79544-27-7 | 2-Bromo-6-fluorobenzonitrile

CAS:79544-27-7 | 2-Bromo-6-fluorobenzonitrile,Description

2-Bromo-6-fluorobenzonitrile is a chemical compound with the molecular formula C7H3BrFN. It is used as an initial raw material in the synthesis of 2-bromo-6-fluorobenzoic acid.

Synthesis Analysis

The synthesis of 2-Bromo-6-fluorobenzonitrile involves several steps. One method involves the nitration reaction of adjacent fluorobenzonitrile with vitriol oil. The ratio range of the amount of substance of the used vitriol oil and adjacent fluorobenzonitrile is 5.0:1～15.0:1, and slowly adding nitrating agent is stirred down in-5～20 ℃ of temperature controls.

Molecular Structure Analysis

The molecular structure of 2-Bromo-6-fluorobenzonitrile can be represented by the InChI code 1S/C7H3BrFN/c8-6-2-1-3-7 (9)5 (6)4-10/h1-3H. The Canonical SMILES string representation is C1=CC (=C (C (=C1)Br)C#N)F.

Chemical Reactions Analysis

The chemical reactions involving 2-Bromo-6-fluorobenzonitrile are complex and varied. For instance, it can be used as a raw material in the synthesis of 2-bromo-6-fluorobenzoic acid.

Physical And Chemical Properties Analysis

2-Bromo-6-fluorobenzonitrile has a molecular weight of 200.01 g/mol. It has a computed XLogP3-AA value of 2.4, indicating its lipophilicity. It has zero hydrogen bond donor count and two hydrogen bond acceptor count. The exact mass and monoisotopic mass are 198.94329 g/mol. The topological polar surface area is 23.8 Ų. The heavy atom count is 10.

Scientific Research Applications

Synthesis and Chemical Transformation

• The synthesis and chemical transformation of related compounds like 2-bromo-3-fluorobenzonitrile have been studied, showcasing methods such as bromodeboronation of aryl boronic acids (Szumigala et al., 2004).

Material Science and Spectroscopy

• Vibrational spectroscopic investigations and density functional theory computations on similar compounds like 3-bromo-5-fluorobenzonitrile provide insights into molecular properties, nonlinear optical properties, and electron density transfer (Jeyavijayan et al., 2018).

Synthesis of Derivatives and Intermediates

• The synthesis of derivatives such as 3-Bromo-2-fluorobenzoic acid from compounds like 2-amino-6-fluorobenzonitrile demonstrates the potential for creating various chemical intermediates (Zhou Peng-peng, 2013).

Advanced Imaging Applications

• Compounds like 3-{2-[2-(Bromomethyl)thiazol-4-yl]-ethynyl}-5-fluorobenzonitrile, derived from 3-bromo-5-fluorobenzonitrile, serve as precursors for advanced imaging techniques like PET radioligands (Gopinathan et al., 2009).

Analytical Chemistry and Crystallography

• Research on small molecule structures, including compounds similar to 2-bromo-6-fluorobenzonitrile, involves X-ray crystallography to understand intermolecular interactions, aiding in the field of analytical chemistry (Aldeborgh et al., 2014).

Medicinal Chemistry and Drug Development

• The compound's derivatives have potential applications in medicinal chemistry, as seen in the synthesis of novel ketamine derivatives from related fluorobenzonitriles for potential therapeutic use (Moghimi et al., 2014).

Safety And Hazards

2-Bromo-6-fluorobenzonitrile is harmful if swallowed, in contact with skin, or if inhaled. It causes skin irritation, serious eye irritation, and may cause respiratory irritation.

Relevant Papers

There are several papers and documents related to 2-Bromo-6-fluorobenzonitrile. These papers provide valuable insights into the properties, synthesis, and applications of this compound. Further analysis of these papers could provide more detailed information.

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