1-(2-Amino-3-chlorophenyl)ethanone - ≥97% , CAS No.56762-32-4

CAS: 56762-32-4 Cat. No.: E731102 Formule: C₈H₈ClNO Poids moléculaire: 169.61 Numéro CE: 187-366-6 PubChem CID: 23380945

QUALITÉ & PURETÉ ≥97%

Synonyms

2-Amino-3-chloro-acetophenone

Storage

Store at 2-8°C,Protected from light,Argon charged

Shipped In

Wet ice

Spécifications

Synonymes

2-Amino-3-chloro-acetophenone

Spécifications et pureté

≥97%

Conditions de stockage de stockage

Store at 2-8°C,Protected from light,Argon charged

Expédié en

Wet ice

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Pureté

≥97%

Noms et identifiants

Sourires canoniques

CC(=O)C1=C(C(=CC=C1)Cl)N

IUPAC Name

1-(2-amino-3-chlorophenyl)ethanone

InChIKey

RVYRSQRMEZKASP-UHFFFAOYSA-N

INCHI

1S/C8H8ClNO/c1-5(11)6-3-2-4-7(9)8(6)10/h2-4H,10H2,1H3

Isomères SMILES

CC(=O)C1=C(C(=CC=C1)Cl)N

PubChem CID

23380945

Poids moléculaire

169.61

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Carbonyl compounds
        • Level5 Ketones
          • Level6 Aryl ketones
            • Level7 Phenylketones
              • Level8 Alkyl-phenylketones

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Carbonyl compounds
• Intermediate Tree Nodes: Ketones - Aryl ketones - Phenylketones
• Direct Parent: Alkyl-phenylketones
• Alternative Parents: Acetophenones Benzoyl derivatives Aryl alkyl ketones Aniline and substituted anilines Chlorobenzenes Aryl chlorides Vinylogous amides Primary amines Organochlorides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Alkyl-phenylketone - Acetophenone - Aniline or substituted anilines - Aryl alkyl ketone - Benzoyl - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Vinylogous amide - Organochloride - Organonitrogen compound - Primary amine - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Amine - Organohalogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
• 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

• Sensibilité: light & air sensitive
• Poids moléculaire: 169.610 g/mol
• XLogP3: 2.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 169.029 Da
• Monoisotopic Mass: 169.029 Da
• Topological Polar Surface Area: 43.100 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 160.000
• 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

Application Protocols

Not applicable. There are no immunoassay or bioassay protocols (e.g., WB, IHC, IF, FC) associated with a small-molecule building block. For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections for general laboratory guidance.

Biological Roles

This product is a synthetic organic building block, not a biomolecule. No intrinsic biological function or metabolic role is assigned to 1-(2-amino-3-chlorophenyl)ethanone.

• General chemistry perspective:

  • The aniline moiety can interact with biomacromolecules via hydrogen bonding and π-stacking, but any such interactions are context-dependent and pertain to derivatives, not the reagent itself.
  • In medicinal chemistry, the o-aminoacetophenone motif is used as a precursor to heterocycles (e.g., quinazolinones), which may have biological activities; however, that is a property of the final scaffolds and not of this starting material.

• Research Use Note: For research use only. Not intended for diagnostic, therapeutic, or clinical applications.

Buffer Applications

Not typically applicable. 1-(2-Amino-3-chlorophenyl)ethanone is an organic building block rather than a buffering agent. It is not used to prepare standard laboratory buffers. For work requiring aqueous handling, consider dissolving in a miscible organic co-solvent (e.g., DMSO, MeCN) before dilution, and control pH with an appropriate buffer system (e.g., phosphate, acetate) as needed.

Green Alternatives

For an aryl amine/aryl chloride ketone building block, substitution is typically structure-driven; true “drop-in” greener alternatives are rare. However, greener choices can be made in how this material is used and transformed.

• Greener solvent choices (for typical operations):

  • Workup/extraction: Prefer ethyl acetate or MTBE over DCM/chloroform when feasible.
  • Reactions: 2-MeTHF or CPME can replace THF/Et2O in many condensations; MeCN or EtOAc can often substitute for DMF/DMAc if solubility allows.
  • Crystallization/recrystallization: Ethyl acetate/hexanes blends are generally greener than chlorinated systems.

• Catalysis and conditions:

  • Use modern Pd catalysts that enable aryl chloride couplings at lower catalyst loadings and milder temperatures (energy savings, fewer byproducts).
  • Replace stoichiometric inorganic oxidants with catalytic aerobic oxidation for cyclizations to quinazolinones where literature supports it.

• Waste minimization:

  • Segregate halogenated waste streams; optimize concentration to minimize solvent usage.
  • Apply telescoped steps (e.g., in situ imine formation followed by cyclization) to reduce isolation and solvent swaps.

• Comparison (general):

  • DMF vs MeCN: MeCN offers lower boiling point and easier removal; DMF provides superior solvation but presents more challenging EHS profile.
  • DCM vs EtOAc: EtOAc is biodegradable with lower toxicity; DCM offers superior solvency for stubborn residues but is less green.

Always validate greener substitutions on small scale to ensure yield and selectivity are preserved.

Pharmaceutical Uses

No excipient or pharmacopeial role is specified for this item. It is supplied for research use only.

• General context (non-clinical):

  • This scaffold can serve as an intermediate in the synthesis of heterocycles (e.g., quinazolinones, benzimidazoles) frequently explored in medicinal chemistry campaigns.
  • Any application in drug substance/process development would require independent qualification, impurity profiling, and compliance with applicable regulatory standards.

• Compliance:

  • Not listed with a pharmacopeial grade in the provided data. For GMP or clinical manufacturing, source or qualify material to relevant monographs/specifications as needed.

Physical Properties

Item-specific physical specifications have not been provided for this SKU. Do not treat the values below as specifications; consult the CoA/Spec Sheet for release criteria.

• Item-specific (from Product Data):

  • Appearance: 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.

• Computed/literature values (for the neutral molecule; guidance only):

  • Empirical formula (from structure): C8H8ClNO (computed)
  • Average molecular weight: ~169.61 g/mol (computed)
  • Monoisotopic mass: 169.0295 Da (computed)
  • pKa (anilinium conjugate acid): typically ~4–6 for anilines (literature, class value; exact value for this specific substitution not verified)
  • LogP: anilide/aromatic ketone with chloro substituent typically displays moderate hydrophobicity (literature, class behavior; no specific value assigned)
  • Solubility: expected to be soluble in common organic solvents (EtOAc, DCM, MeOH, acetonitrile, DMF/DMSO) and sparingly soluble in water (literature, class behavior; verify experimentally).

• Thermal properties:

  • Melting point, boiling point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.

Important: Always confirm exact physical constants for your batch on the CoA or by in-house characterization prior to scale-up.

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, water content, residual solvents, metals profile: Not specified for this item; refer to CoA/Spec Sheet.

• Guidance on interpreting grades (general):

  • Research/technical grade materials are intended for laboratory research and development and may not meet pharmacopeial monographs.
  • Where “puriss.” or “≥98%” type designations appear on a CoA, they typically reflect assay by GC/HPLC/quantitative NMR with defined acceptance criteria. For building blocks, impurity profiles may include isomeric regioisomers, residual solvents, and halogen-containing byproducts.
  • If low-UV or LC/MS suitability is critical, specify HPLC-grade solvents for sample prep and request low-UV impurity data if needed.

• Batch documentation:

  • For this SKU, release specifications (assay, ID by NMR/IR/HRMS, appearance, and limits on related substances) should be confirmed on the CoA/Spec Sheet. Request additional QC data (stereochemical confirmation not applicable here; no chiral centers) if your application is sensitive to trace anilines/halides.

• Research Use Note: For research use only.

Reaction and Applications

As an ortho-amino, meta-chloro acetophenone, this building block is versatile for heterocycle construction and diversification of aryl frameworks (general synthetic chemistry guidance).

• Transformations via the aniline:

  • Electrophilic acylation/carbamoylation/sulfonylation to access anilides, ureas, and sulfonamides. Control chemoselectivity vs the ketone using protecting groups (e.g., Boc on the amine) when needed.
  • Diazotization (NaNO2/HX, 0–5 °C) enabling Sandmeyer-type substitutions (–N2+ → –Cl, –Br, –CN) or azo coupling; ensure compatibility with the aryl chloride already present.
  • Reductive amination with aldehydes/ketones to form secondary/tertiary anilines; protect/reduce the adjacent aryl ketone as required to avoid undesired imine formation at the ketone carbonyl.

• Transformations via the ketone:

  • Oxime/hydrazone formation; subsequent Beckmann rearrangement to amides or Wolff–Kishner/Clemmensen reductions to the ethyl analogue.
  • Enamine formation and alpha-functionalization (halogenation, alkylation) using LDA or weaker bases, mindful of aniline protonation state.

• Cross-coupling at aryl chloride:

  • Pd-catalyzed Suzuki–Miyaura, Buchwald–Hartwig, or Sonogashira couplings are feasible with modern ligands (e.g., BrettPhos/XPhos) and bases (K3PO4, Cs2CO3), enabling rapid library synthesis.

• Heterocycle synthesis (from o-aminoacetophenone motif):

  • Quinazolinones and quinazolines via condensation with formamide, amidines, or nitriles (often oxidative cyclization).
  • Benzimidazoles/quinazolines through cyclocondensation with carboxylic acid derivatives or aldehydes (e.g., o-aminoacetophenone + aldehyde + oxidant).

• Applications:

  • Fragment for medicinal chemistry SAR studies, agrochemical intermediate, and materials precursors (general uses; no clinical claims).

Reaction Conditions

General literature-guided conditions for typical transformations of o-amino, m-chloro acetophenone motifs (verify and optimize for your substrate and scale):

• Protection of aniline:

  • Boc protection: (Boc)2O, DMAP catalytic, Et3N, DCM or MeCN, 0 °C to RT, 1–4 h. Typical isolated yields: high.
  • Sulfonylation: TsCl, pyridine or Et3N, DCM, 0 °C→RT.

• Imine/oxime formation at the ketone:

  • With hydroxylamine·HCl: EtOH or MeOH, pyridine/AcONa, RT–reflux, 2–16 h.
  • Reductive amination (external carbonyl): NaBH3CN or NaBH(OAc)3, MeOH/MeCN, catalytic AcOH, RT.

• α-Halogenation/functionalization:

  • NBS/NCS in AcOH or DCM with acid catalysis, 0 °C→RT; or enolate generation with LDA in THF at −78→0 °C followed by electrophile addition.

• Cross-coupling at aryl chloride:

  • Suzuki–Miyaura: aryl/alkenyl boron (1.2–1.5 eq), Pd2(dba)3 (0.5–1 mol%), XPhos/BrettPhos (1–3 mol%), K3PO4 or Cs2CO3 (2–3 eq), dioxane/H2O (10:1), 80–110 °C, 2–16 h. Many examples tolerate protected anilines.
  • Buchwald–Hartwig amination: amine nucleophile (1.2–2 eq), Pd(allyl)Cl dimer or Pd2(dba)3 (1–2 mol%), tBuBrettPhos or RuPhos (2–4 mol%), NaOtBu or Cs2CO3, toluene/dioxane, 80–110 °C.
  • Sonogashira: terminal alkyne, Pd(PPh3)2Cl2/CuI, Et3N or iPr2NH, 50–80 °C.

• Quinazolinone formation (from o-aminoacetophenone motif):

  • Condense with formamide or formamidine under oxidative/cyclodehydrative conditions (e.g., I2/DMSO or Cu-catalyzed aerobic), 80–140 °C.

• Workup/purification:

  • Control protonation state of the aniline during extractions (acid–base toggling) to improve separations. Use silica gel with optional NEt3 modifier to minimize amine streaking.

All parameters above are general literature guidance; optimize for your exact substrate and scale.

Safety and Handling

Safety details specific to this catalog item (GHS, pictograms, hazard statements) are not provided here; consult the SDS for authoritative information.

• Item-specific hazard data (from Product Data):

  • 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 laboratory safety considerations (general chemistry guidance for aryl amines/aryl ketones; not item-specific):

  • Potential hazards: Aromatic amines can be harmful if inhaled, swallowed, or absorbed through skin and may cause skin/eye irritation and sensitization. Aryl ketones can be irritants. Avoid dust or vapor formation.
  • PPE: Use lab coat, safety glasses or face shield, and appropriate chemically resistant gloves (e.g., nitrile). Handle in a fume hood.
  • Incompatibilities: Strong oxidizers; nitrosating agents (anilines can form nitroso species); strong acids/bases that may cause salt formation or degradation. Avoid prolonged exposure to air/heat if oxidative discoloration is observed.
  • First aid (summary): Inhalation—move to fresh air; Skin—wash with soap/water; Eyes—rinse cautiously with water for several minutes; Ingestion—rinse mouth, seek medical attention. Follow SDS instructions.
  • Spills/Waste: Absorb small spills with inert material; collect for disposal per institutional and regulatory requirements. For halogenated organics, segregate waste streams appropriately.

• Storage (per Product Data):

  • Store at room temperature. Keep container tightly closed in a dry, well-ventilated area. Refer to SDS for detailed guidance.

Solvent Selection

This compound is an aniline-bearing aryl methyl ketone with a chloro substituent. It displays moderate polarity and is typically soluble in common organic solvents.

• Polarity/miscibility (general behavior; verify experimentally):

  • Good: DMSO, DMF, NMP, acetonitrile, ethyl acetate, dichloromethane, chloroform, methanol, ethanol.
  • Limited: Nonpolar hydrocarbons (hexanes, heptane) depending on temperature.
  • Aqueous: Likely low solubility at neutral pH; increases under acidic conditions via anilinium salt formation.

• Selection by task:

  • NMR: DMSO-d6 or CDCl3 are typical; consider DMSO-d6 if limited solubility in CDCl3.
  • Crystallization: Ethyl acetate/hexane or DCM/hexane systems can be effective; acidify mother liquor to control protonation state if necessary.
  • Reactions involving the amine (acylation, imine formation): Use anhydrous polar aprotic solvents (DCM, THF, MeCN); manage basicity with tertiary amine bases.
  • Cross-coupling on the aryl chloride: High-boiling polar aprotics (dioxane, toluene, DMAc) under Pd catalysis.

• Small comparison (general):

  • DCM vs EtOAc: DCM offers faster dissolution and lower boiling point; EtOAc is greener and easier to remove than DMF.
  • DMSO/DMF vs MeCN: DMSO/DMF improve solubility and coupling efficiency but are harder to remove; MeCN balances polarity and volatility.

Always confirm solvent compatibility with downstream steps and regulatory requirements.

Storage and Reconstitution

• Storage (item-specific):

  • Storage Conditions: Room temperature (per Product Data). Keep container tightly closed in a dry, well-ventilated place. Protect from moisture and incompatible materials. Refer to the SDS for detailed handling/storage instructions.

• Shipping: Not specified for this item; refer to CoA/Spec Sheet.

• Reconstitution/Preparation:

  • Physical form and appearance are not specified; if received as a solid, prepare stock solutions in dry organic solvents compatible with your application (e.g., DMSO, MeCN, DCM, EtOAc). If received as an oil, handle under inert atmosphere if prolonged storage is anticipated.
  • For solution storage, use dry, oxygen-impermeable containers; aliquot to minimize headspace and freeze–thaw cycles. Verify solution stability empirically before long-term storage.

• Stability considerations (general):

  • Anilines can slowly oxidize/discolor on exposure to air/light; if sensitivity is observed, store under inert gas and/or protect from light.
  • Avoid prolonged exposure to strong acids/bases and oxidizers.

• Documentation:

  • For exact shelf-life, purity release limits, and any stabilizers used, consult the item’s CoA/Spec Sheet.

• Research Use Note: For research use only.

Structure and Identity

A substituted acetophenone bearing an ortho-amino and meta-chloro substituent on the aromatic ring; useful as an aniline-containing aryl ketone building block.

• Item-specific identifiers (from Product Data):

  • CAS: 56762-32-4
  • CID (PubChem): 23380945
  • InChIKey: 327505 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Synonyms (general/literature): 2-amino-3-chloroacetophenone; o-amino-m-chloroacetophenone (literature)

• Computed/literature structural details (not item-specific specifications):

  • Core scaffold: acetophenone (phenyl–CO–CH3) with an –NH2 at the 2-position and –Cl at the 3-position relative to the acyl substituent.
  • Functional groups: aniline (primary aryl amine), aryl chloride, aryl methyl ketone.
  • Molecular formula (from structure, computed): C8H8ClNO
  • Average molecular weight (from formula, computed): ~169.61 g/mol
  • Monoisotopic mass (computed): 169.0295 Da
  • 2D description: A benzene ring bearing three substituents in adjacent positions: carbonyl methyl (acyl) at C1 (–COCH3), amino at C2 (–NH2), and chloro at C3 (–Cl). No stereocenters.

• Notes:

  • Any definitive structural string (SMILES/InChI) and exact identifiers for this specific item should be confirmed on the item’s CoA/Spec Sheet. All computed values above are for general reference only.

Synthetic Utility

This molecule combines three reactive handles: an aniline (nucleophilic, basic), an aryl chloride (cross-coupling handle), and an aryl methyl ketone (electrophilic carbonyl with α-reactivity). This convergence enables orthogonal diversification.

• Aniline-directed chemistry:

  • Protection strategies: Boc, Cbz, or sulfonyl protections to manage chemoselectivity during α-functionalization of the ketone or cross-coupling at Ar–Cl.
  • Electrophile capture: Acylation, sulfonylation, and isocyanate trapping to form amides/ureas; subsequent intramolecular condensation with the ketone can furnish bicyclic systems under dehydrating conditions.

• Ketone-centered chemistry:

  • Oxime/hydrazone formation, followed by Beckmann or Fischer-type transformations.
  • α-Functionalization: Halogenation (NBS/NCS under acidic conditions), alkylation (via enolate), or oxidation to the corresponding aryl glyoxal (via SeO2 or catalytic methods) enabling further condensations.
  • Reductive transformations: Clemmensen/Wolff–Kishner to install ethyl group while retaining the aniline/Cl handles.

• Aryl chloride as coupling locus:

  • Pd/Ni-catalyzed cross-couplings (Suzuki, Buchwald–Hartwig, Sonogashira) with ligands tailored for aryl chlorides (BrettPhos, XPhos, SPhos). Orthogonal to amine when protected or under carefully chosen bases.

• Heterocycle assembly from o-aminoacetophenone motif:

  • Quinazolinones via condensation with formamide/amidines; benzimidazoles via condensation with aldehydes and oxidants; 1,2-dihydroquinazolines via reductive cyclization.

Strategically, this building block is valuable in retrosynthesis to converge amine-derived diversity, cross-coupling diversity, and carbonyl-derived diversity on a single aryl core.

Target Specificity

Not applicable. This product is a small-molecule chemical building block and is not an antibody, enzyme, or affinity reagent. No antigen/epitope or biological target specificity is associated with this item.