6327-52-2

Basic information

• Product Name: octyl phenylcarbamate
• CAS NO: 6327-52-2
• Molecular Formula: C₁₅H₂₃NO₂
• Molecular Weight: 249.3486
• Mol File: 6327-52-2.mol

Chemical Properties

• Boiling Point: 317.6°C at 760 mmHg
• Flash Point: 145.9°C
• Density: 1.02g/cm³
• Vapor Pressure: 0.000381mmHg at 25°C
• Refractive Index: 1.523
• CAS DataBase Reference: octyl phenylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: octyl phenylcarbamate(6327-52-2)
• EPA Substance Registry System: octyl phenylcarbamate(6327-52-2)

Safety Data

• Hazardous Substances Data: 6327-52-2(Hazardous Substances Data)

Upstream product

• 111-87-5 octanol 
• 103-71-9 phenyl isocyanate 
• 10160-16-4 (3Z,5Z)-3,5-octadien-1-ol 
• 102-07-8 bis(diphenyl)urea 
• 10160-11-9 3,5-octadiyn-1-ol 
• 201230-82-2 carbon monoxide 
• 62-53-3 aniline 
• 2603-10-3 N-phenyl methyl carbamate 
• 98-88-4 benzoyl chloride 
• 582-61-6 benzoyl azide 
• 103-70-8 Formanilid 
• 2617-79-0 N-(4-chlorophenyl)formamide 

Downstream Products

• 103-71-9 phenyl isocyanate 
• 67-56-1 methanol 
• 111-87-5 octanol 
• 62-53-3 aniline 
• 66606-08-4 N-tolyl-O-decyl urethane 
• 2589-21-1 1,1'-dibutyl-3-phenylurea 

Relevant articles and documents

Hydrogenation of alkenes via cooperative hydrogen atom transfer

Radical hydrogenation via hydrogen atom transfer (HAT) to alkenes is an increasingly important transformation for the formation of thermodynamic alkane isomers. Current single-catalyst methods require stoichiometric oxidant in addition to hydride (H-) source to function. Here we report a new approach to radical hydrogenation: cooperative hydrogen atom transfer (cHAT), where each hydrogen atom donated to the alkene arrives from a different catalyst. Further, these hydrogen atom (H?) equivalents are generated from complementary hydrogen atom precursors, with each alkane requiring one hydride (H-) and one proton (H+) equivalent and no added oxidants. Preliminary mechanistic study supports this reaction manifold and shows the intersection of metal-catalyzed HAT and thiol radical trapping HAT catalytic cycles to be essential for effective catalysis. Together, this unique catalyst system allows us to reduce a variety of unactivated alkene substrates to their respective alkanes in high yields and diastereoselectivities and introduces a new approach to radical hydrogenation.

Mechanistic Study of Stress Relaxation in Urethane-Containing Polymer Networks

Cross-linked polymers are used in many commercial products and are traditionally incapable of recycling via melt reprocessing. Recently, tough and reprocessable cross-linked polymers have been realized by incorporating cross-links that undergo associative exchange reactions, such as transesterification, at elevated temperatures. Here we investigate how cross-linked polymers containing urethane linkages relax stress under similar conditions, which enables their reprocessing. Materials based on hydroxyl-terminated star-shaped poly(ethylene oxide) and poly((±)-lactide) were cross-linked with methylene diphenyldiisocyanate in the presence of stannous octoate catalyst. Polymers with lower plateau moduli exhibit faster rates of relaxation. Reactions of model urethanes suggest that exchange occurs through the tin-mediated exchange of the urethanes that does not require free hydroxyl groups. Furthermore, samples were incapable of elevated-temperature dissolution in a low-polarity solvent (1,2,4-trichlorobenzene) but readily dissolved in a high-polarity aprotic solvent (DMSO, 24 to 48 h). These findings indicate that urethane linkages, which are straightforward to incorporate, impart dynamic character to polymer networks of diverse chemical composition, likely through a urethane reversion mechanism.

Formamides as Isocyanate Surrogates: A Mechanistically Driven Approach to the Development of Atom-Efficient, Selective Catalytic Syntheses of Ureas, Carbamates, and Heterocycles

Despite the hazardous nature of isocyanates, they remain key building blocks in bulk and fine chemical synthesis. By surrogating them with less potent and readily available formamide precursors, we herein demonstrate an alternative, mechanistic approach to selectively access a broad range of ureas, carbamates, and heterocycles via ruthenium-based pincer complex catalyzed acceptorless dehydrogenative coupling reactions. The design of these highly atom-efficient procedures was driven by the identification and characterization of the relevant organometallic complexes, uniquely exhibiting the trapping of an isocyanate intermediate. Density functional theory (DFT) calculations further contributed to shed light on the remarkably orchestrated chain of catalytic events, involving metal-ligand cooperation.

Synthesis of Amines, Carbamates and Amides by Multi-Step Continuous Flow Synthesis

We report the continuous flow synthesis of acyl azides in various continuous flow systems and demonstrate that liquid–liquid separation may be incorporated to prepare anhydrous solutions of the acyl azide, which may be subsequently reacted with appropriate nucleophiles to prepare amines, carbamates and amides within a fully integrated multi-step process in high yields (> 80 %). Interesting effects were also observed when preparing carbamates with long chain alcohols, whereby as the chain length of the alcohol increased the products could be made in high yield even without incorporation of the liquid–liquid separation module.

Base-Catalyzed Transcarbamoylation

Inorganic bases such as NaH, KO t -Bu, NaOH, or KOH are efficient catalysts to promote the transcarbamoylation reaction between urethanes and a variety of primary and secondary alcohols under mild conditions. They constitute an alternative to organometallic catalysis and can be applied to aliphatic or aromatic urethanes.

Selenium-catalyzed oxidative carbonylation of aniline and alcohols to n-phenylcarbamates

A facile one-pot, phosgene-free synthesis of N-phenylcarbamates is demonstrated. Catalyzed by selenium, oxidative carbonylation of aniline with alcohols in the presence of carbon monoxide and oxygen affords the corresponding N-phenylcarbamates, mostly in fair to good yields. Selenium can be easily recovered because of its phase-transfer catalysis function. Copyright

The influence of the structure of alcohols on the rate of N,N'-diphenylurea alcoholysis

The kinetics and mechanism of the reaction between symmetrical diphenylurea and various alcohols in the absence of inert solvents were studied. The activation parameters of alcoholysis were determined. A correlation equation that described the influence of the nature of the alcohol on the rate of the reaction was obtained. Copyright

Medium Effects on the Rate of Interaction between N,N′-Diphenylurea and Alcohols

The kinetics and mechanism of alcoholysis of symmetrical diphenylurea in inert solvents was studied. The reaction rate was found to be independent of the nature and concentration of the alcohol, which was evidence of the dissociative character of interactions. The reaction involved the decomposition of urea followed by the interaction of the decomposition product (phenylisocyanate) with alcohols. The activation and transition state parameters that characterized the alcoholysis of diphenylurea in various media were found. The influence of the nature of the solvent on the rate of the reaction under consideration was studied.

The kinetics and mechanism of alcoholysis of symmetrical substituted diphenylureas

The kinetics of the reaction between n-octyl alcohol and symmetrical substituted diphenylureas was studied. An analytic technique based on the use of high-performance liquid chromatography was developed. Substituent and temperature effects on the rate of alcoholysis were determined. The activation and transition state parameters were calculated. A dissociative mechanism of the reaction was suggested.