2-Aminobenzhydrol - ≥97% , CAS No.13209-38-6

CAS: 13209-38-6 Cat. No.: A166953 Formule: C₁₃H₁₃NO Poids moléculaire: 199.25 Numéro CE: 639-294-6

QUALITÉ & PURETÉ ≥97%

Synonyms

(2-Aminophenyl)(phenyl)methanol # | SY308250 | 2-Aminobenzhydrol, 97% | AKOS016842789 | DTXSID20297071 | AKOS000125387 | PS-5345 | MFCD00017097 | (2-Aminophenyl)(phenyl)methanol | SCHEMBL1740565 | (2-aminophenyl)-phenylmethanol | (2-aminophenyl)-phenyl-me

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Spécifications

Synonymes

(2-Aminophenyl)(phenyl)methanol # | SY308250 | 2-Aminobenzhydrol, 97% | AKOS016842789 | DTXSID20297071 | AKOS000125387 | PS-5345 | MFCD00017097 | (2-Aminophenyl)(phenyl)methanol | SCHEMBL1740565 | (2-aminophenyl)-phenylmethanol | (2-aminophenyl)-phenyl-me

Spécifications et pureté

≥97%

Conditions de stockage de stockage

Store at 2-8°C,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

Pubchem Sid

504758244

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504758244

Sourires canoniques

C1=CC=C(C=C1)C(C2=CC=CC=C2N)O

IUPAC Name

(2-aminophenyl)-phenylmethanol

InChIKey

NAWYZLGDGZTAPN-UHFFFAOYSA-N

INCHI

1S/C13H13NO/c14-12-9-5-4-8-11(12)13(15)10-6-2-1-3-7-10/h1-9,13,15H,14H2

Isomères SMILES

C1=CC=C(C=C1)C(C2=CC=CC=C2N)O

WGK Allemagne

3

Poids moléculaire

199.25

Reaxy-Rn

1212446

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1212446&ln=

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Diphenylmethanes
• Intermediate Tree Nodes: Not available
• Direct Parent: Diphenylmethanes
• Alternative Parents: Aniline and substituted anilines Secondary alcohols Primary amines Organopnictogen compounds Hydrocarbon derivatives Aromatic alcohols
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Diphenylmethane - Aniline or substituted anilines - Secondary alcohol - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Aromatic alcohol - Primary amine - Organooxygen compound - Organonitrogen compound - Amine - Alcohol - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
• 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 sensitive
• Point de fusion (°C): 113-118 °C
• Poids moléculaire: 199.250 g/mol
• XLogP3: 2.600
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 199.1 Da
• Monoisotopic Mass: 199.1 Da
• Topological Polar Surface Area: 46.300 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 189.000
• 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

No tested bioassay or immunoassay protocols are provided for this small-molecule reagent. For synthetic use, see Reaction Conditions and Synthetic Utility. If using as a reference standard or for analytical method development, develop fit-for-purpose dilution and handling protocols based on solvent compatibility and detector response (e.g., UV at 254 nm for aromatics).

Biological Roles

This product is supplied strictly for research use. No biological or clinical roles are claimed for the material as sold.

General biochemical context (literature; not claims)

• Aromatic amines may participate in acylation/condensation to generate bioactive scaffolds, but the parent aniline alcohol itself is primarily a synthetic intermediate.
• The aniline nitrogen can be derivatized to amides, sulfonamides, ureas, or carbamates that are common in medicinal chemistry libraries; the benzhydryl motif appears in drug-like molecules as a lipophilic anchor.

Caveats

• Do not infer pharmacology from presence of an aniline and benzhydryl alcohol. Any biological evaluation requires independent testing and validation.

Buffer Applications

Not typically applicable. 2-Aminobenzhydrol is not used as a buffering agent or pH calibrant. For aqueous handling, the aniline can be protonated to form water-soluble salts, but this serves solubility/workup purposes rather than buffering. Consider other sections (Reaction & Applications, Synthetic Utility) for more relevant information.

Green Alternatives

Context: 2-Aminobenzhydrol is a solid building block; greener considerations revolve around solvent and reagent choices during its transformations.

Greener solvent options (literature/general)

• Prefer ethyl acetate, 2-methyltetrahydrofuran (2-MeTHF), or cyclopentyl methyl ether (CPME) over chlorinated solvents when compatible.
• Use bio-derived alcohols (ethanol) for recrystallization/workups in place of isopropanol or methanol where feasible.

Reagent alternatives and process intensification

• Oxidation to benzophenone analog: swap chromium(VI) reagents for DMP, TEMPO/bleach, or O2 with catalytic TEMPO/metal salts.
• Benzylic activation: employ sulfonyl carbonates or green leaving group strategies instead of halogenations when possible.
• Acid-catalyzed dehydrations: use solid acids (e.g., Amberlyst-15) in toluene/MeTHF with water removal instead of strong mineral acids.

Illustrative comparison (general, not item-specific specs)

• PCC in DCM vs DMP in EtOAc
  • Hazardous waste: high for PCC (Cr(VI)) vs low for DMP.
  • Solvent: chlorinated vs greener ester.
  • Workup: silica/filtration for DMP; heavy metal disposal for PCC.

Trade-offs

• Benzylic cation chemistry can require strong acids; solid acids or catalytic Brønsted acids may reduce corrosivity but can affect rates/selectivity. Validate on small scale.

Pharmaceutical Uses

No excipient or pharmacopeial role is specified for this item; refer to CoA/Spec Sheet for any regulatory statements.

General formulation/manufacturing context (literature; not therapeutic claims)

• The benzhydryl group is used as a protecting group and as a lipophilic fragment in medicinal chemistry synthesis. 2-Aminobenzhydrol can serve as an intermediate toward amide/sulfonamide libraries or toward 2-aminobenzophenone analogs after oxidation.
• Salt formation (e.g., hydrochloride) can aid isolation/purification during process development; choice of counterion affects crystallinity and polymorphism.

Quality considerations

• Residual solvents, metals, and nitrosamine risk assessments are process-dependent and Not specified for this item; refer to CoA/Spec Sheet and internal QA for GMP-related projects. This product is for research use only.

Physical Properties

Item-specific specifications (from Product Data)

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Any numeric specs (mp/bp/density/UV cutoff, etc.): Not specified for this item; refer to CoA/Spec Sheet.

Literature/computed information (general guidance; not item specifications)

• Expected physical state: crystalline solid for many aminobenzhydrol isomers (literature); actual form may vary.
• Solubility profile (qualitative):
  • Good solubility in polar organic solvents (e.g., ethanol, methanol, acetone, DMF, DMSO) due to –OH and –NH2 functionality (literature).
  • Limited solubility in nonpolar hydrocarbons; sparingly soluble in water as the free base (literature). Water solubility increases upon forming salts (e.g., hydrochloride) (literature).
• Acid–base properties (literature):
  • Aromatic amine basicity similar to aniline; conjugate acid pKa typically ~4.5–5.5 depending on ring substitution. The adjacent benzylic alcohol and ortho position may modestly influence basicity.
• Partitioning/logP (qualitative): moderate hydrophobicity from diaryl framework, tempered by one –OH and one –NH2 group (literature qualitative assessment).

General chemistry notes

• The benzylic –CH(OH)– in a diphenyl system is readily oxidized to the corresponding benzophenone derivative under standard oxidation conditions (literature).
• Hydrogen bonding: intramolecular and intermolecular H-bonding between –OH and –NH2 possible; can influence melting point and crystallinity (literature).

Quality and Grades

Item-specific grade/purity

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

Guidance on typical grade meaning (general)

• Research-grade aromatic building blocks are commonly supplied with assay by HPLC/GC and identity by NMR/IR/HRMS. If “98%” or higher purity is indicated on the CoA, this typically supports use in synthesis without further purification.
• UV/LC suitability: When used in analytical or photochemical contexts, low UV-absorbing solvents/impurities are desirable; for this item, specific UV-cutoff or trace impurity limits are Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/inhibitors: None indicated in the Product Data. If stabilizers are used, they will appear on the CoA and may influence downstream reactivity (e.g., acid scavengers affecting acylations).

What to check on receipt

• Verify identity by 1H/13C NMR; benzylic –CH(OH)– appears typically at δ ~5–6 ppm (1H) with characteristic coupling; aniline –NH2 often broad near δ ~3–5 ppm (solvent-dependent) (literature patterns).
• Assess purity by HPLC/UPLC (UV at 254 nm commonly used for aromatics) and confirm residual solvents/water as needed for moisture-sensitive reactions.

Reaction and Applications

Manufacturer applications: Not specified in the Product Data. The following are literature/general synthetic uses of 2-aminobenzhydrol-type scaffolds.

Representative applications (literature)

• Oxidation to 2-aminobenzophenone: benzylic alcohol oxidation (e.g., DMP, PCC, MnO2) furnishes the corresponding benzophenone, a valuable intermediate for heterocycle synthesis (e.g., quinazolinones, benzoxazoles via further amidation/condensation).
• Electrophile generation at benzylic position: convert –OH to better leaving groups (mesylate/tosylate, halides) enabling SN1/SN2 (often SN1-like due to stabilized benzhydryl cation) to install benzhydryl substituents on N, O, S nucleophiles.
• Dehydration/arylation: acid-catalyzed elimination to diarylmethane derivatives; Friedel–Crafts-type transformations exploiting benzhydryl cation character (literature).
• Mitsunobu variations: benzylic alcohols can undergo Mitsunobu substitution with inversion (here, stereochemical inversion is moot because the center is prochiral) to introduce heteroatoms.
• Protection strategies: diphenylmethyl (benzhydryl) groups are classical protecting groups; the substrate can be a precursor to benzhydryl donors for N-/O-protection after activation.
• Ligand/auxiliary exploration: an ortho-amino group can be derivatized (acylation, sulfonylation, urea/carbamate formation) to create bidentate motifs.

Practical notes

• Keep moisture low for activation reactions (MsCl/TsCl, SOCl2, PBr3); use base scavengers (Et3N, pyridine) and inert atmosphere.
• The aniline may need temporary protection (e.g., Boc, sulfonamide) to direct selectivity during benzylic transformations.

Reaction Conditions

General conditions from literature (guidance; not product specifications)

• Oxidation to 2-aminobenzophenone:
  • Dess–Martin periodinane (1.2–1.5 equiv) in DCM or EtOAc, 0 °C to rt, 1–3 h; typical isolated yields often 70–95% for benzhydrols.
  • MnO2 (excess) in DCM/toluene, rt to reflux, several hours.
• Benzylic activation/substitution:
  • MsCl (1.2–1.5 equiv), Et3N or DIPEA (2–3 equiv), DCM/THF, 0 °C→rt, 1–2 h; subsequent SN with nucleophile (amine, alcohol, thiol) in DMF/MeCN at rt–60 °C.
  • SOCl2 (1.5–2 equiv) with catalytic DMF, DCM, 0 °C→rt; quench carefully; follow with substitution under SN1/SN2 conditions.
• Dehydration to diarylmethane:
  • p-TsOH (5–20 mol%) in toluene or DCE, reflux, Dean–Stark as needed, 2–8 h.
• Protection of aniline:
  • Boc2O (1.1–1.5 equiv), base (Et3N, Na2CO3) in DCM/MeCN, 0 °C→rt; or sulfonyl chloride (e.g., TsCl) in pyridine/DCM.

Practical tips

• The aniline can compete/react during benzylic activation; protect N when selectivity demands. Monitor by TLC/HPLC at 254 nm.
• Maintain inert atmosphere to minimize adventitious oxidation during moisture-/air-sensitive steps, aligning with the item’s storage recommendation.

All conditions should be optimized for the specific substrate and scale.

Safety and Handling

Item-specific hazard details

• Signal word: Not specified for this item; refer to CoA/Spec Sheet.
• H-statements: Not specified for this item; refer to CoA/Spec Sheet.
• GHS classification: Not specified for this item; refer to CoA/Spec Sheet.
• Pictograms: Not specified for this item; refer to CoA/Spec Sheet.

General safety guidance for aromatic amine/benzylic alcohols (informational only; defer to SDS)

• Potential hazards: may cause skin/eye irritation; aromatic amines can be harmful if swallowed or inhaled and may cause sensitization in some cases (literature, class-based). Avoid dust formation.
• Personal protective equipment: lab coat, chemical-resistant gloves (e.g., nitrile), safety goggles or face shield. Use in a fume hood to minimize inhalation exposure.
• Handling: avoid contact with strong oxidizers and acylating agents unless controlled; amines can react with acid chlorides/anhydrides and isocyanates. Benzylic alcohols can be dehydrated by strong acids.
• First aid (overview):
  • Skin/eye contact: rinse immediately with plenty of water for at least 15 minutes; remove contaminated clothing; seek medical attention.
  • Ingestion/inhalation: move to fresh air; rinse mouth; do not induce vomiting; obtain medical attention.
• Fire safety: use CO2, dry chemical, or alcohol-resistant foam. Combustible organic solid; combustion may produce NOx and CO/CO2 (literature).

Always consult the product SDS for authoritative hazard classifications and response procedures.

Solvent Selection

Applicability: This compound is a solid aromatic amine/benzylic alcohol used as a building block. Solvent selection pertains to dissolution for reactions, recrystallization, or chromatography.

General solvent behavior (literature)

• Polarity class: moderately polar organic compound; dissolves well in polar aprotic and protic organic solvents (e.g., EtOAc, acetone, MeCN, MeOH, EtOH, DCM, DMF, DMSO).
• Dielectric/miscibility: prefers solvents with moderate-to-high polarity; insoluble or only sparingly soluble in aliphatic hexanes/heptane unless warmed or with additives.
• Aqueous handling: free base has low water solubility; protonation with HCl or other acids markedly increases water solubility for extractions or salt formation.

Practical choices by task

• Nucleophilic substitutions/activations: use dry DCM, THF, MeCN, or DMF with base (e.g., for mesylation/tosylation) — choose based on base/catalyst compatibility.
• Oxidation to benzophenone analog: DCM, EtOAc, or MeCN commonly used with DMP, PCC, or TEMPO/bleach (literature).
• Dehydration to diarylmethane: toluene or DCE under acid catalysis (e.g., TsOH) with Dean–Stark if water removal is needed (literature).
• Recrystallization: alcohols (EtOH/i-PrOH) or ethyl acetate/hexanes mixtures; optimize empirically.

Mini-comparison (general)

• DCM: fast dissolution, easy removal; non-green, halogenated.
• EtOAc/MeTHF: greener options for workup and recrystallization; may require warming.
• MeOH/EtOH: enable salt formation and facilitate H-bonding; can participate in reactions under strong acids.

Storage and Reconstitution

Item-specific conditions (from Product Data)

• Storage: Store at 2–8 °C, under argon (argon charged).
• Shipping: Shipped on wet ice.

Practical guidance

• Rationale: Inert atmosphere minimizes slow oxidative changes of benzylic alcohols/anilines and suppresses moisture uptake or acid/base-catalyzed side reactions during long-term storage.
• Container: Keep tightly closed in amber glass or other light-protective container to minimize photochemical discoloration of anilines (general precaution).
• Handling: Allow vial to warm to room temperature under inert gas before opening to prevent condensation. Reseal under inert gas after use.
• Solid handling: If caked from cold storage, gently warm to ambient in a desiccator. Use dry spatulas; avoid prolonged exposure to air.
• Reconstitution/dissolution: Choose dry, oxygen-free solvents when sensitive transformations follow. Typical solvents include DCM, EtOAc, THF, MeCN, MeOH, DMF, or DMSO; select based on downstream reaction needs. Final concentration and solvent choice are application-specific.

Stability notes

• Exact shelf life and impurity limits are Not specified for this item; refer to CoA/Spec Sheet. Always consult the SDS and perform a small-scale assay (e.g., NMR/HPLC) after extended storage.

Structure and Identity

Brief overview: 2-Aminobenzhydrol is an aniline-substituted benzhydrol (diphenylmethanol) featuring a benzylic secondary alcohol adjacent to two aryl rings, with an ortho-amino group on one ring.

• Item-specific identifiers (from Product Data)
  • SKU: A166953
  • CAS: 13209-38-6
  • CID: 270810
  • InChIKey: 233676 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Computed/literature identity (informational)
  • Common name: 2-aminodiphenylmethanol; o-aminobenzhydrol (literature)
  • Molecular formula (derived from structure): C13H13NO (literature/structure-based)
  • Molecular weight: ~199.25 g/mol (literature/structure-based)
  • Functional groups: aniline (primary aromatic amine), benzylic secondary alcohol, two phenyl rings.
  • Structural description (2D): a diphenylmethanol core (Ph–CH(OH)–Ph) where one phenyl carries an ortho –NH2 substituent relative to the benzylic linkage.
  • Stereochemistry: none (achiral benzylic center due to two identical aryl substituents).

Notes:

• Where exact identifiers (e.g., SMILES) are required for computation, consult the CoA/Spec Sheet or vendor SDS to avoid ambiguity of substitution pattern.

Synthetic Utility

Key functional groups and reactivity (literature)

• Benzylic secondary alcohol: readily forms stabilized benzhydryl cations; amenable to oxidation (→ 2-aminobenzophenone), dehydration (→ diarylmethanes), and substitution after activation (Ms/Ts, halides).
• Aniline (ortho to benzylic linkage): nucleophilic at N; can be protected (Boc, Cbz, sulfonyl), acylated, or converted to ureas/carbamates. Ortho position may enable intramolecular cyclizations after carbonyl introduction (e.g., quinazolin-4-ones from 2-aminobenzophenones).

Retrosynthetic value

• As a convergent node: couples an aniline-bearing aryl fragment with a second aryl ring via benzylic center. From 2-aminobenzophenone, reduction furnishes this alcohol; conversely, oxidation of this alcohol returns the ketone, enabling redox shuttling across a project.

Named/typical transformations

• Oxidations: DMP, PCC, MnO2, TEMPO-based systems.
• Activations: MsCl/TsCl + base; SOCl2 or PBr3 to halides; Appel variants (PPh3/CX4).
• Dehydrations/Friedel–Crafts: acids (TsOH, H2SO4) or Lewis acids (AlCl3, BF3·OEt2) to generate diarylmethanes/triarylmethanes (with additional aryl sources).
• Mitsunobu: installation of N/O/S nucleophiles at the benzylic position (stereochemical inversion not consequential here).

Target Specificity

Not applicable. This product is a small-molecule building block, not a biological targeting reagent. No antigen/epitope specificity, clone, isotype, or species reactivity applies.

Foire aux questions

What is the purity of this product?

This product is supplied at ≥97% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at 2–8 °C under argon. It is supplied under an argon blanket; reseal under inert gas after each use.

How is this product shipped?

This product ships chilled on wet ice. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 13209-38-6, the molecular formula is C13H13NO, and the molecular weight is 199.25 g/mol. InChIKey NAWYZLGDGZTAPN-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.