83594-83-6

Basic information

• Product Name: 3,5-DIFLUOROPHENYLISOCYANATE
• Synonyms: 1,3-difluoro-5-isocyanatobenzene(SALTDATA: FREE);1-Isocyanato-3,5-difluorobenzene;3,5-Difluoro-1-isocyanatobenzene;Benzene,1,3-difluoro-5-isocyanato-;3,5-Difluorophenyl isocyanate 97%;516562_ALDRICH;ZINC02389320;3,5-DIFLUOROPHENYLISOCYANATE
• CAS NO: 83594-83-6
• Molecular Formula: C7H3F2NO
• Molecular Weight: 155.1
• Product Categories: Organic Building Blocks;Aryl Fluorinated Building Blocks;Building Blocks;C7;Chemical Synthesis;Fluorinated Building Blocks;Nitrogen Compounds;Organic Building Blocks;Organic Fluorinated Building Blocks;Other Fluorinated Organic Building Blocks;ISOCYANATE;Phenyl isocyanate&Phenyl isothiocyanate;Isocyanates;Nitrogen Compounds
• Mol File: 83594-83-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 159 °C(lit.)
• Flash Point: 130 °F
• Appearance: /
• Density: 1.31 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.493(lit.)
• Sensitive: Moisture Sensitive/Lachrymatory
• CAS DataBase Reference: 3,5-DIFLUOROPHENYLISOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIFLUOROPHENYLISOCYANATE(83594-83-6)
• EPA Substance Registry System: 3,5-DIFLUOROPHENYLISOCYANATE(83594-83-6)

Safety Data

• Hazard Codes: Xn,T,Xi
• Statements: 10-20/21/22-36/37/38
• Safety Statements: 16-26-36/37/39
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 83594-83-6(Hazardous Substances Data)

Usage

General Description

3,5-Difluorophenylisocyanate is a chemical compound that belongs to the isocyanate family. It is derived from the fluorinated phenyl group and contains an isocyanate functional group, which makes it highly reactive. 3,5-DIFLUOROPHENYLISOCYANATE is commonly used in organic synthesis and as a building block for creating various chemical compounds and materials. Due to its reactivity and potential health hazards, it should be handled with care and protective equipment should be worn when working with it. Its properties make it a valuable component in the production of pharmaceuticals, agrochemicals, and advanced materials. Additionally, 3,5-difluorophenylisocyanate has applications in the manufacturing of pesticides and herbicides. Therefore, it is an important and versatile chemical in the field of organic chemistry.

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 372-39-4 3,5-difluoroaniline 

Downstream Products

• 785827-33-0 3-benzyloxy-2-[3-(3,5-difluoro-phenyl)-ureido]-N-octadecyl-propionamide 
• 929195-03-9 C₂₂H₂₉F₂N₃O 
• 1013032-05-7 C₂₁H₂₂ClF₂N₃O 
• 1314678-67-5 1-(3,5-difluorophenyl)-3-(4-nicotinoylpyrimidin-2-yl)urea 
• 1587045-04-2 C₂₅H₃₁F₄N₇O₂ 
• 1616685-08-5 N-(3,5-difluorophenyl)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carboxamide 

Relevant articles and documents

Novel 5-fluorouracil sensitizers for colorectal cancer therapy: Design and synthesis of S1P receptor 2 (S1PR2) antagonists

Sphingosine-1-phosphate receptor 2 (S1PR2) has been identified as a brand-new GPCR target for designing antagonists to reverse 5-FU resistance. We herein report the structural optimization and structure-activity relationship of JTE-013 derivatives as S1PR2 antagonists. Compound 9d was the most potent S1PR2 antagonist (KD = 34.8 nM) among developed compounds. Here, compound 9d could significantly inhibit the expression of dihydropyrimidine dehydrogenase (DPD) to reverse 5-FU-resistance in HCT116DPD and SW620/5-FU cells. Further mechanism studies demonstrated that compound 9d not only inhibited S1PR2 but also affected the transcription of S1PR2. In addition, compound 9d also showed acceptable selectivity to normal cells (NCM460). Importantly, compound 9d with suitable pharmacokinetic properties could significantly reverse 5-FU-resistance in the HCT116DPD and SW620/5-FU xenograft models without obvious toxicity, in which the inhibition rates of 5-FU were increased from 23.97% to 65.29% and 27.23% to 60.81%, respectively. Further immunohistochemistry and western blotting analysis also demonstrated that compound 9d significantly decreases the expression of DPD in tumor and liver tissues. These results indicated that compound 9d is a promising lead compound to reverse 5-FU-resistance for colorectal cancer therapy.

Synthesis and in vitro antitumor activity of novel diaryl urea derivatives

A series of novel diaryl ureas containing 4-[(2-amino-6-trifluromethyl) pyrimidine-4-yl]piperazine-1-yl group were synthesized and evaluated for their cytotoxic activities in a panel of human cancer cell lines. Compared with the reference drug Sorafenib, some compounds showed more potent and a broader spectrum of anti-cancer activities. Among them, compound 2p demonstrated significant inhibitory activities against MDA-MB-231, HT-29 and MCF-7 cell lines with IC50 values of 0.016, 0.63, 0.001 μmol/L, respectively.