393-52-2

Basic information

• Product Name: 2-Fluorobenzoyl chloride
• Synonyms: 2-Fluorbenzoylchlorid;2-Fluorobenzoyl chlo;2-Fluorobenzoyl chloride, 97% 100ML;2-Fluorobenzoyl chloride, 97% 25ML;2-Fluorobenzenecarbonyl Chloride;NSC 88304;2-Fluorobenzoyl;Orthofluorine benzoyl chloride
• CAS NO: 393-52-2
• Molecular Formula: C₇H₄ClFO
• Molecular Weight: 158.56
• EINECS: 206-887-2
• Product Categories: Aromatics;Miscellaneous Reagents;Acid Halides;Aryl Fluorinated Building Blocks;Building Blocks;C7;Carbonyl Compounds;Chemical Synthesis;Fluorinated Building Blocks;Organic Building Blocks;Organic Fluorinated Building Blocks;Other Fluorinated Organic Building Blocks;Fluorobenzene;Acid Halides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 393-52-2.mol

Chemical Properties

• Melting Point: 4 °C(lit.)
• Boiling Point: 90-92 °C15 mm Hg(lit.)
• Flash Point: 180 °F
• Appearance: Clear colorless to faintly colored/Liquid
• Density: 1.328 g/mL at 25 °C(lit.)
• Vapor Pressure: 8.22E-06mmHg at 25°C
• Refractive Index: n20/D 1.536(lit.)
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: Chloroform (Slightly)
• Water Solubility: Decomposition
• Sensitive: Lachrymatory
• BRN: 636864
• CAS DataBase Reference: 2-Fluorobenzoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Fluorobenzoyl chloride(393-52-2)
• EPA Substance Registry System: 2-Fluorobenzoyl chloride(393-52-2)

Safety Data

• Hazard Codes: C
• Statements: 34-37-36/37-14
• Safety Statements: 26-36/37/39-45-28A-27
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• RTECS: DM6640000
• F: 10-19-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 393-52-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-Fluorobenzoyl chloride is used as a synthetic intermediate for the preparation of various organic compounds. Its unique reactivity, due to the presence of the fluorine atom, makes it a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in the Preparation of 3-(N-Hydroxycarbamimidoyl)-benzoic Acid Methyl Ester:
2-Fluorobenzoyl chloride is utilized in the synthesis of 3-(N-Hydroxycarbamimidoyl)-benzoic acid methyl ester, a compound that may have potential applications in medicinal chemistry and drug development.
Used in Hollow-Fiber Liquid Phase Microextraction with In Situ Derivatization Method:
2-Fluorobenzoyl chloride has been employed in the development of a hollow-fiber liquid phase microextraction with in situ derivatization method coupled with HPLC-UV. This technique is used for the determination of metformin hydrochloride in biological fluids, providing a sensitive and efficient analytical approach for the detection and quantification of this important pharmaceutical compound.

Air & Water Reactions

Decomposes in water to form HCl with generation of heat

Reactivity Profile

2-Fluorobenzoyl chloride is sensitive to moisture. Incompatible with water, alcohol, bases (including amines) and with oxidizing agents . May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].

Fire Hazard

2-Fluorobenzoyl chloride is combustible.

InChI:InChI:1S/C7H4ClFO/c8-7(10)5-3-1-2-4-6(5)9/h1-4H

Upstream product

• 320-11-6 1-(tert-butyl)-2-fluorobenzene 
• 69038-73-9 2-flourobenzoic acid tert-butyl 
• 3416-93-1 2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline 
• 445-29-4 o-fluoro-benzoic acid 
• 10026-13-8 phosphorus pentachloride 
• 108-95-2 phenol 
• 79-37-8 oxalyl dichloride 
• 724-37-8 2-fluoro-N-(phenylmethyl)benzamide 

Downstream Products

• 1978-64-9 (2-fluorophenyl)(morpholino)methanone 
• 784-65-6 2-fluoro-N-(4-chlorophenyl)benzamide 
• 66938-29-2 (2-fluorophenyl)(4-methoxyphenyl)methanone 
• 342-25-6 2,4'-difluorobenzophenone 
• 369-72-2 2-fluoro-benzoic acid-(3-fluoro-anilide) 
• 1494-54-8 4'-ethyl-2-fluoro-benzophenone 
• 436-44-2 2'-fluoro-2,3,5,6-tetramethyl-benzophenone 
• 7609-76-9 (1R:2S)-2-[methyl-(2-fluoro-benzoyl)-amino]-1-phenyl-propanol 
• 386-31-2 2-fluoro-benzoic acid-(5-amino-9,10-dioxo-9,10-dihydro-[1]anthrylamide) 
• 7609-76-9 (1S:2S)-2-[methyl-(2-fluoro-benzoyl)-amino]-1-phenyl-propanol-⁽¹⁾ 
• 575-77-9 2-fluoro-benzoic acid phenacylamide 
• 427-24-7 diphenyl-ortho-fluorophenyl-methanol 
• 803-94-1 1,4-bis-(2-fluoro-benzoylamino)-benzene 
• 388-90-9 2-fluoro-benzoic acid-(4-phenylazo-[1]naphthylamide) 

Relevant articles and documents

The smart 2-(2-fluorobenzoyl)-n-(2-methoxyphenyl)hydrazinecarbothioamide functionalized as Ni(II) sensor in micromolar concentration level and its application in live cell imaging

In recent years, fluorescent probes for the detection of environmentally and biologically important metal cations have received extensive attention for designing and development of fluorescent chemosensors. Herein, we report the photophysical results of 2

Pyrido[2,3-b][1,5]benzoxazepin-5(6H)-one derivatives as CDK8 inhibitors

CDK8 is a cyclin-dependent kinase that forms part of the mediator complex, and modulates the transcriptional output from distinct transcription factors involved in oncogenic control. Overexpression of CDK8 has been observed in various cancers, representing a potential target for developing novel CDK8 inhibitors in cancer therapeutics. In the course of our investigations to discover new CDK8 inhibitors, we designed and synthesized tricyclic pyrido[2,3-b][1,5]benzoxazepin-5(6H)-one derivatives, by introduction of chemical complexity in the multi-kinase inhibitor Sorafenib taking into account the flexibility of the P-loop motif of CDK8 protein observed after analysis of structural information of co-crystallized CDK8 inhibitors. In vitro evaluation of the inhibitory activity of the prepared compounds against CDK8 led us to identify compound 2 as the most potent inhibitor of the series (IC50 = 8.25 nM). Co-crystal studies and the remarkable selectivity profile of compound 2 are presented. Compound 2 showed moderate reduction of phosphorylation of CDK8 substrate STAT1 in cells, in line with other reported Type II CDK8 inhibitors. We propose herein an alternative to find a potential therapeutic use for this chemical series.

Imidazo[4,5-c]pyridine derivative and application thereof

The invention relates to a novel imidazo[4,5-c]pyridine derivative represented by a general formula I, and pharmaceutically acceptable salts, solvates or prodrugs of the novel imidazo[4,5-c]pyridine derivative, wherein the substituent R and R' are defined as in the specification. The invention also relates to an effect of the compound represented by the general formula I in inhibiting an NS5B RNA-dependent RNA polymerase (NS5B polymerase for short) which is necessary in a replication process of hepatitis c virus, also relates to an application of the compound, and pharmaceutically acceptable salts, hydrates or prodrugs of the compound in preparation of medicines for treating viral diseases, and especially relates to an application in preparation of medicines for treating and/or preventinghepatitis c.

Design and synthesis of arylamidine derivatives as serotonin/norepinephrine dual reuptake inhibitors

To improve the in vivo antidepressant activity of previously reported serotonin (5-HT) and norepinephrine (NE) dual reuptake inhibitors, three series of arylamidine derivatives were designed and synthesized. The in vitro 5-HT and NE reuptake inhibitory activities of these compounds were evaluated, and compound II-5 was identified as the most potent 5-HT (IC50 = 620 nM) and NE (IC50 = 10 nM) dual reuptake inhibitor. Compound II-5 exhibited potent antidepressant activity in the rat tail suspension test and showed an acceptable safety profile in a preliminary acute toxicity test in mice. Our results show that these arylamidine derivatives exhibit potent 5-HT/NE dual reuptake inhibition and should be explored further as antidepressant drug candidates.

Optimization of a 1,3,4-oxadiazole series for inhibition of Ca2+/calmodulin-stimulated activity of adenylyl cyclases 1 and 8 for the treatment of chronic pain

Adenylyl cyclases type 1 (AC1) and 8 (AC8) are group 1 transmembrane adenylyl cyclases (AC) that are stimulated by Ca2+/calmodulin. Studies have shown that mice depleted of AC1 have attenuated inflammatory pain response, while AC1/AC8 double-knockout mice display both attenuated pain response and opioid dependence. Thus, AC1 has emerged as a promising new target for treating chronic pain and opioid abuse. We discovered that the 1,3,4-oxadiazole scaffold inhibits Ca2+/calmodulin-stimulated cyclic adenosine 3‘,5‘-monophosphate (cAMP) production in cells stably expressing either AC1 or AC8. We then carried out structure-activity relationship studies, in which we designed and synthesized 65 analogs, to modulate potency and selectivity versus each AC isoform in cells. Furthermore, molecular docking of the analogs into an AC1 homology model suggests the molecules may bind at the ATP binding site. Finally, a prioritized analog was tested in a mouse model of inflammatory pain and exhibited modest analgesic properties. In summary, our data indicate the 1,3,4-oxadiazoles represent a novel scaffold for the cellular inhibition of Ca2+/calmodulin-stimulated AC1- and AC8 cAMP and warrant further exploration as potential lead compounds for the treatment of chronic inflammatory pain.

CoIII-Catalyzed Isonitrile Insertion/Acyl Group Migration Between C?H and N?H bonds of Arylamides

A general efficient and site-selective cobalt-catalyzed insertion of isonitrile into C?H and N?H bonds of arylamides through C?H bond activation and alcohol assisted intramolecular trans-amidation is demonstrated. This straightforward approach overcomes the limitation by the presence of strongly chelating groups. Isolation of CoIII-isonitrile complex B has been achieved for the first time to understand the reaction mechanism.

Novel quinazoline derivatives bearing various 6-benzamide moieties as highly selective and potent EGFR inhibitors

A series of novel quinazoline derivatives bearing various C-6 benzamide substituents were synthesized and evaluated as EGFR inhibitors, and most showed significant inhibitory potency against EGFR kinase. In particular, compound 6g possessed potent inhibitory activity against EGFR wild-type (IC50 = 5 nM), and strong antiproliferative activity against HCC827 and Ba/F3 (L858R) cell lines. Kinase profiling against a panel of 365 kinases showed that 6g was highly selective for EGFR. Furthermore, 6g showed desirable properties in assays of liver microsome metabolic stability and cytochromes P450 inhibition and preliminary pharmacokinetic study. The overall attractive profile of 6g made it an interesting compound for further development.

Synthesis and enzyme inhibitory kinetics of some novel 3-(substituted benzoyl)-2-thioxoimidazolidin-4-one derivatives as α-glucosidase/α-amylase inhibitors

The present work describes an efficient and convenient synthesis of a library of novel 3-(substituted benzoyl)-2-thioxoimidazolidin-4-ones (3a–j). The benzoyl isothiocyanates were treated with glycine in the presence of pyridine, the reactants got consumed giving a variety of thioxoimidazolidin-4-ones derivatives under mild reaction conditions. The structures of the compounds were determined by elemental analysis, FTIR, 1H, 13C NMR and mass spectral data. The title compounds were tested for their potential to inhibit the activity of enzymes α-glucosidase and α-amylase. It was found that most of the derivatives showed good enzyme inhibitory activity while compound 3j exhibited excellent activity with IC50 values 0.051 and 0.0082 mM for α-glucosidase and α-amylase, respectively. The presence of 3,5-di-NO2 functional groups at aromatic ring in compound 3j play important role in enzyme inhibitory activity. The enzyme inhibitory kinetic analysis of the most potent derivative 3j revealed that it is a mixed type inhibitor of α-glucosidase with Ki and Ki? values 0.0339 and 0.1562 mM, respectively. It was further investigated that compound 3j formed reversible enzyme inhibitor complex with α-glucosidase. The cytotoxicity of all the synthesized compounds was also evaluated and results showed that none of these compounds displayed toxicity against brine shrimps. Based upon results, it is suggested that compound 3j may act as a lead structure for the development of most potent α-glucosidase inhibitors.

Design, synthesis, structure-activity relationships study and X-ray crystallography of 3-substituted-indolin-2-one-5-carboxamide derivatives as PAK4 inhibitors

We have previously described the identification of indolin-2-one-5-carboxamides as potent PAK4 inhibitors. This study expands the structure-activity relationships on our original series by presenting several modifications in the lead compounds, 2 and 3. A series of novel derivatives was designed, synthesized, and evaluated in biochemical and cellular assay. Most of this series displayed nanomolar biochemical activity and potent antiproliferative activity against A549 and HCT116 cells. The representative compound 10a exhibited excellent enzyme inhibition (PAK4 IC50 = 25 nM) and cellular potency (A549 IC50 = 0.58 μM, HCT116 IC50 = 0.095 μM). An X-ray structure of compound 10a bound to PAK4 was obtained. Crystallographic analysis confirmed predictions from molecular modeling and helped refine SAR results. In addition, Compound 10a displayed focused multi-targeted kinase inhibition, good calculated drug-likeness properties. Further profiling of compound 10a revealed it showed weak inhibitory activity against various isoforms of human cytochrome P450.

Nickel(ii)-catalyzed tandem C(sp2)-H bond activation and annulation of arenes with gem-dibromoalkenes

A nickel(ii)/silver(i)-catalyzed tandem C(sp2)-H activation and intramolecular annulation of arenes with dibromoalkenes has been successfully achieved, which offers an efficient approach to the 3-methyleneisoindolin-1-one scaffold. Attractive features of this system include its low cost, ease of operation, and its ability to access a wide range of isoindolinones.