This compound belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.
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.
Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
Molekulargewicht
155.170 g/mol
XLogP3
1.800
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Exact Mass
155.075 Da
Monoisotopic Mass
155.075 Da
Topological Polar Surface Area
23.500 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
129.000
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
Lösungsrechner
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Application Protocols
No manufacturer-tested biological application protocols are provided for this item. As a synthetic building block, usage protocols depend on the intended chemical transformation.
General guidance
For solution preparation, dissolve in dry organic solvent (e.g., DMSO, DMF, MeCN, or alcohols) at the required concentration; filter if necessary.
For chromatographic purification, add 0.1–1% triethylamine to silica eluents to reduce tailing of the basic amine, or use reverse-phase chromatography.
Assay-related protocols (WB, IHC, IF, FC) are not applicable to this chemical reagent.
Biological Roles
Item-specific biological information: Not specified for this item; no biological characterization is provided in the Product Data. For research use only.
General context (literature)
Structural motif relevance: Aromatic phenol–tertiary amine scaffolds appear in enzyme ligands, dyes, and materials due to their hydrogen-bonding and electron-donating capacity. The presence of fluorine can modulate lipophilicity, metabolic stability, and electronic distribution.
Ionization: At acidic pH, the tertiary aniline is protonated (anilinium), potentially interacting with acidic biomolecular sites; at basic pH, the phenolic OH may deprotonate to phenoxide.
Caution: No specific biological activity or target engagement is ascribed to 3-(Dimethylamino)-5-fluorophenol here; any use in biochemical assays should include appropriate controls and concentration–response evaluation.
Practical note
For in vitro screening, prepare fresh DMSO stocks; assess assay interference (e.g., fluorescence, redox activity) because aminophenols can engage in redox or metal-chelation under some conditions.
No clinical or therapeutic claims are made or implied.
Buffer Applications
This compound is not a conventional buffering agent. It lacks a conjugate acid/base pair with a well-defined pKa spacing suitable for maintaining physiological pH like phosphate, Tris, or HEPES.
Guidance
Not typically used to prepare buffers for biochemical assays or electrophoresis.
If present in assay media, buffer choice should consider its ionization: acidic buffers (pH 4–5) favor amine protonation and solubility; basic buffers (pH >9) favor phenoxide formation which may alter activity/solubility.
For buffer preparation details, use standard buffering systems (e.g., phosphate, acetate, Tris, HEPES) rather than this reagent.
Green Alternatives
This product is a solid building block rather than a process solvent; “green alternatives” are best considered for the solvents and reagents used with it.
Greener solvent choices (literature/general)
Preferred: 2-MeTHF, CPME, EtOAc, MeCN (over chlorinated solvents) when compatible with reaction/selectivity.
Aqueous/biobased media: For O-alkylations, aqueous micellar catalysis (TPGS-750-M, Savie) can sometimes replace DMF/DMSO; verify substrate compatibility.
Reagent substitutions
Base: K2CO3/Cs2CO3 in greener solvents (EtOH/2-MeTHF) can replace NaH in DMF for some etherifications.
Acylation catalysts: Catalytic DMAP can be replaced or minimized; use greener bases like NEt3 or DBU in EtOAc/MeCN.
Oxidations: For N-oxide formation, consider H2O2/acetic acid systems in place of peracids where feasible.
Comparison snapshot (general)
DMF/DMSO vs 2-MeTHF/EtOAc: Lower EHS risk and easier workup with 2-MeTHF/EtOAc; however, some reactions require higher polarity of DMF/DMSO.
Chlorinated solvents vs MeCN/CPME: Reduced environmental impact with MeCN/CPME; watch for solubility and rate impacts.
Item-specific “green metrics” (e.g., solvent/energy intensity, certified bio-based content): Not specified for this item; consult your process development guidelines.
Pharmaceutical Uses
Item-specific information: Not specified for this item; no pharmacopeial grade or excipient designation is provided. For research use only.
General context (literature)
Role: Aromatic phenol/tertiary amine motifs are common in discovery chemistry as fragments or intermediates en route to candidate molecules. This compound may serve as a synthetic intermediate to generate libraries (ethers, carbonates, quaternary ammonium salts) for SAR studies.
Formulation relevance: As a free base, it is not an established excipient. If converted to a salt (e.g., HCl, mesylate), physicochemical properties (melting point, hygroscopicity, solubility) change and can assist in crystallization or purification during API route scouting.
No therapeutic indications or clinical uses are claimed or implied for this item.
Physical Properties
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.
Literature/computed (non-authoritative; typical values for reference)
Formula (literature): C8H10FNO
Molecular weight (literature): ~155.17 g/mol
Expected physical state: organic solid or low-melting solid/oil depending on purity and solvate content (general for substituted aminophenols).
Acid–base properties: tertiary anilinium pKaH typically ~4.5–5.5 (literature, class value); phenolic pKa typically ~9–10 (literature, class value). Protonation increases aqueous solubility.
Solubility profile (qualitative, literature):
Organic: good solubility in polar aprotic solvents (DMF, DMSO, MeCN) and moderately in alcohols/ethyl acetate; limited in alkanes.
Aqueous: low at neutral pH; increased in acidic media (as anilinium salt) or basic media (as phenoxide), noting possible competing protonation/deprotonation.
Partitioning: aromatic tertiary amines with one phenolic OH often show moderate logP (literature class ~1.5–2.5), tunable by pH via ionization state.
Note: Do not treat the above literature values as product specifications; consult the item’s CoA/Spec Sheet for authoritative physical property data.
Quality and Grades
Item-specific (from Product Data)
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)
Research grade: Typical for building-block organics; suitable for synthetic and analytical research. Purity is usually reported by HPLC/GC/NMR on the CoA.
Low-UV/HPLC grade (when applicable to solvents): Ensures minimal baseline noise; not typically relevant for solid reagents unless stated.
Metal specifications, residual solvents, water/peroxide content: Not specified for this item; refer to CoA/Spec Sheet.
Practical considerations specific to aminophenols (general)
Coloration: Minor coloration does not necessarily indicate impurity; aminophenols can darken on storage due to trace oxidation—store tightly closed, minimize air/light exposure.
Salt vs free base: Tertiary anilines may be supplied as free base or as a salt. This listing does not specify; verify on CoA, as it affects solubility, handling, and exact MW.
QC verification: Confirm identity by 1H/13C NMR (diagnostic phenolic OH, NMe2 singlet), HRMS, and suitable chromatographic purity before critical applications.
Reaction and Applications
As a multifunctional aryl building block, 3-(Dimethylamino)-5-fluorophenol offers orthogonal handles for chemical diversification.
Transformations at the phenol (literature/general)
O-alkylation: Williamson ether synthesis with alkyl halides or sulfate esters (bases: K2CO3, Cs2CO3, NaH; solvents: acetone, DMF, DMSO).
O-acylation/carbamate/carbonate formation: Using acyl chlorides/anhydrides (pyridine, DMAP catalysis) or chloroformates for protecting group or pro-moiety installation.
Silylation: TBS/TBDPS protection (imidazole or DMAP, DMF/CH2Cl2) to mask the OH during reactions sensitive to hydrogen bonding.
Transformations at the tertiary amine (literature/general)
Quaternization: Alkylation with MeI, MeOTf, or benzyl halides to form quaternary ammonium salts (useful for phase-transfer or crystallinity control).
Oxidation to amine N-oxide: m-CPBA or peracids, enabling Polonovski-type chemistry or altering electronics for subsequent substitution.
Aromatic functionalization (literature/general)
Electrophilic substitution: The NMe2 and OH strongly activate ortho/para positions; regioselectivity can be leveraged after appropriate protection of the phenol or amine.
Halogen exchange/cross-coupling: Aryl–F is typically inert; direct Pd-catalyzed cross-coupling at C–F is challenging. Strategies include converting the phenol to a leaving group (e.g., triflate) for Suzuki/Negishi couplings, or ipso-substitution via diazotization if converted to an aniline (not directly applicable here) or via directed ortho metalation.
Applications
Intermediate for dyes/fluorophores and advanced materials where electron-rich rings and fluorine tuning are desired.
SAR exploration in medicinal chemistry: Allows variation at O (ethers/esters/carbonates) and N (quaternary salts, amides via N-demethylation sequences) to modulate solubility and binding.
Manufacturer application notes: Not provided for this item; general uses above are literature-based.
Reaction Conditions
General literature guidance for common transformations of 3-(Dimethylamino)-5-fluorophenol and closely related scaffolds. Optimize for your substrate and scale.
O-alkylation (Williamson ether)
Typical: Alkyl bromide/iodide (1.2–1.5 eq), K2CO3 or Cs2CO3 (2.0 eq) in acetone, MeCN, or DMF, 25–60 °C, 2–16 h.
For hindered electrophiles: NaH (1.1–1.5 eq) in THF/DMF at 0–25 °C, then add electrophile; monitor to avoid competitive N-alkylation.
O-acylation/carbonate formation
Acyl chloride (1.1 eq), pyridine or NEt3 (2 eq), catalytic DMAP (5–10 mol%), CH2Cl2 or MeCN, 0–25 °C, 1–4 h.
Chloroformates (1.1 eq) for carbonates; similar base/catalyst.
N-oxide formation
m-CPBA (1.1–1.5 eq) in CH2Cl2, 0–25 °C, 1–3 h; or H2O2/acetic acid (excess) in MeOH, rt. Work up with base wash to remove acids.
Quaternization (salt formation)
MeI or BnBr (1.2–2.0 eq) in MeCN or acetone, 25–60 °C, 2–24 h; isolate quaternary ammonium salt by precipitation with ether.
Aryl triflation (for cross-coupling entry)
Tf2O (1.2 eq), 2,6-lutidine or pyridine (2–3 eq), CH2Cl2, −20 to 0 °C then warm to rt; subsequent Suzuki with Ar–B(OH)2, Pd(dppf)Cl2 (2–5 mol%), base (K3PO4), 2-MeTHF/H2O, 50–80 °C.
Notes
Protecting the phenol or controlling base strength often improves selectivity between O- vs N-functionalization.
Fluorine provides useful 19F NMR handle for rapid reaction monitoring.
Conditions are literature-style guidance and not product specifications.
Safety and Handling
Item-specific (from Product Data)
GHS Classification / Signal word / H-statements / Pictograms: Not specified for this item; refer to the SDS.
Storage conditions: Room temperature.
General safety guidance (literature/analogous chemicals; not a substitute for the SDS)
Likely hazards: Aromatic phenols and tertiary anilines may cause skin/eye irritation and are harmful if swallowed or inhaled. Avoid contact and inhalation of dust/vapors/aerosols.
PPE: Use lab coat, safety glasses or splash goggles, and suitable gloves (e.g., nitrile). Handle in a fume hood to control vapors and dust.
Incompatibilities: Strong oxidizers; strong acids/bases may induce salt formation or deprotonation and can affect stability/handling. Avoid reactive acylating/alkylating agents unless intended.
Phenolic/amine reactivity: Phenols can undergo slow air oxidation; minimize prolonged exposure to air and light. Tertiary amines can form salts with acids; avoid unintended neutralization.
First aid (overview):
Skin/eye contact: Rinse with water for ≥15 minutes; remove contaminated clothing; seek medical advice.
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Fire safety: Combustible organic; use CO2, dry chemical, or foam. Thermal decomposition may release NOx and HF-containing species.
Always consult the product’s SDS for definitive hazard classification and response procedures.
Solvent Selection
This product is an aromatic tertiary amine bearing a phenolic OH; solvent choice should consider both hydrogen bonding and basicity.
Polarity and miscibility (general/literature)
Preferred solvents: Polar aprotic media (DMF, DMSO, NMP, MeCN) dissolve both free base and salts (to varying degrees). Alcohols (MeOH, EtOH, i-PrOH) are often adequate. Ethyl acetate and acetone provide moderate solubility; toluene shows limited solubility.
Aqueous systems: The free base shows low aqueous solubility at neutral pH. In acidic media (e.g., pH < 5), protonation of the amine increases water solubility; in strongly basic media, phenoxide forms but the amine may remain neutral.
Selection tips by operation
O-alkylation/acylation: Dry acetone, MeCN, DMF, or DMSO with K2CO3/Cs2CO3/NaH.
Salt formation/crystallization: Ether/ethyl acetate/hexanes mixtures can precipitate amine salts (e.g., HCl, p-TsOH) from alcohol or MeCN solutions.
Purification: Normal-phase silica is feasible; the basic amine may tail—use 0.1–1% NEt3 in eluents or convert to a protected/salt form. Reverse-phase preparative HPLC works well if needed.
Comparison (general)
vs Phenol-only analogs: Greater solubility in moderately polar organics due to the tertiary amine.
vs Dialkylaminoanilines without OH: Slightly higher polarity; H-bonding to stationary phases is stronger—adjust eluent accordingly.
Item-specific solvent specs (e.g., water content, UV cutoff): Not specified for this item; refer to CoA/Spec Sheet.
Storage and Reconstitution
Item-specific (from Product Data)
Storage conditions: Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General handling and storage (literature/best practice for aminophenols)
Keep container tightly closed in a dry, well-ventilated place. Minimize exposure to air and light to limit slow oxidative discoloration typical of aminophenols.
If long-term storage is planned, consider storing under inert gas and segregate from strong oxidizers, acids, and bases.
Reconstitution/preparation
Solubility: Readily prepared stock solutions in DMSO, DMF, MeCN, or alcohols. For aqueous work, adjust pH (acidify to protonate amine) to enhance solubility as needed.
Filtration: Use PTFE or PVDF syringe filters for organic solutions; avoid nylon if reactive acylating agents are present in solution.
Stability notes
Avoid prolonged heating; phenolic/amine functionalities can undergo side reactions upon extended exposure to air at elevated temperatures.
For analytical reference solutions, prepare fresh or store aliquots at −20 °C (general practice) to maintain integrity; verify by NMR/LC before critical use.
Refer to the product’s CoA and SDS for definitive storage constraints and compatibility.
Structure and Identity
Brief description: 3-(Dimethylamino)-5-fluorophenol is an anilide-like phenolic aromatic bearing a tertiary dimethylamino group meta to the phenolic OH and a fluorine substituent para to the amino group.
Item-specific (from Product Data)
SKU: D979227
Product name: 3-(Dimethylamino)-5-fluorophenol
CAS: 1243401-81-1
PubChem CID: 20258784
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identifiers (non-authoritative, for reference only)
2D structure (described): A benzene ring bearing an OH at position 1 (phenol), a dimethylamino N(CH3)2 at position 3 (meta to OH), and an F at position 5 (para to the amino group). No stereocenters; fully aromatic.
Electronic character: Strongly electron-donating NMe2 and OH activate the ring (ortho/para directing), while F is deactivating but ortho/para directing; net reactivity is governed by competing resonance/inductive effects.
Coordination/basic sites: Tertiary amine (protonation, salt formation); phenoxide under basic conditions.
Synthetic Utility
Functional group handles
Phenol (Ar–OH): Enables rapid diversification to ethers, esters, carbonates, carbamates; serves as a directing group after conversion to sulfonates/triflates.
Tertiary aniline (Ar–NMe2): Tunable basic site for salt formation; convertible to N-oxide; quaternization provides a handle for phase-transfer or further functionalization.
Aryl fluoride (Ar–F): Strong C–F bond; typically inert to standard cross-couplings, but can modulate electronics and site-selectivity; niche SNAr possible only under forcing conditions on suitably activated positions.
Retrosynthetic value (literature/general)
Acts as an electron-rich nucleus for downstream electrophilic substitution once OH/N functions are protected.
Phenol-to-triflate strategy: Convert OH to aryl triflate (Tf2O, base) to access cross-coupling (Suzuki, Negishi, Buchwald–Hartwig) manifolds—bypassing the inert C–F.
Demethylation/refunctionalization pathways: While direct N-demethylation of tertiary anilines can be achieved (e.g., via N-oxide/Polonovski or oxidative protocols), planning should consider over-oxidation risks.
Protecting group tactics
O-protection: TBS, TBDPS, benzyl; choose orthogonality vs N-protection.
N-protection: Quaternization (reversible via Hofmann elimination is not practical on anilines), or acylation to amide (after N-demethylation sequences); alternatively, form the N-oxide transiently to alter reactivity.
Analytics
1H NMR: Diagnostic singlet for NMe2 (~2.9–3.1 ppm, literature), phenolic OH often broad/variable; aromatic pattern influenced by F (JHF coupling).
19F NMR: One aryl F resonance; useful for tracking reactions.
Target Specificity
Not applicable. This product is a small-molecule chemical building block and not a biological macromolecule or affinity reagent. No target, antigen, clone, isotype, or species reactivity is defined in the Product Data.
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