383-50-6

Basic information

• Product Name: 2-Fluoroethyl 4-methylbenzenesulfonate
• Synonyms: Fluoroethylp-tosylate;FLUOROETHYL 4-TOLUENESULFONATE;2-FLUOROETHYL TOSYLATE;2-Fluoro-(4-methylbenzenesulfonate)ethanol;L-TRYPTOPHAN/D-TRYPTOPHAN;2-fluoroethyl 4-methylbenzenesulfonate;Fluoroethyl p-toluenesulfonate;4-Methylbenzenesulfonic acid 2-fluoro-ethyl ester
• CAS NO: 383-50-6
• Molecular Formula: C₉H₁₁FO₃S
• Molecular Weight: 218.25
• Mol File: 383-50-6.mol
• Article Data: 78

Chemical Properties

• Boiling Point: 140°C/1mmHg(lit.)
• Flash Point: 156.4 °C
• Appearance: colorless or light-yellow liquid
• Density: 1.241 g/cm³
• Vapor Pressure: 0.000239mmHg at 25°C
• Refractive Index: 1.5060 to 1.5100
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 2-Fluoroethyl 4-methylbenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Fluoroethyl 4-methylbenzenesulfonate(383-50-6)
• EPA Substance Registry System: 2-Fluoroethyl 4-methylbenzenesulfonate(383-50-6)

Safety Data

• Hazardous Substances Data: 383-50-6(Hazardous Substances Data)

Usage

Uses

2-Fluoroethyl Tosylate is an intermediate used in the preparation and pre-clinical evaluation of new class of high-affinity 18F-labeled PSMA ligands for detection of prostate cancer by positron emission tomography (PET) imaging.

InChI:InChI=1/C9H11FO3S/c1-8-2-4-9(5-3-8)14(11,12)13-7-6-10/h2-5H,6-7H2,1H3

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 42772-85-0 2-hydroxyethyl 4-methylbenzenesulfonate 
• 657-83-0 4-methylphenylsulfur trifluoride 
• 1207989-43-2 2-fluoroethyl 4-toluenesulfinate 
• 6315-52-2 1,2-bis-tosyloxyethane 
• 371-62-0 2-fluoroethanol 
• 104-15-4 toluene-4-sulfonic acid 
• 4124-41-8 p-toluenesulfonylanhydride 

Downstream Products

• 505-13-5 fluoro-2 ethylthiocyanate 
• 462-31-7 thioacetic acid-2-fluoroethyl ester 
• 126434-49-9 [1-Fluoro-2-(2-fluoro-ethoxy)-ethyl]-benzene 
• 108270-06-0 N-(benzyloxycarbonyl)-N-(2-fluoroethyl)aniline 
• 97280-21-2 diethyl N-<4-<(2-fluoroethyl)amino>benzoyl>-L-glutamate 
• 286-20-4 cyclohexane-1,2-epoxide 
• 126434-51-3 (1R,2R)-1-Fluoro-2-(2-fluoro-ethoxy)-cyclohexane 
• 130485-84-6 (S)-(-)-1-(2-fluoroethyl)-2-pyrrolidinecarboxamide 
• 134202-60-1 ethyl 1-(2-fluoroethyl)-6-fluoro-4(1H)-oxo-7-(p-tolylthio)pyrido<2,3-c>pyridazine-3-carboxylate 
• 162308-79-4 benzyl(2-fluoroethyl)sulfane 
• 702-18-1 1-Fluor-2-(p-methyl)phenoxyethan 
• 194351-12-7 1-tert-butoxycarbonyl-4-(2-fluoroethyl)-3-oxopiperazine 
• 870997-08-3 7-bromo-2-[2-(2-fluoroethoxy)-4-(3-piperidin-1-ylpropoxy)phenyl]-3-methylquinazolin-4(3H)-one 
• 870997-13-0 2-{4-[(1-cyclobutylpiperidin-4-yl)oxy]phenyl}-7-(2-fluoroethyl)-3-methyl-3,7-dihydropyrido[3,4-d]pyrimidine-4,8-dione 

Relevant articles and documents

Radiosynthesis and preliminary evaluation of an 18F-labeled tubastatin A analog for PET imaging of histone deacetylase 6

Histone deacetylase 6 (HDAC6) is a unique member of the HDAC family because of its characteristics, namely, its cytoplasmic localization and ubiquitin binding. HDAC6 has been implicated in cancer metastasis and neurodegeneration. In the present study, we performed radiosynthesis and biological evaluation of a fluorine-18–labeled ligand [18F]3, which is an analog of the HDAC6-selective inhibitor tubastatin A, for positron emission tomography (PET) imaging. [18F]3 was synthesized by a two-step reaction composed of 18F-fluorination and formation of a hydroxamic acid group. IC50 values of 3 against HDAC1 and HDAC6 activities were 996 nM and 33.1 nM, respectively. A biodistribution study in mice demonstrated low brain uptake of [18F]3. Furthermore, bone radioactivity was stable at around 2% ID/g after injection, suggesting high tolerance to defluorination. Regarding metabolic stability, 70% of the compound was observed as the unchanged form at 30 minutes post injection in mouse plasma. A small animal PET study in mice showed that pretreatment with cyclosporine A had no effect on initial brain uptake of [18F]3, suggesting low brain uptake of [18F]3 was not caused by the P-glycoprotein–mediated efflux. While PET imaging using [18F]3 has a limitation with respect to neurodegenerative diseases, further studies evaluating its utility for certain cancers are worth evaluating.

An unusual substitution reaction directed by an intramolecular re-arrangement

Secondary amines and thiols undertake a substitution reaction on the side chain of 2-bromoethyl-pyridinium derivatives 'directed' by an intramolecular re-arrangement. Experimental investigations strongly indicate that the reaction is initiated by an alpha

Radiosynthesis of [18F]DPA-714, a selective radioligand for imaging the translocator protein (18 kDa) with PET

Recently, a novel series of 2-phenylpyrazolo[1,5-α] pyrimidineacetamides has been reported as selective ligands of the translocator protein (18 kDa). Within this series, DPA-714 (N,N-diethyl-2-(2-(4-(2- fluoroethoxy)phenyl)-5,7-dimethylpyrazolo[1,5-α]pyri

Development of Novel 18F-PET Agents for Tumor Hypoxia Imaging

Tumor hypoxia is a major factor responsible for tumor progression, metastasis, invasion, and treatment resistance, leading to low local tumor control and recurrence after radiotherapy in cancers. Here,18F-positron emission tomography (PET) probes are developed for visualizing viable hypoxic cells in biopsies. Pimonidazole derivatives and nitroimidazole-based agents bearing sulfonyl linkers were evaluated. A small-animal PET study showed that the tumor uptake of [18F]-23 [poly(ethylene glycols) (PEG)-sulfonyl linker] of 3.36 ± 0.29%ID/g was significantly higher (P 0.01) than that of [18F]-20 (piperazine-linker tracer, 2.55 ± 0.49%ID/g) at 2 h postinjection in UPPL tumors. The tumor-to-muscle uptake ratio of [18F]-23 (2.46 ± 0.48 at 2 h pi) was well improved compared with that of [18F]-FMISO (1.25 ± 0.14 at 2 h pi). A comparable distribution pattern was observed between ex vivo autoradiography of [18F]-23 and pimonidazole staining of the neighboring slice, indicating that [18F]-23 is a promising PET agent for hypoxia imaging.

A novel18F-labeled clickable substrate for targeted imaging of SNAP-tag expressing cells by PETin vivo

Bioorthogonal covalent labeling with self-labeling enzymes like SNAP-tag bears a high potential for specific targeting of cells for imagingin vitroand alsoin vivo. To this end, fluorescent SNAP substrates have been established and used in microscopy and fluorescence imaging while radioactive substrates for the highly sensitive and whole-body positron emission tomography (PET) have been lacking. Here, we show for the first time successful and high-contrast PET imaging of subcutaneous SNAP-tag expressing tumor xenografts by bioorthogonal covalent targeting with a novel18F-based radioligandin vivo.