18354-35-3

Basic information

• Product Name: 4-Fluorobenzoyl isocyanate
• Synonyms: 4-Fluorobenzoyl isocyanate
• CAS NO: 18354-35-3
• Molecular Formula: C₈H₄FNO₂
• Molecular Weight: 165.1212632
• Mol File: 18354-35-3.mol

Chemical Properties

• Boiling Point: 213.8 °C at 760 mmHg
• Flash Point: 79.2 °C
• Appearance: /
• Density: 1.2870
• Vapor Pressure: 0.161mmHg at 25°C
• Refractive Index: 1.527
• CAS DataBase Reference: 4-Fluorobenzoyl isocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Fluorobenzoyl isocyanate(18354-35-3)
• EPA Substance Registry System: 4-Fluorobenzoyl isocyanate(18354-35-3)

Safety Data

• Hazardous Substances Data: 18354-35-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Fluorobenzoyl isocyanate is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to form active drug molecules with specific therapeutic properties.
Used in Agrochemical Industry:
4-Fluorobenzoyl isocyanate is used as a building block in the development of agrochemicals, contributing to the creation of effective compounds for crop protection and pest control.
Used in Organic Synthesis:
4-Fluorobenzoyl isocyanate is utilized as a versatile reagent in organic synthesis, particularly for the production of compounds that incorporate fluorobenzoyl moieties, enhancing their chemical and biological properties.
It is important to handle 4-Fluorobenzoyl isocyanate with care due to its reactivity and potential to cause irritation to the skin, eyes, and respiratory system.

InChI:InChI=1/C8H4FNO2/c9-7-3-1-6(2-4-7)8(12)10-5-11/h1-4H

Upstream product

• 79-37-8 oxalyl dichloride 
• 824-75-9 p-fluorobenzamide 
• 456-22-4 4-Fluorobenzoic acid 
• 403-43-0 4-fluorobenzoyl chloride 
• 917-61-3 sodium isocyanate 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 18354-38-6 N-(p-Fluor-benzoyl)-N'-phenyl-harnstoff 
• 18354-42-2 2--5-acetyl-5-methyl-1,3-oxazolin-4-on 
• 21631-69-6 5-benzoyl-2-(4-fluoro-phenyl)-oxazol-4-one 
• 132981-04-5 1-(4-Fluoro-benzoyl)-3-[(S)-3-(2,3,5,6-tetrahydro-imidazo[2,1-b]thiazol-6-yl)-phenyl]-urea 
• 18354-46-6 2-Acetyl-2-(4-fluorbenzoyloxy)-propionsaeureamid) 
• 21631-72-1 [2-(4-fluoro-phenyl)-4-methoxy-oxazol-5-yl]-phenyl-methanone 
• 897027-68-8 2-(4-fluorophenyl)oxazol-4(5H)-one 
• 897027-51-9 2-(4-fluorophenyl)-1,3-oxazol-4-yl trifluoromethanesulfonate 
• 1188301-82-7 5-(2-(4-fluorophenyl)oxazol-4-yl)-3-methoxypyridin-2-amine 
• 1188301-84-9 5-(5-bromo-2-(4-fluorophenyl)oxazol-4-yl)-3-methoxypyridin-2-amine 
• 1188298-68-1 5-(2-(4-fluorophenyl)-5-(pyridin-4-yl)oxazol-4-yl)-3-methoxypyridin-2-amine 

Relevant articles and documents

Scalable Synthetic Strategy for Unsymmetrical Trisubstituted s-Triazines

A scalable synthetic strategy to produce a large variety of unsymmetrical trisubstituted 1,3,5-triazines was developed. This protocol applied in situ formed acyl isocyanate from amide to react with amidine, introducing two substituents to the 1,3,5-triazinone ring with a low production cost and a simple workup procedure. The scalability of this method was demonstrated by translating a small-scale procedure to a multi-kilogram-scale synthesis. Chlorination and a further coupling reaction with various nucleophiles could provide unsymmetrical trisubstituted 1,3,5-triazines bearing diverse functional groups.

Design, Synthesis, and Insecticidal Activity of Novel Doramectin Derivatives Containing Acylurea and Acylthiourea Based on Hydrogen Bonding

Our recent investigation on the insecticidal activities of several doramectin derivatives preliminarily revealed that the presence of hydrogen bonds at the C4″ position of the molecule with target protein γ-aminobutyric acid (GABA) receptor was crucial for retaining high insecticidal activity. As a continuation of our research work on the development of new insecticides, two series of novel acylurea and acylthiourea doramectin derivatives were designed and synthesized. The bioassay results indicated that the newly synthesized compounds (5o, 5t, and 6t) exhibited higher insecticidal activity against diamondback moth, oriental armyworm, and corn borer than the control compounds doramectin, commercial avermectins, chlorbenzuron, and lead compound 3g in our laboratory. Specifically, compound 5t was identified as the most promising insecticide against diamondback moth, with a final mortality rate of 80.00% at the low concentration of 12.50 mg/L, showing approximately 7.75-fold higher potency than the parent doramectin (LC50 value of 48.1547 mg/L), 6.52-fold higher potency than commercial avermectins (LC50 value of 40.5507 mg/L), and 3.98-fold higher potency than compound 3g (LC50 value of 24.7742 mg/L). Additionally, molecular docking simulations revealed that compound 5t (2.17, 2.20, 2.56, and 2.83 ?) displayed stronger hydrogen-bond action in binding with the GABA receptor, better than that of compound 5o (1.64 and 2.15 ?) and compound 6t (2.20 and 2.31 ?) at the C4″ position. This work demonstrated that these compounds containing hydrogen-bond groups might contribute to the improvement of insecticidal activity and supply certain hints toward structure optimization design for the development of new insecticides.

Synthetic method for aryl formyl isocyanate

The invention relates to a preparation method, and mainly relates to a synthetic method for aryl formyl isocyanate, which includes: (1) dropwise adding an aryl formamide solution, dissolved in an organic solvent, to a bis(trichloromethyl)carbonate solution; (2) slowly heating the mixture to a high temperature of 60-180 DEG C, and at the temperature, completely dropwise adding the rest of the bis(trichloromethyl)carbonate to the solution in the step (1) within 0.5-5 h, and then continuously performing the reaction for 1-6 h, after the reaction is finished, recycling the organic solvent, and performing pressure-reduced distillation to the organic solvent to prepare the aryl formyl isocyanate. The method overcome the problems of poor safety and high investment cost due to use of oxalyl chloride or carbonyl chloride in the prior art. The method has reasonable processes, is environment-friendly, low-cost, safe and reliable, is high in yield of the aryl formyl isocyanate, is low in generation of waste water, waste gas and solid wastes, and is suitable for industrial production.

Design, synthesis and fungicidal activity of N-substituted benzoyl-1,2,3,4-tetrahydroquinolyl-1-carboxamide

To find a new lead compound with high biological activity, a series of N-substituted benzoyl-1,2,3,4-tetrahydroquinolyl-1-carboxamide were designed using linking active substructures method. The target compounds were synthesized from substituted benzoic acid by four steps and their structures were confirmed by 1H NMR, IR spectrum and elemental analysis. The in vitro bioassay results indicated that some target compounds exhibited excellent fungicidal activities, and the position of the substituents played an important role in fungicidal activities. Especially, compound 5n, exhibited better fungicidal activities than the commercial fungicide flutolanil against two tested fungi Valsa Mali and Sclerotinia sclerotiorum, with EC50 values of 3.44 and 2.63 mg/L, respectively. And it also displayed good in vivo fungicidal activity against S. sclerotiorum with the EC50 value of 29.52 mg/L.

Novel Heterocyclic Compounds and Uses Thereof

New substituted heterocyclic compounds, compositions containing them, and methods of using them for the inhibition of Raf kinase activity are provided. The new compounds and compositions may be used either alone or in combination with at least one additional agent for the treatment of a Raf kinase mediated disorder, such as cancer.

Acylurea connected straight chain hydroxamates as novel histone deacetylase inhibitors: Synthesis, SAR, and in vivo antitumor activity

Thirty-six novel acylurea connected straight chain hydroxamates were designed and synthesized. Structure-activity relationships (SAR) were established for the length of linear chain linker and substitutions on the benzoylurea group. Compounds 5g, 5i, 5n, and 19 showed 10-20-fold enhanced HDAC1 potency compared to SAHA. In general, the cellular potency pIC50 (COLO205) correlates with enzymatic potency pIC50 (HDAC1). Compound 5b (SB207), a structurally simple and close analogue to SAHA, is more potent against HDAC1 and HDAC6 compared to the latter. As a representative example of this series, good in vitro enzymatic and cellular potency plus an excellent pharmacokinetic profile has translated into better efficacy than SAHA in both prostate cancer (PC3) and colon cancer (HCT116) xenograft models.

NOVEL HETEROCYCLIC COMPOUNDS AND USES THEROF

New substituted heterocyclic compounds, compositions containing them, and methods of using them for the inhibition of Raf kinase activity are provided. The new compounds and compositions may be used either alone or in combination with at least one additional agent for the treatment of a Raf kinase mediated disorder, such as cancer.

1,2,4-TRIAZOLE DERIVATIVES, PROCESSES FOR THE PREPARATION THEREOF, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME

A 1,2,4-triazole derivative of formula 1 or a non-toxic salt thereof, a preparation method thereof, and a pharmaceutical composition containing the derivative or the salt as an active ingredient are provided.

Synthesis and anthelmintic activity of 3'-benzoylurea derivatives of 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole

Reaction of 3-amino derivatives of the nematocides tetramisole and levamisole with variously substituted benzoylisocyanates gave a series of benzoylureas I which were tested for activity against helminths and ectoparasites. Compounds bearing 2,6-difluoro and 4-trifluoromethyl substituents had potent nematocidal activity in both mice and sheep. No antiectoparasitic activity was observed.