2-(2-Chlorophenyl)-2-hydroxypropionic acid - ≥95% , CAS No.171202-07-6

CAS: 171202-07-6 Cat. No.: C1027917 Formule: C₉H₉ClO₃ Poids moléculaire: 200.62 PubChem CID: 18368828

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Spécifications et pureté

≥95%

Conditions de stockage de stockage

Room temperature

Pureté

≥95%

Noms et identifiants

• Sourires canoniques: CC(C1=CC=CC=C1Cl)(C(=O)O)O
• IUPAC Name: 2-(2-chlorophenyl)-2-hydroxypropanoic acid
• InChIKey: ZEXPENITPLXFLY-UHFFFAOYSA-N
• INCHI: 1S/C9H9ClO3/c1-9(13,8(11)12)6-4-2-3-5-7(6)10/h2-5,13H,1H3,(H,11,12)
• Isomères SMILES: CC(C1=CC=CC=C1Cl)(C(=O)O)O
• PubChem CID: 18368828
• Poids moléculaire: 200.62

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Halobenzenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Halobenzenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Chlorobenzenes
• Alternative Parents: Aryl chlorides Alpha hydroxy acids and derivatives Tertiary alcohols Monocarboxylic acids and derivatives Carboxylic acids Organochlorides Organic oxides Hydrocarbon derivatives Carbonyl compounds Aromatic alcohols
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Chlorobenzene - Alpha-hydroxy acid - Aryl chloride - Aryl halide - Hydroxy acid - Tertiary alcohol - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organooxygen compound - Organochloride - Organohalogen compound - Alcohol - Organic oxygen compound - Carbonyl group - Aromatic alcohol - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
• Description: 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

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

Propriétés chimiques et physiques

• Poids moléculaire: 200.620 g/mol
• XLogP3: 1.600
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 200.024 Da
• Monoisotopic Mass: 200.024 Da
• Topological Polar Surface Area: 57.500 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 207.000
• 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 to this product type.

• No validated biological assay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule building block. Application conditions should be developed as appropriate for the intended synthetic or analytical use.

Biological Roles

Applicability

• This is a synthetic small-molecule building block. It is not a natural metabolite nor a biopolymer component.

General biochemical considerations (no clinical claims)

• Functional groups: The α-hydroxy–carboxylic acid motif is common in metabolism (e.g., lactic, mandelic acids), conferring metal-chelating ability and hydrogen-bonding capacity. These features can influence binding in biochemical assay development or fragment screening.
• Ionization: At physiological pH, the carboxyl group would be largely deprotonated, while the α-hydroxyl remains mostly un-ionized. This impacts passive membrane permeability and protein binding when used as a probe or intermediate in biochemical tool synthesis.
• Aromatic substituent: The 2-chlorophenyl ring is hydrophobic and can drive interactions with lipophilic pockets; ortho-chloro substitution alters electronics and sterics relative to phenyl analogs.

Usage note

• Any biological testing should be conducted under appropriate institutional approvals. This product is supplied strictly for research use; no claims are made regarding biological activity or suitability for diagnostic use.

Buffer Applications

Not typically applicable.

• This compound is not a standard buffering agent and is seldom used to prepare pH buffers. If used in biochemical settings, it would more often be a component or intermediate in the synthesis of tool compounds rather than a buffer component.
• For experimental work requiring pH control, select established buffer systems (e.g., phosphate, HEPES, acetate) and dissolve this compound separately in a compatible solvent or as a salt if needed.

Green Alternatives

Context

• This product is a solid organic building block rather than a bulk process solvent. “Green alternatives” therefore center on greener reagents/solvents used with it and on protection/minimization strategies.

Greener choices (literature guidance)

• Solvents: Favor 2-MeTHF, CPME, EtOAc, or propylene carbonate over chlorinated solvents when feasible. For amide couplings, EtOAc or Me-THF can sometimes replace DCM/DMF with suitable coupling agents.
• Coupling reagents: Use greener uronium salts or CDI instead of DCC (to reduce DCU waste). Enzymatic esterifications in tert-amyl alcohol or solvent-free systems can be effective for α-hydroxy acids.
• Protection economy: Consider telescoping steps or using in situ activation to avoid separate protection/deprotection when chemoselectivity allows.

Illustrative comparison (general)

• DCM vs EtOAc: EtOAc has a superior environmental profile (biodegradable, lower toxicity) while offering similar extraction and many reaction capabilities; DCM may still be needed for certain low-temperature chlorination/oxidation steps.
• DMF vs Cyrene/PolarClean: Cyrene or PolarClean can substitute in some coupling reactions but may require re-optimization of bases and activators.

Waste and safety

• Implement aqueous bicarbonate workups to avoid strong mineral acids for phase switches.
• Distill/recycle ethers/esters where possible; segregate halogenated waste from non-halogenated streams to facilitate solvent recovery.

Pharmaceutical Uses

Formulation/CM&C context (general; no therapeutic claims)

• Role: Potential intermediate for active ingredients or advanced intermediates featuring an o-chlorophenyl tertiary carbinol motif. The α-hydroxy–carboxylate handle enables prodrug-like ester formation for medicinal chemistry SAR studies.
• Compendial status: No pharmacopeial monograph is implied for this specific compound. If compendial compliance is required for a program, appropriate internal specifications and validated analytical methods should be established.
• Salt and ester forms: Conversion to sodium/potassium salts enhances aqueous processability; benzyl/methyl esters can be used as protecting groups during multi-step synthesis with subsequent hydrogenolysis/saponification.
• Impurity control: Track potential process impurities such as regioisomeric chlorophenyl analogs, over-oxidation to α-keto acids, and residual coupling reagents. Establish limits and methods (HPLC-UV, LC–MS) for phase-appropriate development.

Regulatory note

• Supplied for research use only. Not for use in human or veterinary medicines, diagnostics, or as a food additive.

Physical Properties

Item-specific specs

• Melting point, boiling point, density, refractive index, elemental limits, water/peroxide content, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general expectations for this structure class (α-hydroxy aryl carboxylic acids; guidance only)

• Physical state: typically crystalline solids for analogous α-hydroxy arylpropionic acids.
• Acidity: α-hydroxy carboxylic acids generally exhibit pKa(COOH) ~2.8–3.6 (literature, compound class-dependent).
• Solubility: often sparingly soluble in water as free acid; readily soluble in polar organic solvents (MeOH, EtOH, acetone) and in basic aqueous media as the carboxylate salt (literature, class behavior). Soluble in DMSO and DMF.
• Partitioning: aryl-substituted hydroxyacids tend to show moderate hydrophobicity in the neutral form; ionization markedly increases aqueous solubility (general observation).

Practical notes

• Dissolution is accelerated by slight warming and/or conversion to a salt with organic bases (e.g., triethylamine) for non-aqueous workups.
• Hygroscopicity is usually low to moderate for this class, but minimize moisture uptake to preserve assay and avoid slow esterification in alcoholic media.

Quality and Grades

Item-specific grade/purity

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

General guidance on quality considerations for this compound type

• Identity: Confirm by 1H/13C NMR (α-hydroxy proton often broad/small, carboxylic proton downfield), IR (broad O–H 2500–3300 cm⁻¹; C=O ~1700–1730 cm⁻¹), and HRMS.
• Chiral purity: The α-carbon is stereogenic. Unless enantiomeric purity is stated, assume racemic. Applications in asymmetric synthesis or chiral resolution may require ee/er documentation (HPLC/GC on chiral stationary phase).
• Residual solvents and inorganic salts: Scrutiny recommended if the material is prepared via nitrile hydrolysis or Grignard-type routes; check CoA for KF moisture and residual metals if relevant to your process. If not specified: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers: Typically not required for this class; if present, they should be disclosed on the CoA. For this item: Not specified for this item; refer to CoA/Spec Sheet.

Documentation

• For chromatographic applications or regulated workflows, request lot-specific CoA including HPLC purity, assay method, and any stabilizer/additive declarations.

Reaction and Applications

Use profile (general for α-hydroxy aryl carboxylic acids)

• Building block: Precursor to esters, amides, and mixed anhydrides; useful in fragment-based assembly for aryl–alkyl tertiary carbinol motifs.
• Chiral chemistry: The α-carbon is stereogenic. Unless an enantiopure variant is specified, material is typically racemic. Resolution or asymmetric synthesis may be employed downstream.

Representative transformations (literature)

• Esterification: Fischer or Steglich/Mitsunobu protocols to access alkyl/aryl esters; attention to retention/inversion at the α-carbon under Mitsunobu.
• Amide formation: Activation via DCC/EDC/HATU in DMF/DCM; coupling to amines affords α-hydroxy amides (potential for intramolecular hydrogen bonding that influences conformation/reactivity).
• Protection strategies: Hydroxyl can be protected as silyl ether (TBDMS/TBS) or as benzyl/allyl ethers; carboxyl protected as methyl/benzyl esters. Orthogonality enables stepwise functionalization.
• Oxidation: α-Hydroxy → α-keto acid using Dess–Martin periodinane, Swern, or TEMPO-based protocols (control conditions to minimize decarboxylation).
• Halogenation/dehydration: Careful treatment with SOCl2/POCl3 can convert OH to chloride or induce elimination; conditions must be optimized to avoid rearrangements.

Applications

• Intermediates in agrochemical or materials leads featuring o-chlorophenyl motifs.
• Ligand/scaffold elaboration where a 2-chlorophenyl–tertiary carbinol handle is desired.

Practical tips

• Maintain anhydrous conditions during activations to suppress O→N acyl transfer or hydrolysis.
• Monitor epimerization: Strong base or elevated temperatures can racemize the α-center; use mild bases, low temperature, and short reaction times when stereochemistry matters.

Reaction Conditions

General literature guidance (optimize per system)

• Esterification (Steglich): Carboxylic acid (1.0 eq), alcohol (1.2–2.0 eq), DCC (1.2 eq), DMAP (0.1 eq) in DCM or EtOAc, 0–25 °C, 2–16 h. Monitor for O→N acyl transfer; filter DCU.
• Amide coupling (HATU/DIPEA): Acid (1.0 eq), amine (1.2 eq), HATU (1.1 eq), DIPEA (2.0 eq) in DMF/MeCN, 0–25 °C, 1–6 h. Minimize base to reduce racemization at the α-center.
• Mitsunobu substitution: Alcohol (from this α-hydroxy acid or its ester), DEAD/DIAD (1.2 eq), PPh3 (1.2 eq), pronucleophile (1.5 eq), THF/THF–toluene, 0–25 °C. Expect inversion at the reacting center; avoid if retention is required.
• Oxidation to α-keto acid: Dess–Martin periodinane (1.3 eq) in DCM, 0–25 °C, 1–3 h; or TEMPO/NaOCl (pH ~9) in biphasic CH2Cl2/H2O, 0–5 °C, 0.5–2 h. Work cold to limit decarboxylation.
• Protection: TBSCl/imidazole in DMF (rt, 2–6 h) for OH; MeI/K2CO3 in acetone (reflux) for methyl ester; BnBr/NaH in DMF (0–25 °C) for benzyl ether/ester followed by hydrogenolysis.

Notes

• Dry, oxygen-free conditions help when sensitive intermediates (acid chlorides, anhydrides) are generated.
• If stereochemical integrity matters, perform reactions at low temperature, with mild bases, and minimize time in solution.
• Verify compatibility of the o-chlorophenyl ring with metal-catalyzed steps (e.g., Pd-catalyzed couplings) if further aryl elaboration is planned.

Safety and Handling

Item-specific hazard data

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

General safety guidance for α-hydroxy aryl carboxylic acids (informational; defer to SDS)

• Likely hazards: May cause skin/eye irritation; dust may be irritating to the respiratory tract. Avoid inhalation and contact with eyes/skin.
• PPE: Use lab coat, safety glasses or face shield, and suitable chemical-resistant gloves (e.g., nitrile). Handle solids in a fume hood to avoid dust exposure.
• Incompatibilities: Strong oxidizers (risk of exotherm/oxidation); strong bases and acylating agents can induce rapid ester/anhydride formation; dehydrating agents may promote rearrangements or elimination.
• Thermal stability: Organic acids are generally thermally stable but can decompose on strong heating, producing irritating fumes (HCl may evolve from chlorinated aromatics under harsh conditions).
• First aid (overview):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; obtain medical advice if irritation continues.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

Always consult the product’s SDS for authoritative hazard classifications, exposure limits, spill response, and disposal guidance in your jurisdiction.

Solvent Selection

Applicability

• This product is a small-molecule α-hydroxy aryl carboxylic acid (building block). Solvent selection is primarily about dissolution for reaction or analysis.

General solvent behavior (literature/class-based)

• Polar aprotic: DMSO, DMF, NMP dissolve both acid and salts well; useful for coupling and substitution chemistry.
• Alcohols: MeOH/EtOH generally dissolve the free acid; watch for slow esterification under acidic conditions or upon heating.
• Aqueous systems: The free acid is only moderately water-soluble; solubility increases strongly upon basification (pH > pKa). Prepare sodium/potassium salts for aqueous-phase work.
• Esters/ethers: EtOAc and THF offer moderate solubility; THF favored for organometallic transformations on protected derivatives.

Selection tips

• For coupling (to make esters/amides): Use dry DMF/DCM/THF with carbodiimides or uronium reagents; keep base mild to avoid elimination/ester exchange.
• For analytical HPLC: Acidic modifiers (0.1% formic) improve peak shape in RP-HPLC; methanol/water or acetonitrile/water gradients are typical. Verify UV response of the aryl ring at 210–254 nm.
• For salt formation/extractions: Partition as carboxylate into aqueous base (NaHCO3/Na2CO3), and back-extract as the free acid after acidification.

Environmental/compatibility notes

• Avoid strong acids in alcohol solvents if ester-free product must be preserved. Minimize water in peptide-coupling contexts to reduce hydrolysis.

Storage and Reconstitution

Item-specific storage/shipping

• Storage condition (from Product Data): Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

General guidance for this compound class

• Container: Store tightly closed in a clean, dry, inert container. Protect from excessive humidity to prevent gradual esterification in alcoholic residues and to maintain assay.
• Light/air: Normal laboratory lighting is acceptable; avoid prolonged exposure to strong UV. No special inerting is typically required for the free acid, but purge with nitrogen for long-term storage of activated derivatives (e.g., acid chlorides, anhydrides).
• Stability: α-Hydroxy carboxylic acids are generally stable at ambient conditions. Avoid strong bases/acids during storage. If long-term storage is anticipated, consider 2–8 °C as a conservative measure.

Reconstitution/dissolution

• Solubility aids: Dissolve in DMSO, DMF, MeOH, or EtOH. For aqueous work, adjust to pH > pKa with NaOH/KOH or prepare a buffer-compatible salt (e.g., sodium salt) immediately before use.
• Filtering: For analytical work, pass solutions through 0.2 µm PTFE/NYLON filters to remove particulates.
• Solution stability: Prepare fresh solutions where possible; organic solutions are best used within days, aqueous salt solutions within 24–48 h unless stability has been verified.

Always refer to the lot-specific CoA/SDS for definitive storage and handling instructions.

Structure and Identity

Item-specific facts (from Product Data)

• Product name: 2-(2-Chlorophenyl)-2-hydroxypropionic acid (SKU: C1027917)
• CAS: 171202-07-6
• Storage: Room temperature
• Research use: For research use only
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Computed/literature identification (general, for the named structure)

• Synonym (descriptive): 2-hydroxy-2-(2-chlorophenyl)propanoic acid; o-chloro-α-methylmandelic acid (naming sense only)
• Molecular formula (theoretical for this name): C9H9ClO3
• Approximate molecular weight (calculated): ~200.6 g/mol
• Structural features: one aromatic ring (o-chlorophenyl), an α-hydroxy carboxylic acid (α-hydroxy–carboxylate motif), one stereogenic center at the α-carbon; configuration not specified (presume racemic unless otherwise indicated).
• 2D description: a propionic-acid backbone with the α-carbon bearing a hydroxyl, a methyl, and an ortho-chlorophenyl substituent; para/meta ring positions unsubstituted aside from the ortho chlorine.

Notes

• Where exact identifiers (SMILES/InChIKey) are required for regulatory or informatics use, consult the product CoA/SDS for this lot.

Synthetic Utility

Key reactive elements

• Carboxylic acid: amenable to esterification, amidation, and activation (acid chlorides, mixed anhydrides, activated esters).
• α-Hydroxyl group: convertible to leaving groups (e.g., via mesylate/tosylate) or protected as silyl/benzyl ethers; oxidizable to α-keto acids.
• Stereogenic α-center: enables access to enantioenriched derivatives via resolution or asymmetric synthesis (diastereomeric salt/ester formation; biocatalytic resolutions).

Named/typical transformations (literature)

• Steglich esterification (DCC/DMAP) to introduce alcohol-derived esters at ambient temperature.
• Mitsunobu reaction for selective inversion at the α-carbon when converting the hydroxyl to various O-substituents (careful condition choice to prevent elimination).
• HATU/EDC-mediated amide couplings with primary/secondary amines.
• Dess–Martin or TEMPO/bleach oxidations to the corresponding α-keto acid; conditions tuned to suppress decarboxylation.
• Halogen substitution or displacement sequences after OH activation (e.g., via MsCl) to build α-substituted derivatives.

Retrosynthetic value

• Serves as a convergent junction: aryl fragment introduced via arylation of an α-oxo/α-halo precursor or by addition of aryl nucleophiles to pyruvate derivatives; downstream diversification at the acid or alcohol increases library reach.

Target Specificity

Not applicable to this product type.

• This item is a small-molecule building block and is not an antibody, protein, or nucleic acid reagent. No antigen/epitope specificity, clone, or isotype applies.