1195-45-5

Basic information

• Product Name: 4-Fluorophenyl isocyanate
• Synonyms: 1-fluoro-4-isocyanato-benzen;AKOS B022528;4-FLUOROPHENYL ISOCYANATE;1-FLUORO-4-ISOCYANATOBENZENE;ISOCYANIC ACID 4-FLUOROPHENYL ESTER;P-FLUOROPHENYL ISOCYANATE;P-FLUORO PHENYL ISOCYANIC ESTER;4-Fluorophenyl isocyanate, 98+%
• CAS NO: 1195-45-5
• Molecular Formula: C₇H₄FNO
• Molecular Weight: 137.11
• EINECS: 214-799-0
• Product Categories: Fluorobenzene;Organics;Isocyanates;Phenyls & Phenyl-Het;Phenyl isocyanate&Phenyl isothiocyanate;Phenyls & Phenyl-Het;Nitrogen Compounds;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;Fluorine series
• Mol File: 1195-45-5.mol
• Article Data: 56

Chemical Properties

• Boiling Point: 55 °C8 mm Hg(lit.)
• Flash Point: 127 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.206 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.74mmHg at 25°C
• Refractive Index: n20/D 1.5141(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Decomposes
• Sensitive: Moisture Sensitive/Lachrymatory
• BRN: 471609
• CAS DataBase Reference: 4-Fluorophenyl isocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Fluorophenyl isocyanate(1195-45-5)
• EPA Substance Registry System: 4-Fluorophenyl isocyanate(1195-45-5)

Safety Data

• Hazard Codes: Xn,T,C,T+
• Statements: 20/21/22-36-42-36/37/38-26
• Safety Statements: 23-26-36/37-45-38-28A
• RIDADR: UN 3080 6.1/PG 2
• WGK Germany: 3
• F: 1-10-19
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 1195-45-5(Hazardous Substances Data)

Usage

Description

4-Fluorophenyl isocyanate is an organic compound with the chemical formula C7H4FNCO, featuring a fluorine atom attached to a phenyl ring and an isocyanate functional group. It is a clear light yellow to amber liquid and is known for its reactivity and versatility in chemical synthesis.

Uses

Used in Pharmaceutical Industry:
4-Fluorophenyl isocyanate is used as a reagent for the preparation of tris-ureas, which serve as transmembrane anion transporters. These transporters play a crucial role in various biological processes and have potential applications in the development of drugs targeting ion transport-related diseases.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4-Fluorophenyl isocyanate is utilized in the solid phase combinatorial synthesis of peptides. Specifically, it is employed to create integrin inhibitors, which are important in the development of therapeutic agents for conditions involving abnormal cell adhesion and tissue remodeling, such as cancer and inflammatory diseases.
These applications highlight the importance of 4-Fluorophenyl isocyanate as a versatile building block in the synthesis of biologically active molecules and its potential impact on the pharmaceutical and chemical industries.

Purification Methods

Purify the isocyanate by repeated fractionation through an efficient column. If IR indicates that there is too much urea (in the presence of moisture the symmetrical urea is formed), then dissolve it in dry EtOH-free CHCl3, filter, evaporate and distil it. It is a pungent LACHRYMATORY liquid. [See Hardy J Chem Soc 2011 1934, and Hickinbottom Reactions of Organic Compounds Longmans p493 1957.] 4-Fluorophenyl isothiocyanate [1544-68 -9] M 153.2, m 24 -26o, 26 -27o, b 66o/2mm, 2 1 5o/atm, 228o/760mm, n D 1.6116. A likely impurity is the symmetrical thiourea. Dissolve the isothiocyanate in dry CHCl3, filter and distil the residue in a vacuum. It can also be steam distilled, the oily layer is separated, dried over CaCl2 and distilled in vacuo. Bis-(4-fluorophenyl)thiourea has m 145o (from aqueous EtOH). [Browne & Dyson J Chem Soc 3285 1931, Buu Hoi et al. J Chem Soc 1573 1955, Olander Org Synth Coll Vol I 448 1941 ].

InChI:InChI=1/C7H4FNO/c8-6-1-3-7(4-2-6)9-5-10/h1-4H

Upstream product

• 154592-66-2 O-cyclododecyl-N-(4-fluorophenyl)selenocarbamate 
• 154592-72-0 N-(4-fluorophenyl)selenocarbamate of cholestanol 
• 371-40-4 4-fluoroaniline 
• 503-38-8 trichloromethyl chloroformate 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 75-44-5 phosgene 
• 33407-00-0 (4-Fluoro-phenyl)-trimethylsilanyl-amine 
• 16664-09-8 4-fluorobenzoyl azide 
• 456-07-5 4-fluorobenzohydroxamic acid 
• 352-34-1 4-fluoro-1-iodobenzene 
• 456-22-4 4-Fluorobenzoic acid 
• 90172-63-7 1-(p-fluorophenylcarbonyl)imidazole 
• 75-15-0 carbon disulfide 

Downstream Products

• 959-65-9 N-(5-chloro-[2]pyridyl)-N'-(4-fluoro-phenyl)-urea 
• 1766-81-0 1-(4,6-dimethyl-pyrimidin-2-yl)-3-(4-fluoro-phenyl)-urea 
• 1766-60-5 N-(4-fluoro-phenyl)-N'-(5-nitro-[2]pyridyl)-urea 
• 1584-63-0 1-(4-acetylphenyl)-3-(4-fluorophenyl)urea 
• 332-33-2 N'-(4-Fluorophenyl)-N,N-dimethylurea 
• 69123-56-4 1-(4-fluorophenyl)-3-(thiazol-2-yl)urea 
• 16352-54-8 4-[(4-fluoro-phenylcarbamoyloxy)-methyl]-4-methyl-oxazolidine-2-thione 
• 43066-09-7 3-(4-fluoro-phenyl)-6-methyl-[1,3]oxazine-2,4-dione 
• 14162-22-2 1-(2,2-Diethoxy-ethyl)-1-(2-dimethylamino-ethyl)-3-(4-fluoro-phenyl)-urea 
• 30094-82-7 2,2,2-Trimethoxy-5-methyl-2λ⁵-[1,3,2]dioxaphosphole-4-carboxylic acid (4-fluoro-phenyl)-amide 
• 28469-05-8 (4-Fluoro-phenyl)-carbamic acid 5-chloro-2-(4-chloro-phenoxy)-phenyl ester 
• 28386-71-2 (4-Fluoro-phenyl)-carbamic acid 5-chloro-2-(2,4-dichloro-phenoxy)-phenyl ester 
• 28396-01-2 (4-Fluoro-phenyl)-carbamic acid 5-bromo-2-(2,4-dichloro-phenoxy)-phenyl ester 
• 28510-84-1 (4-Fluoro-phenyl)-carbamic acid 5-chloro-2-(2,4,5-trichloro-phenoxy)-phenyl ester 

Relevant articles and documents

Efficient Benzimidazolidinone Synthesis via Rhodium-Catalyzed Double-Decarbonylative C-C Activation/Cycloaddition between Isatins and Isocyanates

The first decarbonylative cycloaddition of less-strained cyclic ketones (isatins) with isocyanates is reported. Initiated by C-C activation, this distinct [5 - 2 + 2] transformation provides a rapid entry to access various benzimidazolidinone derivatives, and a wide range of isocyanates can be efficiently coupled with broad functional group tolerance. A modified one-pot process combining a Curtius rearrangement and C-C activation was also achieved by using acyl azides as the starting materials. A detailed mechanistic study revealed a surprising double-decarbonylative reaction pathway. The novel reactivity discovered in this basic research is expected to shed light on the development of new heterocycle formation methods through C-C/isocyanate coupling.

Electrochemically Enabled Intramolecular Aminooxygenation of Alkynes via Amidyl Radical Cyclization

An electrochemical synthesis of oxazol-2-ones and imidazol-2-ones has been developed via 5-exo-dig cyclization of propargylic carbamates- and ureas-derived amidyl radicals. The electrosynthesis relies on the dual function of 2,2,6,6-tetramethylpiperidin- 1-yl)oxyl (TEMPO) as a redox mediator for amidyl radical formation and an oxygen atom donor. The reactions are conducted under mild conditions using a simple setup and provide convenient access to functionalized oxazol-2-ones and imidazol-2-ones from readily available materials.

DERIVATIVES OF PIPERLONGUMINE AND USES THEREOF

The present invention relates to a group of 1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one (piperlongumine) derivatives, analogs and pharmaceutically acceptable salts thereof. The present invention also relates to a pharmaceutical composition and formulation containing a derivative of piperlongumine; and use of the derivatives and analogs for treating cancer, reducing inflammation and/or treating an autoimmune or inflammatory disease.

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.