This compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
External Descriptors
Not available
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.
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Application Protocols
No vendor-validated application protocols are provided for this small-molecule reagent.
Tested applications, dilutions, positive controls: Not specified for this item; refer to CoA/Spec Sheet.
General handling suggestion:
For synthetic use, prepare stock solutions in dry, oxygen-free solvent in an inert atmosphere glovebox or via Schlenk techniques when moisture/air sensitivity is a concern for your transformation.
Biological Roles
This product is supplied strictly for research use; no biological activity or clinical utility is claimed for this SKU.
General biochemical context (literature, not item-specific):
Primary arylalkylamines are structural motifs found across biogenic amines and synthetic analogues; they can engage in acid–base interactions with biomolecules and form salts under physiological conditions.
The para-fluoro substituent is a common medicinal chemistry handle used to modulate lipophilicity, metabolic stability (blocking benzylic/para-oxidation), and electronic properties of aromatic rings.
As a benzylic primary amine, the functional group can be derivatized for probe synthesis (e.g., amide-linked affinity tags) to study binding in biochemical assays.
Caution:
No in vitro, in vivo, or ADME/tox data are provided by the manufacturer for this item.
Any exploration of biochemical interactions should be conducted within appropriate institutional approvals and with reference standards where required.
For any biological testing, generate your own characterization data and controls; use of this product is for research only.
Buffer Applications
This compound is not typically used as a biological buffer component.
General note (literature):
While primary amines are basic, dedicated buffering agents (e.g., Tris, HEPES, phosphate) provide defined pKa values, high water solubility, and minimal biological interference.
Arylalkyl primary amines like this exhibit limited aqueous solubility as free bases and are not suitable for maintaining stable pH in biochemical assays.
If a basic additive is required, consider standard buffering systems; for synthetic reactions, inorganic or organic bases (e.g., DIPEA, triethylamine) are usually more appropriate.
Green Alternatives
Opportunities for greener practice relate primarily to solvent choice, coupling reagents, and protection strategies rather than to the amine itself.
Solvent selection (literature/general):
Replace chlorinated solvents with greener ethers or esters when feasible (e.g., EtOAc, 2-MeTHF, CPME) for acylations and reductive aminations.
Use aqueous biphasic or alcohol media for reductive amination to reduce VOC impact.
Reagent choices:
Prefer catalytic amide bond formations (e.g., enzymatic amidation, boronic acid-catalyzed couplings) or greener carbodiimide alternatives (e.g., ethyl chloroformate replaced by CDI; avoid HOBt hazard).
Electrocatalytic or hydrogenative reductive amination can minimize cyanoborohydride waste.
Workup/purification:
Crystallize as a salt (e.g., hydrochloride) to avoid silica-gel chromatography.
Employ solvent recycling and minimal protecting-group manipulations.
Comparison (general, qualitative):
DCM/chloroform vs. 2-MeTHF/EtOAc: greener options reduce halogenated waste but may change rates/chemo-selectivity.
NaBH3CN vs. H2/Pd: hydrogenation eliminates cyanide waste but requires pressure equipment and can hydrogenolyze sensitive groups.
Trade-offs should be evaluated with small-scale trials; consult process safety when changing solvents or reductants.
Pharmaceutical Uses
No pharmacopeial status or excipient designation is provided for this item.
Item-specific information: Not specified for this item; refer to CoA/Spec Sheet.
General formulation/manufacturing context (literature):
Primary arylalkyl amines are frequently employed as intermediates in the synthesis of active pharmaceutical ingredients, where the amine is transformed into amides, ureas, or heterocycles.
Formation of crystalline salts (e.g., hydrochloride, mesylate, sulfate) can improve handling, stability, and purification in process development.
Para-fluoro substitution is a common strategy to adjust metabolic stability and solid-state properties of drug-like molecules; however, no therapeutic claims are made or implied for this compound.
For any cGMP use, dedicated qualification, impurity profiling, and regulatory assessment are required; this product is supplied for research use only.
Physical Properties
Item-specific physicochemical specifications (bp, mp, density, refractive index, UV cut-off, residual solvents, etc.) are not provided.
Item-specific values: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general expectations for closely related structures (for planning only; not product specifications):
Physical state: low-melting solid or high-boiling liquid for small arylalkyl primary amines; strong odor typical of aliphatic amines.
Basicity: primary benzylic/isopropylamines typically show conjugate-acid pKa around 9–10 (literature), depending on ring substituents; para-fluoro slightly decreases basicity vs. phenyl analog.
Solubility: miscible with many organic solvents (ethers, alcohols, chlorinateds). As free base, limited solubility in water; salts (e.g., HCl) are water-soluble (literature).
LogP: arylalkyl primary amines of this size often have logP ≈ 1.5–2.5 for the free base; protonated forms are much less lipophilic (literature).
Boiling/melting: many benzylic primary amines boil in the 180–230 °C range as free bases; salts have higher mp (literature).
Practical notes:
As a primary amine, it can form reversible CO2 adducts and absorb moisture/acids; item is supplied under argon and prefers low-temperature, light-protected storage (see Storage tab).
If precise values are needed for method development (chromatography, formulation), consult the CoA/SDS or request a specification sheet.
Quality and Grades
Item-specific grade/purity, stabilizers, residual solvent limits, and analytical release criteria: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting common grades (general guidance):
Research grade: suitable for general synthetic and analytical use; impurity profile intended for R&D.
Purified/base-stabilized: primary amines are sometimes offered with trace stabilizers (e.g., small amounts of acid or antioxidant) to minimize discoloration; any such stabilizer would be declared on the CoA (none specified here).
Chromatography-grade or “low UV” is relevant only if the amine is intended as a mobile-phase additive (not typical for this structure).
QC considerations for arylalkyl primary amines (general):
Identity: 1H/13C NMR (benzylic signals, para-F coupling), FTIR (N–H stretches ~3300–3500 cm−1), MS (M+H+ around the literature formula mass), and melting/boiling range.
Purity: GC or HPLC area %; residual solvent and water (Karl Fischer) as needed for moisture-sensitive reactions.
Color: freshly prepared materials are usually colorless to pale; slight yellowing may occur upon aging/oxidation of amines.
For exact acceptance criteria and analytical data for this SKU, please refer to the Aladdin CoA/Spec Sheet for lot-specific details.
Reaction and Applications
This compound is a para-fluorinated arylalkyl primary amine useful as a nucleophilic base and as a building block for benzylic amide, urea, sulfonamide, and imine chemistries.
Acylation to amides with acyl chlorides/anhydrides or via carbodiimide couplings (EDC/HOBt, HATU) under mild base.
Sulfonylation to sulfonamides (TsCl, MsCl) for protection or further derivatization.
Urea/thiourea formation using CDI or isothiocyanates; carbamate formation with chloroformates.
Reductive amination at the benzylic position of partner carbonyls (the amine as nucleophile) using NaBH3CN, NaBH(OAc)3, or catalytic hydrogenation.
Schiff base formation with aldehydes/ketones; subsequent transformations (e.g., Strecker-type, borohydride reduction).
Formation of quaternary ammonium salts via alkylation (for phase-transfer or ionic tags), though over-alkylation control is needed.
Substituent effects (general):
The para-fluoro group subtly reduces electron density on the ring and on the benzylic center, slightly lowering basicity vs. the unsubstituted phenyl analogue and improving oxidative stability of the ring.
Applications in synthesis:
Precursor to ligand fragments, benzylated auxiliaries, or cross-coupling handles after converting the amine to a suitable leaving group (e.g., diazonium-derived transformations from anilines are not applicable; here the amine is benzylic/aliphatic).
Salt formation (HCl, p-TsOH) improves crystallinity and handling for scale-up and purification.
Note: No manufacturer application notes were provided beyond research use; the above are literature-general strategies.
Reaction Conditions
Generalized conditions for typical transformations of benzylic primary amines (literature guidance; adjust to your substrate and scale):
Amide coupling:
Solvent: DMF, DCM, 2-MeTHF, or EtOAc.
Reagents: HATU (1.1–1.5 equiv) or EDC·HCl/HOBt (exercise HOBt safety), base DIPEA (2–3 equiv).
Temperature/time: 0–25 °C, 1–4 h; monitor by TLC/HPLC.
Sulfonamide formation:
Solvent: DCM or acetonitrile; base: pyridine or Et3N (2–3 equiv).
Reagent: TsCl or MsCl (1.1–1.3 equiv) at 0 °C to rt over 2–6 h.
Reductive amination (amine as nucleophile):
Step 1: Mix carbonyl (1.0 equiv) with amine (1.2–2.0 equiv) in MeOH or THF with 3 Å MS; catalytic AcOH to promote imine.
Step 2: Add NaBH3CN (1.2–1.5 equiv) at pH 6–7 (AcOH) or use NaBH(OAc)3 in DCE/MeCN; 0–25 °C, 2–12 h.
Alternative: H2 (1–5 bar), Pd/C (5–10 wt%), MeOH/EtOH, 25–40 °C.
Protection (Boc):
Solvent: THF or dioxane/water; Reagent: (Boc)2O (1.1–1.5 equiv), base: NaHCO3 or Et3N; 0–25 °C, 1–3 h.
Salt formation (HCl):
Dissolve free base in dry ether; add ethereal HCl dropwise at 0–5 °C to pH ~1; precipitate, filter, wash with cold ether; dry under vacuum.
Yields and exact conditions vary with substrate and scale. Always perform small-scale trials and consult primary literature. None of the above are product specifications.
Safety and Handling
Follow standard precautions for handling low-molecular-weight primary amines and benzylic aromatics.
Item-specific hazard data (GHS, H/P statements, pictograms): Not specified for this item; refer to SDS.
General hazards for primary amines (literature/generic guidance):
May be corrosive/irritating to skin, eyes, and respiratory tract; strong, fishy amine odor; can cause sensitization in some individuals.
Flammable/combustible organic base; vapors may form ignitable mixtures with air if sufficiently volatile.
Amines can attack some plastics and elastomers; use compatible materials (PTFE, glass).
Can absorb CO2/moisture leading to carbamate/amine salt formation; keep under inert atmosphere as supplied.
First aid (overview; defer to SDS):
Skin/eye contact: immediate decontamination with running water for ≥15 minutes; remove contaminated clothing.
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Always consult the product SDS for authoritative safety information.
Solvent Selection
As a small, basic, polar organic compound, this primary amine exhibits dual solubility behavior depending on protonation state.
Polarity/miscibility (general behavior):
Free base: good solubility in ethers (THF, MTBE), alcohols (MeOH, EtOH, i-PrOH), chlorinated solvents (DCM, CHCl3), and many hydrocarbons when warmed; moderate water solubility.
Protonated salt (e.g., HCl): high water and alcohol solubility; poor solubility in nonpolar solvents.
Dielectric and donor/acceptor considerations (literature):
Amines act as H-bond acceptors and donors (two N–H protons); coordinate to Lewis acids and transition metals; can deactivate acidic catalysts unless pre-neutralized.
Choosing a medium (practical tips):
For nucleophilic substitution or acylation: use aprotic solvents (DCM, THF, MeCN) and maintain mild base scavenging of HCl/acid byproducts.
For reductive amination: protic or mixed solvents (MeOH/THF) often aid imine formation/reduction balance.
For salt formation/purification: dissolve base in ether and treat with HCl in ether to precipitate the hydrochloride salt; recrystallize from alcohol/ether mixtures.
Comparison (general):
In contrast to secondary/tertiary amines, primary amines are more reactive toward acylation and imine formation but are more prone to oxidative discoloration; solvent choice should minimize exposure to air/heat during workup.
Storage and Reconstitution
Follow the item-specific storage and shipping guidance provided by the manufacturer.
Allow the container to equilibrate to room temperature before opening to minimize moisture condensation.
If repeated access is expected, consider aliquoting under inert gas into amber vials to reduce air/light exposure.
Primary amines can slowly oxidize/discolor; maintain inert headspace and minimize headspace volume.
Reconstitution:
If supplied as a solid or viscous oil, dissolve in a dry, oxygen-free solvent compatible with your application (e.g., anhydrous THF, DCM, MeOH). Filter through a PTFE syringe filter if particulate is present.
For salt formation (optional for handling), generate the hydrochloride in situ and store as a crystalline solid if appropriate to your workflow.
Stability:
Long-term stability depends on exclusion of air, acids, and light. For exact shelf life and retest dates, consult the CoA.
Research Use Note: For research use only.
Structure and Identity
A para-fluorinated arylalkyl primary amine used as a versatile building block and basic organonitrogen reagent.
Item-specific identifiers (from Product Data):
SKU: P727248
Product Name: 2-(4-Fluorophenyl)propan-2-amine
CAS: 17797-10-3
InChIKey: 251054 (as provided)
SMILES: 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.
Literature/structural description (general chemistry, not item-specific):
Preferred IUPAC-style name corresponds to a benzylic, tertiary carbon bearing an NH2 group and two methyl substituents, with a 4-fluorophenyl substituent on the same stereogenic center (2-(4-fluorophenyl)propan-2-amine; sometimes described as a cumylamine analogue).
Functional groups: primary aliphatic amine (basic), para-fluorinated phenyl ring, benzylic tertiary carbon (C attached to aryl, NH2, and two methyls).
Stereochemistry: the C bearing the amine is chiral; commercial material may be racemic unless otherwise stated (no enantiomeric information provided in Product Data).
Typical (literature) empirical formula for this scaffold: C9H12FN; typical formula mass ≈ 153.2 g/mol (literature, for reference only).
2D structure in words: a para-fluorobenzene ring attached at the benzylic position to a quaternary-like center that is actually tertiary carbon bearing NH2 and two methyl groups (–C(NH2)(CH3)2–Ar-4-F).
Synthetic Utility
2-(4-Fluorophenyl)propan-2-amine serves as a versatile synthon owing to its benzylic, sterically encumbered primary amine.
Functional-group reactivity (general):
Nucleophilicity: undergoes rapid acylation/sulfonylation to give amides/sulfonamides with predictable selectivity.
Electrophile activation: the benzylic center enhances rates of imine formation with aldehydes/ketones; reductive amination proceeds under mild conditions.
Protection: Boc, Cbz, or Fmoc protection enables multi-step sequences; deprotection conditions orthogonal to other groups.
Retrosynthetic value:
As a branching point, it can be elaborated to ligands, chiral auxiliaries (if resolved), or to benzylic quaternary centers via N→C transfer chemistry.
Conversion to isocyanate (via phosgene equivalents) or to ureas/carbamates introduces handles for polymer or material attachment.
Substituent effects:
Para-F modulates electronics without drastically changing sterics; facilitates late-stage diversification via metal-catalyzed C–F activation only under specialized conditions, otherwise inert.
Derivatization examples (literature):
Amide coupling (HATU/DIPEA, DMF or 2-MeTHF); urea formation with CDI; sulfonamide formation (TsCl/Et3N, DCM).
Salt formation for isolation (HCl in Et2O leading to crystalline hydrochloride).
This reagent is well-suited as a scaffold in SAR libraries and as a nucleophilic partner in standard organic transformations.
Target Specificity
Not applicable. This product is a small-molecule reagent, not a biological targeting agent.
Item-specific data such as antigen, epitope, species reactivity, clone, and isotype: Not specified for this item; refer to CoA/Spec Sheet.
For biochemical targeting studies, derivatization to tagged probes would be required; no such data are provided for this SKU.
자주 묻는 질문
What is the purity of this product?
This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at 2–8 °C, protected from light, 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 17797-10-3, the molecular formula is C9H12FN, and the molecular weight is 153.2 g/mol. InChIKey NYFSRXOWJXAHOO-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.
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