3158-26-7

Usage

Uses

Used in Polymerization Reactions:
Octyl isocyanate is used as a suppressant for side reactions such as backbiting or chain transfer reactions during polymerization processes. Its incorporation helps in controlling the reaction pathways, leading to the formation of desired polymer structures with improved properties.
Used in Organic Chemistry:
In the field of organic chemistry, Octyl isocyanate is used in the synthesis of various compounds, including:
1. Low molar mass organogelator containing the 2-(2′-hydroxyphenyl)benzoxazole (HPB) unit with a long alkyl chain. This application takes advantage of Octyl isocyanate's ability to form stable gels with unique properties.
2. N-octylurea, a compound synthesized using Octyl isocyanate, which can be further utilized in the development of new materials or pharmaceuticals.
3. N-cyclopropyl-N′-octylurea, another synthesized product that demonstrates the versatility of Octyl isocyanate in creating diverse organic compounds with potential applications.
Overall, Octyl isocyanate plays a significant role in various industries, from polymer synthesis to organic chemistry, showcasing its versatility and importance in creating new materials and compounds with specific properties and applications.

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 257, 1995 DOI: 10.1021/jo00106a044Synthesis, p. 907, 1987

InChI:InChI=1/C9H17NO/c1-2-3-4-5-6-7-8-10-9-11/h2-8H2,1H3

Upstream product

• 75-44-5 phosgene 
• 111-86-4 n-Octylamine 
• 142-95-0 n-octylamine hydrochloride 
• 764-85-2 Nonanoyl chloride 
• 113402-57-6 C₉H₁₇N₃O₂ 
• 124-38-9 carbon dioxide 
• 629-27-6 1-Iodooctane 
• 20236-50-4 silver (I) nitro cyanamide 
• 111-83-1 1-bromo-octane 
• 45035-07-2 octyl-carbamic acid 
• 36598-10-4 methyl N-octylcarbamate 
• 24424-95-1 di-tert-butyl tricarbonate 
• 503-38-8 trichloromethyl chloroformate 
• 111-87-5 octanol 

Downstream Products

• 131254-17-6 1-(4-nitro-phenyl)-4-octyl-seleno semicarbazide 
• 25218-87-5 N-[3-(3-Octyl-ureido)-phenyl]-propionamide 
• 25228-39-1 N-[3-(3-Octyl-ureido)-phenyl]-isobutyramide 
• 5006-92-8 1-(p-Chlor-phenyl)-3-n-octyl-harnstoff 
• 105599-52-8 2-Aza-spiro[5.5]undec-8-ene-2-carboxylic acid octylamide 
• 63321-54-0 4-nitrophenyl-N-n-octyl carbamate 
• 198965-12-7 1-{(3aR,4R,6R,6aS)-6-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-octyl-2-oxo-hexahydro-furo[3,4-d]oxazol-4-yl}-1H-pyrimidine-2,4-dione 
• 226724-39-6 C₁₆H₂₅N₃O₂ 

Relevant academic research and scientific papers

Supporting-Electrolyte-Free Anodic Oxidation of Oxamic Acids into Isocyanates: An Expedient Way to Access Ureas, Carbamates, and Thiocarbamates

We report a new electrochemical supporting-electrolyte-free method for synthesizing ureas, carbamates, and thiocarbamates via the oxidation of oxamic acids. This simple, practical, and phosgene-free route includes the generation of an isocyanate intermediate in situ via anodic decarboxylation of an oxamic acid in the presence of an organic base, followed by the one-pot addition of suitable nucleophiles to afford the corresponding ureas, carbamates, and thiocarbamates. This procedure is applicable to different amines, alcohols, and thiols. Furthermore, when single-pass continuous electrochemical flow conditions were used and this reaction was run in a carbon graphite Cgr/Cgr flow cell, urea compounds could be obtained in high yields within a residence time of 6 min, unlocking access to substrates that were inaccessible under batch conditions while being easily scalable.

ISOCYANATE PRODUCTION METHOD

An isocyanate production method according to the present invention is a method in which an isocyanate is produced by subjecting a carbamate to thermal decomposition, and includes: a step of preparing a mixture liquid containing the carbamate, an inactive solvent and a polyisocyanate compound; a step of conducting a thermal decomposition reaction of the carbamate by continuously introducing the mixture liquid into a thermal decomposition reactor; a step of collecting a low-boiling decomposition product by continuously extracting the low-boiling decomposition product in a gaseous state from the reactor, the low-boiling decomposition product having a boiling point lower than the polyisocyanate compound; and a step of collecting a high-boiling component by continuously extracting, from the reactor, a liquid phase component which is not collected in a gaseous state at the step of collecting the low-boiling decomposition product.

METHOD FOR PRODUCING ISOCYANATES

The invention relates to a method for producing an isocyanate, wherein a carbamate or thiolcarbomate is converted, in the presence of a catalyst, with separation of an alcohol or thioalcohol, at a temperature of at least 150° C., to the corresponding isocyanate, wherein a compound of the general formula (X)(Y)(Z—H) is used as a catalyst, in particular characterized in that the compound has both a proton donor function and a proton acceptor function. In the catalysts according to the invention, a separable proton is bound to a heteroatom, which is more electronegative than carbon. Said heteroatom is either identical to Z or a component thereof. In the catalysts according to the invention, there is additionally a proton acceptor function which is either identical to X or a component thereof. According to the invention, the proton donator and proton acceptor function are connected to each other by the bridge Y.

Oxime-Based and Catalyst-Free Dynamic Covalent Polyurethanes

Polyurethanes (PUs) have many applications resulting from their preeminent properties, but being commonly used toxic catalysts, and the lack of processability for PU thermosets cause limitations. Herein, we report a new class of the PU-like dynamic covalent polymers, poly(oxime-urethanes) (POUs), which are prepared from the uncatalyzed polyaddition of multifunctional oximes and hexamethylene diisocyanate (HDI) at ambient temperature. Kinetics studies reveal that almost complete polymerization (～99% conversion) can be achieved in 3 h at 30 °C in dichloromethane (DCM), the most effective among the solvents evaluated, producing linear POUs with comparable molecular weights to the catalyzed PUs. We find that the oxime-carbamate structures are reversible at about 100 °C through oxime-enabled transcarbamoylation via a thermally dissociative mechanism. The cross-linked POUs based on oxime-carbamate bonds show efficient catalyst-free healable/recyclable properties. Density functional theory (DFT) calculations suggest that the fast oxime-urethanation and the mild thermoreversible nature are mediated by the characteristic nitrone tautomer of the oxime. Given widespread urethane-containing materials, POUs are of promising potential in applications because of the excellent mechanical performances, facile preparation, and dynamic property without using catalysts.

N-Guanidino Derivatives of 1,5-Dideoxy-1,5-imino-d-xylitol are Potent, Selective, and Stable Inhibitors of β-Glucocerebrosidase

A series of lipidated guanidino and urea derivatives of 1,5-dideoxy-1,5-imino-d-xylitol were prepared from d-xylose using a concise synthetic protocol. Inhibition assays with a panel of glycosidases revealed that the guanidino analogues display potent inhibition against human recombinant β-glucocerebrosidase with IC50 values in the low nanomolar range. Related urea analogues of 1,5-dideoxy-1,5-imino-d-xylitol were also synthesized and evaluated in the same fashion and found to be selective for β-galactosidase from bovine liver. No inhibition of human recombinant β-glucocerebrosidase was observed for the urea analogues. Computational studies provided insight into the potent activity of analogues bearing the substituted guanidine moiety in the inhibition of lysosomal glucocerebrosidase (GBA).

One-pot sequential synthesis of isocyanates and urea derivatives via a microwave-assisted Staudinger-aza-Wittig reaction

A fast and efficient protocol for the synthesis of N,N'-disubstituted urea derivatives from alkyl halides and primary or secondary amines has been developed. The synthetic pathway combines nucleophilic substitutions and a Staudinger-aza-Wittig reaction in the presence of polymer-bound diphenylphosphine under 14 bar of CO2 pressure and has been performed in a one-pot two-step process. The protocol has been optimized under microwave irradiation and the scale-up experiment has been conducted under conventional conditions in a Parr reactor. The final compounds were isolated after simple filtration in almost quantitative overall yields which makes this procedure facile and rapid to execute.

Synthesis of new coumarin compounds and its hypoglycemic activity and structure-activity relationship

Novel coumarin compounds were designed and synthesized by combining the active moieties of hypoglycemic drugs. The coumarin compounds were made by sulfanilamide with isocynate, the intermediate sulfanilamide was formed from coumarin by chlorosulfonated and aminated. These targeted compounds were characterized by FT-IR, 1H NMR and MS spectra and their hypoglycemic activities were evaluated in mice. The preliminary results showed that some compounds exhibited evident hypoglycemic effect (P > 0.01, CMC-Na as negative control). The relationship between these compounds structure with their hypoglycemic activities were studied in order to design new antidiabetic agents.

1-Aryl-3-(1-acylpiperidin-4-yl)urea inhibitors of human and murine soluble epoxide hydrolase: Structure-activity relationships, pharmacokinetics, and reduction of inflammatory pain

1,3-Disubstituted ureas possessing a piperidyl moiety have been synthesized to investigate their structure-activity relationships as inhibitors of the human and murine soluble epoxide hydrolase (sEH). Oral administration of 13 1-aryl-3-(1-acylpiperidin-4-yl)urea inhibitors in mice revealed substantial improvements in pharmacokinetic parameters over previously reported 1-adamantylurea based inhibitors. For example, 1-(1-(cyclopropanecarbonyl) piperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea (52) showed a 7-fold increase in potency, a 65-fold increase in Cmax, and a 3300-fold increase in AUC over its adamantane analogue 1-(1-adamantyl)-3-(1-propionylpiperidin-4-yl) urea (2). This novel sEH inhibitor showed a 1000-fold increase in potency when compared to morphine by reducing hyperalgesia as measured by mechanical withdrawal threshold using the in vivo carrageenan induced inflammatory pain model.

Triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone (DDQ)/[n-Bu4N]OCN as a useful system for the efficient conversion of tetrahydropyranyl (THP) ethers to the corresponding alkyl isocyanates

Triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone/tetrabutylammonium cyanate was used as an efficient system for the conversion of tetrahydropyranyl ethers to the corresponding alkyl isocyanates. Taylor & Francis Group, LLC.

Comparison of base-promoted and self-catalyzed conditions in the synthesis of isocyanates from amines using triphosgene

Comparison of base-promoted and self-catalyzed conditions for the synthesis of isocyanates from amines and triphosgene shows no advantage in using an amine base in the majority of cases. The workup and isolation of the product is simplified under base-free conditions. Yields of between 50 and 90% after distillation were common. Only acid-sensitive substrates need a base catalyst. Copyright Taylor & Francis Group, LLC.