This compound belongs to the class of organic compounds known as chlorobenzenes. These are compounds containing one or more chlorine atoms attached to a benzene moiety.
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
200.620 g/mol
XLogP3
1.800
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
3
Exact Mass
200.024 Da
Monoisotopic Mass
200.024 Da
Topological Polar Surface Area
46.500 Ų
Heavy Atom Count
13
Formal Charge
0
Complexity
184.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
1
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
No bioassay or immunoassay protocols apply to this small-molecule building block. For chemical use:
Typical workflow (general)
Dissolve in a suitable dry solvent (e.g., DCM, THF, EtOAc, MeCN) to the desired concentration (commonly 0.05–0.5 M) for reactions.
For chiral analyses, prepare solutions at validated concentrations for chiral HPLC using appropriate mobile phases (e.g., hexanes/IPA with acid/base modifiers on polysaccharide chiral stationary phases).
For hydrolysis or coupling steps, follow Reaction Conditions guidance and monitor by TLC/HPLC/LC–MS.
All procedures should be validated in your laboratory. No item-specific, tested biological applications are provided for this product.
Biological Roles
This product is intended strictly for research use as a synthetic building block. It is not a metabolite or buffer component in standard biochemical pathways.
General context (literature)
α-Hydroxy acids and esters (mandelate family) occur in nature (e.g., mandelic acid in some metabolic/biotransformation contexts), but aryl-chloro-substituted mandelate esters like 3-chloro analogs are synthetic and have no established endogenous roles.
As a small aromatic ester with a secondary alcohol, it may be a substrate for generic esterase- or lipase-mediated transformations in biocatalysis studies, where stereoselective hydrolysis or acyl transfer can be probed.
Potential utility in chemical biology (conceptual)
Chiral probe synthesis: The defined (S) configuration can be transferred or used to prepare labeled ligands or fragments for binding studies (after conversion to amides/alcohol derivatives), but such use remains purely chemical/biophysical.
Enzyme screening: As a model substrate for investigating enantioselective oxidations (alcohol dehydrogenases) or hydrolases, provided proper safety and approvals.
No medical, diagnostic, or therapeutic applications are implied. For any work involving biological systems, confirm DMSO/EtOH solubility and avoid cytotoxic solvent levels.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare aqueous buffer systems. As a hydrophobic chiral α-hydroxy ester, it lacks acid–base pairs suitable for maintaining pH in water around physiological ranges.
Practical note: If used in biochemical assays as a substrate or probe after derivatization, it is typically dissolved in an organic co-solvent (e.g., DMSO, EtOH) and then diluted into the assay buffer. Optimize the co-solvent percentage to avoid denaturation or activity loss in enzymes or proteins.
Green Alternatives
Although (S)-Methyl 2-(3-chlorophenyl)-2-hydroxyacetate is a building block rather than a solvent or process aid, greener choices can be made around its use and derivatization.
Greener solvent choices (literature/general)
Replace DCM with EtOAc or Me-THF/2-MeTHF for extractions and chromatography where feasible.
Prefer alcohols (EtOH, i-PrOH) or esters (EtOAc, CPME) over chlorinated solvents for reactions and workups when compatible with the transformation.
Catalysis and reagents
Mitsunobu alternatives: Employ catalytic Mitsunobu protocols or alternative dehydrative couplings (e.g., PPh3-free systems, or sulfonyl activation followed by substitution) to reduce waste.
Oxidation: Favor TEMPO/bleach or Oxone systems and electrochemical oxidations over chromium(VI) reagents.
Ester hydrolysis: Use enzymatic or aqueous ethanol/water protocols under mild conditions to minimize energy and corrosive waste.
Energy and waste minimization
Conduct reactions at ambient temperature if possible; employ flow chemistry for heat/mass transfer efficiency.
Use buffered silica or greener stationary phases to reduce solvent volumes in purification; consider crystallization/derivatization to avoid chromatography.
Comparative view (qualitative)
DCM vs EtOAc: EtOAc is biodegradable and of lower toxicity, though sometimes less effective for highly lipophilic intermediates.
THF vs 2-MeTHF: 2-MeTHF derives from renewable sources and affords easier phase separations; peroxide formation still requires monitoring but is less pronounced than ethers like THF.
Note: These are process-level recommendations; the product itself has no greener substitute when its specific structure/stereochemistry is required.
Pharmaceutical Uses
No excipient or pharmacopeial role is claimed for this product. It is offered for research use only as a chiral synthetic intermediate.
General formulation/manufacturing context (literature/general)
Chiral building blocks such as mandelate esters are frequently employed in discovery chemistry to generate enantioenriched libraries. The 3-chloro substituent provides a convenient handle for subsequent diversification via cross-coupling or nucleophilic aromatic substitution (where feasible).
In process development settings, related α-hydroxy acid derivatives may appear as transient intermediates or resolving agents, but any use in regulated drug substance manufacturing would require full qualification, impurity profiling, and alignment with regional pharmacopeias—none of which are specified for this item.
Note: No therapeutic, diagnostic, or clinical claims are made. For GMP or clinical manufacturing, obtain a detailed CoA/Spec Sheet and perform internal qualification.
Physical Properties
Item-specific physical properties
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 (for context; not specifications)
Expected physical state: typically a colorless to pale liquid or low-melting solid for mandelate methyl esters; aryl chloride substitution can modestly raise melting/boiling points (literature, class behavior).
Polarity: moderately polar due to secondary alcohol and ester; capable of hydrogen bonding (donor and acceptor) and dipolar interactions (general chemical knowledge).
Solubility profile (qualitative, literature):
Good solubility in common organic solvents (EtOAc, DCM/CH2Cl2, THF, methanol, acetonitrile, toluene).
Low solubility in water; miscibility increases with the presence of alcohol co-solvents.
Partitioning: mandelate esters typically exhibit moderate logP values reflective of aromatic ring plus polar functionalities (literature, class trend). Specific logP/pKa values for this exact compound are not provided here.
Spectroscopic features: benzylic secondary alcohol shows characteristic O–H stretch (IR ~3300 cm−1) and distinct 1H NMR signals for CH(OH) (~4.8–5.5 ppm) and OMe (~3.6–3.8 ppm); aryl chloride impacts aromatic chemical shifts (literature, general guidance).
Important: For exact numerical data (bp/mp/density/refractive index/UV cutoff), consult the product’s CoA/SDS. Do not treat the above as product specifications.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and implications (general guidance)
Research-grade chiral building blocks: When purity/ee are stated on the CoA, they dictate suitability for asymmetric synthesis or chiral method development. For α-hydroxy esters, both chemical purity and enantiomeric excess (ee) are pivotal.
Enantiopurity via chiral HPLC or derivatization (e.g., Mosher esters) with chromatographic/ NMR readout.
Residual solvents and water content (Karl Fischer) when applicable to downstream moisture-sensitive chemistry.
Identity confirmation by HRMS and, when relevant, optical rotation [α]D.
Stabilizers/additives: Not typically required for α-hydroxy esters. If present (rare), they would be listed on the CoA; stabilizers can affect reactivity (e.g., acid scavengers may bias transesterification kinetics).
Suitability notes:
For chiral catalysis or analytical standards, verify ee and absolute configuration assignments relative to a defined reference (e.g., using VCD, ECD, or optical rotation with literature values).
For scale-up, confirm residual metal/halide levels, especially if the material originates from halogenation or catalytic steps.
Conclusion: Please consult the specific lot CoA for numerical purity, ee, and analytical method details before use in regulated or precision applications.
Reaction and Applications
As a chiral α-hydroxy ester (an (S)-mandelate methyl ester bearing a 3-chloro substituent), this compound serves as a versatile building block and stereochemically defined handle in synthesis.
Nucleophilic substitution at the benzylic OH after activation (e.g., Mitsunobu with DEAD/DIAD and PPh3) to introduce O-, N-, or S-nucleophiles with inversion, enabling access to (R)-configured derivatives at that center.
Oxidation of the secondary alcohol to the corresponding α-keto ester (mandelate → benzoylformate methyl ester), useful in further elaboration (e.g., Wittig/olefination, nucleophilic addition).
Hydrolysis of the methyl ester to give the carboxylic acid (3-chloromandelic acid), preserving configuration under mild conditions; then coupling to amines to give amides for SAR libraries.
Protection strategies: conversion of the secondary alcohol to acyl/ carbonate/ silyl ethers to control reactivity; deprotection typically under mild conditions to avoid racemization.
Resolution and chiral transfer: use as a chiral auxiliary/anchor for diastereomeric salt or ester formation in asymmetric synthesis workflows and as a reference standard in chiral analytics.
Aryl chloride handle
Enables cross-coupling (Suzuki, Buchwald–Hartwig after halogen–amine coupling, etc.) once converted to a more reactive aryl halide or with optimized catalysts for aryl chlorides.
Directed metalation at positions ortho to substituents may be explored with strong bases; control conditions to avoid α-proton deprotonation and racemization.
Practical tips
Maintain low temperatures and short exposure to strong base to avoid enolization/racemization.
Use chiral HPLC to verify ee after transformations.
Reaction Conditions
The following conditions summarize literature-typical practices for α-hydroxy aryl esters and should be optimized per substrate and scale. They are general guidance, not specifications for this item.
Ester hydrolysis (to 3-chloromandelic acid)
Basic: K2CO3 or NaOH (0.5–1.0 M) in MeOH/H2O or THF/H2O at 0–25 °C, 1–6 h; quench carefully to maintain configuration. Minimize strong base exposure time to prevent racemization.
Acidic: HCl(g) or H2SO4-catalyzed in MeOH/THF/H2O at reflux or rt, 2–12 h; typically retains stereochemistry.
Mitsunobu substitution at the secondary alcohol
Reagents: DIAD or DEAD (1.1–1.5 equiv), PPh3 (1.2–1.8 equiv), nucleophile (1.5–3.0 equiv), in THF, toluene, or DCM at 0–25 °C for 2–16 h; proceeds with inversion at the stereocenter.
Greener variants: Catalytic PPh3 with azo-reagent recycling or alternative dehydrative couplings.
Oxidation to α-keto ester
TEMPO/BAIB or Dess–Martin periodinane in DCM or MeCN at 0–25 °C, 0.5–4 h. Swern or PCC are alternatives; choose milder options to avoid chlorinated byproducts.
Transesterification
Acid-catalyzed (p-TsOH, catalytic) in alcohol solvent under Dean–Stark (for higher alcohols) at 50–110 °C; or base-catalyzed with NaOMe/ROMe at 0–25 °C.
Cross-coupling on aryl chloride
Suzuki–Miyaura: Pd(dba)2 or Pd-precatalyst with XPhos/BrettPhos; base K3PO4 or Cs2CO3 in toluene/THF/H2O or dioxane/H2O at 60–100 °C, 4–16 h.
Buchwald–Hartwig amination: Pd2(dba)3 + tBuBrettPhos, NaOtBu, toluene or dioxane, 80–110 °C, 8–24 h.
Always verify enantiopurity post-reaction. Control pH and temperature to limit racemization pathways.
Safety and Handling
Item-specific hazard information
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
GHS Classification: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
General safety considerations (literature/general guidance)
Likely hazards: As an aromatic α-hydroxy ester with an aryl chloride, expect at minimum eye/skin irritation potential; avoid inhalation of vapors or aerosols. Handle in a fume hood.
PPE: Use lab coat, chemical-resistant gloves (e.g., nitrile), and splash goggles. For scale-up or aerosol generation, consider face shield and use of local exhaust ventilation.
Storage incompatibilities: Segregate from strong oxidizers and strong bases (which can induce transesterification/saponification). Avoid strong reducing agents and dehydrating agents that could promote side reactions.
Handling notes: Keep container tightly closed. Minimize exposure to moisture if enantio- or chemoselective work requires rigorous conditions; although esters are generally stable, strong base can racemize the α-hydroxy stereocenter via enolate formation.
First aid (overview, defer to SDS):
Skin: Wash with soap and water; remove contaminated clothing.
Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy.
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Ingestion: Rinse mouth; do not induce vomiting unless directed by medical personnel.
Always consult the product-specific SDS for authoritative hazard, exposure limits, and spill/fire-fighting guidance.
Solvent Selection
This compound is a moderately polar, hydrogen-bonding-capable aryl α-hydroxy methyl ester. Solvent choice depends on the operation (reaction, purification, or analytical work).
Poorly soluble: water; solubility improves with alcohol co-solvents or pH adjustment if converted to its carboxylate (after hydrolysis).
Reaction media considerations
Nucleophilic substitutions at the benzylic OH (e.g., via Mitsunobu or activation) typically proceed well in THF, DCM, or toluene.
Ester transformations (hydrolysis, transesterification) are commonly performed in MeOH/EtOH (acidic or basic) or in toluene with azeotropic water removal for Fischer esterification routes.
Oxidations of the secondary alcohol (to keto-ester) often use CH2Cl2, MeCN, or EtOAc under TEMPO/Swern/PCC-type conditions.
Purification
Normal-phase flash chromatography with hexanes/EtOAc gradients is typical; aryl chloride increases retention in nonpolar eluents. Avoid overly basic silica if racemization is a concern; neutral/alumina or buffered silica can help.
Small comparison (literature, qualitative)
DCM vs EtOAc: DCM offers faster chromatography and better solubility; EtOAc is greener and less dense.
THF vs 2-MeTHF: comparable polarity; 2-MeTHF offers improved sustainability and water tolerance.
Note: No solvent-related specifications are assigned to this item; adjust choices to your specific transformation and sensitivity to racemization.
Storage and Reconstitution
Storage conditions (from Product Data)
Store at: Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance (literature/general)
Keep tightly closed in a dry, inert atmosphere (e.g., with desiccant). Protect from strong light and prolonged heat.
If long-term storage is anticipated, consider storing under nitrogen/argon to minimize oxidative discoloration of benzylic alcohols.
Avoid prolonged exposure to strong bases or acids during storage to prevent transesterification, hydrolysis, or racemization.
Reconstitution/handling
The material typically dissolves readily in common organic solvents (DCM, EtOAc, THF, MeOH, MeCN, toluene). Choose anhydrous grades for moisture-sensitive transformations.
For analytical work, prepare fresh solutions and record concentration by weight/volume. If stock solutions are necessary, store at 2–8 °C in sealed vials and bring to room temperature before use; verify stability by HPLC prior to critical experiments.
Freeze–thaw guidance
Not generally required. If the compound is a low-melting solid or exhibits supersaturation effects, minimize repeated temperature cycling and aliquot if needed.
Always consult the product’s CoA/SDS for definitive storage and stability information.
Structure and Identity
Brief description: (S)-Methyl 2-(3-chlorophenyl)-2-hydroxyacetate is a chiral aryl-substituted α-hydroxy acetate methyl ester (an (S)-mandelate derivative bearing a meta-chloro substituent on the aromatic ring).
Stereochemistry: single stereogenic center at the α-carbon; absolute configuration (S) as named.
Ring systems: one monosubstituted benzene ring bearing a chlorine at the meta position relative to the benzylic carbon.
2D description in words: a benzene ring with a chlorine at position 3, attached via the 1-position to a chiral benzylic carbon that bears a hydroxyl group and a methoxycarbonyl (methyl ester) substituent.
Computed/literature identifiers (for context; not item-specific)
Typical molecular formula (literature): C9H9ClO3
Typical formula weight (literature): ~200.62 g/mol
Note: Definitive structural string identifiers for this specific catalog item should be confirmed from the CoA/Spec Sheet.
Synthetic Utility
The (S)-configured α-hydroxy center and the methyl ester render this molecule a highly adaptable handle for asymmetric synthesis and library diversification.
Functional group leverage
Secondary alcohol (benzylic): amenable to selective oxidation (to α-keto ester), substitution (via Mitsunobu or sulfonate formation), or protection (silyl, carbonate, or acyl groups). Inversion/retention can be programmed via reaction choice.
Methyl ester: hydrolyze to acid for amide coupling; transesterify to alternative alcohols; reduce (e.g., DIBAL-H, LiBH4) to diols or aldehyde equivalents under controlled conditions.
Aryl chloride: gateway to cross-coupling (Suzuki–Miyaura, Buchwald–Hartwig amination) under chloride-competent catalytic systems (e.g., BrettPhos/XPhos Pd complexes, Ni catalysis). Ortho-functionalization strategies may be considered with directing groups.
Strategic roles (literature/general)
Chiral relay: preserve or transfer stereochemical information in multi-step sequences; the α-carbon stereocenter can direct diastereoselective additions to adjacent carbonyl after oxidation to keto-ester.
Resolution platform: formation of diastereomeric esters or amides with racemic partners to enable chromatographic/crystallization-based resolutions.
Fragment for medicinal chemistry: aryl-chloro motif supports late-stage diversification while the mandelate core offers hydrogen-bonding vectors.
Practical considerations
Avoid strong base and elevated temperatures in protic media to minimize racemization via enolate formation.
Monitor enantiopurity after transformations with chiral HPLC/GC or derivatization (e.g., Mosher analysis).
Choose protecting groups compatible with planned cross-couplings (e.g., TBS vs acyl) to balance stability and deprotection conditions.
Target Specificity
Not applicable. This product is a small-molecule chemical building block and does not have biological target specificity data (no antigen/epitope/clone/isotype). Refer to the Synthetic Utility and Reaction & Applications sections for relevant use cases.
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