17318-08-0 | 5-Bromo-1,3-dichloro-2-fluorobenzene

CAS:17318-08-0 | 5-Bromo-1,3-dichloro-2-fluorobenzene,Description

5-Bromo-1,3-dichloro-2-fluorobenzene, also known as 3,5-Dichloro-4-fluorobromobenzene (CAS: 17318-08-0), is a halogenated benzene used in laboratory organic synthesis and pharmaceutical research and development.

Synthesis Analysis

The synthesis of 5-Bromo-1,3-dichloro-2-fluorobenzene involves a two-step process. The first step involves the simultaneous feeding of ammonium salt and a sodium nitrite aqueous solution into a tubular reactor for tubular diazotization reaction to obtain a diazonium salt intermediate. The second step involves dissolving cuprous bromide in hydrobromic acid, heating to 100-130 DEG C, dropwise adding the diazonium salt intermediate prepared in the first step for reaction, and after the complete reaction, performing after-treatment to obtain the 5-bromo-1,3-dichloro-2-fluorobenzene.

Molecular Structure Analysis

The molecular structure of 5-Bromo-1,3-dichloro-2-fluorobenzene can be found in various databases. The InChI code is 1S/C6H2BrCl2F/c7-3-1-4(8)6(10)5(9)2-3/h1-2H and the Canonical SMILES is C1=C(C=C(C(=C1Cl)F)Cl)Br.

Chemical Reactions Analysis

5-Bromo-1,3-dichloro-2-fluorobenzene is a halogenated benzene and can participate in various chemical reactions. For example, it can be used in the preparation of ligand 5-fluoro-1,3-di (2-pyridyl)benzene, by a Stille reaction with 2- (tri- n butylstannyl)pyridine.

Physical And Chemical Properties Analysis

5-Bromo-1,3-dichloro-2-fluorobenzene has a molecular weight of 243.88 g/mol. It is a pale-yellow to yellow-brown solid or liquid at room temperature. It has a density of 1.8±0.1 g/cm3, a boiling point of 234.3±35.0 °C at 760 mmHg, and a flash point of 95.5±25.9 °C.

Scientific Research Applications

Use as an Intermediate in Chemical Synthesis

• Application : 5-Bromo-1,3-dichloro-2-fluorobenzene is used as an intermediate in the synthesis of various organic compounds.
• Results : The use of this compound as an intermediate can lead to the synthesis of a wide range of other compounds, depending on the specific reactions involved.

Use in the Synthesis of Pharmaceuticals and Agrochemicals

• Application : This compound is used as an intermediate in the synthesis of pharmaceuticals and agrochemicals.
• Results : The use of this compound in the synthesis of pharmaceuticals and agrochemicals can lead to the production of a wide range of useful compounds.

Use in Tubular Diazotization Reaction Technology

• Application : This compound is used in tubular diazotization reaction technology. This technology is adopted to prepare diazonium salt, reducing side reactions including diazonium salt coupling and decomposition.
• Method : The method involves simultaneously feeding ammonium salt and a sodium nitrite aqueous solution into a tubular reactor for tubular diazotization reaction to obtain a diazonium salt intermediate. This intermediate is then reacted with cuprous bromide dissolved in hydrobromic acid.
• Results : The use of this technology makes the diazotization reaction more stable and improves the final yield. It also has advantages of continuity in production, safety, short reaction time, and energy saving.

Use in the Preparation of Active Compounds

• Application : 5-Bromo-1,3-dichloro-2-fluorobenzene is used in the preparation of active compounds.
• Method : The method involves diazotization and reduction of 6-bromo-2,4-dichloro-3-fluoro-aniline, which is obtained by bromination of 2,4-dichloro-3-fluoro-aniline. This is obtained by reduction of 1,3-dichloro-2-fluoro-4-nitro-benzene.
• Results : The compound of formula I obtained from 2,4-dichloro-3-fluoro-aniline by this process is a valuable intermediate for the preparation of active compounds.

Use in the Preparation of Fluorine-Containing Products

• Application : This compound is used in the preparation of various fluorine-containing products.
• Method : The method involves diazotization and reduction of 6-bromo-2,4-dichloro-3-fluoro-aniline, which is obtained by bromination of 2,4-dichloro-3-fluoro-aniline. This is obtained by reduction of 1,3-dichloro-2-fluoro-4-nitro-benzene.
• Results : The compound of formula I obtained from 2,4-dichloro-3-fluoro-aniline by this process is a valuable intermediate for the preparation of active compounds.

Use in the Preparation of Active Compounds of Formula V

• Application : 5-Bromo-1,3-dichloro-2-fluorobenzene is used in the preparation of active compounds of formula V.
• Method : The method involves further transforming 5-bromo-1,3-dichloro-2-fluoro-benzene obtained from 2,4-dichloro-3-fluoro-aniline by the process according to the invention.
• Results : Compound of formula I is a valuable intermediate for the preparation of active compounds of formula V.

Safety And Hazards

5-Bromo-1,3-dichloro-2-fluorobenzene may be fatal if swallowed and enters airways. It causes skin irritation and may cause an allergic skin reaction. It may cause respiratory irritation and causes damage to organs through prolonged or repeated exposure. It is very toxic to aquatic life with long-lasting effects.

Future Directions

5-Bromo-1,3-dichloro-2-fluorobenzene is a useful building block in organic synthesis and pharmaceutical research and development. Its future directions could involve its use in the synthesis of more complex molecules and in the development of new pharmaceuticals.

Relevant Papers Relevant papers and technical documents related to 5-Bromo-1,3-dichloro-2-fluorobenzene can be found on various databases.

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