16668-83-0

Basic information

• Product Name: 2-Fluoroadamantane
• Synonyms: 2-Fluoroadamantane
• CAS NO: 16668-83-0
• Molecular Formula: C₁₀H₁₅F
• Molecular Weight: 154.224503
• Mol File: 16668-83-0.mol

Chemical Properties

• Boiling Point: 197 °C at 760 mmHg
• Flash Point: 68.7 °C
• Appearance: /
• Density: 1.05 g/cm³
• Vapor Pressure: 0.545mmHg at 25°C
• Refractive Index: 1.49
• CAS DataBase Reference: 2-Fluoroadamantane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Fluoroadamantane(16668-83-0)
• EPA Substance Registry System: 2-Fluoroadamantane(16668-83-0)

Safety Data

• Hazardous Substances Data: 16668-83-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Fluoroadamantane is used as a key intermediate in the synthesis of various pharmaceuticals for its unique structural properties. Its cage-like adamantane backbone and fluorine substitution provide a stable and versatile template for the development of new drugs with improved pharmacological profiles.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 2-Fluoroadamantane serves as a valuable building block for the design and synthesis of bioactive molecules. Its unique structure allows for the exploration of novel chemical space and the development of compounds with potential therapeutic applications.
Used in Organic Chemistry:
2-Fluoroadamantane is utilized in organic chemistry for the synthesis of complex molecules. Its adamantane framework and fluorine substitution offer a robust and reactive platform for the creation of intricate organic structures with potential applications in various industries.
Used in Drug Development:
2-Fluoroadamantane plays a crucial role in drug development, where its unique properties can be leveraged to enhance the efficacy, selectivity, and pharmacokinetics of new drug candidates. Its potential applications in this field underscore the importance of innovative chemical structures in advancing therapeutic options for various diseases and conditions.

InChI:InChI=1/C10H15F/c11-10-8-2-6-1-7(4-8)5-9(10)3-6/h6-10H,1-5H2

Upstream product

• 700-57-2 1-adamantanol 
• 64-17-5 ethanol 
• 18971-91-0 2-iodoadamantane 
• 7314-85-4 2-adamantyl bromide 
• 281-23-2 adamantane 
• 77550-20-0 (E/Z)-5-bromoadamantan-2-ol 
• 700-58-3 2-Adamantanone 
• 20098-20-8 5-bromoadamantan-2-one 
• 38368-92-2 O-(adamantan-2-yl) S-methyl carbonodithioate 
• 33019-95-3 (trimethylsilyl)sodium 
• 133603-13-1 (Z)-2-bromo-5-fluoroadamantane 
• 65115-51-7 2-(trimethylsiloxy)adamantane 

Downstream Products

• 281-23-2 adamantane 

Relevant articles and documents

Oxygenation of alkane C-H bonds with methyl(trifluoromethyl)dioxirane: Effect of the substituents and the solvent on the reaction rate

The mechanism of the oxygenation of alkane C-H bonds with methyl(trifluoromethyl)dioxirane (1a) is studied through the effect of the substituent and solvent on the rate of oxygenation of 2-substituted adamantanes (2). The results suggest a remarkable elec

Hyperconjugative control by remote substituents of diastereoselectivity in the oxygenation of hydrocarbons

(figure presented) The oxidation of 2-substituted adamantanes (2) with TFDO (1) is reported. The data show a stereodifferentiation of the chemical environments induced by remote electron-withdrawing substituents which produces remarkable Z/E diastereosele

SYNTHESES AND 13C NMR SPECTRA OF FLUORINATED ADAMANTANE DERIVATIVES

The syntheses of a variety of fluorine-containing adamantane derivatives are described.The 13C NMR spectra of those compounds with different configurations are interpreted in terms of through-bond and through-space substituent interactions.

ELECTROPHILIC ATTACK OF ELEMENTAL FLUORINE ON ORGANIC HALOGENS. SYNTHESIS OF FLUOROADAMANTANES

Elemental fluorine acts on bromo- and iodoadamantanes in an electrophilic mode to produce the corresponding fluoroadamantanes.The course of the reaction was investigated in several solvents.It was found that the best yields of the fluoroadamantanes were obtained when Freon (CFCl3) or Freon-chloroform was used.Using methylene chloride as a solvent with iodoadamantanes-but not with the bromo derivatives-resulted in considerable amounts of the corresponding chloro compounds.

Applications of the bloch-siegert shift in solid-state proton-dipolar-decoupled 19F MAS NMR

In solid-state proton-dipolar-decoupled 19F MAS NMR spectroscopy, 19F chemical-shift data need to be corrected for the BlochSiegert shift. Assigning the single sharp 19F resonance of 2-fluoroadamantane to its proton-coupled 19F shift of -174.4 ppm results in chemical-shift referencing that is independent of the amplitude of the proton-decoupling field. The Bloch-Siegert shift is also a useful tool to characterize the amplitude and homogeneity of the proton-decoupling field, H1H, and to monitor probe performance. Considerable inhomogeneity in H1H along the long axis of the rightcylinder sample rotor was detected. In our commercial 7 mm H-F MAS probe, the proton field strength, A HH1H, decreases to 25% of the maximum value across the usable sample volume. Measurement of the Bloch-Siegert shift revealed that the proton-decoupling field strength decreases during the first few scans of an acquisition. Reductions in the proton field strengths can exceed 10%, and they are explained by the heating of the RF coil circuitry which is caused by high-power proton decoupling. The extent of reduction in field amplitude is a function of the decoupling duty cycle. Losses in A HH1H can be avoided by tuning the probe proton RF circuitry at the operating temperature of the probe, using the Bloch-Siegert shift as an optimization parameter.

FLUORINATION WITH CAESIUM FLUOROXYSULPHATE. PART XI. MILD FUNCTIONALIZATION OF SATURATED HYDROCARBONS

Several hydrocarbons reacted with caesium fluoroxysulphate in acetonitrile at 35 deg C yielding mono and disubstituted products.Fluorocyclohexane, fluorocycloheptane, and 2-exo-fluoronorbornane formed in the reactions with the corresponding hydrocarbons were accompanied by up to 15percent of other unidentified fluoro products, but their amount was strongly diminished when fluoronation was performed in the presence of nitrobenzene.Fluorination of adamantane resulted in 1-fluoro, 2-fluoro, and 1,3-difluoro substituted products, with the substitution at the tertiary carbon atom strongly predominating.The presence of nitrobenzene did not influence the rate of reaction and the product distribution when the reaction was carried out in acetonitrile, while the introduction of methanol or methanol and nitrobenzene into the reaction mixture slowed down the reaction, with no evidence of the presence of methoxy derivatives.

Photoredox-catalyzed deoxyfluorination of activated alcohols with Selectfluor

Herein we disclose a deoxyfluorination of alcohols with an electrophilic fluorine source via visible-light photoredox catalysis. This radical-mediated C–F coupling is capable of fluorinating secondary and tertiary alcohols efficiently, complementing previously reported nucleophilic deoxyfluorination protocols.

2-Substituted and 2,2-disubstituted adamantane derivatives as models for studying substituent chemical shifts and C-Hax?Yax cyclohexane contacts - results from experimental and theoretical NMR spectroscopic chemical shifts and DFT structures

Abstract The complete 1H and 13C NMR chemical shifts assignment for various 2-substituted and 2,2-disubstituted adamantane derivatives 1-38 in CDCl3 solution was realized on the basis of NMR experiments combined with chemical structure information and DFT-GIAO (B3LYP/6-31+G(d,p)-GIAO) calculations of chemical shifts in solution. Substituent-induced 13C NMR chemical shifts (SCS) are discussed. C-Hax?Yax contacts are a textbook prototype of steric hindrance in organic chemistry. The nature of these contacts will be further investigated in this work on basis of new adamantane derivatives, which are substituted at C-2 to provide models for 1,4-C-Hax?Yax and 1,5-C-Hax?Yax contacts. The B3LYP/6-31+G(d,p) calculations predicted the presence of NBO hyperconjugative attractive interactions between C-Hax and Yax groups along C-Hax?Yax contacts. The 1H NMR signal separation, Δδ(γ-CH2), reflects the strength of the H-bonded C-Haxa?Yax contact.

C-HALOGEN BOND FORMATION

Methods of halogenating a carbon containing compound having an sp3 C-H bond are provided. Methods of fluorinating a carbon containing compound comprising halogenation with Cl or Br followed by nucleophilic substitution with F are provided. Methods of direct oxidative C-H fluorination of a carbon containing compound having an sp3 C-H bond are provided. The halogenated products of the methods are provided.

Oxidative aliphatic C-H fluorination with fluoride ion catalyzed by a manganese porphyrin

Despite the growing importance of fluorinated organic compounds in drug development, there are no direct protocols for the fluorination of aliphatic C-H bonds using conveniently handled fluoride salts. We have discovered that a manganese porphyrin complex catalyzes alkyl fluorination by fluoride ion under mild conditions in conjunction with stoichiometric oxidation by iodosylbenzene. Simple alkanes, terpenoids, and even steroids were selectively fluorinated at otherwise inaccessible sites in 50 to 60% yield. Decalin was fluorinated predominantly at the C2 and C3 methylene positions. Bornyl acetate was converted to exo-5-fluoro-bornyl acetate, and 5a-androstan-17-one was fluorinated selectively in the A ring. Mechanistic analysis suggests that the regioselectivity for C-H bond cleavage is directed by an oxomanganese(V) catalytic intermediate followed by F delivery via an unusual manganese(IV) fluoride that has been isolated and structurally characterized.