Methyl 2-(3-bromophenyl)alaninate - ≥95% , CAS No.1183581-39-6

CAS: 1183581-39-6 Cat. No.: M1037267 Formula: C₁₀H₁₂BrNO₂ Peso molecolare: 258.110 Numero EC: 873-419-7

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

• Sorrisi canonici: CC(C1=CC(=CC=C1)Br)(C(=O)OC)N
• IUPAC Name: methyl 2-amino-2-(3-bromophenyl)propanoate
• InChIKey: SBLKKJBRKIWUQH-UHFFFAOYSA-N
• INCHI: 1S/C10H12BrNO2/c1-10(12,9(13)14-2)7-4-3-5-8(11)6-7/h3-6H,12H2,1-2H3
• Peso molecolare: 258.110

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives
• Direct Parent: Alpha amino acids and derivatives
• Alternative Parents: Bromobenzenes Aralkylamines Aryl bromides Methyl esters Monocarboxylic acids and derivatives Organobromides Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Alpha-amino acid or derivatives - Bromobenzene - Halobenzene - Aralkylamine - Aryl bromide - Aryl halide - Monocyclic benzene moiety - Benzenoid - Methyl ester - Carboxylic acid ester - Monocarboxylic acid or derivatives - Organooxygen compound - Organonitrogen compound - Organobromide - Organohalogen compound - Primary aliphatic amine - Organic oxide - Carbonyl group - Organic oxygen compound - Amine - Primary amine - Organic nitrogen compound - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
• 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: 258.110 g/mol
• XLogP3: 1.800
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 257.005 Da
• Monoisotopic Mass: 257.005 Da
• Topological Polar Surface Area: 52.300 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 222.000
• 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 as standardized bioassay protocols (e.g., WB, IHC, IF, FC) are for biomolecular reagents. For this small-molecule building block, follow general organic synthesis procedures appropriate to your transformation (see Reaction Conditions and Synthetic Utility). Batch-specific handling or dissolution instructions beyond standard organic techniques are Not specified for this item; refer to CoA/SDS.

Biological Roles

This product is an amino-acid derivative intended for research and synthesis. No clinical or therapeutic claims are made.

• General biochemical context (literature)

  • Phenylalanine analogs bearing halogens (e.g., 3-bromo) are widely used as probes to modulate hydrophobic interactions, π-stacking, and electronic effects in peptides and proteins.
  • The free-base methyl ester is non-natural and is typically a synthetic intermediate; it does not participate directly in ribosomal incorporation without deprotection/hydrolysis or specialized translation systems.
  • Halogenated aromatic residues can influence binding through halogen bonding and altered polarizability; meta-bromine substitution can subtly affect conformational preferences and aromatic interactions.

• Typical research uses

  • Precursor to the corresponding amino acid (after ester hydrolysis) for solid-phase peptide synthesis (SPPS) once properly protected (e.g., Fmoc/Boc) and converted to the free acid.
  • Scaffold for preparing photoaffinity or cross-coupling-derived labels (via the aryl–Br) to interrogate protein–ligand interfaces in biochemical assays.

• Metabolic/enzymatic considerations

  • Esterases can hydrolyze methyl esters in biological matrices; however, this product is designated for research use and is not intended for in vivo applications.

• Item-specific data such as transporter affinity, enzyme inhibition, or metabolic clearance are Not specified for this item; consult primary literature when designing biochemical experiments.

Buffer Applications

This compound is not a buffering agent and is not typically used to prepare pH buffer systems.

• Guidance
  • If aqueous handling is required (e.g., for hydrolysis or salt formation), use appropriate laboratory buffers separately (e.g., phosphate, bicarbonate) and confirm that conditions do not hydrolyze the methyl ester or alter stereochemistry.
  • For peptide coupling steps, employ non-buffered anhydrous media or controlled pH two-phase systems rather than relying on this compound as a buffer.

Green Alternatives

While the molecule itself is fixed, greener choices can be implemented in solvent and reagent selection across typical transformations.

• Solvent substitutions (general guidance)

  • Replace DCM with EtOAc or 2-MeTHF for amine protection and extractions when feasible.
  • Use 2-MeTHF, CPME, or toluene/EtOH–H2O blends for cross-couplings instead of dioxane or DMF where performance allows.
  • Favor MeCN over DMF for amidations if solubility and reactivity are adequate; MeCN is easier to remove and has a better EHS profile.

• Bases and reagents

  • Employ aqueous K2CO3/K3PO4 in biphasic couplings instead of strong inorganic bases in polar aprotics.
  • Choose modern coupling reagents with improved safety profiles (e.g., COMU) and catalysis (low-Pd loading, ligand-optimized) to reduce waste.

• Energy and workup

  • Conduct reactions at ambient temperature where possible; exploit micellar catalysis (e.g., surfactant media) for cross-couplings of aryl bromides to cut organic solvent use.
  • Implement solvent recycling (distillation of EtOAc, MeOH, 2-MeTHF) and minimize halogenated waste streams.

• Small comparison (illustrative)

  • Dioxane/H2O vs 2-MeTHF/H2O in Suzuki: 2-MeTHF is bio-based and has lower toxicity; may require ligand/base tuning for comparable rates.
  • DCM vs EtOAc for Boc protection: EtOAc reduces chlorinated waste; reaction times may be slightly longer but typically acceptable.

• Note: Item-specific green metrics (PMI, E-factor) and stabilizers are Not specified for this item; process optimization is advised.

Pharmaceutical Uses

No medicinal use is claimed. For research and manufacturing development only.

• Formulation/excipient role

  • Not employed as a standard excipient. Any presence in a dosage form would be as a synthetic intermediate only, not as a functional excipient.

• Process chemistry context (general)

  • Useful intermediate for preparing halogenated phenylalanine derivatives for medicinal chemistry SAR studies.
  • The aryl–Br enables rapid library diversification via cross-couplings, facilitating lead optimization.

• Regulatory notes

  • No pharmacopeial monograph is indicated for this specific derivative. Any GMP use would require full specification, impurity profiling, and control of stereochemistry and residual catalysts.

• Item-specific pharmacopeial grade/status, residual catalysts, and elemental impurities limits: Not specified for this item; refer to CoA/Spec Sheet.

Physical Properties

Only item-specific specifications should be taken from the CoA/Spec Sheet. Values below are general literature/computed guidance for this structural class and are not specifications.

• 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.
  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed (informational)

  • Approximate molecular formula: C10H12BrNO2 (literature)
  • Approximate molecular weight: ~258.12 g/mol (literature)
  • Acid/base character: primary amine (basic), methyl ester (neutral); conjugate acid pKa of α-amine typically ~9–10 (literature for amino esters).
  • LogP: aryl bromides with amino ester functionality often have moderate lipophilicity (estimated cLogP ~1–2.5; literature/estimation for closely related analogs).
  • Solubility (qualitative, literature):
    • Good in polar aprotic organics (DCM, THF, MeCN), alcohols, and chlorinated solvents.
    • Often soluble in DMSO and DMF; limited solubility in water as free-base; increased aqueous solubility as acid salts.
  • Optical activity: A single stereocenter is present; optical rotation depends on enantiomeric composition. This item’s stereochemistry is not specified.

• Not provided for this item; refer to CoA/Spec Sheet

  • Melting/boiling point, density, refractive index, UV cutoff, residual solvents, trace metals, water/peroxide content.

Quality and Grades

• Item-specific quality information

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
  • UV cutoff, trace metals, residual solvents, water/peroxide limits: Not specified for this item; refer to CoA/Spec Sheet.

• Interpreting common grades (general guidance)

  • Research/biochemical grade typically indicates suitability for synthetic and discovery workflows with routine impurity control.
  • HPLC grade solvents/reagents emphasize low UV background and particulate; for this amino ester, “HPLC-grade” would be relevant primarily to solvents used for purification, not the solid itself.
  • Peptide-synthesis grade amino acid derivatives usually specify enantiomeric excess (ee), specific rotation, and low levels of inorganic/organic contaminants; stereochemistry for this item is not specified — verify on the CoA if chiral purity matters.

• Practical quality considerations for this compound class

  • Primary amines can bind adventitious CO2/acid; verify assay by titration or qNMR when stoichiometry is critical.
  • Methyl esters can undergo partial hydrolysis during workup; monitor by HPLC/LC–MS, especially after aqueous exposures.
  • For cross-coupling use (via aryl–Br), trace Pd-catalyst poisons (sulfur-containing impurities) and water can impact conversion; pre-dry and use appropriate base quality.

• Documentation

  • Always consult the Aladdin CoA and Spec Sheet for batch-specific assay, residual solvent profile, chiral analysis (if applicable), and recommended analytical methods.

Reaction and Applications

Methyl 2-(3-bromophenyl)alaninate is a versatile bifunctional building block bridging amino-acid chemistry and aryl–halide cross-coupling.

• Functional group leverage

  • Aryl bromide: platform for Pd-catalyzed cross-couplings (Suzuki–Miyaura, Buchwald–Hartwig, Sonogashira) to diversify the aromatic substituent without altering the amino-ester backbone.
  • Primary amine: amenable to protection (Boc, Fmoc, Cbz), acylation, urea/carbamate formation, or reductive amination (on derivatives).
  • Methyl ester: convertible to acid (saponification) for peptide couplings; transesterification to alternate esters.

• Representative application scenarios (literature/general)

  • Late-stage aryl diversification: Suzuki of the meta-bromide using boronic acids/esters to access libraries of substituted phenylalanine esters.
  • Peptidomimetic synthesis: Hydrolysis to the acid followed by EDCI/HOBt or HATU-mediated amide coupling; stereochemical integrity preserved by mild bases and low temperatures.
  • Arylamination/etherification: Buchwald–Hartwig coupling on the aryl–Br using dialkylamines or phenoxides to provide anilines or aryl ethers.

• Practical tips

  • Protect the amine during cross-coupling to avoid catalyst binding and side reactions; Boc protection is commonly effective.
  • Avoid strong base/long exposures to water to minimize ester hydrolysis and racemization at the α-center.
  • For parallel synthesis, prepare acid salts (e.g., HCl, TsOH) to enhance handling and crystallinity; deprotect immediately prior to use.

• Analytics

  • Monitor transformations by LC–MS (M+H+ ~258 for free base; literature) and 1H/13C NMR; aryl–Br disappearance in 13C NMR/HRMS corroborates coupling.

Reaction Conditions

The following representative conditions are drawn from literature precedents for closely related α-amino methyl esters bearing aryl bromides. Optimize for your substrate and setup.

• Suzuki–Miyaura cross-coupling (general)

  • Substrate: aryl–Br amino ester (amine typically Boc-protected).
  • Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd2(dba)3 (1–2 mol%) with SPhos/XPhos (2–5 mol%).
  • Base: K2CO3 or K3PO4 (2–3 equiv).
  • Solvent: 2-MeTHF/H2O or dioxane/H2O (3:1 to 1:1).
  • Temp/Time: 60–90 °C, 2–16 h.
  • Notes: Maintain inert atmosphere; pre-activation of boronic acid (if sluggish) can help. Protect amine to reduce Pd-binding.

• Buchwald–Hartwig amination (general)

  • Catalyst: Pd2(dba)3 (1 mol%) with BINAP or BrettPhos (2–4 mol%).
  • Base: NaOtBu or Cs2CO3 (2 equiv).
  • Solvent: toluene or t-BuOH/PhMe.
  • Temp: 80–110 °C.
  • Notes: Amine protection recommended; avoid strong base if ester sensitivity is an issue.

• Saponification to free acid (general)

  • Reagent: LiOH (1–3 equiv).
  • Solvent: THF/MeOH/H2O (2:1:1).
  • Temp: 0–25 °C, 1–4 h.
  • Workup: Quench with 1 M HCl to pH ~2, extract, or proceed directly to coupling.

• Amine Boc protection (general)

  • Reagents: (Boc)2O (1.1–1.5 equiv), base (NEt3 or NaHCO3).
  • Solvent: DCM or THF, 0–25 °C, 1–3 h.

• Peptide coupling (general)

  • Reagents: HATU (1.1 equiv), DIPEA (2–3 equiv).
  • Solvent: DMF or MeCN.
  • Temp: 0–25 °C.

• Analytical expectations (general)

  • Aryl–Br starting material: HRMS shows 79/81Br isotope doublet; LC–MS [M+H]+ ~258 (literature for free base). Post-coupling mass shift consistent with installed group.

Safety and Handling

Authoritative safety information resides in the product SDS. The following provides general guidance for amino ester aryl bromides.

• GHS/Classification (item-specific)

  • Signal Word: Not specified for this item; refer to SDS.
  • H-Statements: Not specified for this item; refer to SDS.
  • GHS Classification/Pictograms: Not specified for this item; refer to SDS.

• General hazards (literature/analog-based)

  • May cause irritation to skin, eyes, and respiratory tract.
  • Free-base amines can be sensitizers in some individuals; handle to avoid dermal contact.
  • Aryl bromides are not strongly volatile but should be handled in a fume hood to avoid aerosol/inhalation.

• PPE and engineering controls

  • Use chemical-resistant gloves (e.g., nitrile), lab coat, and splash goggles.
  • Handle in a certified chemical fume hood; avoid inhalation of dust or mists.

• Incompatibilities and precautions (general)

  • Avoid strong oxidizers. Amines can react with acylating agents, acid chlorides, and isocyanates.
  • The methyl ester can hydrolyze under strong acidic or basic conditions; avoid prolonged exposure to aqueous media if structure must be preserved.
  • If converting to salts, control exotherms when adding strong acids.

• First aid (overview; consult SDS)

  • Skin/eye contact: Rinse with water for ≥15 min; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; support breathing; seek medical attention.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

• Spill/fire response (general)

  • Absorb small spills with inert material; collect for disposal.
  • Use CO2, dry chemical, or foam for fires; combustion may release HBr and NOx.

Solvent Selection

This molecule combines a basic primary amine, an aryl bromide, and a methyl ester. Solvent choice should balance solubility, base compatibility, and protection of the ester from hydrolysis.

• Polarity/miscibility profile (general)

  • Polar aprotic: DMF, DMSO, NMP, MeCN — excellent solvency for coupling and cross-coupling; watch for amide formation with strong acylating agents.
  • Moderately polar/chlorinated: DCM, DCE, chloroform — good for protection steps (Boc) and extractions.
  • Protic: MeOH, EtOH, i-PrOH — good solvency; can promote transesterification or hydrolysis under basic/acidic conditions.
  • Hydrocarbons/ethers: THF, 2-MeTHF, toluene, MTBE — useful for organometallic or Pd-catalyzed chemistry (with co-solvents).

• Practical selection guidance

  • For amine protection (Boc/CBz): DCM or THF with mild base (NEt3, NaHCO3); avoid strong aqueous base to protect ester.
  • For Suzuki on aryl–Br: dioxane/H2O, THF/H2O, or toluene/EtOH/H2O mixtures; adjust to maintain solubility of base and boronate.
  • For amidation after saponification: THF/MeOH/H2O for hydrolysis, then DMF/MeCN for coupling.

• Small comparison (general)

  • THF vs 2-MeTHF: 2-MeTHF offers improved sustainability and higher bp; both dissolve amino esters well.
  • DCM vs EtOAc for workup: EtOAc provides greener profile and can be preferable for extractions if solubility permits.

• Note

  • Item-specific solubility and water content are Not specified for this item; refer to CoA/Spec Sheet and assess experimentally.

Storage and Reconstitution

• Item-specific storage/shipping

  • Storage Conditions: Room temperature (per Product Data). Store tightly capped in a dry, well-ventilated area.
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• General storage guidance for amino esters with aryl bromide

  • Protect from moisture and prolonged exposure to strong acids/bases to prevent ester hydrolysis and amine salt formation.
  • Minimize light/heat to preserve integrity; although aryl bromides are reasonably stable, avoid elevated temperatures during long-term storage.
  • For long-term archiving, consider inert-atmosphere storage (N2/Ar) and desiccation.

• Reconstitution/solution preparation (general)

  • Not supplied as a lyophilized biomolecule; no aqueous reconstitution is required.
  • For stock solutions, dissolve in dry organic solvents (e.g., DCM, THF, MeCN, DMF, DMSO) appropriate to the planned reaction. Filter if particulates are observed (PTFE syringe filter, 0.2–0.45 µm).
  • Prepare acid salts (e.g., HCl) in situ if increased aqueous solubility is desired for brief manipulations; avoid extended aqueous storage to minimize hydrolysis.

• Stability notes

  • Avoid repeated warming/cooling cycles that may introduce condensation; keep container tightly closed.
  • Periodically verify purity by HPLC/LC–MS for materials kept beyond 12 months or after exposure to humidity.

• Research use only

  • Research Use Note (per Product Data): For research use only.

Structure and Identity

Brief description: Methyl 2-(3-bromophenyl)alaninate is the methyl ester of a brominated phenylalanine analog featuring three key motifs: a primary amine, a methyl carboxylate, and a meta-bromophenyl ring suitable for cross-coupling.

• Item-specific (from Product Data)

  • SKU: M1037267
  • Product Name: Methyl 2-(3-bromophenyl)alaninate
  • CAS: 1183581-39-6
  • CID: 50989094
  • InChIKey: 331569 (provided; truncated/not standard length as given)
  • Storage Conditions: Room temperature
  • Category Path: 全部 / 可售 / 生命科学

• Literature/computed identifiers and description (informational; verify against CoA/SDS)

  • Suggested molecular framework: methyl 2-amino-3-(3-bromophenyl)propanoate (free-base amino ester)
  • Typical molecular formula (literature): C10H12BrNO2
  • Typical molecular weight (literature): ~258.12 g/mol
  • Representative SMILES (literature): COC(=O)C(N)CC1=CC(Br)=CC=C1
  • Structural features:
    • Aromatic ring bearing a meta-bromine (C–Br aryl halide)
    • Primary aliphatic amine at the α-carbon
    • Methyl ester (–CO2Me) at the carboxyl terminus
    • One stereogenic center at the α-carbon; stereochemistry for this item is Not specified for this item; refer to CoA/Spec Sheet.

• 2D structure in words (general): An aromatic ring substituted with bromine at the meta position is connected via a –CH2– to an α-carbon bearing an –NH2 group and a methyl ester –CO2CH3. The α-carbon is potentially chiral; configuration not specified for this listing.

Synthetic Utility

This amino ester offers orthogonal handles that support convergent synthesis strategies in peptidomimetics and small-molecule diversification.

• Strategic disconnections

  • Aryl diversification at the meta-bromide via Suzuki–Miyaura coupling to introduce heteroaryl, alkyl, or substituted aryl groups without perturbing the α-amino ester.
  • Hydrolysis of the methyl ester to the acid, followed by amide coupling to introduce peptide linkages or small-molecule amides.
  • Amino protection (Boc/Fmoc/Cbz) to enable selective transformations on the aryl bromide or the ester.

• Typical transformations (literature)

  • Suzuki: Ar–Br + R–B(OH)2 (Pd0/PdII, base) → biaryl.
  • Buchwald–Hartwig: Ar–Br + R2NH (Pd/Ligand, base) → aniline derivatives.
  • Sonogashira: Ar–Br + terminal alkyne (Pd/Cu, base) → aryl alkyne, followed by hydrogenation or cycloadditions.
  • Saponification: MeOH-sensitive; use LiOH or NaOH in THF/MeOH/H2O at 0–25 °C to access the acid while minimizing racemization.
  • Carbamate formation: Boc protection using (Boc)2O and mild base in DCM/THF.

• Selectivity and protection

  • Free amine can chelate Pd; temporary protection increases coupling efficiency and suppresses side reactions.
  • Maintain anhydrous conditions during acylations and use base scavengers (e.g., DIPEA) to control salt formation.

• Analytical control

  • Track ee (if enantioenriched) by chiral HPLC.
  • Confirm loss of aryl–Br by HRMS and disappearance of ~1:1 79/81Br isotope pattern after coupling.

Target Specificity

Not applicable. This product is a small-molecule amino-acid derivative, not a biological targeting reagent (e.g., antibody, ligand-protein conjugate). No antigen, epitope, species reactivity, clone, or isotype information applies.