2-Bromo-4'-cyanoacetophenone
[CAS# 20099-89-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic ketone
• Name: 2-Bromo-4'-cyanoacetophenone
• Synonyms: 4-(2-Bromoacetyl)benzonitrile; 4-Cyanophenacyl bromide
• Molecular Formula: C₉H₆BrNO
• Molecular Weight: 224.05
• CAS Registry Number: 20099-89-2
• EC Number: 606-435-8
• SMILES: C1=CC(=CC=C1C#N)C(=O)CBr

Properties

• Density: 1.6±0.1 g/cm³, Calc.^*
• Melting point: 92-96 ºC (Expl.)
• Index of Refraction: 1.590, Calc.^*
• Boiling Point: 342.4±22.0 ºC (760 mmHg), Calc.^*
• Flash Point: 160.9±22.3 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H302-H312-H314-H332
• Precautionary Statements: P260-P261-P264-P270-P271-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P330-P362+P364-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H332
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	3	H311
Skin corrosion	Skin Corr.	1C	H314
Acute toxicity	Acute Tox.	3	H301

• Transport Information: UN 2928

Discovory and Applicatios

2-Bromo-4'-cyanoacetophenone is an organic compound that belongs to the class of substituted acetophenones. It features a bromine atom at the 2-position and a cyano group at the 4'-position on the phenyl ring, along with an acetophenone backbone. The molecular formula of 2-bromo-4'-cyanoacetophenone is C8H6BrNO2, and it is a solid at room temperature, typically appearing as a yellow to off-white powder. This compound is soluble in organic solvents such as acetone and ethanol, but has limited solubility in water due to its relatively hydrophobic nature.

The discovery of 2-bromo-4'-cyanoacetophenone is part of the broader exploration of halogenated and nitrated aromatic compounds, which have garnered significant interest due to their wide range of applications. The introduction of both the bromine and cyano functional groups onto the acetophenone structure allows for a high degree of reactivity and versatility in synthetic chemistry. These substitutions make the compound a valuable intermediate in the synthesis of more complex organic molecules, as well as a key building block in various chemical processes.

2-Bromo-4'-cyanoacetophenone finds significant application in the field of organic synthesis. The bromine atom at the 2-position facilitates nucleophilic substitution reactions, while the cyano group at the para-position of the phenyl ring serves as an electron-withdrawing group, enhancing the electrophilicity of the carbonyl group in the acetophenone structure. These properties allow the compound to participate in a wide range of chemical transformations, including Friedel–Crafts acylation, nucleophilic aromatic substitution, and cross-coupling reactions.

In pharmaceutical chemistry, 2-bromo-4'-cyanoacetophenone serves as a key intermediate in the synthesis of bioactive molecules. The cyano group can undergo reduction to an amine, which can then be further functionalized to yield a variety of pharmaceutical compounds. Additionally, the presence of the acetophenone backbone makes this compound a useful precursor in the synthesis of other acetophenone derivatives that exhibit therapeutic properties. These derivatives are often investigated for their potential anti-inflammatory, analgesic, and anticancer activities.

The compound is also used in the production of agrochemicals, where its reactivity allows it to be incorporated into the synthesis of herbicides, fungicides, and pesticides. The cyano and bromo groups on the phenyl ring are known to contribute to the bioactivity of agrochemical compounds by enhancing their interaction with specific biological targets, such as enzymes or receptors. This makes 2-bromo-4'-cyanoacetophenone an important intermediate in the development of crop protection products.

Another significant application of 2-bromo-4'-cyanoacetophenone lies in materials science. The compound’s ability to undergo various chemical reactions allows it to be used in the production of specialty polymers and materials with tailored properties. For instance, it can be employed in the synthesis of polycarbonates or polyesters, where it imparts stability and resistance to environmental degradation. Additionally, 2-bromo-4'-cyanoacetophenone is a potential precursor for the development of organic semiconductors and optoelectronic materials used in displays, solar cells, and light-emitting devices.

2-Bromo-4'-cyanoacetophenone’s versatility in organic synthesis, pharmaceutical applications, agrochemical development, and materials science highlights its importance as a chemical building block. Its combination of halogen and cyano functional groups makes it an essential intermediate for the creation of a wide range of compounds with diverse applications. The compound’s ability to participate in numerous reactions also ensures its continued use in research and industrial processes, contributing to the advancement of chemical and material sciences.

In conclusion, 2-bromo-4'-cyanoacetophenone is a valuable organic compound with a broad spectrum of applications in various industries. Its role as an intermediate in the synthesis of pharmaceutical compounds, agrochemicals, and materials demonstrates its importance in both research and manufacturing. As new synthetic techniques and applications continue to emerge, the potential uses of 2-bromo-4'-cyanoacetophenone are likely to expand, solidifying its position as a crucial compound in the chemical sciences.

References

2023. Recent synthetic approaches towards thienothiophenes: a potential template for biologically active compounds. *Molecular Diversity*.
DOI: 10.1007/s11030-023-10647-1

2020. 2-Amino- and 2-hydroxymethylbenzimidazolium bromides as protein tyrosine phosphatase 1? (PTP1?) inhibitors and other targets associated with diabetes mellitus. *Russian Chemical Bulletin*.
DOI: 10.1007/s11172-020-2832-5

2019. Synthesis, antimicrobial activity, and determination of the lipophilicity of ((cyclohex-3-enylmethylene)hydrazinyl)thiazole derivatives. *Medicinal Chemistry Research*.
DOI: 10.1007/s00044-019-02433-2

2018. Thiazoles with cyclopropyl fragment as antifungal, anticonvulsant, and anti-Toxoplasma gondii agents: synthesis, toxicity evaluation, and molecular docking study. *Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents*.
DOI: 10.1007/s00044-018-2221-x

2016. Synthesis of Thioethers Using Triethylamine-Activated Phosphorus Decasulfide (P4S10). *Synthesis*.
DOI: 10.1055/s-0035-1561673