2,4-Dihydroxybenzylamine - ≥95% , CAS No.63452-56-2

CAS: 63452-56-2 Cat. No.: D1073379 Summenformel: C7H10ClNO2 Molekulargewicht: 175.62 PubChem CID: 124993

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥95%

Storage

Room temperature

Reinheit

≥95%

Namen und Kennungen

• Kanonisches Lächeln: C1=CC(=C(C=C1O)O)CN
• IUPAC Name: 4-(aminomethyl)benzene-1,3-diol
• InChIKey: BJJYHNCUAZNAOP-UHFFFAOYSA-N
• INCHI: 1S/C7H9NO2/c8-4-5-1-2-6(9)3-7(5)10/h1-3,9-10H,4,8H2
• Isomere SMILES: C1=CC(=C(C=C1O)O)CN
• PubChem CID: 124993
• Molekulargewicht: 175.62

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Klasse Phenols
      • Subclass Benzenediols

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Klasse: Phenols
• Subclass: Benzenediols
• Intermediate Tree Nodes: Not available
• Direct Parent: Resorcinols
• Alternative Parents: Phenylmethylamines Benzylamines Aralkylamines 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Organopnictogen compounds Organooxygen compounds Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzylamine - Phenylmethylamine - Resorcinol - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Aralkylamine - Monocyclic benzene moiety - Amine - Hydrocarbon derivative - Primary amine - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Primary aliphatic amine - Organic oxygen compound - Organic nitrogen compound - Aromatic homomonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as resorcinols. These are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3.
• 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

Chemische und physikalische Eigenschaften

• Molekulargewicht: 139.150 g/mol
• XLogP3: 0.600
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 139.063 Da
• Monoisotopic Mass: 139.063 Da
• Topological Polar Surface Area: 66.500 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 108.000
• 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

No assay or kit-style application protocols are specified for this item.

• Typical laboratory uses (general)

  • Prepare stock solutions in DMSO, methanol, or ethanol for combinatorial synthesis or screening; filter sterilize if required for biochemical assays.
  • For reductive amination screens: combine carbonyl partner and 2,4-dihydroxybenzylamine in alcohol or MeCN with acetic acid and NaBH(OAc)3; monitor by LC–MS.
  • For amide coupling: dissolve amine and acid partner in DMF or DCM, add coupling agent and base, stir at 0–25°C; quench and purify by flash chromatography.

• Analytical considerations

  • Use acidic modifiers (0.1% formic acid or TFA) in LC to minimize amine tailing; detect by UV at 210–280 nm or by MS (ESI+).

For any validated, product-specific protocols or recommended dilutions, refer to the CoA/Spec Sheet.

Biological Roles

Applicability note: 2,4-Dihydroxybenzylamine is a synthetic research chemical and not an endogenous metabolite. Content below is general biochemical context for related functional groups and is not a claim of biological activity for this specific product.

• Phenolic/benzylamine motif

  • Phenolic rings participate in hydrogen bonding and π–π interactions with proteins; dihydroxy substitution can modulate redox behavior and metal chelation.
  • Primary benzylamines are protonated near physiological pH (pKaH ~9–10, literature), influencing transport and interaction with acidic binding sites.

• Enzymology context (literature)

  • Phenolic benzylamines can serve as model substrates/inhibitors in assays involving oxidases (e.g., tyrosinase, peroxidases) due to their phenolic groups and benzylic amine.
  • Schiff base formation with aldehydes is a common step in cofactor/enzyme-mimetic chemistry (e.g., imine formation with PLP mimics in vitro), assisting mechanistic studies.

• Metal binding and redox

  • Ortho/para dihydroxy patterns influence catechol-like coordination, potentially enabling O,N-chelation in metal-binding studies (purely in vitro, research use).

• Assay development uses

  • Frequently employed as a scaffold to construct fluorescent/chelating probes or affinity ligands by derivatizing the amine or phenolic positions.

Note: No medical, diagnostic, or therapeutic use is intended or implied. Any biological experimentation should be designed and reviewed under appropriate institutional guidelines.

Buffer Applications

This compound is not a conventional buffering agent. It lacks a well-defined, narrow pKa window and salt pair commonly used in standardized biological buffers.

• Practical guidance
  • If used in aqueous systems, its amine will be protonated under mildly acidic conditions (literature pKaH for benzylamines ~9–10), but this does not make it a reliable buffer component.
  • For pH control, select established buffers (e.g., phosphate, HEPES, MOPS, Tris) tailored to your target pH range.
  • The compound may be dissolved in buffered media for assays, but the buffer capacity should come from a dedicated buffer system.

For recipes and pH ranges, consult standard buffering agents rather than relying on 2,4-dihydroxybenzylamine.

Green Alternatives

Context: While 2,4-dihydroxybenzylamine itself is the chosen building block, greener choices can be made for solvents and reagents used with it.

• Greener solvent swaps (general guidance)

  • Replace DMF/DMAc/NMP with safer polar aprotics where possible (e.g., propylene carbonate, dimethyl sulfone, Cyrene) or aqueous/ethanol systems for imine/reductive amination chemistry.
  • Substitute dichloromethane with ethyl acetate, 2-MeTHF, or CPME for acylation/extractions.
  • Use ethanol or water–ethanol mixtures instead of methanol where reactivity permits.

• Reductive amination systems

  • Prefer NaBH(OAc)3 in acetic acid/EtOAc or ethanol over cyanoborohydride in acetonitrile when feasible; or catalytic hydrogenation in ethanol under mild pressure with proper safety controls.

• Base and coupling reagents

  • Consider green coupling agents (e.g., COMU/ethyl cyano(hydroxyimino)acetate alternatives) and minimize excess. Explore enzyme-mediated acylations in water/green solvents for selective amide formation.

• Energy and waste reduction

  • Microwave or flow chemistry can reduce reaction times and solvent volumes.
  • Employ in situ protection strategies and telescoped sequences to minimize isolations and solvent-intensive workups.

Small comparison (illustrative; literature-based)

• Traditional: DCM/DMF; NaBH3CN; strong inorganic bases (NaH, K2CO3).
• Greener: 2-MeTHF/EtOAc/EtOH; NaBH(OAc)3 or H2/Pd in EtOH; organic superbases in catalytic amounts or aqueous bicarbonate.

Always validate green substitutions on small scale to confirm selectivity with phenolic and amine functionalities.

Pharmaceutical Uses

No direct excipient or pharmacopeial status is provided for this item.

• Item-specific status

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

• General context (non-clinical; research/manufacturing only)

  • Synthetic intermediate: The benzylamine/phenol combination is a useful synthon for assembling more complex scaffolds (e.g., amide-linked, carbamate, or ether derivatives) relevant to medicinal chemistry campaigns.
  • Prodrug/derivatization handle: The primary amine allows formation of salts or pro-moieties in research; phenolic OH groups can be masked as carbonate/carbamate/ether for tunable properties during process development.
  • Ligand precursor: O,N- or O,N,O-dentate motifs derived from this scaffold are explored as coordination ligands in catalyst development, which can be relevant to API synthesis steps.

• Formulation considerations (general)

  • Salt selection (e.g., hydrochloride) may be used to enhance stability, crystallinity, and aqueous handling in process research.
  • Control of oxidative impurities is important for phenolic materials; antioxidants or low-oxygen handling may be considered during development.

Note: Not for human or veterinary use. No therapeutic claims are made for this product.

Physical Properties

Item-specific specifications (for this catalog entry):

• 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.

General/literature characteristics (context only; not product specifications):

• State: Aromatic benzylamine derivatives of this type are commonly low-melting solids or viscous oils, depending on salt form and hydration.
• pKa (conjugate acid of benzylic amine, literature): typically ~9–10 for benzylamines; phenolic pKa values often ~9–10 (substitution pattern can shift values modestly).
• LogP/logD (qualitative): Polyfunctional; expected moderate polarity with hydrogen-bond donor/acceptor capability; logD is pH-dependent due to amine protonation and phenolic deprotonation.
• Solubility (qualitative): Generally soluble in polar organic solvents (MeOH, EtOH, DMSO, DMF). Aqueous solubility improves under acidic conditions (formation of ammonium salt) and may decrease near neutral pH if the free base predominates.
• UV/Vis: Phenolic aromatics typically show strong UV absorbance around 210–280 nm (literature). Exact cutoffs and absorptivity are system-dependent.

Handling note: Polyphenolic amines can exhibit gradual oxidation/discoloration on air exposure; minimizing prolonged exposure to air/alkaline conditions and storing tightly closed can help preserve appearance.

For exact numeric values (mp/bp, density, refractive index, water/peroxide/metal content, UV cutoff), refer to the item’s CoA/Spec Sheet.

Quality and Grades

• Item-specific details

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

• Guidance on grades (general, for context)

  • Research grade: Suitable for most synthetic and screening workflows. Typical focus is identity and assay purity; trace metals/UV profile usually not controlled tightly unless declared.
  • Analytical/HPLC grade (if offered): Emphasizes low non-volatile residue and low UV baseline; useful where spectroscopic detection is critical.
  • Salt forms: For amines, hydrochloride or other salt forms may be offered by some suppliers to enhance stability/handling; specifications differ from free-base materials.

• What to verify on the CoA for this item

  • Assay purity method (e.g., HPLC/GC), and acceptance limits.
  • Identity confirmation (NMR, MS, IR) and any additional tests (e.g., water by Karl Fischer).
  • Residual solvents and inorganic impurities; for phenolic amines, trace oxidation products may be monitored.
  • If intended for metal-mediated synthesis, low trace-metal content can be beneficial; check if reported.

• Practical notes

  • Phenolic amines can self-associate; purity assessment may require multiple orthogonal methods (HPLC with acidic mobile phase and complementary NMR).
  • If low baseline drift is critical (e.g., for UV-based analytics), consider requesting UV cut-off or absorbance profile; otherwise, treat as research grade.

All item-specific numeric limits should be taken from the CoA/Spec Sheet when supplied.

Reaction and Applications

2,4-Dihydroxybenzylamine is a versatile bifunctional building block; the benzylic primary amine and two phenolic OH groups enable orthogonal transformations.

• Representative application families (literature/general)

  • Amide/urea/carbamate formation: Acylation or carbamylation of the primary amine to generate amides, ureas, and carbamates. Phenols can be protected (e.g., benzyl, silyl, carbonate) to steer selectivity.
  • Schiff bases and reductive amination: Condensation with aldehydes/ketones to imines, followed by reduction (NaBH3CN, NaBH(OAc)3, or catalytic hydrogenation). Useful in library synthesis and ligand design.
  • O-alkylation/acylation of phenols: Formation of aryl ethers or esters; the ortho/para arrangement allows tuning H-bonding and coordination properties.
  • Chelating ligands and salen-type scaffolds: Condensation with salicylaldehydes or diformyl aromatics to give O,N-bidentate or O,N,O-tridentate ligands for transition metals.
  • Polymer/solid support conjugation: The amine can anchor to activated esters or isocyanates; phenols provide additional points for functionalization or crosslinking.
  • Tyrosinase/oxidase probe precursors: Phenolic benzylamines are used as substrates or inhibitors in enzymology studies (assay development, not therapeutic use).

• Practical tips

  • Selective protection: Protect phenols (e.g., TBDMS, MOM, benzyl) when amine-selective acylation or cross-coupling on the ring is planned. Alternatively, protect the amine (Boc, Cbz, Fmoc) for O-functionalization.
  • Oxidation control: Work under inert atmosphere for strongly basic or prolonged reactions to limit phenol oxidation; include antioxidants if compatible.
  • Purification: Use acidic modifiers in flash chromatography to suppress amine tailing (e.g., 0.1–1% Et3N in hexanes/EtOAc or 0.1% AcOH when needed).

Reaction Conditions

General literature guidance for typical transformations with 2,4-dihydroxybenzylamine. These are not specifications for this item; optimize for your substrate and scale.

• Reductive amination

  • Solvent: MeOH, EtOH, or MeCN; include 3Å molecular sieves for water removal.
  • Conditions: Aldehyde/ketone (1.0 eq), amine (1.2–1.5 eq), AcOH (0.2–0.5 eq) to adjust pH 5–6; NaBH(OAc)3 (1.5–2.0 eq) at rt to 40°C, 2–16 h.
  • Notes: Phenolic OH generally tolerated; avoid strong base to limit side oxidations.

• Amide formation (N-acylation)

  • Coupling reagents: EDCI/HOBt, HATU, or CDI in DMF/DCM; base DIPEA or lutidine; 0–25°C, 1–12 h.
  • Selectivity: Protect phenols if N-acyl selectivity is required; otherwise competitive O-acylation may occur.

• O-alkylation of phenols

  • Conditions: Alkyl halide (1.2–2.0 eq), K2CO3 or Cs2CO3, acetone/MeCN/DMF, 25–60°C, 2–18 h.
  • Strategy: Protect amine (Boc) to suppress N-alkylation. Phase-transfer catalysis can enhance rates in greener solvents (2-MeTHF, toluene/H2O).

• Carbamate/urea formation

  • Reagents: Chloroformates for carbamates (0–25°C), or CDI + amines for ureas.

• Oxidation to quinone-like species (if desired)

  • Mild oxidants (e.g., Fremy’s salt, DDQ) under controlled conditions; monitor closely to avoid over-oxidation.

• Workup tips

  • Acid/base toggling (pH 2–3 then 9–10) can facilitate removal of neutral/byproduct species and recover either salt or free base forms.

Always run small-scale pilots; reaction outcomes depend on substitution pattern, protection, and solvent/base choice.

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 for benzylamines bearing phenolic groups (literature/industry practice):

• Likely hazards: May cause skin/eye/respiratory irritation; amines can be sensitizers in some cases. Phenolic compounds can cause irritation and may be harmful if swallowed.
• PPE: Use appropriate gloves (e.g., nitrile), lab coat, and eye protection. Handle in a fume hood to avoid inhalation of vapors/aerosols.
• Incompatibilities: Strong oxidizers (risk of exothermic reaction/oxidation), acyl/alkyl halides and anhydrides (reactive toward amine/phenols), isocyanates, strong bases (can accelerate air oxidation of phenols), and strong acids (may form salts with heat release).
• Air/light sensitivity: Phenolic aromatics may slowly oxidize or discolor upon prolonged air/light exposure, especially in alkaline media.
• First aid overview (consult SDS for full guidance):
  • 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 for persistent irritation.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Spill/cleanup: Absorb small spills with inert material; avoid skin contact; ventilate area. Dispose according to local regulations.

Always consult the product-specific SDS for authoritative hazard classification and response measures.

Solvent Selection

Applicability: This section discusses solvent choices for dissolving and reacting 2,4-dihydroxybenzylamine in synthesis and analysis.

• Solubility profile (general/literature)

  • Polar protic: Good solubility expected in methanol and ethanol; isopropanol may require warming.
  • Polar aprotic: Typically soluble in DMSO, DMF, DMAc, NMP; MeCN often usable for moderately concentrated solutions.
  • Water: Solubility increases under acidic conditions (formation of ammonium salts). Near neutral pH, the free base may have limited solubility.

• Polarity/acid–base considerations

  • The benzylic amine is basic and readily protonated (use acidic media for aqueous work). Phenolic OH groups deprotonate in basic media, potentially increasing water solubility but also promoting oxidation.

• Selection tips by use case

  • Coupling/acylation: Use dry polar aprotics (DMF, DCM/DIPEA systems, or MeCN) with base control; avoid strong base if phenolic O-acylation is undesired.
  • Reductive amination/imine formation: Alcohols (MeOH, EtOH) or MeCN with molecular sieves; choose reducing system compatible with phenols (e.g., NaBH3CN, NaBH(OAc)3) and buffer pH 5–6.
  • Metal-catalyzed steps (if derivatized): Prefer amide-protected amine and phenol-protected substrates; use anhydrous, oxygen-lean solvents.

• Small comparison (general)

  • DMSO vs DMF: DMSO is greener/less volatile; DMF offers lower viscosity and easier removal. For moisture-sensitive steps, both should be rigorously dried.
  • MeOH vs EtOH: EtOH is greener and less toxic; MeOH dissolves many salts more effectively and often accelerates imine chemistry.

Always confirm actual solubility with a small-scale trial under your specific conditions.

Storage and Reconstitution

• Item-specific storage

  • Storage Conditions: Room temperature (as provided). Store tightly closed in a dry place. Protect from excessive heat and light.
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• Stability considerations (general)

  • Phenolic amines can slowly oxidize/discolor upon prolonged exposure to air, light, or alkaline conditions. Minimize headspace oxygen and avoid strong base during storage.
  • If long-term storage is planned, consider keeping material in amber glass under inert gas, especially after opening.

• Reconstitution/solution preparation (general guidance)

  • Solvents: Readily dissolves in polar organics such as methanol, ethanol, DMSO, DMF. For aqueous use, prepare as an acidified solution (e.g., dilute HCl) to form the ammonium salt.
  • Concentration: Prepare concentrated stock solutions (e.g., 10–100 mM) as required for screening; filter (0.2 µm PTFE/NYLON) if particulates are present.
  • Freeze–thaw: If storing solutions, aliquot to avoid repeated freeze–thaw. DMSO or ethanol stocks are commonly stable at −20°C for weeks to months; verify by LC–MS before critical experiments.

• Compatibility and containers

  • Use compatible closures (PTFE-lined caps) to limit amine adsorption and permeation. Avoid reactive plastics when storing in strong solvents.

Always defer to the product’s CoA/SDS for lot-specific guidance on storage and handling.

Structure and Identity

Brief overview: 2,4-Dihydroxybenzylamine is a polyfunctional aromatic building block combining a benzylic primary amine with two phenolic hydroxyls in the 2- and 4-positions of the ring.

• Item-specific (from Product Data)

  • SKU: D1073379
  • Product Name: 2,4-Dihydroxybenzylamine
  • CAS: 63452-56-2
  • InChIKey: 26470 (as provided)
  • Storage Conditions: Room temperature
  • Research Use: For research use only

• Literature/computed identity (for context; not item specifications)

  • Synonyms: 2,4-dihydroxybenzyl-1-amine; 2,4-dihydroxyphenylmethylamine (common names)
  • Molecular formula (neutral free base, literature): C7H9NO2
  • Molecular weight (literature): ~139.15 g/mol
  • SMILES (literature): Oc1ccc(O)cc1CN
  • Structural features: primary benzylic amine (–CH2–NH2); two phenolic OH groups ortho and para to the benzylic carbon; no stereogenic centers; planar aromatic core with benzylic substituent out of plane.

• 2D structure (described in words)

  • A benzene ring bearing: (i) a –CH2–NH2 substituent (benzylamine) at position 1, (ii) a phenolic –OH at position 2 (ortho to –CH2NH2), and (iii) a phenolic –OH at position 4 (para to –CH2NH2). The amine is primary and exocyclic; the two hydroxyls can engage in intra/intermolecular hydrogen bonding.

Note: Where authoritative identifiers are required for regulatory or database matching, consult the CoA/Spec Sheet for this specific lot.

Synthetic Utility

Key functional groups and their reactivity make 2,4-dihydroxybenzylamine a strategically valuable building block.

• Functional handles

  • Primary benzylic amine: N-acylation, N-alkylation, imine formation, reductive amination, urea/carbamate synthesis, diazotization (through derived amides), and as a nucleophile in SNAr on activated systems.
  • Phenolic OH (2,4-positions): O-alkylation/acylation to access diaryl ethers/esters; conversion to carbonate/carbamate protecting groups; potential entry to quinone/quinone-imine systems under oxidation.

• Orthogonal protection strategy

  • Protect phenols (e.g., MOM, benzyl, silyl) to focus transformations on the amine.
  • Protect the amine (Boc, Cbz, Fmoc) for selective O-functionalization or electrophilic aromatic substitution.

• Ring functionalization

  • Electrophilic substitutions guided by existing OH groups (directing effects), enabling halogenation, nitration (mild), or formylation (e.g., Reimer–Tiemann, Duff) on appropriately protected substrates.
  • Cross-coupling after prefunctionalization (e.g., convert to aryl halide or triflate if needed) to elaborate the aromatic core.

• Retrosynthetic value

  • Serves as an entry to catechol/resorcinol-like derivatives with pendant amines, frequently used in ligand frameworks and bioactive analog series.

• Purification/analysis tips

  • Employ acid/base extraction to switch between free base and ammonium salt for phase manipulation.
  • Use buffered HPLC (volatile acid modifiers) to reduce peak tailing from the basic amine while retaining phenolic signatures in UV detection.

Target Specificity

Not applicable. This product is a small-molecule chemical building block, not a biological targeting reagent (e.g., antibody, aptamer, enzyme). No antigen/epitope, species reactivity, clone, or isotype information pertains to this item.