Ethyl 2-bromo-3-phenylpropanoate - ≥95% , CAS No.39149-82-1

CAS: 39149-82-1 Cat. No.: E1067829 Summenformel: C₁₁H₁₃BrO₂ Molekulargewicht: 257.13 EG-Nummer: 815-428-0 PubChem CID: 4737529

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥95%

Storage

Room temperature

Reinheit

≥95%

Namen und Kennungen

Kanonisches Lächeln

CCOC(=O)C(CC1=CC=CC=C1)Br

IUPAC Name

ethyl 2-bromo-3-phenylpropanoate

InChIKey

MVCUFNYFDQMSTE-UHFFFAOYSA-N

INCHI

1S/C11H13BrO2/c1-2-14-11(13)10(12)8-9-6-4-3-5-7-9/h3-7,10H,2,8H2,1H3

Isomere SMILES

CCOC(=O)C(CC1=CC=CC=C1)Br

PubChem CID

4737529

Molekulargewicht

257.13

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Klasse Fatty Acyls
      • Subclass Fatty acid esters

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Klasse: Fatty Acyls
• Subclass: Fatty acid esters
• Intermediate Tree Nodes: Not available
• Direct Parent: Fatty acid esters
• Alternative Parents: Benzene and substituted derivatives Alpha-halocarboxylic acid derivatives Carboxylic acid esters Monocarboxylic acids and derivatives Organobromides Organic oxides Hydrocarbon derivatives Carbonyl compounds Alkyl bromides
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Fatty acid ester - Monocyclic benzene moiety - Benzenoid - Alpha-halocarboxylic acid derivative - Alpha-halocarboxylic acid or derivatives - Carboxylic acid ester - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Alkyl bromide - Organohalogen compound - Organobromide - Organooxygen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Alkyl halide - Aromatic homomonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
• 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: 257.120 g/mol
• XLogP3: 3.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 256.01 Da
• Monoisotopic Mass: 256.01 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 176.000
• 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

Not applicable. No biological assay protocols (WB, IHC, IF, FC) are associated with this small-molecule reagent in the provided data. For synthetic applications, refer to the Reaction Conditions section for literature-style procedures.

Biological Roles

This product is a synthetic organic intermediate (α-bromo aromatic ester) and is not a naturally occurring biomolecule. No endogenous biological role is expected.

• No biochemical pathway participation is known for this specific structure (literature, general).
• Any biological testing should be performed in accordance with institutional EHS policies.
• Research Use Note: For research use only; not for human or veterinary use.

Buffer Applications

Not typically applicable. Ethyl 2-bromo-3-phenylpropanoate is a hydrophobic organic electrophile, not used as a buffering agent. For aqueous work, focus on extraction/phase-transfer or non-aqueous reaction media as discussed under Solvent Selection and Reaction Conditions.

Green Alternatives

Guidance below is literature-based and intended to help reduce environmental and safety impact while using this α-bromo ester.

Strategy 1: Prefer greener solvents when feasible

• Replace DMF/DMSO with MeCN, EtOAc, 2-MeTHF, or CPME for SN2 and cross-couplings, provided rates/selectivity remain acceptable.

Strategy 2: Tune base/nucleophile to minimize byproducts

• Use carbonate bases in acetone/MeCN for thiolations to reduce elimination and salt waste vs strong alkoxides in protic solvents.

Strategy 3: Consider alternative leaving groups (project-dependent)

• In contexts where halogen waste is critical, generating the analogous mesylate/tosylate in situ from the corresponding alcohol can avoid bromide salts; tradeoff: potentially lower reactivity and additional step.

Small comparison (literature, general):

• DMF/DMSO: high SN2 rates; EHS concerns (reproductive toxicity for DMF), difficult workup.
• MeCN: good SN2 rates; flammable; lower toxicity than DMF; easy removal.
• 2-MeTHF/CPME: bio-based or greener ethers; enable phase split workups; good for photoredox/Ni couplings; form peroxides over long storage—monitor.
• EtOAc: greener ester solvent; suitable for some substitutions and for extractions; may reduce rates with very hard nucleophiles.

Waste minimization:

• Capture inorganic bromide in dedicated halide waste; optimize stoichiometry to limit excess nucleophile.
• Explore continuous flow for hazardous nucleophiles (e.g., azide) to reduce inventory and improve heat/mass transfer.

Pharmaceutical Uses

As a reactive α-bromo ester, this material is used as a synthetic intermediate in research-scale molecule construction. It is not an excipient and has no pharmacopeial monograph specified in the provided data.

• Typical roles (literature, general): intermediate in the preparation of β-aryl ethylamine derivatives, cinnamate esters, and other fine chemicals.
• Formulation/excipient status: Not applicable; not specified for this item.
• Regulatory status: Not specified for this item; refer to institutional and regional regulations when using in GMP-adjacent research.
• Reminder: For research use only; not for human or veterinary use.

Physical Properties

Item-specific physicochemical specifications are not listed in the provided Product Data. Consult the CoA/Spec Sheet for authoritative values.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
  • α-Bromo esters of comparable size typically distill under reduced pressure (literature, qualitative).
• Melting point: Not applicable/typically liquid for analogous compounds (literature, qualitative). Specific value: Not specified for this item; refer to CoA/Spec Sheet.
• Density, refractive index, UV cutoff, water/peroxide/metal content: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility: Not specified for this item; refer to CoA/Spec Sheet.
  • General expectation (literature): miscible with common organic solvents (EtOAc, DCM, THF, toluene, MeCN) and insoluble in water.
• LogP/pKa: Not specified for this item; refer to CoA/Spec Sheet.
  • Qualitative: nonpolar–moderately polar organic liquid; no titratable groups; ester carbonyl can be deprotonated α to C=O under strong base only (literature).

Notes for method development (literature, general):

• For GC/GC–MS, the compound is thermally labile toward HBr elimination at high injector temperatures; use split/splitless conditions with moderated inlet temperature and deactivated liners.
• For HPLC, reversed-phase methods with UV detection at 210–230 nm are typical for esters with aromatic chromophores.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for actual assay, impurity profile, and stabilizer (if any).

Context for this compound class (literature/generic guidance):

• α-Bromo esters can undergo elimination or hydrolysis; rigorous control of acid/base impurities and water content improves shelf-life and performance in SN2 or coupling reactions.
• For synthesis workflows requiring high selectivity (e.g., asymmetric substitutions), chemists often prefer material with:
  • Low residual halide ions and HBr (to minimize catalyst poisoning and side reactions).
  • Low UV-absorbing impurities for chromatographic monitoring.
  • Specified enantiopurity when a single enantiomer is required (this listing does not specify stereochemistry; treat as racemic unless the CoA indicates otherwise).
• If offered in “anhydrous” or “high-purity” variants, these usually imply tighter specs on water and volatile acidity and may be packaged under inert gas; no such claims are made in the provided data for this SKU.

What to check on receipt (best practice):

• Confirm identity by 1H/13C NMR (diagnostic: α-CH–Br at ~4.0–4.5 ppm; benzylic CH2 at ~2.9–3.2 ppm; ethyl ester quartet/triplet), GC/LC purity, and accurate mass.
• Review the CoA for assay, residual solvents, and stabilizer content (if present).

Reaction and Applications

This α-bromo benzylic ester is a versatile electrophile and radical precursor. The benzylic position and α-carbonyl activation provide complementary reactivity modes (literature, general):

• Nucleophilic substitutions (SN2):
  • Amination: displacement with primary/secondary amines to access β-aryl ethylamino esters (precursors to phenethylamine motifs). Phase-transfer or polar aprotic media increase rates.
  • Azidation/cyanation: NaN3 or KCN in MeCN/DMF give the corresponding α-azido or α-cyano esters; the azide can be reduced to primary amines (Staudinger/hydrogenation).
  • Thiolation/selenation: RS− or Se-nucleophiles furnish thio/seleno esters, valuable in further cross-couplings or oxidations.

• Elimination (E2): Strong, non-nucleophilic bases (t-BuOK, DBU) yield ethyl cinnamate via dehydrohalogenation. Benzylic stabilization favors clean alkene formation under controlled conditions.

• Enolate and umpolung strategies: The parent ester enolizes; however, here the C–Br provides direct electrophilic handle. Post-substitution, the ester can be elaborated (hydrolysis, reduction to alcohol, amidation, Curtius/HWE sequences).

• Radical and cross-coupling:
  • Single-electron activation of the C–Br bond enables Ni/photoredox couplings to form C(sp3)–C(sp2) bonds with aryl/alkenyl partners (Merger of SET with Ni catalysis).
  • Giese-type additions using photoredox catalysis deliver new C–C bonds at the α position.
  • Atom transfer (Kharasch) reactions with alkenes are feasible under radical initiators.

• Stereochemical applications: When used in asymmetric SN2 or radical processes with chiral catalysts or auxiliaries, enantioenriched α-substituted products are accessible (literature reports). If stereochemical control is required, start from or resolve enantioenriched material (this item’s enantiopurity is not specified).

Reaction Conditions

The following are literature-style general conditions for α-bromo aromatic esters; optimize for your substrate and scale. Item-specific validated conditions are not provided in the Product Data.

• Azidation (to α-azido ester): NaN3 (1.2–1.5 equiv) in MeCN or DMF, 0–25 °C, 2–8 h; monitor by TLC/LC. Workup by aqueous quench and extraction. Caution: hydrazoic acid hazards—use fume hood and proper scrubbing.
• Amination: Primary amine (2.0–3.0 equiv) in MeCN or THF with K2CO3 or i-Pr2NEt (1–2 equiv), 20–60 °C, 4–16 h. For less nucleophilic amines, add catalytic KI or employ phase-transfer (TBAB) in toluene/50% aq. NaOH (biphasic). Minimize temperature to suppress elimination.
• Thiolation: Thiol (1.1–1.5 equiv), K2CO3 (2 equiv), acetone or MeCN, 20–30 °C, 2–6 h; typically high conversions with limited side products.
• Elimination to ethyl cinnamate: t-BuOK (1.2 equiv) in THF or t-BuOH, 0–25 °C, 0.5–2 h. Quench carefully; HBr formation possible.
• Cross-coupling (Ni/photoredox, C(sp3)–C(sp2)):
  • Catalyst: NiBr2·glyme (5–10 mol%) + bipyridine ligand (5–15 mol%).
  • Photocatalyst: Ir(ppy)3 (0.5–1.0 mol%) or organic dyes.
  • Base: K3PO4 or Cs2CO3 (2 equiv).
  • Solvent: 2-MeTHF, MeCN, or DMA; blue LEDs; 25–40 °C; 4–16 h.
  • Provides coupling at the α-carbon via SET reduction of C–Br.

Notes:

• Dry, oxygen-minimized conditions improve outcomes for nucleophilic substitutions and radical couplings.
• For chiral synthesis, use enantiopure starting material or asymmetric catalysis; racemization can occur through enolization under base.

Safety and Handling

Always consult the SDS for definitive hazard information and regulatory guidance for this SKU.

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

General safety considerations for α-bromo esters (literature, general):

• Hazards: Combustible liquid; harmful if swallowed or in contact with skin; causes skin and eye irritation; may cause respiratory irritation. α-Bromo carbonyls are alkylating agents and can be lachrymatory.
• PPE: Wear lab coat, safety glasses/goggles, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood to avoid inhalation of vapors.
• Handling: Avoid moisture and bases unless intended; α-bromo esters can undergo base-promoted elimination to give alkenes (e.g., ethyl cinnamate) and can hydrolyze under strongly basic/aqueous conditions.
• Incompatibilities: Strong bases, strong nucleophiles (uncontrolled reactions), strong oxidizers, powdered metals. Avoid prolonged contact with amines unless in controlled reaction conditions.
• First aid (overview):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin: Wash with soap and water; remove contaminated clothing.
  • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if easy.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
• Spill/Fire: For small spills, absorb with inert material. For fire, use CO2, dry chemical, or foam; cool containers with water spray.
• Waste: Collect halogenated organic waste separately according to institutional and local regulations.

Solvent Selection

Selection depends on the intended transformation (substitution vs elimination vs radical/cross-coupling). Item-specific solubility is not provided; guidance below is literature-based and general for α-bromo aromatic esters.

• Polarity/miscibility (literature, general):
  • Expected to be soluble in common organic solvents (DCM, chloroform, toluene, EtOAc, THF, MeCN); poorly soluble in water.
  • Polar aprotics (DMF, DMSO, MeCN) accelerate SN2 with hard nucleophiles (azide, cyanide, alkoxides).
  • Protic solvents (EtOH, i-PrOH) enable substitutions with amines/alcohols but increase risk of solvolysis.

• Choosing solvents by reaction class:
  • SN2 (N/S/C nucleophiles): MeCN, acetone, or DMF; add phase-transfer catalyst for heterogeneous systems.
  • Thiolation: acetone/MeCN with K2CO3 or Cs2CO3.
  • Amination: MeCN, THF, or toluene with amine base; avoid excess free base at high temperature to limit elimination.
  • Elimination to ethyl cinnamate: employ strong base (t-BuOK) in THF or t-BuOH; non-nucleophilic conditions suppress substitution.
  • Cross-coupling/radical: polar ethers (THF/2-MeTHF) or CPME for metallaphotoredox; DME/THF for Ni-catalyzed couplings.

• Practical tips:
  • Dry solvents reduce hydrolysis and minimize HBr formation.
  • For scale-up, consider greener choices (2-MeTHF, CPME, EtOAc) when compatible; they facilitate workup and reduce EHS footprint compared with DMF/DMSO.

Storage and Reconstitution

• Storage conditions: Room temperature (as provided). Store tightly closed in the original container. Protect from moisture and strong bases to minimize hydrolysis and elimination.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizer: Not specified for this item; refer to CoA/Spec Sheet.
• Shelf-life: Not specified for this item; monitor by NMR/GC for signs of elimination (formation of ethyl cinnamate) or hydrolysis.
• Handling practices (literature, general):
  • Keep under inert atmosphere (N2/Ar) for long-term storage to limit oxidative or hydrolytic degradation.
  • If cold storage is desired for longevity, avoid freezing; store cool and dry (e.g., desiccator). Follow the product label over generic advice if they differ.
  • Warm to ambient temperature before opening to prevent moisture condensation.
• Reconstitution: Not applicable; supplied as a neat reagent. If dilution is required for dosing or stock solutions, prepare in a dry, compatible solvent (e.g., MeCN, THF, DCM) immediately before use.

Structure and Identity

Ethyl 2-bromo-3-phenylpropanoate is an α-bromo ester bearing a benzylic substituent, useful as an electrophile and coupling synthon.

• SKU: E1067829
• Product name: Ethyl 2-bromo-3-phenylpropanoate
• CAS: 39149-82-1
• PubChem CID: 4737529
• InChIKey: 229298 (as provided; consult CoA/SDS for the full identifier)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Typical literature SMILES: CCOC(=O)CH(Br)CH2c1ccccc1 (literature)
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Typical composition (literature): C11H13BrO2
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Calculated from literature formula: ~257.13 g/mol (literature)

Structural features (descriptive, literature):

• Contains an ethyl ester (–CO2Et) and an α-brominated methine adjacent to the carbonyl (activated for substitution/elimination).
• The side chain terminates in a phenyl ring (benzylic CH2–Ph), providing additional stabilization in anionic/radical pathways.
• No defined stereochemistry is specified; the α-carbon is stereogenic. Commercial material is often racemic unless stated otherwise.
• 2D description: Ethyl ester carbonyl linked to a chiral center bearing Br and a benzylic methylene, which is attached to a phenyl ring.

Synthetic Utility

Key functional motifs and their reactivity (literature, general):

• α-Bromo carbonyl: Excellent leaving group at the α-position; enables high-yield SN2 substitutions with N-, S-, and C-nucleophiles. The adjacent carbonyl stabilizes developing charge in the transition state.
• Benzylic stabilization: The β-aryl substituent (Ph–CH2–) stabilizes carbocationic/radical character, broadening scope for SET and radical pathways under photoredox or Ni catalysis.
• Ester handle: Downstream diversification via hydrolysis (acid/base), reduction to alcohol (DIBAL-H/LiAlH4/NaBH4 under modified conditions), or amidation (amine coupling, CDI/EDC methods).

Representative transformations:

• Synthesis of α-amino esters: Displacement with azide (NaN3, MeCN), followed by reduction to give racemic phenylalanine ethyl ester analogs; or direct amination with benzylamine/alkylamines under phase-transfer catalysis.
• Construction of cinnamates: Base-induced E2 to ethyl cinnamate; subsequent cross-coupling or hydrogenation to saturated esters.
• C(sp3)–C(sp2) bond formation: Ni/photoredox coupling with aryl bromides/boronates to forge substituted benzylic stereocenters.
• Thioether synthesis: K2CO3-promoted substitution with thiols in acetone/MeCN at ambient temperature.

Retrosynthetic value:

• Serves as a bench-stable equivalent of the corresponding enolate electrophile, enabling convergent assembly of α-substituted esters without strong base.

Target Specificity

Not applicable. This product is a small-molecule reagent, not a biological targeting agent (e.g., antibody, probe). No antigen/epitope specificity or species reactivity applies.