1-Adamantyl fluoroformate - ≥90% , CAS No.62087-82-5

CAS: 62087-82-5 Cat. No.: A463147 Formula: C₁₁H₁₅FO₂ Peso molecolare: 198.23 Numero EC: 263-400-6

GRADE & PURITY ≥90%

Synonyms

SCHEMBL2517522 | AS-60455 | Adamantan-1-yl carbonofluoridate | A930304 | (Tricyclo(3,3,1,1',3,7)decan-1-yl) fluoroformate | Carbonofluoridic acid,tricyclo[3.3.1.13,7]dec-1-yl ester | Carbonofluoridic acid, tricyclo[3.3.1.13,7]dec-1-yl ester | EINECS 263-4

Storage

Store at 2-8°C

Shipped In

Wet ice

Specifications

Sinonimi

SCHEMBL2517522 | AS-60455 | Adamantan-1-yl carbonofluoridate | A930304 | (Tricyclo(3,3,1,1',3,7)decan-1-yl) fluoroformate | Carbonofluoridic acid,tricyclo[3.3.1.13,7]dec-1-yl ester | Carbonofluoridic acid, tricyclo[3.3.1.13,7]dec-1-yl ester | EINECS 263-4

Specifiche e purezza

≥90%

Condizioni di conservazione di stoccaggio

Store at 2-8°C

Spedito in

Wet ice

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Purezza

≥90%

Nomi e identificatori

Sorrisi canonici

C1C2CC3CC1CC(C2)(C3)OC(=O)F

IUPAC Name

1-adamantyl carbonofluoridate

InChIKey

PNLZKVOKOVFGMZ-UHFFFAOYSA-N

INCHI

1S/C11H15FO2/c12-10(13)14-11-4-7-1-8(5-11)3-9(2-7)6-11/h7-9H,1-6H2

Isomeri SMILES

C1C2CC3CC1CC(C2)(C3)OC(=O)F

WGK Germania

3

Peso molecolare

198.23

Reaxy-Rn

3590131

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=3590131&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Organic carbonic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Organic carbonic acids and derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Organic carbonic acids and derivatives
• Alternative Parents: Organofluorides Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Carbonic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organofluoride - Organohalogen compound - Carbonyl group - Aliphatic homopolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as organic carbonic acids and derivatives. These are compounds comprising the organic carbonic acid or a derivative thereof.
• 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

Proprietà chimiche e fisiche

• Punto di infiammabilità (°F): 190.4 °F
• Punto di infiammabilità (°C): 88 °C
• Peso molecolare: 198.230 g/mol
• XLogP3: 3.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 198.106 Da
• Monoisotopic Mass: 198.106 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 233.000
• 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 standardized bioassay or immunoassay protocols apply to this small-molecule reagent.

• Synthetic usage notes
  • Dry glassware and inert atmosphere setup (N2/Ar).
  • Charge substrate and base first; cool, then add 1-adamantyl fluoroformate dropwise.
  • Monitor by TLC/LC–MS; quench cautiously with buffered aqueous solution; extract and purify by standard chromatographic methods under minimal moisture exposure.

For any assay-like use in your workflow, develop substrate-specific procedures and validate analytically. Refer to the SDS and CoA for handling specifics.

Biological Roles

• Item-specific biological data: Not specified for this item; for research use only (as noted in Product Data).

• General context (literature)

  • 1-Adamantyl fluoroformate is a synthetic reagent; it is not a naturally occurring metabolite or cofactor.
  • The adamantyl group is a rigid, lipophilic cage that can modulate physicochemical properties (hydrophobicity, steric bulk) when incorporated as the adamantyloxycarbonyl (Adoc) group on amines or alcohols.
  • In chemical biology and probe development, installation of bulky carbamate/carbonate protecting groups can be used to attenuate nucleophilicity or alter membrane permeability and metabolic stability of small molecules or linkers, enabling controlled release after deprotection under defined conditions.
  • Any biochemical interactions of Adoc-modified molecules stem from the parent scaffold; the reagent itself serves purely as a chemical modifier in synthetic steps, not as a biological effector.

• Practical note

  • Because Adoc is bulky, enzymatic hydrolysis of adamantyl carbonates/carbamates is often slowed relative to smaller groups; this can be leveraged in stability studies—but specific rates are substrate- and system-dependent and should be determined empirically.

Buffer Applications

This compound is not a buffering agent and is reactive toward water and protic media. It is therefore not used to prepare aqueous buffers.

• Guidance
  • Avoid aqueous or protic buffers during handling and reactions; hydrolysis generates CO2 and fluoride/HF.
  • For workup, buffered aqueous bicarbonate or dilute carbonate solutions can be used cautiously to neutralize acidity while minimizing uncontrolled HF formation; ensure appropriate fluoride handling protocols.

Green Alternatives

When choosing an Adoc-introducing reagent or a carbonylating strategy, consider greener options and trade-offs.

• Alternative reagents/approaches (literature/general)

  • 1-Adamantyl chloroformate (AdOCOCl): similar reactivity but typically derived from phosgene equivalents; chloride is a less benign halide than fluoride in some contexts; may have higher hydrolytic persistence in water but similar hazard profile overall.
  • Carbonyldiimidazole (CDI) strategies: Form AdO–C(=O)–Im from adamantanol and CDI, then transfer to amines/alcohols. Avoids halogenated byproducts; imidazole byproduct is easier to handle.
  • Organic carbonates (dimethyl/diethyl carbonate): Greener carbonyl sources but generally less reactive; may require catalysts (e.g., DBU, organocatalysts) and elevated temperature; not ideal for hindered Ad derivatives.

• Solvent substitution

  • Swap DCM with 2-MeTHF, CPME, or EtOAc when compatible. Rates may differ; verify on small scale.

• Small comparison (qualitative)

  • Fluoroformate: fast, mild, water-sensitive; potential HF formation on hydrolysis; works at low temp.
  • CDI route: greener byproducts; may require pre-activation; sometimes slower but operationally simple.
  • Dialkyl carbonates: green solvents/reagents; highest atom economy but less reactive—often unsuitable for very hindered amines.

• Practical green tips

  • Use minimal excess; run at higher concentration to reduce solvent.
  • Implement in-line quench/neutralization for fluoride and capture CO2 off-gas responsibly.
  • Choose greener solvent and energy-efficient conditions where performance allows.

Pharmaceutical Uses

• Item-specific pharmacopeial status: Not specified for this item; refer to CoA/Spec Sheet if pharmacopeial compliance is required.

• General formulation/manufacturing context (no therapeutic claims)

  • Role in process chemistry: 1-Adamantyl fluoroformate can be used to introduce the adamantyloxycarbonyl (Adoc) protecting group onto amines or alcohols during the synthesis of drug intermediates, enabling orthogonal protection/deprotection strategies.
  • Advantages: Mild conditions, short reaction times, and compatibility with many functional groups can reduce impurity generation in multi-step API syntheses.
  • Considerations: Hydrolytic sensitivity necessitates controlled addition and anhydrous processing. Fluoride/HF management must be addressed in equipment selection and waste treatment.
  • Residuals and purge: Validate removal of residual reagent and byproducts (fluoride, 1-adamantanol, carbonate impurities) by appropriate analytical methods (e.g., IC for F−, GC/LC for organics).
  • Scale-up notes: Gas evolution (CO2) during quench requires controlled venting. Incorporate in-process controls for assay and moisture. Materials of construction should be compatible with potential fluoride formation.

Physical Properties

Only item-specific specifications provided by the catalog are listed as such. All other values below are literature/computed for general reference and must not be construed as specifications for this SKU.

• Item-specific specifications

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

• Literature/computed properties (reference only; verify in your system prior to use)

  • Molecular formula: C11H15FO2 (computed from structure)
  • Molecular weight: ~198.23 g/mol (computed)
  • Physical state: typically a moisture-sensitive liquid or low-melting solid for analogous fluoroformates (literature, general)
  • Density, refractive index, melting/boiling point, vapor pressure: Not specified for this item; consult primary literature/SDS for representative ranges.
  • Solubility profile (qualitative, literature): expected to be soluble in common aprotic organic solvents (e.g., DCM, THF, EtOAc, acetonitrile); reacts/hydrolyzes in water and alcohols.
  • Partitioning: adamantyl substituent is hydrophobic; overall high logP expected relative to simple alkyl fluoroformates (qualitative, literature).

• Practical implications

  • Hydrolytically sensitive: contact with moisture/protic media leads to decomposition (CO2 evolution) and formation of 1-adamantanol and fluoride (HF in acidic media). Work under anhydrous conditions.
  • Volatility/odor: acyl fluorides/fluoroformates can be lachrymators; minimize vapor exposure and use efficient containment (hood, cold traps as needed).

Quality and Grades

• Item-specific grade/purity

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

• General guidance on quality for this reagent class

  • Fluoroformates are hydrolytically sensitive; real-world purity can change with handling. Review water content, fluoride content, and assay on the current Certificate of Analysis.
  • Low UV background is typically not critical unless the reagent will be used in photochemical steps or monitored by UV-HPLC; in such cases, ensure impurity profile is suitable.
  • Stabilizers: Some commercial activated carbonates may be stabilized or packaged under inert gas. This listing does not specify a stabilizer. If present in the CoA, consider its impact on downstream chemistry and purification.

• Practical QA/QC tips

  • On receipt, inspect container integrity and ensure cold-chain compliance (shipped on wet ice for this item).
  • If needed, assay by quantitative 19F NMR or titration with a standardized amine under controlled conditions. Monitor for hydrolysis products (1-adamantanol) by GC/LC.
  • For sensitive applications (e.g., protecting-group installation in complex intermediates), run a small-scale test to confirm reactivity and selectivity with your substrate lot.

Reaction and Applications

1-Adamantyl fluoroformate is an activated carbonate used to introduce the adamantyloxycarbonyl (Adoc) group under mild conditions.

• Representative applications (literature/general)

  • Protection of amines as Adoc-carbamates: R–NH2 + AdO–C(=O)–F → R–NH–C(=O)–O–Ad (base-promoted). Bulky Adoc can impart stability to nucleophilic or basic conditions while being removable under specific acidic or hydrogenolytic protocols (check substrate compatibility).
  • Carbonate formation from alcohols/phenols: R–OH + AdO–C(=O)–F → R–O–C(=O)–O–Ad using base and often catalytic DMAP.
  • Preparation of adamantyl esters via transcarbonylation to probe steric effects in catalysis, materials, or pro-moiety studies.

• Advantages of the fluoroformate leaving group

  • High electrophilicity; typically faster and cleaner than corresponding chloroformates with certain nucleophiles.
  • Avoids handling phosgene-derived reagents during use-phase (though upstream sourcing varies; consult supplier documentation).

• Practical tips

  • Use 1.0–1.2 equiv of fluoroformate; 1.5–2.0 equiv of tertiary amine base (Et3N, DIPEA). For alcohols, include 5–10 mol% DMAP.
  • Temperature: 0–25°C is generally sufficient; cool during initial addition to control exotherm.
  • Order of addition: add reagent slowly to a cooled solution of substrate and base to minimize over-acylation and hydrolysis.
  • Quench: cautiously with buffered aqueous bicarbonate at low temperature; fluoride/HF scavenging with CaCO3/Ca(OH)2 may be beneficial (follow EHS protocols).

• Monitoring

  • TLC/LC–MS; 19F NMR can track consumption/formation of fluoride species; IR shows carbonyl shifts (fluoroformate ~1800–1850 cm−1; product carbamates/carbonates lower).

Reaction Conditions

General literature guidance for using 1-adamantyl fluoroformate; adjust to your substrate and consult primary references. Values below are not item specifications.

• Amines → Adoc-carbamates

  • Solvent: dry DCM or THF (0.05–0.5 M).
  • Base: Et3N or DIPEA (1.5–2.5 equiv relative to amine).
  • Reagent: 1.0–1.2 equiv of 1-adamantyl fluoroformate.
  • Temperature/time: 0–25°C, 0.5–4 h; exotherm on addition—dose slowly.
  • Additives: none typically required; for less nucleophilic anilines, DMAP (5–10 mol%) can accelerate.
  • Typical outcomes: high conversions with minimal urea formation under dry conditions (yields often good to excellent in literature reports).

• Alcohols/phenols → Adoc-carbonates

  • Solvent: dry DCM or MeCN (0.05–0.3 M).
  • Base: Et3N or pyridine (2.0–3.0 equiv); catalytic DMAP (5–10 mol%).
  • Temperature/time: 0–25°C, 1–6 h.

• Workup

  • Quench at 0–5°C with aqueous NaHCO3 or dilute carbonate buffer. Control gas evolution (CO2). Consider fluoride scavengers (CaCO3/Ca(OH)2) and compatible glassware/contact materials.

• Monitoring/analytics

  • TLC/LC–MS; IR: disappearance of fluoroformate C=O (~1800–1850 cm−1) and appearance of carbamate/carbonate C=O (~1700–1770 cm−1). 19F NMR for reagent consumption/byproducts.

• Common pitfalls

  • Moisture ingress leading to hydrolysis and reduced assay.
  • Over-acylation or carbonate scrambling with excess DMAP—optimize catalyst loading.
  • Accumulation of salts (amine·HF) impairing stirrability—adjust solvent volume or add base incrementally.

Safety and Handling

The following guidance is general best practice for acyl fluorides/fluoroformates. Always review the product-specific SDS and your institutional EHS protocols before use.

• GHS/SDS information for this item

  • Signal word, H-statements, pictograms, and classification: Not specified for this item; refer to SDS.

• Key hazards (general for fluoroformates)

  • Corrosive/irritant potential: Hydrolysis can generate fluoride species; in acidic aqueous conditions this includes HF, which is highly corrosive and systemically toxic.
  • Respiratory/eye irritation: Many acyl fluorides are potent lachrymators. Avoid inhalation and eye contact.
  • Reactivity: Hydrolyzes with moisture; reacts vigorously with nucleophiles (amines, alcohols, strong bases). Avoid contact with water, alcohols, strong bases, and strong acids.

• Handling

  • Use in a fume hood; employ anhydrous techniques (dry glassware, inert atmosphere).
  • Avoid glass etching by fluoride in prolonged contact with strongly acidic mixtures; use compatible materials (PTFE) if HF formation is possible.
  • Recommended PPE: lab coat, safety goggles/face shield, chemical-resistant gloves (e.g., nitrile; consider laminate gloves for extended contact), and appropriate HF-calcium gluconate availability per site policy.

• First aid (overview; defer to SDS)

  • Skin/eye: Immediate irrigation with water for ≥15 min. For suspected HF exposure, follow HF-specific medical protocols and apply calcium gluconate gel per site SOP.
  • Inhalation: Move to fresh air; seek medical attention.
  • Ingestion: Do not induce vomiting; seek immediate medical attention.

• Storage incompatibilities

  • Keep away from moisture, alcohols, amines, bases, and acids. Store tightly closed at 2–8°C (per item data).

Solvent Selection

Choosing a solvent for 1-adamantyl fluoroformate focuses on maintaining anhydrous conditions while enabling efficient nucleophilic substitution to form carbamates (with amines) or carbonates (with alcohols/phenols).

• Polarity/miscibility (general expectations for this reagent class)

  • Preferred aprotic, anhydrous solvents: dichloromethane (DCM), 1,2-dichloroethane (DCE), tetrahydrofuran (THF), acetonitrile (MeCN), toluene, ethyl acetate (dry).
  • Avoid protic solvents (water, alcohols) which cause hydrolysis.

• Selection guidance by transformation

  • Amines → carbamates: DCM or THF with a non-nucleophilic base (e.g., DIPEA, Et3N). DCM often affords cleaner profiles at 0–25°C.
  • Alcohols/phenols → carbonates: DCM or MeCN with catalytic DMAP and a tertiary amine base to accelerate acyl transfer.
  • Heterogeneous systems: Add co-solvents (e.g., THF/hexanes) to dissolve bulky adamantyl substrates while keeping reagents anhydrous.

• Practical considerations

  • Ensure solvents are thoroughly dried (molecular sieves, solvent purification systems) and degassed if required.
  • Temperature control is easier in halogenated solvents (DCM/DCE) due to higher heat capacity and boiling range.

• Brief comparison (literature, general)

  • DCM: excellent for room-temperature reactions; easy workup; not green.
  • THF: good nucleophile solvation; peroxide-prone, must be dry.
  • MeCN: polar aprotic, often increases rate with hindered amines; miscible with water (undesirable for storage/charging, but fine when kept dry).

Storage and Reconstitution

• Item-specific storage and shipping

  • Storage conditions: Store at 2–8°C (per Product Data). Keep container tightly closed.
  • Shipped on: Wet ice (per Product Data).

• General best practices for this reagent class

  • Moisture sensitive: store under inert gas (N2/Ar) in a tightly sealed, preferably amber container with a PTFE-lined cap. Consider adding a desiccant in the outer secondary container; do not place desiccant in direct contact with product.
  • Minimize headspace and temperature cycling. After each use, purge with inert gas and return to 2–8°C promptly.
  • Do not freeze unless stability is documented for your lot; some activated carbonates can crystallize or decompose upon freeze–thaw.

• Reconstitution

  • Supplied neat; no reconstitution is required. If dilution is desired for dosing, prepare single-use anhydrous stock solutions in a dry solvent (e.g., DCM, THF, MeCN) immediately before use; store on ice during the operation and discard remaining solution after the session.

• Stability checks

  • Periodically verify assay by 19F NMR or LC/GC for hydrolysis to 1-adamantanol. Any visible moisture ingress or pressure build-up (CO2) warrants precautionary evaluation before opening.

• Waste

  • Collect fluoride-containing wastes separately. Neutralize appropriately and follow institutional HF waste disposal procedures.

Structure and Identity

Brief description: 1-Adamantyl fluoroformate is an activated carbonate (fluoroformate) bearing the adamantyloxy moiety; it functions as a carbonylating/Adoc-protecting reagent for amines and alcohols.

• Item-specific identifiers (from Product Data)

  • SKU: A463147
  • Product name: 1-Adamantyl fluoroformate
  • CAS: 62087-82-5
  • PubChem CID: 64433
  • InChIKey: 282126 (as provided)
  • Storage: 2–8°C; shipped on wet ice

• Computed/literature structural information (for reference; not an item specification)

  • Functional groups: secondary alkyl-oxy carbonyl fluoride (RO–C(=O)–F); bridged tricyclic adamantyl substituent (rigid, hydrophobic cage)
  • Molecular formula (derived from structure): C11H15FO2 (literature/computed)
  • Molecular weight (calculated): ~198.23 g/mol (literature/computed)
  • 2D description: An adamantyl oxygen (from 1-adamantanol) is bound to the carbonyl carbon of a fluoroformate; the carbonyl bears fluorine as the leaving group. No stereocenters are present; the adamantane cage is symmetric and rigid.
  • Representative SMILES (literature/computed): O(C1C2CC3CC(C1)CC(C2)C3)C(=O)F

• Structural features of interest

  • The acyl fluoride motif confers high electrophilicity at the carbonyl carbon and good leaving-group ability (F−), enabling rapid carbamate/carbonate formation under mild base.
  • The adamantyl group is bulky and lipophilic, useful as a protecting/probing group (Adoc) to modulate sterics and solubility.

Synthetic Utility

• Functional group reactivity

  • Electrophilic carbonyl center activated by an –F leaving group; reacts readily with nucleophiles to form carbamates (amines) and carbonates (alcohols/phenols).
  • The adamantyl fragment imparts steric hindrance and lipophilicity to the product, providing a robust protecting or modulating group (Adoc).

• Use cases (literature/general)

  • Protecting-group installation on primary/secondary amines under mild base at 0–25°C.
  • Formation of mixed carbonates from hindered alcohols/phenols using catalytic DMAP.
  • Step-economical introduction of the Adoc group without generating chloride salts in situ.

• Selectivity considerations

  • In bifunctional substrates, amines typically outcompete alcohols for acylation; chemoselectivity can be tuned by base strength, catalyst (DMAP), solvent polarity, and temperature.
  • Bulky Adoc reduces over-acylation and can block neighboring group participation, aiding in regioselective protection.

• Retrosynthetic value

  • Adoc as a temporary mask of –NH/–OH facilitates transformations incompatible with free nucleophiles (e.g., strong base, metal-catalyzed couplings).
  • Deprotection options depend on substrate: acidic conditions, hydrogenolysis, or nucleophilic cleavage are reported for Adoc-type groups; optimization is substrate-specific and should be established experimentally.

Target Specificity

Not applicable. This product is a small-molecule synthetic reagent, not a biological targeting agent or antibody. No antigen/epitope, clone, isotype, or species reactivity information applies.