6948-72-7

Basic information

• Product Name: 2-(4-NITROPHENYL)-ETHYLTOSYLATE
• Synonyms: 2-(4-NITROPHENYL)-ETHYLTOSYLATE
• CAS NO: 6948-72-7
• Molecular Formula: C₁₅H₁₅NO₅S
• Molecular Weight: 321.35
• Mol File: 6948-72-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 508.8 ºC at 760 mmHg
• Flash Point: 261.5ºC
• Appearance: /
• Density: 1.322 g/cm³
• Vapor Pressure: 5.74E-10mmHg at 25°C
• Refractive Index: 1.589
• CAS DataBase Reference: 2-(4-NITROPHENYL)-ETHYLTOSYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-NITROPHENYL)-ETHYLTOSYLATE(6948-72-7)
• EPA Substance Registry System: 2-(4-NITROPHENYL)-ETHYLTOSYLATE(6948-72-7)

Safety Data

• Hazardous Substances Data: 6948-72-7(Hazardous Substances Data)

Usage

Structure

Tosylate ester derivative of 4-nitrophenethylamine

Use

+ Protecting group for amines
+ Reagent for the synthesis of complex organic molecules

Properties

+ Strong electrophilic
+ Useful in the formation of carbon-carbon and carbon-nitrogen bonds in organic synthesis

Physical form

Pale yellow to brown solid

Stability

Stable and relatively non-reactive under normal conditions

InChI:InChI=1/C15H15NO5S/c1-12-2-8-15(9-3-12)22(19,20)21-11-10-13-4-6-14(7-5-13)16(17)18/h2-9H,10-11H2,1H3

Upstream product

• 100-27-6 2-(4-nitrophenyl)ethanol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 37043-94-0 N-(4-nitro-phenethyl)-p-toluidine 
• 104-15-4 toluene-4-sulfonic acid 
• 19904-92-8 4-methoxy-N-(4-nitrophenethyl)aniline 
• 841-19-0 N-phenyl-4-nitrophenethylamine 
• 104-30-3 2-(4-nitrophenyl)ethyl acetate 
• 176090-64-5 6-[3-[N-methoxyethyl-N-[2-(4-nitrophenyl)ethyl]amino]propyl]-1,3-dimethyl-2,4(1H,3H)pyrimidinedione 
• 176090-62-3 1,3-dimethyl-6-[3-[N-[2-(4-nitrophenyl)ethyl]amino]propyl]-2,4(1H,3H)pyrimidinedione 
• 210158-20-6 4-[2-(4-nitro-phenyl)-ethyl]-morpholine 

Relevant articles and documents

Improved synthesis of the bifunctional chelator p-SCN-Bn-HOPO

The bifunctional ligand p-SCN-Bn-HOPO, which has four 1,2-hydroxypyridinone groups on a spermine backbone with an isothiocyanate linker, has been shown to be an efficient and stable chelator for Zr(iv) and, more importantly, the radioisotope 89Zr for use in radiolabeling antibodies for positron emission tomography (PET) imaging. Previous studies of 89Zr-HOPO-trastuzumab in mice showed low background, good tumor to organ contrast, and very low bone uptake which show p-SCN-Bn-HOPO to be an important next-generation bifunctional chelator for radioimmunoPET imaging with 89Zr. However, the reported synthesis of p-SCN-Bn-HOPO involves nine steps and multiple HPLC purifications with an overall yield of about 1.4%. Herein we report an improved and efficient synthesis of p-SCN-Bn-HOPO in four steps with 14.3% overall yield which will improve its availability for further biological studies and wider application in PET imaging. The new synthetic route also allows variation in linker length and chemistries which may be helpful in modifying in vivo clearance behaviors of future agents.

COMPOUNDS

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