Phenyl N-phenylcarbamate
[CAS# 4930-03-4]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Phenyl N-phenylcarbamate
• Molecular Formula: C₁₃H₁₁NO₂
• Molecular Weight: 213.23
• CAS Registry Number: 4930-03-4
• SMILES: C1=CC=C(C=C1)NC(=O)OC2=CC=CC=C2

Properties

• Density: 1.2$+/-$0.1 g/cm³ Calc.^*
• Melting point: 136 $degree$C (Expl.)
• Boiling point: 315.6$+/-$15.0 $degree$C 760 mmHg (Calc.)^*
• Flash point: 144.6$+/-$20.4 $degree$C (Calc.)^*
• Index of refraction: 1.631 (Calc.)^*

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

Discovery and Applications

Phenyl N-phenylcarbamate is an aromatic carbamate compound that belongs to a class of substances formed from the reaction of phenols with carbamic acid derivatives. Carbamates have been studied since the nineteenth century, when chemists investigating the chemistry of urea and related compounds began to explore reactions between alcohols, phenols, and isocyanates. These studies established the general methods for preparing carbamate esters and revealed their structural relationship to both esters and amides. The compound phenyl N-phenylcarbamate represents a symmetrical aromatic carbamate in which both the alcohol and amine components are derived from phenyl groups. The preparation of aromatic carbamates became more systematic after the discovery that isocyanates react readily with alcohols and phenols to form carbamate esters. In a typical synthesis, phenyl isocyanate reacts with phenol to yield phenyl N-phenylcarbamate through formation of a carbamate linkage connecting the oxygen atom of the phenol to the carbonyl carbon of the isocyanate. This reaction proceeds under relatively mild conditions and produces a stable crystalline product. The development of isocyanate chemistry in the early twentieth century greatly expanded the availability of carbamate derivatives and allowed chemists to investigate their physical and chemical properties in detail. Carbamate compounds occupy an important position in organic chemistry because the carbamate functional group combines structural features of both amides and esters. The presence of a carbonyl group adjacent to both nitrogen and oxygen atoms influences the stability and reactivity of the molecule. In phenyl N-phenylcarbamate, the two aromatic rings contribute additional stabilization through conjugation with the carbamate group. This structural arrangement has made aromatic carbamates valuable as model compounds for studying resonance effects and substituent influences in aromatic systems. Phenyl N-phenylcarbamate and related compounds have been used as intermediates in organic synthesis. The carbamate group can undergo a variety of chemical transformations, including hydrolysis to yield the corresponding phenol and amine derivatives. Because of this behavior, carbamates can serve as protected forms of amines or phenols during multistep synthetic procedures. The ability to introduce and later remove the carbamate functionality has made such compounds useful tools in laboratory synthesis and in the preparation of more complex organic molecules. Another important area of application for aromatic carbamates involves their role in polymer and materials chemistry. The reactions of isocyanates with alcohols and phenols that produce carbamates are closely related to the chemistry used to form urethane linkages in polyurethane materials. Although phenyl N-phenylcarbamate itself is primarily encountered as a discrete organic compound rather than a polymer component, its formation illustrates the fundamental reaction that underlies the synthesis of many urethane-based materials. Studies of simple carbamates helped clarify the mechanisms and conditions involved in these reactions, contributing to the development of large-scale industrial polyurethane production. In addition, carbamate derivatives have long been investigated in the field of medicinal and agricultural chemistry. The carbamate functional group appears in numerous biologically active molecules, and research into simple carbamate structures helped establish the chemical principles underlying their stability and reactivity. Aromatic carbamates such as phenyl N-phenylcarbamate have therefore served as reference compounds for examining how structural variations affect chemical behavior. The continued study of carbamate chemistry reflects the versatility of this functional group in both fundamental and applied contexts. Phenyl N-phenylcarbamate exemplifies a relatively simple aromatic carbamate whose preparation, stability, and reactivity illustrate key aspects of carbamate formation and transformation. Through its role as a representative compound in studies of isocyanate reactions, protective group chemistry, and aromatic substitution effects, it contributes to the broader understanding of carbamate derivatives and their applications in organic chemistry.

References

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DOI: 10.1016/j.jbc.2022.102228

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DOI: 10.1016/j.celrep.2021.109040