407-97-6 | 1-Bromo-5-fluoropentane

CAS:407-97-6 | 1-Bromo-5-fluoropentane,Description

1-Bromo-5-fluoropentane is a halogenated alkane with both bromine and fluorine atoms attached to a five-carbon chain. The presence of these halogens suggests that the compound could exhibit interesting chemical and physical properties, which may be useful in various chemical synthesis processes.

Synthesis Analysis

The synthesis of related fluorinated compounds has been described in the literature. For instance, the synthesis of 1-fluoro-4,4-di-hydroxymethyl-pentane, a compound with a similar fluorinated pentane structure, involves the alkylation of methylmalonic ester with 1-bromo-3-fluoro-propane followed by reduction with lithium aluminum hydride (LiAlH4). This method could potentially be adapted for the synthesis of 1-Bromo-5-fluoropentane by altering the carbon chain length and the position of the halogen substituents.

Molecular Structure Analysis

The study of vibration spectra and rotational isomerism in chain molecules, including 1-bromo-pentane, provides insights into the molecular structure of such compounds. Although the study does not directly address 1-Bromo-5-fluoropentane, it suggests that halogenated pentanes can exist in different rotational isomeric forms. In the crystalline state, 1-bromo-pentane adopts a trans-trans-trans conformation. This information could be relevant when considering the molecular structure of 1-Bromo-5-fluoropentane, as the addition of a fluorine atom may influence the preferred conformational state.

Chemical Reactions Analysis

The chemical reactivity of 1-Bromo-5-fluoropentane would likely be influenced by the presence of the bromine and fluorine atoms. Bromine is typically more reactive than fluorine due to its lower electronegativity and larger atomic size, which could make the bromine atom a site for nucleophilic substitution reactions. The abstracts provided do not detail specific reactions for 1-Bromo-5-fluoropentane, but the synthesis of related compounds suggests that it could be involved in alkylation reactions.

Physical and Chemical Properties Analysis

The physical and chemical properties of 1-Bromo-5-fluoropentane can be inferred from studies on similar halogenated alkanes. The Raman and infrared spectra of 1-bromo-pentane have been measured in various states of aggregation, which provides information on the vibrational modes of the molecule. These vibrational modes are directly related to the molecular structure and can affect properties such as boiling point, melting point, and solubility. The presence of both bromine and fluorine in 1-Bromo-5-fluoropentane would likely result in a higher density and boiling point compared to non-halogenated alkanes due to the increased molecular weight and potential for intermolecular halogen bonding.

Scientific Research Applications

Catalytic Dehydrohalogenation

1-Bromo-5-fluoropentane is involved in the catalytic dehydrohalogenation process. Nb, Mo, Ta, and W halide clusters have been used as catalysts in the dehydrohalogenation of alkyl halides like 1-bromo-5-fluoropentane, yielding pentene and its isomers (Kamiguchi et al., 2003).

Chirality Probes

1-Bromo-5-fluoropentane has been used as a chirality probe in the synthesis of pseudotetrahedral polyhaloadamantanes. These compounds are significant in the study of absolute configuration and molecular chirality (Schreiner et al., 2002).

Synthesis of Fluorinated Amino Acids

It plays a role in the stereoselective synthesis of γ-fluorinated α-amino acids. These amino acids are synthesized using 1-bromo-5-fluoropentane and have applications in medicinal chemistry and biology (Laue et al., 2000) .

Organic Synthesis

In organic synthesis, 1-bromo-5-fluoropentane is used for the preparation of various derivatives, such as 1-fluoro-4,4-di-hydroxymethyl-pentane (Cherbuliez et al., 1960) .

Electrochemical Studies

This compound is also studied in electrochemical reduction processes. The reduction of 1,5-dihalopentanes at carbon electrodes provides insights into the electrochemistry of such halogenated compounds (Pritts & Peters, 1994) .

Ornithine Decarboxylase Inhibitors

1-Bromo-5-fluoropentane derivatives have been explored as ornithine decarboxylase inhibitors, indicating potential applications in biochemical research (Danzin et al., 1982) .

Catalytic Hydrodefluorination

The compound is used in catalytic hydrodefluorination studies, transforming strong C(sp3)-F bonds in fluoroalkanes to alkanes at room temperature (Scott, Çelenligil-Çetin, & Ozerov, 2005).

Anticancer Activity Studies

Its derivatives have been synthesized and analyzed for anticancer activity. One such study involved the synthesis of 1-[(5-bromo-2-thienyl)sulfonyl]-5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione and its effect on cancer cells (Miao, Yan, & Zhao, 2010).

Safety And Hazards

1-Bromo-5-fluoropentane is considered hazardous. It causes skin irritation, serious eye irritation, and may cause respiratory irritation. It is classified as Acute Tox. 4 Oral, Eye Irrit. 2, Skin Irrit. 2, and STOT SE 3. It is recommended to avoid breathing dust/fume/gas/mist/vapors/spray and to use personal protective equipment.

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