4-Methoxybut-1-ene - ≥95% , CAS No.4696-30-4

CAS: 4696-30-4 Cat. No.: M1035773 Summenformel: C₅H₁₀O Molekulargewicht: 86.130 EG-Nummer: 851-453-3

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥95%

Storage

Room temperature

Reinheit

≥95%

Namen und Kennungen

Kanonisches Lächeln

COCCC=C

IUPAC Name

4-methoxybut-1-ene

InChIKey

VDTUJQCSPFYIKZ-UHFFFAOYSA-N

INCHI

1S/C5H10O/c1-3-4-5-6-2/h3H,1,4-5H2,2H3

Molekulargewicht

86.130

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Klasse Organooxygen compounds
      • Subclass Ethers

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Klasse: Organooxygen compounds
• Subclass: Ethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Dialkyl ethers
• Alternative Parents: Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Dialkyl ether - Hydrocarbon derivative - Aliphatic acyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as dialkyl ethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are alkyl groups.
• 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

Chemische und physikalische Eigenschaften

• Molekulargewicht: 86.130 g/mol
• XLogP3: 1.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 86.0732 Da
• Monoisotopic Mass: 86.0732 Da
• Topological Polar Surface Area: 9.200 Ų
• Heavy Atom Count: 6
• Formal Charge: 0
• Complexity: 32.900
• 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 biological assay protocols are specified for this item. As a synthetic building block, typical procedures follow standard organic synthesis practices.

For example workflows (general, literature-based):

• Hydroboration–oxidation sequence to 4‑methoxybutan-1-ol: Charge anhydrous THF, cool to 0 °C, add BH3·THF dropwise under N2, stir to rt, then quench with H2O2/NaOH at 0–10 °C; standard aqueous workup and purification by distillation or column chromatography. Optimize stoichiometry and temperature for your scale.
• Peracid epoxidation: Dissolve substrate in cold DCM, add mCPBA portionwise with NaHCO3 buffer to control acidity, stir at 0–25 °C, then quench, wash with bisulfite and bicarbonate, dry, and purify.

These are illustrative and must be adapted/validated for your specific application. Consult primary literature and your institutional SOPs.

Biological Roles

This compound is a small, non-natural organic building block. It is not typically associated with endogenous biochemical pathways or recognized biological roles.

• No known role as a metabolite in primary metabolism has been broadly reported for simple ω‑methoxy alkenes of this chain length (literature perspective).
• The terminal alkene may undergo generic oxidative metabolism in biological systems (e.g., P450-mediated epoxidation) and the ether could be cleaved under strong acidic or enzymatic conditions, but such considerations are mainly relevant for environmental fate or toxicology studies rather than lab synthesis.

For research applications involving biology, this material is best treated as a synthetic intermediate or hydrophobic modifier for small-molecule probe synthesis, rather than as a buffer component or biomolecule.

All uses are restricted to research and laboratory development; this product is not intended for diagnostic, therapeutic, or in vivo applications.

Buffer Applications

Not typically applicable. 4-Methoxybut-1-ene is a hydrophobic organic reagent and is not used to prepare aqueous buffer systems or maintain pH in biochemical assays.

• If your workflow requires aqueous handling (e.g., biphasic oxidations or extractions), select an appropriate buffer independently (e.g., phosphate, acetate) based on your reaction’s pH needs, and verify the organic phase compatibility with your chosen solvent system.
• For any emulsions or phase-transfer processes, consider a phase-transfer catalyst rather than attempting to solubilize this reagent via buffers.

Green Alternatives

While 4-methoxybut-1-ene is a purpose-built synthon, greener choices can be applied to the surrounding process (solvents, oxidants, workups):

• Greener reaction media for common transformations:

  • Hydroboration–oxidation: 2‑MeTHF (bio-based) often substitutes for THF while offering similar reactivity and easier phase separations.
  • Epoxidation: aqueous H2O2 with appropriate catalysts (e.g., tungstate, Ti-silicates) can replace peracids such as mCPBA, reducing halogenated waste.
  • Radical additions/thiol–ene: ethanol or ethyl acetate may be viable if substrates and catalysts are compatible, reducing reliance on chlorinated solvents.

• Process intensification:

  • Use continuous-flow microreactors for ozonolysis or photochemistry to lower solvent volumes and improve safety.
  • Solvent recycling and vacuum-assisted solvent recovery to reduce VOC emissions.

• Tradeoffs (balanced view):

  • 2‑MeTHF can introduce additional impurities (levulinic derivatives) and has a higher boiling point than THF, affecting cycle times.
  • Aqueous H2O2 systems may demand catalyst development and careful control to avoid over-oxidation.

Comparison snapshot (general):

• THF vs 2‑MeTHF: similar polarity; 2‑MeTHF is partially water-immiscible, aiding separations but sometimes slowing rates.
• DCM vs EtOAc: EtOAc is greener but more nucleophilic; verify compatibility with electrophilic reagents used on the alkene.

Pharmaceutical Uses

No pharmacopeial or excipient role is specified for this item; it is supplied for research use only.

• As a synthetic intermediate (general chemistry context), 4-methoxybut-1-ene may be used in discovery-phase route scouting to introduce an ω‑methoxy group via alkene chemistry, later unmasked or further elaborated. However, it is not a formulated excipient, processing aid, or API.
• If materials are to be advanced toward GMP settings, source control, impurity fate-and-purge, and residual solvent profiles must be established independently; consult QA/Regulatory teams and pharmacopeial monographs for analogous functional groups if relevant.

No clinical or therapeutic claims are made or implied.

Physical Properties

Item-specific specs

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

Literature/general properties (for planning; not item-specific)

• State at RT: low-viscosity liquid (typical for C5 alkoxy-alkenes).
• Molecular formula: C5H10O; Molecular weight: ~86.13 g/mol (literature).
• Volatility: expected moderately volatile; handle in a fume hood to minimize losses.
• Solubility: expected to be miscible with common nonpolar and moderately polar organic solvents (e.g., hexanes, toluene, diethyl ether, THF, DCM); low solubility in water (literature trend for alkyl ethers of this size).
• Partitioning: positive logP expected (nonpolar backbone with one ether oxygen).
• Refractive index, density, boiling point, melting point: Not specified for this item; refer to CoA/Spec Sheet.

Notes for use

• As with many terminal alkenes, the bulk properties are dominated by hydrophobic interactions; the single ether oxygen imparts modest polarity without conferring water miscibility.
• If precise values (bp, density, nD, UV cutoff) are critical for your application, consult the item-specific CoA/Spec Sheet.

Quality and Grades

Item-specific grade/purity

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

Guidance on grades (general)

• Research grade vs. analytical grades: For reactive alkene ethers, common catalog offerings include research grade (suitable for synthesis), ≥95–99% purity lines for demanding applications, and inhibitor-stabilized variants to suppress polymerization or peroxide formation. Your specific lot’s grade, inhibitor content, and purity profile will be listed on the CoA.
• HPLC/GC suitability: If using in trace analysis or kinetic studies, look for low residual solvent and narrow impurity profiles; low UV background is generally expected for simple alkenes, but item-specific UV cutoffs should be confirmed on the CoA.
• Stabilizers/Inhibitors: None are specified for this item. If present in your lot, the stabilizer type and level will be declared on the CoA/Spec Sheet. Stabilizers can subtly affect radical or acid-catalyzed reactions; remove as needed by appropriate pre-treatment (e.g., inhibitor removal cartridges) if compatible with your chemistry.
• Trace impurities (water, peroxides, metals): Not specified for this item; refer to CoA/Spec Sheet for quantitative limits.

Reaction and Applications

4-Methoxybut-1-ene is a bifunctional synthon combining a terminal alkene (C=C) with a masked alcohol (methyl ether). It is valuable for introducing a four-carbon spacer terminating in –OCH3, which can later be transformed.

Key application families (literature examples):

• Hydroboration–oxidation (anti-Markovnikov): converts the terminal alkene into 4-methoxybutan-1-ol, a useful intermediate for further derivatization (esters, mesylates/tosylates, intramolecular cyclizations to tetrahydrofurans after deprotection/activation).
• Epoxidation and subsequent ring opening: epoxide formation at C1–C2 followed by nucleophilic opening allows access to 1,2‑difunctionalized derivatives bearing a distal methoxy group.
• Ozonolysis/oxidative cleavage: terminal alkene cleavage yields formaldehyde and 3‑methoxypropionaldehyde or corresponding acids after oxidative workups—useful for aldehyde-bearing linkers.
• Radical thiol–ene and hydrosilylation: efficient addition across the double bond to install thioether or silyl groups under photochemical or catalytic conditions.
• Polymer and surface functionalization: the terminal alkene can undergo UV‑initiated grafting; the ether end imparts modest polarity to modify surface energy.

Practical tips:

• Work under inert atmosphere for air/moisture‑sensitive steps (e.g., with boranes).
• Avoid strong acids that can cleave the methyl ether or initiate cationic polymerization.
• Test for peroxides before distillation; pass through basic alumina if appropriate to remove peroxides (general practice for ethers).

Reaction Conditions

General literature guidance for common transformations of terminal alkenes/alkyl methyl ethers (not item-specific; optimize for your system):

• Hydroboration–oxidation:

  • Solvent: THF or 2‑MeTHF (anhydrous)
  • Reagents: BH3·THF or 9‑BBN; then H2O2/NaOH
  • Temperature: 0 °C to rt for hydroboration; 0–25 °C for oxidation
  • Notes: exclude moisture/air during hydroboration; anti‑Markovnikov alcohol formation expected.

• Epoxidation (peracid):

  • Solvent: DCM/CHCl3
  • Reagent: mCPBA (1.1–1.5 equiv) with NaHCO3 buffer
  • Temperature: 0–25 °C
  • Notes: control exotherm; subsequent nucleophilic opening expands functionality.

• Ozonolysis:

  • Solvent: DCM, MeOH, or MeOH/DCM; −78 to −40 °C
  • Workup: reductive (Me2S, PPh3) to aldehydes or oxidative (H2O2) to acids
  • Notes: handle ozone with appropriate destruction and ventilation; flow chemistry improves safety.

• Thiol–ene (radical):

  • Solvent: toluene, MeCN, or neat; inert atmosphere
  • Initiation: UV (365 nm) with photoinitiator or AIBN/thermal
  • Temperature: rt to 80 °C, depending on initiator
  • Notes: oxygen quenches radicals—degassing improves conversion.

Always monitor by GC/GC–MS or NMR; terminal alkenes can isomerize under acidic/metal-catalyzed conditions—use neutral ligands/bases as needed.

Safety and Handling

GHS/SDS status for this item

• Signal Word: Not specified for this item; refer to SDS.
• Hazard Statements (H-codes): Not specified for this item; refer to SDS.
• GHS Classification and Pictograms: Not specified for this item; refer to SDS.

General safety considerations (class-based, literature guidance)

• Likely hazards: flammable liquid and vapor (typical for low-MW alkene ethers); may cause irritation to eyes/skin/respiratory tract upon exposure. Always verify with the SDS for this specific product.
• PPE: safety glasses or chemical splash goggles, lab coat, appropriate chemical-resistant gloves (nitrile commonly used), and work in a fume hood.
• Handling: minimize ignition sources; ground/bond containers during transfer; avoid aerosol formation and inhalation of vapors.
• Incompatibilities: strong oxidizers; strong acids/Lewis acids (which can catalyze cationic polymerization of the alkene or ether cleavage); halogens; peroxides.
• Peroxide formation: ethers may form peroxides on air/oxygen exposure over time. Store away from light/air where practical; test for peroxides before distillation or concentration to dryness.

First aid (overview; defer to SDS)

• Inhalation: move to fresh air; seek medical attention if symptoms persist.
• Skin/eyes: rinse with water for at least 15 minutes; remove contaminated clothing; seek medical advice if irritation continues.
• Fire: use dry chemical, CO2, or alcohol-resistant foam; water spray to cool containers.

Solvent Selection

This product is a reactive liquid building block rather than a routine chromatography solvent. Nevertheless, solvent choice is key for reactions involving 4-methoxybut-1-ene.

• Polarity class (general): nonpolar to moderately polar aprotic (one ether oxygen); behaves similarly to other C5 alkyl ethers.
• Miscibility profile (literature trends): miscible with many organic solvents (hexanes, toluene, Et2O, THF, DCM, EtOAc); limited water miscibility.
• Solvent selection for transformations:
  • Electrophilic additions/halofunctionalizations: use inert, non-nucleophilic media (DCM, ClCH2CH2Cl) at 0–25 °C to control regioselectivity.
  • Radical additions or thiol–ene chemistry: employ oxygen-free, aprotic solvents (toluene, MeCN) with photoredox or thermal initiators; degas thoroughly.
  • Hydroboration–oxidation: THF or 2-MeTHF commonly used to solubilize boranes; maintain anhydrous conditions during hydroboration.
  • Epoxidation: DCM or CHCl3 for peracid epoxidations (mCPBA), or MeCN for H2O2/UHP systems with catalysts.
• Removal from reaction mixtures: its moderate volatility allows removal by rotary evaporation; avoid concentrating to dryness if peroxide risk is suspected.
• When to choose alternatives: If higher boiling/greater polarity is required, consider longer-chain methoxyalkenes; for greener media, see Green Alternatives.

Storage and Reconstitution

Item-specific storage

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

General handling/stability (class-based guidance)

• Store tightly closed in a cool, well-ventilated area away from heat, sparks, and open flame.
• Protect from light and air when practical to limit peroxide formation; consider storing under inert gas for extended periods.
• Avoid contact with strong acids and oxidizers.
• Do not freeze–thaw; this is a liquid reagent and does not require reconstitution.

Before use

• If high sensitivity is required (e.g., for polymerizations or low-temperature distillations), test for peroxides (KI–starch test) and remove if detected using appropriate treatments (e.g., passage through basic alumina) per your SOPs.
• For moisture-sensitive reactions, dry the liquid over suitable agents (e.g., molecular sieves) and handle under inert atmosphere.

Always refer to the product’s SDS and lot-specific CoA for authoritative storage stability, inhibitor content (if any), and shelf-life information.

Structure and Identity

Item-specific identifiers (from Product Data)

• SKU: M1035773
• Product Name: 4-Methoxybut-1-ene
• CAS: 4696-30-4
• Storage Conditions: Room temperature
• Research Use Note: For research use only

Core identifiers (literature/computed; not item-specific specs)

• Preferred IUPAC name (literature): 4-Methoxybut-1-ene
• Molecular formula (literature): C5H10O
• Molecular weight (literature): ~86.13 g/mol
• SMILES (literature): C=CCCOC (depicts CH2=CH–CH2–CH2–O–CH3)
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general chemistry)

• Functional groups: terminal alkene (vinyl) and alkyl methyl ether. No stereocenters; planar C=C with E/Z not applicable (terminal alkene).
• Connectivity in words: A four‑carbon chain bearing a terminal double bond at C1; the distal C4 is substituted with a methoxy group (–O–CH3), yielding an ω‑methoxy alkene.
• Reactivity handles: the C=C enables typical alkene transformations (epoxidation, hydroboration–oxidation, ozonolysis, radical additions). The ether is generally inert under neutral/basic conditions but cleavable under strong Lewis/Brønsted acids.

Synthetic Utility

Functional group set: terminal alkene + methyl ether (masked alcohol). This combination offers orthogonal reactivity and strategic flexibility.

• Chain extension and alcohol unveiling:
  • Hydroboration–oxidation furnishes 4‑methoxybutan-1-ol; subsequent ether deprotection (e.g., BBr3 or HBr under controlled conditions) gives 1,4‑butanediol derivatives after appropriate protection strategies.
• Electrophilic additions and rearrangements:
  • Halogenation/halohydrin formation then cyclization can yield tetrahydrofuran frameworks when paired with deprotection/activation steps (literature strategy for THF ring construction).
• Oxidative cleavage and homologation:
  • Ozonolysis produces 3‑methoxypropionaldehyde, a versatile handle for reductive amination, Wittig/HWE olefinations, or acetal formation.
• Ligation and surface chemistry:
  • Radical thiol–ene coupling provides rapid access to thioether-linked spacers useful in materials and linker design.
• Protecting-group logic:
  • The methyl ether is stable to many bases/nucleophiles and mild oxidants, enabling selective alkene manipulation first, followed by ether transformation at a later stage.

Overall, 4-methoxybut-1-ene serves as a compact synthon to install a four-carbon tether terminating in an oxygen substituent, enabling subsequent elaboration in target- and diversity-oriented synthesis.

Target Specificity

Not applicable. This product is a small-molecule chemical reagent (alkene ether) and does not possess immunological target specificity (no antigen/epitope, clone, isotype, or species reactivity).