Chroman-7-amine - ≥95% , CAS No.50386-68-0

CAS: 50386-68-0 Cat. No.: C942583 분자식: C₉H₁₁NO 분자량: 149.19 PubChem CID: 21827044

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

사양 및 순도

≥95%

보관 조건

Room temperature

순수함

≥95%

이름과 식별자

정식 스마일

C1CC2=C(C=C(C=C2)N)OC1

IUPAC Name

3,4-dihydro-2H-chromen-7-amine

InChIKey

SPTKRFYLJBPEBL-UHFFFAOYSA-N

INCHI

1S/C9H11NO/c10-8-4-3-7-2-1-5-11-9(7)6-8/h3-4,6H,1-2,5,10H2

이성체 SMILES

C1CC2=C(C=C(C=C2)N)OC1

PubChem CID

21827044

분자량

149.19

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • 분류 Benzopyrans
      • Subclass 1-benzopyrans

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• 분류: Benzopyrans
• Subclass: 1-benzopyrans
• Intermediate Tree Nodes: Not available
• Direct Parent: 1-benzopyrans
• Alternative Parents: Alkyl aryl ethers Benzenoids Oxacyclic compounds Primary amines Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 1-benzopyran - Alkyl aryl ether - Benzenoid - Oxacycle - Ether - Organic nitrogen compound - Organic oxygen compound - Hydrocarbon derivative - Primary amine - Organooxygen compound - Organonitrogen compound - Amine - Aromatic heteropolycyclic compound
• 설명: This compound belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.
• 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

화학 및 물리적 특성

• 분자량: 149.190 g/mol
• XLogP3: 1.600
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 149.084 Da
• Monoisotopic Mass: 149.084 Da
• Topological Polar Surface Area: 35.300 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 138.000
• 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. No validated bioassay protocols (e.g., WB, IHC, FC) are associated with this small-molecule reagent.

General lab use suggestions:

• For stock solutions, prepare 10–100 mM in DMSO or MeOH; filter-sterilize if required for cell-free assays. Determine solubility experimentally.
• For aqueous work, consider forming a salt (e.g., HCl) to improve solubility; adjust pH with standard buffers. Validate stability before use.

Always adapt protocols to your specific application and consult the SDS for safe handling.

Biological Roles

Item-specific biological data are not provided. The content below reflects general, literature-based context for chroman scaffolds and aryl amines.

• Chroman motif in biology: The chroman (benzopyran) framework is a privileged structure present in numerous natural products. Notably, tocopherols (vitamin E) feature a chromanol core, underscoring redox and antioxidant relevance of certain substituted chromans. Chroman-7-amine differs (aryl amine vs phenolic chromanol), but the bicyclic heteroaromatic scaffold is widely explored in chemical biology.
• Aryl amines in biochemistry: Primary aryl amines can engage in diazotization and azo coupling, enabling probe/dye conjugation chemistry. They can serve as precursors to cationic species (diazonium) for covalent labeling of electron-rich biomolecules in vitro (method development context).
• Physicochemical profile: The aniline nitrogen modulates basicity and hydrogen-bonding capacity, affecting membrane permeability and target engagement in screening libraries. Salt formation can increase aqueous compatibility for biochemical assays.

No claims are made regarding physiological activity or therapeutic use of this product. Use is restricted to research and laboratory investigations.

Buffer Applications

Chroman-7-amine is a small-molecule building block, not a buffering reagent. It does not constitute a conventional buffer system.

• If used in biochemical assays, prepare assay buffers separately (e.g., phosphate, HEPES, MES) and dissolve the compound as a DMSO or aqueous acid salt stock as appropriate.
• For increased aqueous solubility, consider forming the hydrochloride or another suitable acid salt and adjust pH with standard buffers. Validate compound stability across the assay pH range.

No specific buffering capacity or recipes apply to this item.

Green Alternatives

While specific green metrics for this item are not provided, several strategies can improve the sustainability profile when working with chroman-7-amine.

Greener solvent choices (literature guidance):

• Prefer ethyl acetate, 2-MeTHF, CPME, or IPA over chlorinated solvents where feasible. For extractions, EtOAc or MTBE can replace DCM in many cases.
• For cross-couplings, bio-derived solvents (2-MeTHF) or greener ethers (CPME) often substitute for dioxane/toluene with appropriate ligands/bases.
• For amide couplings, use greener coupling systems (e.g., T3P in EtOAc/MeTHF) to reduce urea waste relative to HATU/HBTU.

Example comparison (conceptual):

• DCM vs EtOAc

  • Worker exposure: DCM is a suspected carcinogen; EtOAc has a better safety profile.
  • Performance: EtOAc often matches DCM for acylations and workups with similar partitioning behavior.

• Dioxane vs 2-MeTHF/CPME

  • Regulatory: Dioxane is a problematic solvent; 2-MeTHF/CPME are preferred in many solvent guides.
  • Tradeoffs: Different boiling points and polarity; drying and catalyst solubility should be validated.

Process tips:

• Use catalytic rather than stoichiometric halogenation/activation steps when possible.
• Salt formation (e.g., HCl salt) can improve crystallinity and reduce reliance on chlorinated solvents for purification.
• Employ solvent recycling and minimize amide-coupling reagent excess.

Pharmaceutical Uses

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

General research/manufacturing context (non-clinical, literature):

• Discovery intermediate: Chroman-7-amine serves as a versatile starting point for SAR campaigns owing to the privileged chroman core and aniline handle. It enables rapid access to amides, sulfonamides, ureas, and N-arylated derivatives for screening libraries.
• Salt selection studies: Conversion to crystalline salts (e.g., hydrochloride, sulfate, mesylate) can facilitate purification and solid-state characterization during process development.
• Analytical reference: May be used as a synthetic reference or impurity marker in development workflows for chroman-containing candidates.

This product is offered strictly for research use only and is not intended for human or veterinary use, clinical applications, or as an excipient in drug products.

Physical Properties

Item-specific physicochemical specifications (BP/MP, density, refractive index, UV cutoff, water/metal limits) are not provided.

• Boiling point / melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (general, literature expectations for aryl amines):
  • Moderate solubility in polar organic solvents (e.g., alcohols, acetone, acetonitrile, ethyl acetate).
  • Enhanced aqueous solubility upon protonation (e.g., as the hydrochloride salt) relative to the free base.
  • Good solubility in chlorinated solvents and aromatics (DCM, chloroform, toluene).
• pKaH (anilinium-type conjugate acid, literature): typically ~4.6–5.5 for primary anilines; substituents and the chroman oxygen can modulate basicity slightly.
• LogP/logD (qualitative, literature): aryl amines on benzenoid scaffolds commonly show logP in the ~1–2.5 range as free bases; protonation reduces logD at acidic pH.
• Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Vapor pressure/volatility: Not specified for this item; refer to SDS.

Notes:

• The above are generalized literature expectations for a chromanyl aniline and are provided for planning purposes only. For regulated or specification-sensitive work, rely on the batch CoA/SDS.

Quality and Grades

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

Interpretation and guidance:

• In the absence of a declared grade, treat this as a research-grade small-molecule building block. For analytical or GMP-adjacent work, verify impurity profile, residual solvents, and metal content via the batch CoA.
• Aryl amines can discolor upon storage due to trace oxidation; color is not always indicative of purity but may correlate with oxidative impurities. If low UV background is critical (e.g., HPLC assay development), consider purifying or preparing as a salt.
• If supplied as free base, you may optionally convert to an HCl salt for improved handling and crystallinity (verify stoichiometry and dryness by titration/Karl Fischer as needed). Any such conversion should be documented if specifications are required.

Recommended verifications (as applicable to your workflow):

• Identity by 1H/13C NMR and HRMS; purity by HPLC/GC. Anilines typically show diagnostic NH2 signals (broad) and aromatic patterns; chroman O-CH2- protons appear around 3.8–4.4 ppm (literature).
• Residual metals: if used after Pd-catalyzed steps or in coupling reactions, ICP-MS may be warranted. Limits: Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

Chroman-7-amine functions as a versatile aryl amine building block on a privileged chroman scaffold. Typical research applications (literature):

• Electrophile capture via the aniline nitrogen:
  • Amide formation (acyl chlorides/anhydrides, CDI, EDCI/HATU systems) to access chroman-7-anilides.
  • Sulfonamide formation (sulfonyl chlorides) for SAR exploration and polarity tuning.
  • Carbamate/urea synthesis (chloroformates or phosgene substitutes such as triphosgene/carbonyl diimidazole; isocyanate coupling or CDI-mediated union with amines).
• Cross-coupling and N-arylation:
  • Buchwald–Hartwig amination of aryl (pseudo)halides to elaborate diarylamine derivatives; BrettPhos/BINAP/XPhos ligands frequently employed with Pd(0/II), base (NaOtBu, Cs2CO3), 60–110 C (literature ranges).
• Diazotization/Sandmeyer manifold:
  • Formation of the diazonium salt (NaNO2/HCl at 0–5 C), enabling substitution to phenols, halides (CuX), or azo coupling for dye/probe synthesis.
• Directed electrophilic aromatic substitution:
  • The –NH2 group is ortho/para-directing and activating; within the chroman framework, regiochemistry is influenced by the heteroatom and ring fusion. Protection (e.g., acylation to acetanilide) can moderate reactivity and steer outcomes.
• Protection/deprotection:
  • Boc, Cbz, or tosyl protection to manage basicity and chemoselectivity. Standard deprotections (TFA for Boc, hydrogenolysis for Cbz) are applicable.
• Scaffold derivatization:
  • Oxidation at the chroman ring (to chromanone/chromene under specific conditions) and benzylic functionalization of the O-CH2- can enable further diversification.

These use cases are general literature guidance for aryl amines on a chroman core; tailor conditions to your substrate and objective.

Reaction Conditions

Representative literature-style conditions for common transformations of aryl amines on chroman scaffolds (adjust to your substrate and scale):

• Amide coupling:
  • Reagents: HATU (1.1–1.5 equiv) or T3P (50% in EtOAc), base (DIPEA 2–3 equiv).
  • Solvent: DMF, MeCN, DCM, or greener EtOAc/2-MeTHF.
  • Temperature/time: 20–40 C, 1–16 h. Typical isolated yields: 70–95% (literature ranges depending on acid partner).
• Sulfonamide formation:
  • Reagents: sulfonyl chloride (1.05–1.2 equiv), base (TEA/NaHCO3).
  • Solvent: DCM or aqueous biphasic (NaHCO3).
  • 0–25 C, 0.5–4 h.
• Buchwald–Hartwig N-arylation:
  • Catalyst: Pd2(dba)3 (0.5–2 mol%) or Pd(OAc)2 (1–3 mol%) with BrettPhos/SPhos (2–6 mol%).
  • Base: NaOtBu, KOtBu, or Cs2CO3 (2–3 equiv).
  • Solvent: toluene, dioxane, CPME, or t-BuOH.
  • 80–110 C, 4–20 h; many substrates 60–90% yield (literature).
• Diazotization/Sandmeyer:
  • NaNO2 (1.1–1.5 equiv) in 2–4 M HCl at 0–5 C; subsequent CuX-mediated substitution in aqueous/organic media.
  • Maintain low temperature during diazotization; quench/extract carefully due to energetic diazonium salts.
• Protection (Boc):
  • Boc2O (1.2–1.5 equiv), base (Na2CO3 or TEA), DCM/MeCN, 0–25 C, 1–4 h.

Always perform small-scale trials, monitor by TLC/LCMS, and consult primary literature for your specific substrate.

Safety and Handling

GHS classification, pictograms, and H-statements are not provided for this specific item. Always consult the SDS for authoritative hazard and first-aid information.

General safety guidance for aryl amines (literature-based best practice):

• Potential hazards: skin/eye irritation; some aromatic amines can be harmful if inhaled or absorbed. Avoid dust/aerosol formation.
• PPE: lab coat, safety glasses or face shield, and appropriate chemically resistant gloves (e.g., nitrile). Work in a fume hood to minimize inhalation exposure.
• Handling: avoid contact with oxidizing agents; aromatic amines may slowly oxidize on air/light to colored byproducts. Minimize air exposure of solutions; cap containers tightly.
• Incompatibilities: strong oxidizers, acylating/sulfonylating agents (unless intended), nitrosating agents under acidic conditions (can form N-nitroso species).
• First aid (overview; see SDS):
  • Inhalation: move to fresh air; seek medical attention if symptoms occur.
  • Skin: wash with soap and water; remove contaminated clothing.
  • Eyes: rinse cautiously with water for several minutes; seek medical advice if irritation persists.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
• Fire fighting: many organic amines are combustible. Use CO2, dry chemical, or foam; cool containers with water spray.
• Spill response: absorb with inert material, collect for disposal. Prevent entry to drains.

SDS and local regulations take precedence over the above general guidance.

Solvent Selection

Chroman-7-amine is a moderately polar aryl amine. Solvent choice depends on whether you use it as a free base or a protonated salt.

• Polarity/miscibility (general):
  • Free base dissolves well in DCM, chloroform, ethyl acetate, acetone, methanol/ethanol, acetonitrile, and aromatic solvents (toluene). Limited water solubility at neutral pH.
  • Protonated salts (e.g., HCl) display improved water/alcohol solubility and reduced solubility in nonpolar solvents.
• Acid/base handling: To extract from aqueous media, basify to liberate the free base; to partition into water, acidify to form the ammonium salt.
• Typical use scenarios:
  • Couplings (acylation/sulfonylation/urea formation): DCM, DMF, DCM/DMF, or MeCN with a base (DIPEA/TEA).
  • Pd-catalyzed N-arylation (Buchwald–Hartwig): toluene, dioxane, or t-BuOH with strong base (NaOtBu) and appropriate ligand.
  • Diazotization/Sandmeyer: aqueous mineral acid with in situ generation of diazonium at 0–5 C; subsequent solvent depends on trapping reaction.
• Comparison notes:
  • Versus aliphatic amines, aryl amines are less basic; protonation (and hence aqueous solubility) is less complete at mildly acidic pH.
  • Polar aprotics (DMF/DMSO) maximize solubility for high-loading reactions but consider workup and environmental profile. Greener options include 2-MeTHF or CPME when compatible.

Storage and Reconstitution

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

General guidance for aryl amines (literature best practice):

• Keep container tightly closed in a dry, well-ventilated place. Minimize exposure to air and light to limit slow oxidative discoloration.
• If long-term storage is anticipated, consider aliquoting under inert gas and storing with a desiccant. Periodically verify purity by HPLC/GC/NMR if used for sensitive applications.

Reconstitution/solution preparation:

• Organic stocks: Dissolve to 10–100 mM in DMSO, MeOH, or acetonitrile. Filter if particulate is present.
• Aqueous stocks: Prepare as an acid salt (e.g., dissolve in minimal HCl, then dilute with water or buffer) to enhance solubility. Record final pH and ionic strength when relevant to assays.
• Freeze-thaw: If preparing frozen aliquots, avoid repeated freeze–thaw cycles; thaw at room temperature and use promptly.

Disposal: Follow institutional and local regulations for organic amine waste. Do not release to the environment.

Research use only (from Product Data): For research use only.

Structure and Identity

Chroman-7-amine is an aniline-type aryl amine on the chroman (2,3-dihydro-1-benzopyran) scaffold, useful as a heteroaromatic building block.

• SKU: C942583
• Product name: Chroman-7-amine
• CAS: 50386-68-0
• Category: Life Science research reagent (research use only)
• InChIKey (from Product Data): 342136 (note: appears truncated/non-standard; see CoA/SDS for definitive identifier)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet. (C9H11NO, literature)
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (~149.19 g/mol, literature)

Structural features (general/literature description):

• Core: chroman (2,3-dihydro-1-benzopyran) bicyclic system with an ether oxygen in the heterocycle.
• Substituent: primary aromatic amine at the 7-position (para to the chroman O across the benzene subring, by common numbering).
• Functional groups: aryl amine (–NH2), cyclic ether (chroman O), benzenoid aromatic ring fused to a saturated O-containing ring.
• Stereochemistry: none specified; the parent chroman ring is achiral in the absence of additional stereocenters.

2D structure in words (literature):

• A benzene ring fused to a tetrahydropyran-like ring (oxygen at position 1 of the heterocycle), with an –NH2 substituent on the benzene ring meta to the fusion and para/para′ relative to the heteroatom by common chroman numbering.

Synthetic Utility

Functional handles and reactivity (literature, chroman anilines):

• Nucleophilicity/basicity: The aniline nitrogen reacts with acylating, sulfonylating, and carbonyl-activating reagents. Reduced basicity vs aliphatic amines affords greater chemoselectivity in multi-functional settings.
• Cross-coupling: Acts as the amine partner in Pd-catalyzed Buchwald–Hartwig reactions. Ligand tuning (e.g., BrettPhos, SPhos, XPhos) accommodates less nucleophilic anilines.
• Diazotization gateway: Transforms to diazonium salts enabling access to phenols, aryl halides (CuX), cyanides (CuCN), and azo dyes—useful for late-stage diversification.
• Directing effects: –NH2 is ortho/para-directing and ring-activating; in the chroman system, interplay with the oxygen heteroatom influences regioselectivity for EAS and metalation.
• Protection strategies: Boc/Ts/Ac protection to modulate reactivity and enable orthogonal sequences. Deprotections are well-established (TFA, NaOH/MeOH, hydrogenolysis as appropriate).
• Scaffold elaboration: Benzylic functionalization at the chroman O–CH2– site (e.g., oxidation to aldehydes/ketones, or halogenation) opens further C–C or C–X bond formations.

Retrosynthetic value:

• Chroman-7-amine can be traced back to nitro precursors (reduction of chroman-7-nitro) or from halogenated chromans via Buchwald–Hartwig amination. These routes provide entry points for analog series by varying the amine or ring substituents.

Target Specificity

Not applicable. This product is a small-molecule chemical building block, not a biological targeting reagent (e.g., antibody, enzyme, or ligand with defined biological specificity). No antigen/epitope or species reactivity information applies.

자주 묻는 질문

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

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

The CAS Number is 50386-68-0, the molecular formula is C9H11NO, and the molecular weight is 149.19 g/mol. InChIKey SPTKRFYLJBPEBL-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.