3-Bromopropyl Acetate - ≥97% , CAS No.592-33-6

CAS: 592-33-6 Cat. No.: B405317 Fórmula: C₅H₉BrO₂ Peso molecular: 181.03

GRADE & PURITY ≥97%

Synonyms

Acetic Acid 3-Bromopropyl Ester

Storage

Store at 2-8°C

Shipped In

Wet ice

Specifications

Sinónimos

Acetic Acid 3-Bromopropyl Ester

Especificações e pureza

≥97%

Condições de armazenamento de armazenamento

Store at 2-8°C

Enviado em

Wet ice

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

Pureza

≥97%

Nomes e identificadores

Peso molecular

181.03

Reaxy-Rn

1745615

Propriedades químicas e físicas

• Sensibilidade: Heat Sensitive
• Índice de refração: 1.46
• Ponto de inflamação (°C): 89 °C
• Ponto de ebulição (°C): 163 °C

Application Protocols

No standardized biological assay protocols are associated with this small-molecule reagent.

General laboratory protocol templates (chemistry-focused):

• Representative O-alkylation: To a dry flask charge phenol (1.0 eq) and K2CO3 (1.5 eq) in acetonitrile (0.1–0.5 M). Stir 10–20 min, then add 3-bromopropyl acetate (1.2 eq) dropwise at 25–35°C. Stir 4–12 h (monitor by TLC/LC). Filter salts, concentrate, and purify. Optional: deprotect with K2CO3/MeOH to yield the 3-hydroxypropyl ether.
• Representative S-alkylation: Dissolve thiol (1.0 eq) and Et3N (1.1 eq) in acetone (0.2 M), cool to 0–5°C, add 3-bromopropyl acetate (1.1–1.3 eq). Warm to RT and stir 1–3 h.

These are illustrative, literature-style procedures to aid planning. Optimize equivalents, solvent, and temperature for your specific substrate and scale.

Biological Roles

This compound is a synthetic organic reagent with no intrinsic biological role. Any references below describe general chemistry context rather than bioactivity claims.

• Functional class: Electrophilic alkylating agent bearing a protected alcohol. It is used to introduce a 3-acetoxypropyl (and, after deprotection, 3-hydroxypropyl) substituent into small molecules, polymers, and surfaces.
• Relevance to bioconjugation workflows (general): After SN2 installation onto nucleophilic biomolecule mimics (e.g., thiol-bearing linkers), the acetate can be removed to expose a hydroxyl group, which can then be transformed into carbonate, carbamate, or activated esters for subsequent coupling steps.
• Metabolic/biochemical activity: None established; not a metabolite or cofactor. Hydrolysis to 3-bromopropanol and acetic acid can occur chemically; such transformations are not enzymatic roles of the intact molecule.

Note: This product is for research use only and is not intended for use in humans or animals. No medical, diagnostic, or therapeutic claims are made.

Buffer Applications

Not typically applicable. 3-Bromopropyl acetate is a reactive organic reagent and is neither a buffering agent nor a component of common biochemical buffer systems.

• Recommendation: For work in aqueous media, avoid buffers containing strong nucleophiles or bases that would promote hydrolysis or substitution. Conduct reactions in suitable organic solvents as outlined under Solvent Selection and Reaction Conditions.

Green Alternatives

Greener choices relate to both the electrophile and the reaction medium.

Electrophile strategy (literature/practice):

• Replace bromide with alternative leaving groups when feasible:
  • 3-Tosyloxypropyl acetate: Comparable SN2 reactivity; avoids halogenated waste but introduces sulfonate byproducts (higher E-factor if not recovered).
  • 3-Mesyloxypropyl acetate: High reactivity; potentially less persistent than bromides but requires careful handling.
  • 3-Chloropropyl acetate: Less reactive; may necessitate higher temperature/longer time, but reduces brominated waste.
• Two-step alternative: Alkylate with 3-bromopropanol (then acetylate) or alkylate with 3-chloropropanol and acetylate; can reduce overalkylation but may increase step count.

Solvent choices (typical tradeoffs):

• 2-MeTHF vs DMF/DMSO: 2-MeTHF offers lower toxicity, biorenewable sourcing, easier workup; SN2 rates may be slower than DMF/DMSO.
• Acetonitrile vs chlorinated solvents: MeCN provides good SN2 performance and easy removal; chlorinated solvents (DCM) are effective for handling but less preferred environmentally.
• Propylene carbonate or Cyrene: High-boiling polar aprotics with improved EHS profiles; may require higher temperatures and careful product isolation.

Comparison snapshot (general):

• Metric: Worker exposure/EHS — 2-MeTHF, MeCN, propylene carbonate often score better than DMF/DMSO/DCM.
• Metric: Reactivity — DMF/DMSO > MeCN ≈ acetone > 2-MeTHF > esters.

Adopt closed handling, solvent recycling, and minimized halogenated waste streams to further improve process sustainability.

Pharmaceutical Uses

No excipient or pharmacopeial status is provided for this item; it is offered for research use only.

General context (non-clinical, process-oriented):

• Role as an intermediate: 3-Bromopropyl acetate can be used to introduce 3-hydroxypropyl groups (after deprotection) into small-molecule scaffolds, enabling fine-tuning of solubility, hydrogen-bonding capacity, and linker length in discovery chemistry.
• Protecting-group strategy: The acetate serves as a temporary protecting group for the terminal alcohol during N-, O-, or S-alkylation steps, improving selectivity in stepwise synthesis.
• Quaternary ammonium salt formation: Tertiary amines can be quaternized to generate 3-acetoxypropyl ammonium salts, which may subsequently be deprotected to furnish hydroxypropyl ammonium derivatives (used as intermediates in material or API precursor synthesis).

No claims are made regarding therapeutic efficacy, safety in humans, or regulatory listing. For GMP or pharmacopeial applications, consult your quality unit and request additional documentation for the specific lot if appropriate.

Physical Properties

Item-specific physical property specifications are not provided for this catalog entry.

• Boiling point: Not specified for this item; refer to CoA/Spec Sheet. (General note: primary bromoalkyl acetates typically distill under reduced pressure to limit decomposition.)
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Vapor pressure: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (general/literature expectations):
  • Miscible with many organic solvents (e.g., dichloromethane, chloroform, toluene, THF, acetone, acetonitrile, ethyl acetate).
  • Limited solubility in water; may undergo slow hydrolysis in aqueous media, especially under basic conditions.
• Partitioning: As a moderately nonpolar halogenated ester, logP is expected to be positive (literature expectation), supporting extraction into organic phases.

Practical notes (general):

• Distillation should be performed under inert atmosphere and reduced pressure to minimize hydrolysis and elimination (to allyl acetate).
• Drying over neutral salts (e.g., CaCl2, MgSO4) is typical after aqueous workups; avoid prolonged contact with strong bases to prevent side reactions.

Always consult the product’s CoA/Spec Sheet for any item-specific certified values; literature values are provided only as general guidance.

Quality and Grades

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

Interpretation and implications (general guidance):

• When a specific grade is not stated, users should rely on the lot-specific Certificate of Analysis (CoA) for assay, GC purity profile, and limits on common impurities (e.g., starting 3-bromopropanol, allyl acetate from elimination, acetic acid, moisture).
• For sensitive applications (e.g., anhydrous SN2, polymer end-group functionalization), consider confirming residual water content (e.g., Karl Fischer), acidity, and halide content as relevant to your process requirements.
• UV cutoffs and trace metal limits are typically not critical for this class of reagent; if needed for analytical photochemical or catalytic applications, request supporting documentation.
• Stabilizers: None are indicated in the product data. If your process is base-catalyzed or prolonged at elevated temperature, evaluate the need for inhibitor-free handling and verify absence of added stabilizers via CoA.
• If HPLC/GC suitability is required, pre-test a small aliquot to confirm baseline stability under your chromatographic conditions (esters can undergo partial hydrolysis in moist solvents).

For procurement specifications or compliance needs (e.g., ISO, RoHS), contact Aladdin Scientific with the SKU and lot number for documentation.

Reaction and Applications

3-Bromopropyl acetate is a versatile electrophile for installing a masked 3-hydroxypropyl handle via SN2 alkylation, followed by acetate deprotection.

Key application families (literature/practice):

• O-Alkylation (Williamson ether synthesis): Phenols and alcohols to afford 3-acetoxypropyl ethers; subsequent hydrolysis gives 3-hydroxypropyl ethers commonly used to tune polarity and H-bonding in ligands and materials.
• S-Alkylation: Thiols to 3-acetoxypropyl thioethers; useful in bioconjugation precursors and crosslinker synthesis.
• N-Alkylation/Quaternization: Amines, amidines, imidazoles, pyridines to introduce pendant 3-acetoxypropyl or produce quaternary ammonium salts; deacetylation generates 3-hydroxypropyl-functionalized amines.
• Polymer and surface modification: Grafting of 3-acetoxypropyl groups onto polymers (e.g., polyethers, polysiloxanes) or silica surfaces; acetate deprotection unveils hydroxyls for further elaboration (carbonate/urethane formation, click-like sequences after activation).
• Intramolecular cyclization precursors: After deprotection, 1,3-diols can be formed or further converted to cyclic carbonates/ethers.

Practical tips:

• Favor SN2: Use polar aprotic media (MeCN, DMF, DMSO), moderate temperatures (0–50°C), and non-nucleophilic bases (K2CO3, Cs2CO3). Avoid strong base/heat that promote β-elimination to allyl acetate.
• Water control: Ester hydrolysis competes in wet media; keep solvents dry and minimize aqueous exposure during workup.
• Leaving group strength: Bromide offers a good rate–selectivity balance; chloride analogs react more slowly; tosylates/mesylates are alternatives when halides are restricted.
• Deprotection: Acetate removal under mild basic (e.g., K2CO3/MeOH) or acidic (e.g., AcOH/H2O, catalytic acid in alcohol) conditions reveals the 3-hydroxyl.

Reaction Conditions

Typical conditions (literature guidance; optimize per substrate):

• O-Alkylation (phenols/alcohols):

  • Base: K2CO3 (1.2–2.0 eq) or Cs2CO3 (1.1–1.5 eq).
  • Solvent: Acetonitrile, acetone, 2-MeTHF, or DMF.
  • Temperature/time: 20–50°C, 2–16 h.
  • Notes: Dry conditions; add halide slowly to minimize local excess and elimination.

• S-Alkylation (thiols):

  • Base: K2CO3, Et3N, or NaH; often proceeds at RT.
  • Solvent: MeCN, acetone, or DMSO.
  • Temperature/time: 0–25°C, 0.5–6 h.

• N-Alkylation / quaternization:

  • For secondary amines: K2CO3 or DIPEA; MeCN or DMF; 20–40°C.
  • For tertiary amines (quaternization): Neat or MeCN; 20–60°C; monitor to avoid overreaction elsewhere in the molecule.

• Phase-transfer conditions (for weakly soluble nucleophiles):

  • Base: K2CO3 or Na2CO3 (aq) with PTC (e.g., TBAB, TBAHS).
  • Solvent: Toluene or DCM; biphasic 20–40°C.

• Workup/purification:

  • Quench with neutral buffer or saturated NH4Cl; avoid strong base in aqueous quench to limit hydrolysis.
  • Extract with EtOAc or DCM; dry and concentrate under reduced pressure.
  • Purify by distillation (reduced pressure) or flash chromatography as appropriate.

• Expected outcomes: SN2 products generally in good yields when elimination and hydrolysis are suppressed; actual yields are substrate-dependent (consult literature for closely related systems).

Caution: All values above are general literature norms; they are not item-specific specifications.

Safety and Handling

Hazard classification details are not provided in the product data for this item; consult the SDS for authoritative information.

• GHS/Signal word, H-statements, pictograms: Not specified for this item; refer to SDS.
• Likely hazards (general for primary bromoalkyl esters):
  • Harmful if swallowed, inhaled, or in contact with skin; may cause skin and eye irritation.
  • Alkylating character may cause lachrymation and respiratory irritation; handle in a fume hood.
• PPE: Lab coat, nitrile gloves (change regularly), splash goggles; consider a face shield for larger scale pouring.
• Engineering controls: Use in a certified chemical fume hood. Maintain closed transfer systems on scale when feasible.
• Incompatibilities: Strong bases and nucleophiles (promote substitution/elimination), strong oxidizers, moisture (hydrolysis), and strong acids/bases for storage.
• Reactivity/instability (general): Primary alkyl bromide can undergo SN2 with nucleophiles; ester moiety can hydrolyze under acidic or basic conditions. Under strong base/heat, β-elimination can generate allyl acetate.
• First aid overview (general):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin contact: Remove contaminated clothing; wash with soap and water.
  • Eye contact: Rinse cautiously with water for several minutes; seek medical advice.
  • Ingestion: Rinse mouth; do not induce vomiting; get medical attention.
• Storage: Store at 2–8°C (per Product Data), tightly closed, under inert gas recommended for long-term storage. Keep away from moisture and bases.

Always defer to the SDS and your institutional EHS policies for definitive guidance.

Solvent Selection

This product is a reactive alkylating reagent rather than a process solvent. Solvent selection here refers to media for its use in synthesis and handling.

General solvent compatibility (literature/practice):

• Polar aprotic solvents (preferred for SN2): acetonitrile, DMF, DMSO, nitromethane, DMA. These enhance nucleophilicity and minimize elimination.
• Moderately polar solvents: acetone, MEK, ethyl acetate, 2-MeTHF; often suitable with inorganic bases (e.g., K2CO3) or phase-transfer catalysts (PTC).
• Nonpolar/aromatic: toluene, chlorobenzene; used with PTC or strong soluble bases.
• Halogenated: DCM, chloroform; good solvency and stability for workups and extractions; limited for strongly basic reactions.
• Alcohols/water: generally avoided for alkylation steps due to competing hydrolysis/solvolysis, but may be used intentionally for deprotection.

Selection tips:

• For O-alkylations (Williamson-type) of phenols/alcohols: K2CO3 or Cs2CO3 in acetonitrile, acetone, or 2-MeTHF at 0–50°C.
• For S-alkylations: acetone or MeCN at ambient temperature; weaker bases often suffice.
• For N-alkylations: MeCN, DMF, or DMSO with tertiary amines (quaternization) or with base for primary/secondary amines.

Small comparison (general):

• DMF/DMSO: highest SN2 rates, but more challenging workup and EHS profile.
• MeCN/acetone: balanced reactivity and easy removal; lower EHS burden.
• 2-MeTHF/EtOAc: greener options; may require longer reaction time or higher temperature versus DMF.

Storage and Reconstitution

• Storage conditions (from Product Data): Store at 2–8°C.
• Shipping: Shipped on wet ice (from Product Data).
• Container: Keep tightly closed in original container; recommend amber glass to limit light exposure.
• Atmosphere: Store under inert gas (nitrogen or argon) if possible to minimize hydrolysis during long-term storage.
• Handling: Bring to ambient temperature before opening to minimize moisture condensation. Dispense quickly and reseal immediately.
• Stability considerations (general): Susceptible to hydrolysis (ester cleavage) and to base-promoted elimination; avoid contact with strong bases or aqueous alkaline media during storage.
• Reconstitution: Not applicable; supplied as a neat liquid reagent (appearance not specified for this item; refer to CoA/Spec Sheet.).
• Shelf-life: Not specified for this item; refer to CoA/Spec Sheet.

For best results, minimize headspace, use dry transfer tools/syringes when appropriate, and record opening dates for inventory control.

Structure and Identity

3-Bromopropyl acetate is a bifunctional alkylating reagent bearing a primary alkyl bromide and an acetate-protected alcohol, useful for installing 3-hydroxypropyl motifs after deprotection.

• SKU: B405317
• Product name: 3-Bromopropyl Acetate
• CAS: 592-33-6
• Category: Chemical and Biochemical Reagents (research use only)
• Molecular formula (literature): C5H9BrO2
• Molecular weight (literature): ~181.03 g/mol
• SMILES (literature): CC(=O)OCCCBr
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• CID: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general description):

• Contains an acetate ester (–O–C(O)CH3) linked via oxygen to a 3-carbon chain terminating in a primary bromide (–CH2–CH2–CH2–Br).
• Functional groups: primary alkyl bromide (good SN2 electrophile), acetate ester (alcohol protecting group; hydrolyzable under acidic or basic conditions).
• No stereocenters; achiral molecule.
• 2D structure in words: Acetyl group (CH3–C(=O)–) attached to an oxygen that connects to a three-methylene chain ending with bromide: CH3–C(=O)–O–CH2–CH2–CH2–Br.

Synthetic Utility

Reactivity overview:

• Electrophile: Primary alkyl bromide exhibits robust SN2 reactivity with O-, N-, S-, and selected C-nucleophiles.
• Protecting group synergy: The acetate masks the terminal alcohol, permitting selective mono-alkylation and orthogonal deprotection.

Common transformations (literature/practice):

• Williamson ether synthesis: Phenols/alcohols + base (K2CO3, Cs2CO3) → 3-acetoxypropyl ethers; deacetylation → 3-hydroxypropyl ethers.
• Thioether formation: Thiols + mild base (NaHCO3, K2CO3) or neat tertiary amines → 3-acetoxypropyl thioethers.
• Amine alkylation and quaternization: Primary/secondary amines (controlled monoalkylation) or tertiary amines (R3N → R3N+–(CH2)3–OAc Br−).
• C-alkylation: Active methylene compounds (β-dicarbonyls, malonates) under phase-transfer or strong base conditions.

Selectivity/side reactions:

• Competing E2 elimination can yield allyl acetate under strong base/heat; mitigate with lower temperatures, polar aprotic solvents, and non-nucleophilic bases.
• Ester hydrolysis in moist/basic media reduces effective electrophile concentration; maintain anhydrous conditions.

Downstream elaboration:

• Deprotect acetate with K2CO3/MeOH, NaOMe/MeOH, or mild acid to unmask the alcohol, enabling carbonate/carbamate formation, tosylation/mesylation (to create di-functional linkers), or intramolecular cyclizations.

Target Specificity

Not applicable. This product is a small-molecule chemical reagent and is not an antibody, probe, or biologic. No antigen, epitope, or isotype information applies.

Perguntas frequentes

What is the purity of this product?

This product is supplied at ≥97% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at 2–8 °C. Refrigerated storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships chilled on wet ice. Unpack on arrival and transfer it to the storage condition stated above.

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

The CAS Number is 592-33-6, the molecular formula is C5H9BrO2, and the molecular weight is 181.03 g/mol.

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.