2-Chloro-4-fluorobenzaldehyde
[CAS# 84194-36-5]

Identification

• Classification: Organic raw materials >> Organic fluorine compound >> Fluorobenzaldehyde series
• Name: 2-Chloro-4-fluorobenzaldehyde
• Molecular Formula: C₇H₄ClFO
• Molecular Weight: 158.56
• CAS Registry Number: 84194-36-5
• EC Number: 617-548-7
• SMILES: C1=CC(=C(C=C1F)Cl)C=O

Properties

• Melting point: 59-62 °C
• Boiling point: 118-120 °C (50 mmHg)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2-Chloro-4-fluorobenzaldehyde, with the chemical formula C₇H₄ClFO, is an aromatic aldehyde characterized by chlorine and fluorine atoms at the 2- and 4-positions of the benzene ring, respectively. The compound has reactive formyl and halogen substituents, making it a valuable intermediate in organic synthesis and various industrial applications.

The discovery of 2-chloro-4-fluorobenzaldehyde stems from the extensive exploration of halogenated benzaldehydes. These compounds have attracted much attention due to their potential to participate in a variety of chemical reactions. The development of this compound is driven by the demand for versatile intermediates in pharmaceuticals, agrochemicals, and materials science. The synthesis of 2-chloro-4-fluorobenzaldehyde generally involves halogenation and formylation reactions. A common method is to start with benzene and perform chlorination and fluorination in sequence to introduce chlorine and fluorine atoms at the desired positions. The resulting halogenated benzene is then formylated using a formylation reagent such as the Vilsmeier-Haack reagent. These steps yield 2-chloro-4-fluorobenzaldehyde, which can be purified and characterized for further use.

2-Chloro-4-fluorobenzaldehyde is widely used as an intermediate in pharmaceutical synthesis. Its halogen atoms and aldehyde groups make it an ideal precursor for the creation of complex drug molecules, including those with anti-inflammatory, anticancer, and antimicrobial properties.

In agrochemical development, this compound is a key component in the synthesis of herbicides, fungicides, and insecticides. The presence of chlorine and fluorine enhances the biological activity and environmental stability of the resulting agrochemicals.

2-Chloro-4-fluorobenzaldehyde is used in the synthesis of specialty polymers and advanced materials. Its reactivity allows the creation of materials with unique properties, such as increased thermal stability and resistance to chemical degradation.

The compound can be used as a versatile reagent in organic synthesis. The formyl group can participate in a variety of reactions, including condensation, reduction, and cyclization, while the halogen atom can undergo substitution or coupling reactions. This versatility makes it a valuable tool for chemists in the development of new synthetic methods and compounds.

In academic and industrial research, 2-chloro-4-fluorobenzaldehyde is used to study reaction mechanisms and develop new synthetic pathways. Its unique structure allows researchers to explore the effects of halogen substituents on reactivity and stability, thereby advancing the development of organic chemistry.

References

2019. Structure-activity relationships in a series of antiplasmodial thieno[2,3-b]pyridines. Malaria Journal, 18(1).
DOI: 10.1186/s12936-019-2725-y

2009. Trimethyl 5-(2-chloro-4-fluoro-phen-yl)-2-phenyl-pyrrolidine-2,3,4-tricarboxyl-ate. Acta crystallographica. Section E, Structure reports online, 65(11).
DOI: 10.1107/s1600536809044274

2007. A Novel Nickel(0)-Catalyzed Cascade Ullmann-Pinacol Coupling: From o-Bromobenzaldehyde to trans-9,10-Dihydroxy-9,10-dihydrophenanthrene. Synlett, 2007(12).
DOI: 10.1055/s-2007-984543