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

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

Uses

Used in Organic Synthesis:
3,5-Difluorophenylisocyanate is used as a building block in organic synthesis for creating a wide range of chemical compounds and materials. Its unique properties and reactivity contribute to the development of new and innovative products in the chemical industry.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 3,5-difluorophenylisocyanate is used as a key component in the synthesis of various drugs. Its versatility and reactivity enable the creation of new pharmaceutical compounds with potential therapeutic benefits.
Used in Agrochemical Manufacturing:
3,5-Difluorophenylisocyanate is utilized in the production of agrochemicals, including pesticides and herbicides. Its incorporation into these products enhances their effectiveness in controlling pests and weeds, contributing to improved agricultural yields.
Used in Advanced Material Development:
This chemical compound is also employed in the development of advanced materials with specific properties, such as high thermal stability, chemical resistance, or unique optical characteristics. Its reactivity and ability to form various chemical bonds make it an essential component in the creation of these materials.

Upstream product

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

Downstream Products

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

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 biological evaluation of a new series of 1-aryl-3-[4-(pyridin-2-ylmethoxy)phenyl]urea derivatives as new anticancer agents

The diaryl ureas are very important fragments in medicinal chemistry. By means of computer-aided design, 1-aryl-3-[4-(pyridin-2-ylmethoxy)phenyl]urea derivatives were designed and synthesized, and evaluated for their antiproliferative activity against A549, HCT-116, PC-3 cancer cell lines, and HL7702 human normal liver cell lines in vitro by using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide colorimetric assay. Most of the target compounds demonstrate significant antiproliferative effects on all the selective cancer cell lines. The calculated IC50 values were reported. The target compound 1-(4-chlorophenyl)-3-{4-{[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methoxy}phenyl}urea (7u) demonstrated the most potent inhibitory activity (IC50 = 2.39 ± 0.10 μM for A549 and IC50 = 3.90 ± 0.33 μM for HCT-116), comparable to the positive-control sorafenib (IC50 = 2.12 ± 0.18 μM for A549 and IC50 = 2.25 ± 0.71 μM for HCT-116). Conclusively, 1-aryl-3-[4-(pyridin-2-ylmethoxy)phenyl]urea derivatives as the new anticancer agents were discovered, and could be used as the potential BRAF inhibitors for further research.

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.

Specific inhibitors of puromycin-sensitive aminopeptidase with a 3-(halogenated phenyl)-2,4(1H,3H)-quinazolinedione skeleton

Specific puromycin-sensitive aminopeptidase (PSA) inhibitors with a 3-(halogenated phenyl)-2,4(1H,3H)-quinazolinedione skeleton were prepared and their structure-activity relationships were investigated. The nature (F, Cl or Br), number and position(s) of the halogen atom(s) introduced into the 3-phenyl group were concluded to be critical determinants of the inhibitory activity.