzaldehyde
  • CAS: 1032527-40-4
  • PubChem CID: 57785476
  • InChIKey: 293971 (as listed)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed identifiers and features (for reference; not item specifications)

  • Typical molecular formula (literature): C10H10O2
  • Nominal molecular weight (literature): ~162.19 g/mol
  • Representative SMILES (literature): O=Cc1cccc(OC2CC2)c1
  • Key functional groups: aromatic ring, formyl (aldehyde), aryl–O–cyclopropyl ether
  • Structural features: The benzene ring bears an aldehyde (–CHO) which is meta to an electron-donating cyclopropyloxy substituent (–O–c-C3H5). The ether oxygen is directly attached to the ring; the cyclopropyl ring is a strained three-membered aliphatic ring.

• 2D structure in words

  • A benzene core with an aldehyde at C1 and an –O–cyclopropyl at C3. The aldehyde carbonyl is conjugated with the ring, enabling typical aryl-aldehyde reactivity, while the cyclopropyloxy group is an ortho/para-directing, strongly donating substituent by resonance through the oxygen.

Synthetic Utility

Functional group and reactivity synopsis:

• Electrophile at carbonyl carbon (aldehyde): Enables formation of C–N (imines/enamines), C–C (Wittig/HWE/Julia; nucleophilic additions), and C–O (acetals/hemiacetals) bonds.
• Aryl–O–cyclopropyl ether: Electron-donating substituent that modulates ring electronics and directs EAS. Generally inert to many nucleophiles and mild reductants; susceptible to strong Lewis/Brønsted acids and harsh hydrogenolysis.

Retrosynthetic value:

• Serves as a convergent point for routes targeting benzylamine, benzylic alcohol, or cinnamate/cinnamyl motifs bearing a cyclopropyl ether handle.
• The cyclopropyloxy group can be interconverted: demethylation-type conditions (e.g., BBr3/AlCl3 analogs) are often too harsh for cyclopropyl ethers; milder alternatives include oxidative cleavage (DDQ under constrained conditions) or directed metalation followed by substitution if a leaving group is introduced elsewhere.

Named and common transformations (literature examples):

• Wittig olefination to give 3-(cyclopropyloxy)styrenes; E/Z selectivity tuned by ylide type and solvent.
• Reductive amination with (hetero)arylamines or aliphatic amines to access benzylamines; NaBH(OAc)3 in AcOH-buffered MeCN or EtOH is frequently effective.
• Nucleophilic addition of RMgX/RLi to furnish secondary/tertiary benzylic alcohols; subsequent oxidation/elimination provides access to alkenes.
• Oxidation to acid or nitrile (via oxime then dehydration) expands handles for amide couplings and further diversification.

Protection/compatibility:

• Protect the aldehyde as an acetal during ring functionalization steps that involve strong acids or oxidants; deprotect under mild aqueous acid post-modification.

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.