59025-55-7

Basic information

• Product Name: 2,4-Difluorophenyl isocyanate
• Synonyms: Difluorophenyl isocyanat;250759_ALDRICH;36952_FLUKA;Benzene, 2,4-difluoro-1-isocyanato-;SBB006537;ZINC00164769;2,4-Diflurophenyl isocyanate;TIMTEC-BB SBB006537
• CAS NO: 59025-55-7
• Molecular Formula: C₇H₃F₂NO
• Molecular Weight: 155.1
• Product Categories: ISOCYANATE;Phenyl isocyanate&Phenyl isothiocyanate;Isocyanates;Nitrogen Compounds;Organic Building Blocks
• Mol File: 59025-55-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 42 °C6 mm Hg(lit.)
• Flash Point: 50 °C
• Appearance: Clear colorless to faintly yellow liquid
• Density: 1.309 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.490(lit.)
• Storage Temp.: 2-8°C
• Sensitive: Moisture Sensitive/Lachrymatory
• BRN: 2831577
• CAS DataBase Reference: 2,4-Difluorophenyl isocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Difluorophenyl isocyanate(59025-55-7)
• EPA Substance Registry System: 2,4-Difluorophenyl isocyanate(59025-55-7)

Safety Data

• Hazard Codes: Xn,T,Xi
• Statements: 20/21/22-36/37/38-42-10
• Safety Statements: 26-36/37-45-36/37/39-16
• RIDADR: UN 2478 3/PG 3
• WGK Germany: 3
• F: 10-19-21
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 59025-55-7(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to faintly yellow liquid

Uses

2,4-Difluorophenyl isocyanate has been used:in the synthesis of N,N-disubstituted S,N′-diarylisothioureasas blocking reagent, to modify the hydroxyl, amine and epoxide functional groups of cured MY720/DDS epoxy thin films

InChI:InChI:1S/C7H3F2NO/c8-5-1-2-7(10-4-11)6(9)3-5/h1-3H

Upstream product

• 75-44-5 phosgene 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 367-25-9 2,4-difluorophenylamine 

Downstream Products

• 128830-76-2 4-(2-chlorophenyl)-3-[3-(2,4-difluorophenyl)ureido]-6,8-dimethylquinoline 
• 128831-46-9 TMP-153 
• 139772-88-6 N'-{2,4-difluorophenyl)-N-heptyl-N-5-hydroxypentylurea 
• 139878-67-4 3-(2,4-Difluoro-phenyl)-1-heptyl-1-(5-hydroxy-3,3-dimethyl-pentyl)-urea 

Relevant articles and documents

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.

N-fluorinated phenyl-N′-pyrimidyl urea derivatives: Synthesis, biological evaluation and 3D-qsar study

With the increase of herbicide-resistant weeds, novel, more selective and even more potent herbicides to control weeds are needed. In this paper, a series of N-fluorinated phenyl-N′-pyrimidyl urea derivatives were synthesized and screened for their herbicidal activities against Amaranthus retroflexus (AR) and Setaria viridis (SV). Compound 25 (N-(3-trifluoromethylphenyl)-N′-(2- amino-4-chloro-6-methylpyrimidyl) urea) exhibited marked herbicidal activity against SV (IC50 = 11.67 mg/L) and is more potent than bensulfuron (IC50 = 27.45 mg/L), a commercially available herbicide. A statistically significant CoMFA model with high prediction abilities (q 2 = 0.869, r2 = 0.989) was obtained.

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.