This compound belongs to the class of organic compounds known as bromobenzenes. These are organic compounds containing a bromine atom attached to a benzene ring.
External Descriptors
Not available
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
287.110 g/mol
XLogP3
2.500
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
5
Exact Mass
285.984 Da
Monoisotopic Mass
285.984 Da
Topological Polar Surface Area
52.600 Ų
Heavy Atom Count
16
Formal Charge
0
Complexity
251.000
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
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Recensioni
Recensioni dei clienti
Application Protocols
Not applicable for bioassays. This item is not supplied with tested biological application protocols (e.g., WB, IHC, IF, FC). For chemical synthesis, refer to the literature-style guidance under Reaction Conditions and Synthetic Utility for example setups and conditions.
Biological Roles
This material is a synthetic organic building block rather than a biochemical reagent. No intrinsic biological function or role is typically assigned for dimethyl 2-(3-bromophenyl)malonate in living systems.
Context for researchers
Scaffold utility: Arylmalonate motifs can serve as precursors to arylacetic acids and benzylic derivatives that appear in bioactive compound libraries. The reagent facilitates rapid diversification of such scaffolds for SAR exploration.
Enzyme/biology interface: While malonate is a classical metabolic inhibitor in biochemistry, dialkyl arylmalonates like this compound are not standard metabolic probes and are generally used solely in chemical synthesis.
Good laboratory practice
Use strictly for research and laboratory synthesis. Avoid implying or inferring any therapeutic or diagnostic applications.
If biological testing of downstream derivatives is planned, ensure removal of residual palladium/halides and confirm compound identity/purity by appropriate analytical methods (NMR, LC–MS, HRMS).
Conclusion: The value of this reagent in life-science workflows is as a versatile precursor to benzylic/arylacetic frameworks, not as a molecule with inherent biological activity.
Buffer Applications
Not typically applicable. Dimethyl 2-(3-bromophenyl)malonate is a neutral organic reagent used in synthetic chemistry and is not employed as a buffering agent. For laboratory workflows involving this compound, focus on organic solvent systems and the synthetic guidance provided in Reaction & Applications, Synthetic Utility, and Reaction Conditions.
Green Alternatives
Context: The compound itself is the desired building block; “greener alternatives” mainly concern solvent/catalyst choices and process conditions.
Greener solvent swaps (literature guidance)
Replace DCM/CHCl3 in extraction or chromatography with EtOAc or cyclopentyl methyl ether (CPME) where feasible.
Replace THF with 2-MeTHF for base-mediated α-functionalizations or Pd-catalyzed couplings; 2-MeTHF offers bio-based origin, higher boiling point, and improved phase behavior.
Consider propylene carbonate, Cyrene, or dimethyl carbonate for polar-aprotic needs in select transformations.
Catalysis and bases
Use modern Pd catalysts with ligand efficiency to reduce metal loading in cross-couplings. Explore nickel catalysis for certain couplings to reduce precious-metal use.
Employ milder inorganic bases (K3PO4, Cs2CO3) and aqueous/solvent-minimized protocols to reduce waste from strong bases.
Process intensification
Telescoping: Combine coupling and subsequent hydrolysis/decarboxylation steps where compatible to reduce solvent use and intermediate isolations.
Continuous flow: Improves heat/mass transfer and may allow lower solvent volumes and safer handling of strong bases.
Comparison snapshot (general)
THF vs 2-MeTHF: Similar performance; 2-MeTHF is greener and often recyclable.
DCM vs EtOAc: EtOAc is less hazardous and has a better environmental profile; may require optimization of extraction ratios.
Note: Validate solvent/catalyst substitutions at small scale to ensure chemoselectivity and to avoid unintended ester hydrolysis.
Pharmaceutical Uses
Formulation/excipient role: None. This compound is not used as a pharmaceutical excipient.
Relevance to drug discovery/manufacturing (general, non-clinical)
Intermediate: Useful as a synthetic intermediate to access 3-bromophenylacetic acid derivatives and further elaborated scaffolds via cross-coupling and benzylic functionalization. Such intermediates can be incorporated into candidate molecules during lead optimization.
Protecting/“masking” strategy: The malonate diester can serve as a masked acetic acid functionality, enabling assembly under neutral conditions followed by hydrolysis/decarboxylation at a later stage.
Late-stage diversification: The aryl bromide allows rapid diversification through Pd- (or Ni-) catalyzed cross-couplings to form biaryl, aryl–alkenyl, aryl–alkynyl, or aryl–amine linkages.
Regulatory note
No pharmacopeial monograph is associated with this specific reagent.
For GMP-related work, ensure supplier qualification, traceability, and CoA-backed impurity controls. Remove residual metals/halides in final drug substances according to ICH Q3D/Q3A where applicable.
This information is provided strictly in the context of synthetic intermediate utility for research and development, not for therapeutic use.
Physical Properties
Item-specific (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed values (typical for this structure; not product specifications)
Molecular formula: C11H11BrO4
Molecular weight: ~287.11 g/mol
Physical state: typically an oil or low-melting solid for closely related arylmalonate dimethyl esters (literature)
Boiling point: aryl malonate dimethyl esters commonly exhibit thermal decomposition before distillation; purification generally by chromatography (literature)
Melting point: not widely reported for the 3-bromo isomer (literature)
Density: expected ~1.4–1.5 g/mL for brominated aryl diesters; specific value not established for this exact compound (literature trend)
Solubility: low in water; soluble in common organic solvents (DCM, EtOAc, THF, acetone, toluene, MeCN) (literature)
LogP: anticipated moderate (literature)
Refractive index: not reported (literature)
Practical notes
Due to two ester carbonyls and an aryl bromide, the compound is moderately polar yet nonionic; handle as a typical neutral organic building block. Avoid moisture if subsequent base-mediated steps are planned (to limit hydrolysis). For exact quality attributes (water, peroxides, metals, UV cutoff), consult the item’s CoA/Spec Sheet.
Quality and Grades
Item-specific (from Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
General guidance (how to interpret when CoA is provided)
Research-use building block: Typically supplied as neat material without stabilizers. For sensitive downstream chemistry (e.g., anionic alkylations, cross-coupling), customers commonly verify by 1H/13C NMR, LC/GC purity, and water content (Karl Fischer).
UV/Chromatography suitability: If planning HPLC monitoring at low UV, request LC impurity profile and UV cutoff. For photochemical work, verify absence of chromophoric impurities.
Metal content: For catalysis (Suzuki, Buchwald–Hartwig), pre-screened low-metal content can be helpful; if critical, request ICP data on the batch CoA.
Residual solvents: Check GC for residuals that could interfere with base-mediated steps or cross-couplings (e.g., alcohols that can transesterify).
What the grade implies (when stated)
AR/ACS grade: Tight specs for assay and common impurities.
HPLC grade (solvents): Low UV absorbance and particulate—less relevant here as this is a reagent, not a solvent.
Custom specs: On request, Aladdin can often provide batch CoA detailing assay, key impurities, and handling notes.
Always defer to the specific lot’s CoA/Spec Sheet for definitive grade and impurity limits.
Reaction and Applications
This reagent merges two versatile handles: an activated malonate diester and a meta-bromophenyl ring. Together they enable convergent strategies: manipulate the ring (cross-couplings) before or after transforming the malonate.
Representative application families (literature)
Formation of arylacetic acids: Hydrolysis of both esters → malonic diacid, followed by thermal decarboxylation to give 3-bromophenylacetic acid; subsequent cross-coupling diversifies the arylacetic acid scaffold (or couple first, then hydrolyze/decarboxylate).
α-Functionalization/alkylation: The remaining α-H can be deprotonated (NaH, K2CO3, LDA) to introduce an additional substituent, enabling access to quaternary centers after coupling/hydrolysis steps.
Knoevenagel condensations: Condense with aldehydes/ketones under basic or amine catalysis to give substituted alkenes that retain the diester functionality for later transformations.
Cross-coupling on aryl bromide: Suzuki–Miyaura (aryl/alkenyl boron species), Buchwald–Hartwig amination (amines), Heck (alkenes), and Sonogashira (alkynes). The malonate is usually benign under Pd catalysis; choose bases that do not saponify under conditions used.
Decarboxylative functionalization: After mono-saponification and decarboxylation, generate benzylic carbanions for further elaboration.
Practical tips
Sequence planning: Consider whether to first modify the aryl bromide (e.g., install heteroaryl or amine) and then perform hydrolysis/decarboxylation vs. the reverse order, to manage stability and purification.
Protecting-group logic: The diester can serve as a temporary “masked acetic acid.”
Workup: Avoid prolonged exposure to strong aqueous base at elevated temperature to control ester cleavage.
Reaction Conditions
General literature guidance (optimize per substrate; not product specifications)
α-Deprotonation/alkylation
Base: NaH (60% in mineral oil, 1.1–1.5 equiv) in dry THF or 2-MeTHF; or K2CO3/cesium carbonate in DMF for milder conditions. LDA (1.1–1.5 equiv) at −78 to −20 °C affords high enolate control.
Electrophiles: Benzyl/allyl/alkyl halides, activated sulfonates. Add electrophile after enolate formation; 0 to room temperature, 1–6 h typical.
Notes: Minimize time at elevated temperature to avoid transesterification/hydrolysis.
Hydrolysis and decarboxylation to arylacetic acids
Saponification: NaOH or KOH (2–4 equiv) in MeOH/H2O or EtOH/H2O, 0–25 °C then warm to reflux until complete (TLC/LC). Acidify to pH ~1–2, isolate diacid/monoacid.
Decarboxylation: Heat the diacid in aqueous acid (e.g., 6 M HCl) or organic solvent (toluene/xylene) at reflux to release CO2 and furnish the arylacetic acid.
Suzuki–Miyaura coupling on aryl bromide
Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd2(dba)3 with SPhos/XPhos (1–2 mol% Pd).
Base: K3PO4, K2CO3, or Cs2CO3 (2–3 equiv). Solvent: dioxane/H2O, toluene/H2O, THF/H2O, or 2-MeTHF/H2O. 60–100 °C, 2–16 h.
Buchwald–Hartwig amination
Catalyst/ligand: Pd2(dba)3 or Pd(OAc)2 with BrettPhos/RuPhos (1–3 mol% Pd).
Base: NaOtBu or Cs2CO3. Solvent: toluene, dioxane, or 2-MeTHF. 80–110 °C.
Heck/Sonogashira
Heck: Pd(OAc)2/PPh3, Et3N or K2CO3, DMF or toluene, 80–120 °C.
Sonogashira: Pd/Cu co-catalysis, amine base (iPr2NH/Et3N), THF/DMF, 25–80 °C.
Always monitor for ester stability and adjust base/temperature accordingly.
Safety and Handling
Item-specific (from Product Data)
GHS classification, signal word, H-statements, pictograms: Not specified for this item; refer to SDS.
Storage conditions: Room temperature.
General safety guidance (literature; consult SDS for authoritative data)
Likely hazards: Organic bromides and malonate esters can cause skin/eye irritation and may be harmful if swallowed or inhaled. Avoid aerosol formation. Handle in a fume hood.
Personal protective equipment (PPE): Lab coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). For large-scale operations, consider splash protection and local exhaust ventilation.
Incompatibilities: Strong bases and nucleophiles promote transesterification or hydrolysis; strong acids may also hydrolyze esters. Avoid prolonged contact with aqueous base/acids unless intended. Keep away from strong oxidizers and reducing agents.
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 present and easy to do.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Fire safety: Treat as combustible organic liquid/solid. Use CO2, dry chemical, or foam. Combustion may release CO/CO2 and HBr/Br-containing fumes—firefighters should wear SCBA.
Waste: Dispose according to local regulations. Halogenated organic residues may require specific waste streams.
Always refer to the product’s SDS for definitive hazard classification and response measures.
Solvent Selection
Applicability: Dimethyl 2-(3-bromophenyl)malonate is a neutral, moderately polar organic building block. Solvent choice is primarily for reaction media and workup, not as a buffer or aqueous system.
Poorly soluble: Water and brine (useful for phase separation during workup).
Practical selection by operation
Base-mediated α-functionalization (NaH, LDA, K2CO3): Use dry THF, MTBE, 2-MeTHF, or DMF depending on base/temperature. THF/2-MeTHF are common for NaH; LDA at −78 to −20 °C in THF or THF/hexanes.
Cross-coupling on aryl bromide (Suzuki, Buchwald–Hartwig, Heck): Toluene, dioxane, THF, or DMF with an aqueous base (K3PO4, K2CO3, Cs2CO3). 2-MeTHF or Cyrene can be considered as greener options where compatible.
Hydrolysis/saponification: EtOH/H2O or MeOH/H2O with NaOH or KOH; follow with acidification and extraction into EtOAc or MTBE.
Chromatographic purification: Normal-phase silica using hexanes/EtOAc or cyclohexane/EtOAc; add 0.1–1% Et3N if tailing due to acid–base interactions.
Comparison snapshot (literature)
THF vs 2-MeTHF: Similar polarity; 2-MeTHF offers better water tolerance and greener profile.
DCM vs EtOAc: DCM offers faster extractions but higher environmental/health burdens; EtOAc is a greener alternative for workup and chromatography.
Storage and Reconstitution
Item-specific (from Product Data)
Storage conditions: Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General handling advice (literature; not product specifications)
Container: Store in a tightly closed container under dry, inert atmosphere if possible, to minimize moisture uptake and unintended hydrolysis/transesterification.
Light/heat: Protect from prolonged heat. Room-temperature storage is typically adequate; avoid repeated heating–cooling cycles.
Stability: Aryl bromides and dialkyl malonates are generally stable under neutral, dry conditions. Avoid strong bases/acids during storage.
Reconstitution: Not applicable; supplied neat. If solidified, gently warm to room temperature to liquefy (if oily) or dissolve in a suitable dry organic solvent (e.g., DCM, EtOAc, THF) for use.
Freeze–thaw: Not relevant; no aqueous formulation. If preparing stock solutions, store in amber vials at ambient or refrigerated temperatures as appropriate for the chosen solvent and planned timeline.
Always consult the product’s CoA/SDS for lot-specific stability notes and packaging details. For research use only.
Structure and Identity
Item-specific (from Product Data)
SKU: D1004513
Product name: Dimethyl 2-(3-bromophenyl)malonate
CAS: 773134-24-0
InChIKey: 172737 (as provided)
Storage: Room temperature
Literature/computed identifiers and description (for reference; not specifications)
Preferred IUPAC-style name (literature): Dimethyl 2-(3-bromophenyl)malonate; also written as dimethyl (3-bromophenyl)propanedioate
Structural features: A malonate diester (two methyl esters) with an sp3 α-carbon bearing one hydrogen and a meta-bromophenyl substituent. Functional groups include two ester carbonyls and an aryl bromide handle.
2D structure (verbal): Central tetrahedral carbon attached to two carbonyl carbons (each part of a methyl ester OMe–C(=O)–) and to a 3-bromophenyl ring; the remaining substituent on the α-carbon is hydrogen. The phenyl ring carries bromine at the 3-position relative to the benzylic attachment.
Notes
The aryl bromide enables cross-coupling (e.g., Suzuki, Buchwald–Hartwig, Heck), while the malonate enables α-functionalization, hydrolysis, and decarboxylation to arylacetic-acid derivatives. Clearly separate any use of these literature identifiers from item-specific documentation (CoA/SDS).
Synthetic Utility
Key functional elements and reactivity (literature)
Malonate diester: The α-methine (adjacent to two carbonyls) is moderately acidic, enabling enolate or carbanion formation under base (NaH, K2CO3, LDA). This supports alkylation, Michael addition, and Knoevenagel condensation. Subsequent hydrolysis/decarboxylation yields arylacetic acid derivatives.
Aryl bromide: A robust leaving group for Pd/Ni-catalyzed cross-couplings (Suzuki–Miyaura, Buchwald–Hartwig, Heck, Sonogashira), enabling introduction of heteroaryl, alkenyl, alkynyl, or amine substituents at the meta position.
Strategic applications
Masked acetic acid: Use the malonate as a traceless linchpin—assemble complex frameworks under neutral or mildly basic conditions, then unmask (saponify/decarboxylate) to obtain the benzylic carboxylate/acid.
Quaternary center construction: Sequential α-alkylation on the arylmalonate (forming a tetrasubstituted carbon), followed by ester manipulation, delivers densely substituted benzylic motifs.
Domino sequences: Cross-couple first to install diversity on the ring, then perform Knoevenagel with aldehydes to elaborate the side chain; or invert the order depending on chemoselectivity.
Retrosynthetic value
Enables disconnection of arylacetic-acid fragments back to an arylmalonate synthon. The aryl bromide provides an orthogonal disconnection to simpler boronates/halides/olefins/amines.
Handling considerations
Avoid strong bases in protic solvents if ester integrity must be preserved. Under coupling conditions, prefer bases and temperatures that minimize saponification.
Target Specificity
Not applicable. This product is a small-molecule synthetic reagent and is not an antibody, probe, or biologic with defined binding specificity. No antigen/epitope or isotype information applies.
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