54132-75-1

Usage

Uses

Used in Chiral Chromatography:
3,5-Dimethylphenyl isocyanate is used as a linking agent for oligosaccharides and cyclodextrins in chiral chromatography stationary phases. This application is due to its ability to form stable and selective interactions with chiral molecules, which is crucial for the separation and analysis of enantiomers in various chemical and pharmaceutical processes.
Used in Chemical Synthesis:
3,5-Dimethylphenyl isocyanate can also be used as a building block or intermediate in the synthesis of various organic compounds, particularly those with pharmaceutical or agrochemical applications. Its isocyanate functional group allows for further reactions and modifications, making it a versatile component in the development of new molecules with specific properties and functions.
Used in Coatings and Adhesives:
Due to its reactive isocyanate group, 3,5-Dimethylphenyl isocyanate can be utilized in the formulation of coatings and adhesives. It can improve the performance characteristics of these materials, such as adhesion, flexibility, and durability, by reacting with other components to form strong and stable polymer networks.
Used in Polymer Industry:
3,5-Dimethylphenyl isocyanate can be employed in the polymer industry as a monomer for the synthesis of polyurethanes and other isocyanate-based polymers. These materials have a wide range of applications, including foams, elastomers, and coatings, due to their unique properties such as high mechanical strength, flexibility, and resistance to various environmental factors.

InChI:InChI=1/C9H9NO/c1-7-3-8(2)5-9(4-7)10-6-11/h3-5H,1-2H3

Upstream product

• 108-69-0 3,5-dimethylaminoaniline 
• 503-38-8 trichloromethyl chloroformate 
• 590-28-3 potassium cyanate 
• 75-44-5 phosgene 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 864269-47-6 [((CH(C(Me)N-2,4,6-Me₃C₆H₂)₂)Ni)₂(μ-CO)₂] 
• 70334-59-7 1-azido-3,5-dimethylbenzene 
• 203321-89-5 (3,5-dimethylphenyl)carbamic acid 1,1-dimethylethyl ester 

Downstream Products

• 99841-16-4 N'-(3,5-dimethyl-phenyl)-N-formyl-N-methyl-urea 
• 64392-97-8 1-cyclopropyl-3-(3,5-dimethylphenyl)urea 
• 28395-91-7 (3,5-Dimethyl-phenyl)-carbamic acid 5-chloro-2-(2,4-dichloro-phenoxy)-phenyl ester 
• 38021-40-8 (3,5-Dimethyl-phenyl)-carbamic acid 3-methylsulfanylcarbonylamino-phenyl ester 
• 119872-21-8 1-(3,5-Dimethyl-phenyl)-3-[2-(3,5-dimethyl-phenyl)-3-oxo-2,3-dihydro-[1,2,4]thiadiazol-5-yl]-urea 
• 132314-20-6 3,5-dimethylphenylcarbamate of cellotetraose 
• 88451-14-3 1-Benzyl-1-butyl-3-(3,5-dimethyl-phenyl)-urea 
• 132314-20-6 C₁₅₀H₁₆₈N₁₄O₃₅ 
• 86353-59-5 (3,5-Dimethyl-phenyl)-carbamic acid 1-methyl-1-(4,4,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-yl)-ethyl ester 
• 251091-76-6 3-(3,5-dimethylphenyl)carbamoyl-N-allyl-deoxycholan-24-amide 
• 251091-78-8 3,12-bis-(3,5-dimethylphenyl)carbamoyl-N-allyl-deoxycholan-24-amide 
• 242148-28-3 3',5'-dimethylphenyl-ureido-(Phe-D-Leu)₂-Phe-OMe 
• 251091-81-3 3-(3,5-dichlorophenyl)carbamoyl-12-(3,5-dimethylphenyl)carbamoyl-N-allyl-deoxycholan-24-amide 
• 403607-15-8 N-allyl-N'-methyl-3α-N-(3,5-dimethylbenzoyl)amino-12α-(3,5-dimethylphenyl)carbamoyloxy-5β-cholan-24-amide 

Relevant academic research and scientific papers

Practical one-pot amidation of N -Alloc-, N -Boc-, and N -Cbz protected amines under mild conditions

A facile one-pot synthesis of amides from N-Alloc-, N-Boc-, and N-Cbz-protected amines has been described. The reactions involve the use of isocyanate intermediates, which are generated in situ in the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, to react with Grignard reagents to produce the corresponding amides. Using this reaction protocol, a variety of N-Alloc-, N-Boc-, and N-Cbz-protected aliphatic amines and aryl amines were efficiently converted to amides with high yields. This method is highly effective for the synthesis of amides and offers a promising approach for facile amidation.

Synthesis and in vitro anti-bladder cancer activity evaluation of quinazolinyl-arylurea derivatives

Based on the structural modification of molecular-targeted agent sorafenib, a series of quinazolinyl-arylurea derivatives were synthesized and evaluated for their anti-proliferative activities against six human cancer cell lines. Compared with other cell lines tested, T24 was more sensitive to most compounds. Compound 7j exhibited the best profile with lower IC50 value and favorable selectivity. In this study, we focused on 7j-induced death forms of T24 cells and tried to elucidate the reason for its potent proliferative inhibitory activity. Compound 7j treatment could trigger three different cell death forms including apoptosis, ferroptosis, and autophagy; which form would occur depended on the concentrations and incubation time of 7j: (1) Lower concentrations within the initial 8 h of 7j treatment led to apoptosis-dependent death. (2) Ferroptosis and autophagy occurred in the case of higher concentrations combining with extended incubation time through effectively regulating the Sxc?/GPx4/ROS and PI3K/Akt/mTOR/ULK1 pathways, respectively. (3) The above death forms were closely associated with intracellular ROS generation and decreased mitochondrial membrane potential induced by 7j. In molecular docking and structure-activity relationship analyses, 7j could bind well to the active site of the corresponding receptor glutathione peroxidase 4 (GPx4). Compound 7j could be a promising lead for molecular-targeted anti-bladder cancer agents’ discovery.

Synthesis and nematicidal activity of piperazinedione derivatives based on the natural product Barettin

Nematodes are serious constraints of crop production worldwide. However, the traditional nematicides suffer from the side-effects, including environmental and human toxicity. Herein, more than 70 novel piperazinedione derivatives based on the natural product Barettin were synthesized and evaluated against the root-knot nematode Meloidogyne incognita (M. incognita). While most of synthesized compounds exhibited certain nematicidal activity at high concentration, the best one showed a nematicidal activity of 75% at 2.4 μmol/L.

With anti-tumor effect of a quinazoline-urea derivative and its application (by machine translation)

The present invention relates to a of the general formula (II) anti-tumor function of said quinazoline-urea derivative and its application. The definition of the substituent in the general formula (II) in the specification. This invention, in order to SUO draw non-Buddhist nun and Geftinat compounds as the precursor, retention of SUO draw non-Buddhist nun the pharmocology-carbamido; at the same time, such as in reserved [...] EGFR-TKIs Geftinat, synthesis, and obtain a series of quinazoline-urea derivatives, by the in vitro activity tests, some compounds exhibit excellent anti-tumor activity, such derivatives have high research and utility value. (II). (by machine translation)

Rhenium-catalyzed C-H aminocarbonylation of azobenzenes with isocyanates

The first C-H aminocarbonylation of azobenzenes with isocyanates is achieved by using rhenium-catalysis, which provides an expedient and atom-economical access to varied o-azobenzamides from readily available starting materials. The reaction efficiency can be enhanced by the catalytic use of sodium acetate via accelerated C-H bond activation.

β-diketiminato nickel imides in catalytic nitrene transfer to isocyanides

The β-diketiminato nickel(I) species [Me3NN]Ni(2-picoline) (1) serves as an efficient catalyst for carbodiimide (RN=C=NR′) formation in the reactions of a range of organoazides N3R with isocyanides R′NC. [Me3NN]Ni(CNR)2 (R = tBu, Ar (Ar = 2,6-Me2C6H3)) species provide carbodiimides RN=C=NAr′ upon reaction with Ar′N3 (Ar′ = 3,5-Me2C6H3). Nitrene transfer takes place via the intermediacy of nickel imides. Reaction of [MexNN]Ni(2-picoline) (x = 2 or 3) with Ar′N3 gives the new dinickel imides {[Me xNN]Ni}2(μ-NAr′) (4 (x = 3) and 5 (x = 2)) as deep purple, diamagnetic substances. The X-ray structure of {[Me 2NN]Ni}2(μ-NAr′) (5) features short Ni-N imide distances of 1.747(2) and 1.755(2) A along with a short Ni-Ni distance of 2.7210(3) A. These dinickel imides 4 and 5 react stoichiometrically with tBuNC to provide the corresponding carbodiimides tBuN=C=NAr′ in good yield. Azide transfer takes place upon reaction of 1 with TMS-N3 to give the square planar nickel(II) azide [Me3NN]Ni(N3)(2-picoline) (7). Stoichiometric reaction of dinickel dicarbonyl {[Me3NN]Ni} 2(μ-CO)2 with organoazides such as Ar′N 3 is sluggish, indicating that 1 is not an efficient catalyst for nitrene transfer from organoazides to CO to form isocyanates RN=C=O.

A simple and efficient synthesis of diaryl ureas with reduction of the intermediate isocyanate by triethylamine

Thirty symmetrical diaryl urea derivatives were synthesised in moderate to excellent yields from arylamine and triphosgene with triethylamine as a reducing agent for the intermediate, isocyanate. It was significant that part of the products could be collected in almost quantitative yield without column chromatography. The procedure under mild reaction conditions was tolerant of a wide range of functional groups. The structures of the compounds were determined by NMR, MS and X-ray crystallographic analyses.

Synthesis of aryl urea derivatives from aryl amines and aryl isocyanates

The present study describes the synthesis of novel diaryl urea derivatives derived from aryl amine and aryl isocyanates. The synthesized compounds are analogs of sorafenib [4-[4-[[[4-chloro-3-(trifluoromethyl)phenyl]amino]carbonyl] amino]phenoxy]-N-methylpyridine-2- carboxamide] having potential antiproliferative activity.

Structural optimization of a CXCR2-directed antagonist that indirectly inhibits γ-secretase and reduces Aβ

Amyloid β (Aβ), a key molecule in the pathogenesis of Alzheimer's disease (AD), is derived from the amyloid precursor protein (APP) by sequential proteolysis via β- and γ-secretases. Because of their role in generation of Aβ, these enzymes have emerged as important therapeutic targets for AD. In the case of γ-secretase, progress has been made towards designing potent inhibitors with suitable pharmacological profiles. Direct γ-secretase inhibitors are being evaluated in clinical trials and new strategies are being explored to block γ-secretase activity indirectly as well. In this regard, we have previously reported an indirect regulation of γ-secretase through antagonism of CXCR2, a G-protein coupled receptor (GPCR). We demonstrated that N-(2-hydroxy-4-nitrophenyl)-N′-(2-bromophenyl)urea (SB225002), a selective inhibitor of CXCR2 also plays a role in an indirect inhibition of γ-secretase. Furthermore, we reported a ～5-fold difference in the selective inhibition of APP versus Notch processing via γ-secretase following treatment with SB225002. Herein we describe the synthesis and optimization of SB225002. By determination of the structure-activity relationship (SAR), we derived small molecules that inhibit Aβ40 production with IC50 values in the sub-micromolar range in a cell-based assay and also validated the potential of CXCR2 as a new target for therapeutic intervention in AD.

Substituted N-phenylcarbamates as histamine H3 receptor antagonists with improved in vivo potency

Novel substituted N-phenylcarbamates as derivatives of 3-(1 H-imidazol- 4-yl)propanol were prepared and tested for their antagonist potency in vitro and in vivo at histamine H3 receptors. Structural modifications with different alkyl and acetyl moieties were performed in an attempt to optimize pharmacodynamic and pharmacokinetic effects. Most compounds are active in a functional test for histamine H3 receptors on rat cerebral cortex synaptosomes as well as in a peripheral model on guinea pig ileum. But only carbamates without too bulky lipophilic residues showed pronounced to high antagonist potency on the enhancement of endogenous histamine in brain after p.o. administration to mice (ED50 values of 5.5 to 0.86 mg · kg-1). The tested compounds presented weak activities at histamine H1, H2, and muscarinic M3 receptors thus demonstrating their H3-receptor selectivity.