3-Bromo-1-methoxybutane - ≥95% , CAS No.53424-50-3

CAS: 53424-50-3 Cat. No.: B963012 Fórmula: C₅H₁₁BrO Peso molecular: 167.040 Número CE: 823-021-4

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Especificações e pureza

≥95%

Condições de armazenamento de armazenamento

Room temperature

Pureza

≥95%

Nomes e identificadores

• Sorrisos canónicos: CC(CCOC)Br
• IUPAC Name: 3-bromo-1-methoxybutane
• InChIKey: RKFOMXBDHZVLJX-UHFFFAOYSA-N
• INCHI: 1S/C5H11BrO/c1-5(6)3-4-7-2/h5H,3-4H2,1-2H3
• Peso molecular: 167.040

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Ethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Dialkyl ethers
• Alternative Parents: Organobromides Hydrocarbon derivatives Alkyl bromides
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Dialkyl ether - Hydrocarbon derivative - Organobromide - Organohalogen compound - Alkyl halide - Alkyl bromide - Aliphatic acyclic compound
• Descrição: 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

Propriedades químicas e físicas

• Peso molecular: 167.040 g/mol
• XLogP3: 1.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 165.999 Da
• Monoisotopic Mass: 165.999 Da
• Topological Polar Surface Area: 9.200 Ų
• Heavy Atom Count: 7
• Formal Charge: 0
• Complexity: 39.100
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• 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 standardized bioassay or imaging protocols apply to this small-molecule reagent. For synthetic applications, follow reaction-specific procedures under “Reaction Conditions.” If using in a screening library or as an intermediate, develop appropriate handling SOPs (dosing, quenching, analytical verification) suited to your platform.

Biological Roles

This product is a small organic halogenated ether intended for synthetic and materials chemistry. It does not have established endogenous biological roles. Any discussion of metabolism, signaling, or physiological function is not typically applicable.

General context (literature)

• Alkyl bromides can undergo biotransformation via glutathione conjugation or hydrolysis in vivo, but such information is provided purely for chemical context and is not relevant to intended research use of this reagent.

Note: No medical, diagnostic, or therapeutic uses are implied. For research/lab use only.

Buffer Applications

Not typically applicable. 3-Bromo-1-methoxybutane is a hydrophobic, reactive organic reagent, not a buffering agent. It is not used to prepare aqueous buffer systems or for pH control. For practical handling in aqueous workflows, consider phase-transfer conditions if nucleophilic substitutions are conducted with water-soluble nucleophiles.

Green Alternatives

Greener strategy considerations (literature-based)

• Substitution chemistry: Replace alkyl bromides with less hazardous leaving groups where feasible (e.g., mesylates/tosylates generated in situ from the corresponding alcohol), reducing brominated waste.
• Solvent choice: Favor greener polar aprotics (e.g., propylene carbonate, sulfolane, or NBP) over DMF/NMP where compatible. For etheric media, 2-MeTHF or CPME can substitute for THF/diethyl ether with improved safety and sustainability profiles.
• Methylation steps (if preparing the ether): Dimethyl carbonate can sometimes replace methyl halides for O-methylation under catalytic conditions.

Illustrative comparison (general)

• DMF vs acetonitrile/propylene carbonate: DMF offers high polarity but is reprotoxic and problematic in waste; MeCN or PC may provide acceptable rates with improved EHS profiles.
• THF vs 2-MeTHF/CPME: 2-MeTHF and CPME exhibit lower peroxide formation rates, higher boiling points, and improved lifecycle metrics compared to THF, while maintaining similar solvating ability for many nucleophilic substitutions.

Process notes

• Implement halide recovery or ion-exchange capture for bromide-containing effluents.
• Minimize excess reagent and operate at the highest feasible concentration to reduce solvent use.
• Apply energy-efficient heating (microwave/flow) to shorten reaction times and decrease footprint, where compatible.

Pharmaceutical Uses

This item is not an excipient and is not documented in pharmacopeias as a formulation aid. Its relevance to the pharmaceutical sector is as a synthetic intermediate/alkylating building block in medicinal chemistry or process development.

Formulation/manufacturing context (general)

• If used in API intermediate synthesis, ensure removal of residual alkyl bromide via validated purge steps (e.g., distillation, extraction, or scavenging), and confirm absence by appropriate analytical methods (GC, HS-GC).
• Brominated waste streams should be segregated and treated according to regulatory requirements.

Physical Properties

Item-specific specifications

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

Literature/typical data for 3-bromo-1-methoxybutane (non-binding)

• Phase at ambient conditions: liquid (expected for a small alkyl bromide ether)
• Polarity: low-to-moderate (ether) with increased polarizability due to bromine; miscible with many organic solvents; poorly soluble in water (qualitative, literature-based expectation)
• Volatility: moderate; vapor pressure is expected to be lower than the parent methyl n-butyl ether due to the bromine substituent (qualitative)

General physico-chemical features (context)

• The ether oxygen confers Lewis basicity (can coordinate to metals/serve as ligand/solvate organometallics), while the secondary C–Br bond is reactive toward nucleophilic substitution and β-elimination.
• LogP is expected to be in the lipophilic range typical of C5 alkyl ethers/halides (literature expectation; verify experimentally for critical work).

For exact numerical values (bp, mp, density, refractive index, UV cutoff, water/peroxide/metal limits), consult the product’s CoA/Spec Sheet; not specified for this item.

Quality and Grades

Item-specific

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

Guidance on grades (general context)

• Research grade reagents are suitable for most synthetic and analytical workflows. When trace impurities (e.g., halide content, water, peroxides, UV-absorbing species, metals) matter, select a grade with defined limits (e.g., HPLC, anhydrous, or low-water grades) and verify by CoA.
• For nucleophilic substitution chemistry, residual moisture can suppress reactivity and promote elimination or side reactions. If your application is water-sensitive, consider drying the reagent prior to use (e.g., molecular sieves) or purchasing an anhydrous specification, when available.
• If low UV background is needed (e.g., LC applications), HPLC/UV-cutoff-certified grades reduce baseline noise; confirm UV specs on the CoA.

Batch verification

• Confirm identity by GC-MS or NMR prior to scale-up, as alkyl halides can undergo gradual hydrolysis or elimination on storage, especially in basic/alkaline containers.

Reaction and Applications

Use cases (literature-based)

• Alkylating agent: The secondary alkyl bromide undergoes SN2 displacement with a range of nucleophiles (RS−, N3−, CN−, I−, NH-based nucleophiles) to install the corresponding 3-substituent on a 1-methoxybutyl framework.
• Elimination chemistry: With strong base (KOtBu, DBU), E2 furnishes butene derivatives bearing a remote methoxy substituent; Zaitsev vs Hofmann selectivity depends on base/solvent and temperature.
• Radical and cross-coupling: Secondary alkyl bromides can engage in Ni/Co/Fe-catalyzed cross-couplings (e.g., with aryl/alkenyl partners under reductive or photoredox conditions), enabling C(sp3)–C(sp2) bond formation while the ether acts as a directing/innocent group.
• Intramolecular transformations: Under appropriate conditions, displacement by the pendant ether oxygen (after conversion to a better leaving group) could form cyclic ethers (THF derivatives), though direct intramolecular SN2 is disfavored in this substrate without activation.

Practical tips

• Control moisture: water competes in substitution and can promote hydrolysis to alcohols.
• Competing pathways: secondary substrates invite E2; lower temperatures, stronger nucleophiles, and polar aprotic solvents bias toward SN2.
• Ether stability: The methyl ether is robust to base but cleaves under strong Lewis acids (BBr3, AlCl3) or HX (HI/HBr) at elevated temperatures—avoid such conditions if retention of –OMe is desired.
• Monitoring: GC or GC-MS provides rapid assessment of substitution/elimination progress and byproduct profiles.

Representative applications (examples in literature)

• Formation of 3-azido-1-methoxybutane (precursor to amines via Staudinger/reduction).
• Thioether synthesis via RS− displacement, enabling subsequent oxidation to sulfoxides/sulfones.

Reaction Conditions

General conditions (literature guidance; optimize per system)

• SN2 substitutions

  • Solvents: MeCN, DMF, DMSO, NMP, sulfolane.
  • Nucleophiles: NaN3, KSeCN, NaI (Finkelstein), KCN (with strict safety controls), alkoxides/thiolates, amines.
  • Temperature: 0–80 °C depending on nucleophile strength; cooler temperatures suppress E2.
  • Notes: Use excess nucleophile or phase-transfer catalysts for heterogeneous systems; employ anhydrous conditions. Secondary substrates may require higher nucleophile loading or catalytic assistance.

• E2 eliminations

  • Bases: KOtBu, NaOtBu, LDA, DBU.
  • Solvents: t-BuOH, THF, 2-MeTHF, DMSO.
  • Temperature: typically 40–100 °C; monitor for isomer ratios if multiple alkenes form.

• Cross-coupling/radical chemistry

  • Catalysts: Ni(II)/ligand systems under reductive conditions (e.g., Mn/Zn), or photoredox/nickel dual catalysis.
  • Solvents: DMA, MeCN, THF, 2-MeTHF; additives (halide salts, phosphines/pybox ligands) per literature.
  • Light: blue LEDs for photoredox; control oxygen rigorously.

Workup/analytics

• Quench nucleophiles carefully; wash with aqueous bicarbonate/brine; dry over MgSO4/Na2SO4.
• Analyze by GC-FID/GC-MS; confirm stereochemical inversion in SN2 by chiral GC/NMR if relevant.

Safety and Handling

GHS and regulatory

• Signal word, hazard statements, classification, and pictograms: Not specified for this item; refer to the SDS for authoritative information.

General hazards for alkyl bromide ethers (literature-based guidance)

• Flammability: Organic halide ethers are generally combustible; keep away from ignition sources. Vapors may form flammable mixtures with air.
• Acute toxicity/irritation: Alkyl bromides can be irritating to skin, eyes, and respiratory tract; some may exhibit narcotic effects at high vapor concentrations. Avoid inhalation and contact.
• Peroxide formation: Ethers can form peroxides upon prolonged exposure to air/oxygen and light. Although the presence of bromine may alter rates, prudent practice is to treat as a peroxide-forming chemical.

PPE and engineering controls

• Use in a fume hood with appropriate local exhaust.
• Wear chemical-resistant gloves (e.g., nitrile), lab coat, and splash goggles. Consider double-gloving for extended handling.

Storage and incompatibilities

• Store tightly closed at room temperature as provided; keep in a cool, well-ventilated area, protected from light.
• Keep away from strong bases (risk of E2 elimination), strong nucleophiles (uncontrolled substitution), strong oxidizers, and sources of ignition.
• For ethers: minimize headspace oxygen where feasible; label with date opened; periodically test for peroxides before distillation or concentration.

First aid (overview; defer to SDS)

• Inhalation: Move to fresh air; seek medical attention if symptoms persist.
• Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; get medical advice.
• Ingestion: Rinse mouth; do not induce vomiting; seek medical attention immediately.

Solvent Selection

Applicability

• 3-Bromo-1-methoxybutane is primarily a reactive alkylating agent/building block rather than a general-purpose solvent. Solvent selection here refers to the choice of medium when using it as a substrate/reagent.

Recommended media by transformation (literature guidance)

• SN2 substitutions (e.g., with thiolates, azide, cyanide, alkoxides): polar aprotic solvents such as acetonitrile, DMF, DMSO, NMP, or sulfolane often enhance nucleophilicity and rates. Temperature control is important to limit E2.
• E2 eliminations (to give alkenes): use strong, hindered bases (e.g., t-BuOK) in tert-BuOH, THF, 2-MeTHF, or DMSO; elevate temperature to drive elimination.
• Metal-mediated reactions (e.g., radical/nickel catalyzed cross-coupling of secondary alkyl bromides): employ coordinating ethers (THF, 2-MeTHF, CPME) or polar aprotics, according to catalyst system.

Miscibility profile (general)

• Expected to be miscible with many organic solvents (ethers, hydrocarbons, chlorinated solvents, esters) and poorly soluble in water. Verify experimentally for process design.

Comparison notes

• Compared with non-halogenated methyl n-butyl ether, the bromoether is less suitable as an inert solvent because it is reactive at the C–Br site; prefer truly inert ethers (MTBE, TBME, 2-MeTHF) when solvent function is required.

Storage and Reconstitution

Storage (item-specific)

• Store at room temperature (per Product Data). Keep container tightly closed in a cool, well-ventilated place.

Best practices (general for ethers/alkyl bromides)

• Protect from light and air to minimize peroxide formation and slow side reactions (hydrolysis/elimination). Purge headspace with inert gas for long-term storage when feasible.
• Clearly label the date opened; periodically test for peroxides before any distillation or concentration.
• Avoid contact with strong bases, strong nucleophiles, and strong oxidizers during storage.

Reconstitution/handling

• Supplied neat; no reconstitution required. If a stock solution is desired, prepare in a dry, oxygen-free organic solvent compatible with the intended reaction (e.g., anhydrous MeCN, THF, or 2-MeTHF) and store under inert atmosphere at low temperature for short periods.

Shipping

• Shipped conditions: Not specified for this item; refer to CoA/Spec Sheet.

Disposal

• Treat as a halogenated organic waste. Collect in appropriate halogenated waste containers per institutional and regulatory guidelines.

Structure and Identity

Item-specific (Product Data)

• SKU: B963012
• Product name: 3-Bromo-1-methoxybutane
• CAS: 53424-50-3
• PubChem CID: 23511183
• InChIKey: 318586 (as provided)
• Storage conditions: Room temperature
• Research use: For research use only

Literature/Computed identity (for reference; not item specifications)

• Preferred IUPAC name (literature): 3-bromo-1-methoxybutane
• Molecular formula (literature): C5H11BrO
• Molecular weight (literature): ~167.04 g/mol
• Functional groups: alkyl bromide (secondary), dialkyl ether (methyl n-alkyl ether)
• 2D structural description: a linear butyl chain bearing a terminal methoxy group at C1 (–OCH3) and a bromine substituent on C3. The carbon bearing bromine is secondary [–O–CH2–CH2–CH(Br)–CH3]. No aromatic rings; no stereocenters specified (racemic if generated at C3 during synthesis).
• Representative SMILES (literature): CH3O–CH2–CH2–CH(Br)–CH3 (plain-text depiction)

Notes

• The above “literature” identifiers and descriptors are provided for general reference to the neutral parent compound. Always verify exact identifiers for your lot on the CoA/Spec Sheet.

Synthetic Utility

Functional group landscape

• Reactive site: secondary C–Br at C3 enables SN2 (with inversion) and E2 pathways.
• Latent functionality: –OMe is a stable ether protecting motif for the corresponding alcohol; removable under Lewis acidic or strong protic conditions (e.g., BBr3, HI), allowing two-stage manipulations.

Strategic uses (literature)

• SN2 installation of nitrogen/oxygen/sulfur nucleophiles to access libraries of 3-substituted-1-methoxybutanes; subsequent ether cleavage can unmask 3-substituted butan-1-ols.
• Carbon–carbon formation via radical/catalytic methods (Ni/photoredox) from the alkyl bromide, enabling sp3–sp2 couplings while tolerating the ether.
• Elimination to alkenes, followed by hydrofunctionalizations (epoxidation, hydroboration–oxidation), provides diverse elaboration routes.

Retrosynthetic value

• Viewed as a masked 3-substituted butan-1-ol synthon: finalize substitution first under SN2 conditions, then demethylate the ether to reveal the primary alcohol late in the sequence when desired.

Target Specificity

Not applicable. This product is a small-molecule chemical reagent, not a biological targeting agent (e.g., antibody, inhibitor with defined biochemical target), and no target specificity data are provided in the Product Data.