768-92-3

Basic information

• Product Name: 1-FLUOROADAMANTANE
• Synonyms: 1-FLUOROADAMANTANE;1-ADAMANTYL FLUORIDE
• CAS NO: 768-92-3
• Molecular Formula: C₁₀H₁₅F
• Molecular Weight: 154.22
• Product Categories: Adamantanes
• Mol File: 768-92-3.mol
• Article Data: 14

Chemical Properties

• Melting Point: 225 °C
• Boiling Point: 188.8 °C at 760 mmHg
• Flash Point: 67.3 °C
• Appearance: /
• Density: 1.06 g/cm³
• Vapor Pressure: 0.813mmHg at 25°C
• Refractive Index: 1.494
• CAS DataBase Reference: 1-FLUOROADAMANTANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-FLUOROADAMANTANE(768-92-3)
• EPA Substance Registry System: 1-FLUOROADAMANTANE(768-92-3)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 768-92-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 53, p. 2803, 1988 DOI: 10.1021/jo00247a026Synthesis, p. 713, 1983 DOI: 10.1055/s-1983-30479

Purification Methods

Dissolve it in Et2O, dry over Na2SO4, evaporate to dryness and sublime the residue at 90-100o/12mm. Recrystallise the sublimate from MeOH, m 259-260o. To remove 1-hydroxyadamantane impurity, dissolve it in cyclohexane, cool for many hours, filter off the hydroxyadamantane, and evaporate to dryness or by passage through an Al2O5 column in dry cyclohexane. Recrystallise the residue from pet ether at -77o and sublime it in vacuum, m 210-212odec (sealed tube). [Bhandari & Pinock Synthesis 655 1974, NMR: Fort et al. J Org Chem 30 789 1965.]

InChI:InChI=1/C10H15F/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6H2

Upstream product

• 64-18-6 formic acid 
• 281-23-2 adamantane 
• 768-93-4 1-iodoadamantane 
• 828-51-3 1-Adamantanecarboxylic acid 
• 920-66-1 1,1,1,3',3',3'-hexafluoro-propanol 
• 62087-82-5 1-adamantylfluoroformate 
• 67-63-0 isopropyl alcohol 
• 67-56-1 methanol 
• 64-17-5 ethanol 
• 75-89-8 2,2,2-trifluoroethanol 

Downstream Products

• 768-90-1 1-Adamantyl bromide 
• 41171-83-9 5-fluoroadamantan-2-one 
• 935-56-8 1-chloroadamantane 
• 780-68-7 1-phenyladamantane 
• 770-69-4 1-ethyladamantane 
• 88459-01-2 (1s,3s)-adamantan-1-yl(phenyl)sulfide 
• 56432-99-6 1-tosylaminoadamantane 
• 102402-86-8 2-(adamantan-1-yl)-1,3-diphenylpropane-1,3-dione 
• 74203-39-7 (3r,5r,7r)-1-(phenylethynyl)adamantane 
• 1394826-22-2 1-((4-chlorophenyl)ethynyl)adamantane 
• 40430-66-8 1-ethynyladamantane 
• 82094-48-2 1-(trimethylsilylethynyl)adamantane 
• 6221-74-5 1-methoxyadamantane 
• 32314-61-7 1-nitroxyadamantane 

Relevant articles and documents

Temperature Controls Guest Uptake and Release from Zn4L4 Tetrahedra

We report the preparation of triazatruxene-faced tetrahedral cage 1, which exhibits two diastereomeric configurations (T1 and T2) that differ in the handedness of the ligand faces relative to that of the octahedrally coordinated metal centers. At lower temperatures, T1 is favored, whereas T2 predominates at higher temperatures. Host-guest studies show that T1 binds small aliphatic guests, whereas T2 binds larger aromatic molecules, with these changes in binding preference resulting from differences in cavity size and degree of enclosure. Thus, by a change in temperature the cage system can be triggered to eject one bound guest and take up another.

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.

Fluorodecarboxylation, rearrangement and cyclisation: the influence of structure and environment on the reactions of carboxylic acids with xenon difluoride

The reactions of structurally diverse carboxylic acids with XeF2 in both CH2Cl2/Pyrex and CH2Cl2/PTFE have been studied. Pyrex appears to be a very effective heterogeneous catalyst for an electrophilic mode of reaction of polarised XeF2, leading to rearrangement, cyclisation and cationic products. In CH2Cl2/PTFE, fluorodecarboxylation is the main mode of reaction, in accordance with previous studies, and may occur via a SET reaction of unpolarised XeF2.