4461-34-1

Basic information

• Product Name: 2-Chlorobenzoyl isocyanate
• Synonyms: 2-ChlorobenzoylIsocyanate;N-(2-Chlorobenzoyl) isocyanate
• CAS NO: 4461-34-1
• Molecular Formula: C₈H₄ClNO₂
• Molecular Weight: 181.58
• Mol File: 4461-34-1.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 250 °C
• Flash Point: 95 °C
• Appearance: /
• Density: 1.28
• Vapor Pressure: 0.022mmHg at 25°C
• Refractive Index: 1.568
• CAS DataBase Reference: 2-Chlorobenzoyl isocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chlorobenzoyl isocyanate(4461-34-1)
• EPA Substance Registry System: 2-Chlorobenzoyl isocyanate(4461-34-1)

Safety Data

• Hazardous Substances Data: 4461-34-1(Hazardous Substances Data)

Usage

General Description

2-Chlorobenzoyl isocyanate is a chemical compound featuring an isocyanate group linked to a 2-chlorobenzoyl group. It is used in the field of organic chemistry for the synthesis of numerous substances. Being an isocyanate, it holds the properties of being highly reactive and can participate in a variety of chemical reactions. These qualities make it useful in materials science and in the manufacturing of polymers, coatings, and adhesives. However, due to the reactive nature and toxicity of isocyanates in general, it needs to be handled with due care and strict safety precautions. The exact physiochemical properties of the compound might differ based on the specific conditions and the presence of other substances.

InChI:InChI=1/C8H4ClNO2/c9-7-4-2-1-3-6(7)8(12)10-5-11/h1-4H

Upstream product

• 79-37-8 oxalyl dichloride 
• 609-66-5 2-chlorobenzamide 
• 917-61-3 sodium isocyanate 
• 609-65-4 o-chlorobenzoyl chloride 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 118-91-2 ortho-chlorobenzoic acid 
• 104417-75-6 1,1-Bis-(2-chloro-benzoyl)-3,3-dimethyl-urea 

Downstream Products

• 1248590-23-9 4-(2-chlorobenzoyl)-1-[5-(2,4-difluorophenyl)-2-furoyl]semicarbazide 
• 1248590-17-1 4-(2-chlorobenzoyl)-1-[5-(4-methylphenyl)-2-furoyl]semicarbazide 
• 1248590-14-8 4-(2-chlorobenzoyl)-1-[5-(4-chlorophenyl)-2-furoyl]semicarbazide 
• 1032338-34-3 C₁₉H₁₃ClFNO₄ 
• 1032338-36-5 C₁₉H₁₃ClFNO₄ 
• 1187887-49-5 N-(2-chlorobenzoyl)-N'-(4-heptafluoroisopropylphenyl)urea 
• 1187887-52-0 N-(2-chlorobenzoyl)-N'-(2,6-dimethyl-4-heptafluoroisopropylphenyl)urea 

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.

Investigation of novel pesticides with insecticidal and antifungal activities: Design, synthesis and SAR studies of benzoylpyrimidinylurea derivatives

In order to find pesticides with insecticidal and antifungal activities, a series of novel benzoyl pyrimidinylurea derivatives were designed and synthesized. All target compounds were identified by 1H-NMR spectroscopy and HRMS. Insecticidal and antifungal activity of these compounds were evaluated and the structure-activity relationships (SAR) were clearly and comprehensively illustrated. Compound 7, with low toxicity to zebrafish (LC50 = 378.387 μg mL?1) showed 100% inhibition against mosquito (Culex pipiens pallens) at 0.25 μg mL?1. Both compounds 19 and 25 exhibited broad-spectrum fungicidal activity (>50% inhibitory activities against 13 phytopathogenic fungi), which were better than those of the commercial pesticide pyrimethanil (>50% inhibitory activities against eight phytopathogenic fungi). Furthermore, compounds 19 and 25 exhibited protective activity against Sclerotinia sclerotiorum on leaves of Brassica oleracea L. during in vivo experiments.