N-(4-Cyanophenyl)glycine
[CAS# 42288-26-6]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Glycine derivatives
• Name: N-(4-Cyanophenyl)glycine
• Synonyms: 2-(4-Cyanophenylamino)acetic acid
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.17
• Protein Sequence: G
• CAS Registry Number: 42288-26-6
• EC Number: 459-560-3
• SMILES: C1=CC(=CC=C1C#N)NCC(=O)O

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.594, Calc.^*
• Boiling Point: 447.2±30.0 °C (760 mmHg), Calc.^*
• Flash Point: 224.3±24.6 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302+H312+H332-H302-H312+H332-H312-H315-H319-H332
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P321-P330-P332+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

N-(4-Cyanophenyl)glycine is an important chemical compound that belongs to the class of substituted glycine derivatives. It is formed by the reaction of 4-cyanobenzylamine with glycine, which results in the introduction of a cyano group at the para position of the phenyl group attached to the amino acid backbone. This compound is used in the synthesis of various bioactive molecules and has applications in medicinal chemistry, particularly in the development of pharmaceuticals.

The discovery of N-(4-Cyanophenyl)glycine can be traced back to the growing interest in amino acid derivatives with functionalized aromatic rings. Amino acids are critical building blocks in biochemistry, and modifying their structure to introduce various functional groups, such as the cyano group, can alter their chemical properties and biological activity. The incorporation of a cyano group, in particular, has been shown to influence the reactivity and pharmacological properties of these derivatives, making them useful in the design of bioactive compounds.

N-(4-Cyanophenyl)glycine is often synthesized by reacting glycine with 4-cyanobenzylamine under mild conditions. The reaction typically occurs in the presence of a base, such as sodium hydroxide, which deprotonates the glycine and facilitates the nucleophilic attack of the amine group on the carbonyl carbon of the glycine. This leads to the formation of the desired N-(4-Cyanophenyl)glycine product. The cyano group at the para position of the phenyl ring enhances the compound’s chemical stability and may influence its solubility, making it an ideal candidate for various synthetic routes.

In terms of applications, N-(4-Cyanophenyl)glycine is primarily used as an intermediate in the synthesis of other bioactive compounds. It has been explored in the development of novel drugs and enzyme inhibitors, where the cyano group serves as an important structural feature. The presence of the cyano group can enhance the binding affinity of the compound to its target, improving its efficacy in inhibiting specific enzymes or receptors. This makes N-(4-Cyanophenyl)glycine a valuable compound in the development of treatments for a variety of diseases, including cancer, inflammation, and neurological disorders.

Furthermore, N-(4-Cyanophenyl)glycine has applications in materials science, where its ability to interact with other molecules is utilized in the design of functionalized surfaces and sensors. The cyano group can participate in various types of interactions, such as hydrogen bonding and electrostatic interactions, which are beneficial in creating materials with specific properties for use in sensors, bioactive coatings, and nanomaterials.

In conclusion, N-(4-Cyanophenyl)glycine is a versatile compound that plays a significant role in medicinal chemistry and materials science. Its discovery and subsequent application have led to the development of new drugs and materials with enhanced properties. By modifying the structure of glycine with a cyano group, researchers have been able to create compounds with increased stability, reactivity, and biological activity, making N-(4-Cyanophenyl)glycine an important tool in chemical synthesis and pharmaceutical development.

References

2008. Dabigatran etexilate. Pharmaceutical Substances, (No volume/issue available).
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-04-0169


2015. Synthesis and biological evaluation of novel dabigatran derivatives as thrombin inhibitors. Research on Chemical Intermediates, 41(12).
DOI: 10.1007/s11164-015-2053-y


2016. Design, synthesis, biological evaluation and molecular docking of novel substituted 1-ethyl-1H-benzimidazole fluorinated derivatives as thrombin inhibitors. Journal of the Iranian Chemical Society, 13(7).
DOI: 10.1007/s13738-016-0830-1