4-Cyanobiphenyl
[CAS# 2920-38-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Alkyne
• Name: 4-Cyanobiphenyl
• Synonyms: 4-Phenylbenzonitrile; Biphenyl-4-carbonitrile
• Molecular Formula: C₁₃H₉N
• Molecular Weight: 179.22
• CAS Registry Number: 2920-38-9
• EC Number: 220-860-2
• SMILES: C1=CC=C(C=C1)C2=CC=C(C=C2)C#N

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: 85-87 °C (Expl.)
• Index of Refraction: 1.616, Calc.^*
• Boiling Point: 332.3±21.0 °C (760 mmHg), Calc.^*
• Flash Point: 155.5±14.6 °C, Calc.^*
• Water solubility: limited soluble

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

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H302-H312-H332-H411
• Safety Statements: P261-P264-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P317-P321-P330-P362+P364-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H301
Specific target organ toxicity - single exposure	STOT SE	3	H335

• Transport Information: UN 3439

Discovery and Applications

4-Cyanobiphenyl is an organic compound with the chemical formula C13H9N. It consists of two phenyl groups (C6H5) connected by a single bond, with a cyano group (-CN) attached to one of the phenyl rings at the para position. This compound belongs to the class of aryl nitriles, which are characterized by the presence of a cyano group attached to an aromatic ring.

The discovery of 4-cyanobiphenyl can be traced to the ongoing study and development of aromatic nitriles, which are significant in the synthesis of various organic compounds. The introduction of the cyano group into the biphenyl structure increases the molecule's stability and provides a functional group that is highly reactive in various chemical reactions. This structure has been known and used in organic chemistry for many years, and it has found broad applications due to its versatility in synthesis.

4-Cyanobiphenyl is widely used in organic synthesis, primarily as a building block for the production of more complex compounds. Its structure allows it to participate in a range of reactions, including electrophilic substitution and nucleophilic substitution. The cyano group is an electron-withdrawing group, which influences the reactivity of the aromatic ring and makes it useful for further modifications in synthetic chemistry.

One of the main applications of 4-cyanobiphenyl is in the synthesis of liquid crystals. The compound is a key intermediate in the preparation of liquid crystalline materials, which are essential components of devices such as liquid crystal displays (LCDs). The molecular structure of 4-cyanobiphenyl, which includes both aromatic rings and the electron-withdrawing cyano group, is well-suited for the formation of liquid crystal phases that exhibit the necessary optical properties for display technologies.

In addition to its use in liquid crystals, 4-cyanobiphenyl is also employed in the preparation of various other materials, including polymers and agrochemicals. It can serve as a precursor for the synthesis of specialty chemicals used in the electronics and materials industries. The ability of the cyano group to participate in various chemical reactions makes this compound a valuable intermediate for the production of functionalized materials with specific properties.

Furthermore, 4-cyanobiphenyl has been investigated for its potential biological activity. While it is not widely known for direct medicinal uses, its derivatives may have bioactive properties, and the compound itself can be used in the synthesis of more complex molecules that exhibit pharmaceutical or agricultural activity.

In conclusion, 4-cyanobiphenyl is a versatile and important compound in organic synthesis. It plays a key role in the production of liquid crystal materials and other specialty chemicals. Its structure, featuring a cyano group attached to a biphenyl backbone, allows it to participate in a variety of chemical reactions, making it an important intermediate in both industrial and research applications.

References

2020. Suzuki-Miyaura Coupling on a Triazolyl-Functionalized Hypercrosslinked Polymer-Palladium Catalyst. Synfacts, 16(8).
DOI: 10.1055/s-0040-1706876

2020. A new palladium heterogeneous complex (Pd-Gu@BOEH): chemoselective, phosphine-free and practical nanocatalyst in carbon-carbon cross-coupling reaction. Research on Chemical Intermediates, 47(2).
DOI: 10.1007/s11164-020-04315-4

2022. Bimetallic Ru:Co Mesoporous Nanoparticles Stabilized by PEG and Imidazolium Ionic Liquid Based [KIT-6] as an Efficient Heterogeneous Catalyst for Suzuki-Miyaura Cross-Couplings in H2O:EtOH Solution. Catalysis Letters, 152(12).
DOI: 10.1007/s10562-022-03951-2