53526-74-2

Basic information

• Product Name: 2,3,4,5,6-PENTAFLUOROBENZYL CHLOROFORMATE
• Synonyms: PENTAFLUOROBENZYL CHLOROFORMATE;2,3,4,5,6-PENTAFLUOROBENZYL CHLOROFORMATE;Pentafluorobenzyl chloroformate 97%;Pentafluorobenzylchloroformate97%
• CAS NO: 53526-74-2
• Molecular Formula: C₈H₂ClF₅O₂
• Molecular Weight: 260.55
• Mol File: 53526-74-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 116°C 20mm
• Flash Point: 79.6°C
• Appearance: /
• Density: 1.647g/cm³
• Vapor Pressure: 0.426mmHg at 25°C
• Refractive Index: 1.444
• CAS DataBase Reference: 2,3,4,5,6-PENTAFLUOROBENZYL CHLOROFORMATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,5,6-PENTAFLUOROBENZYL CHLOROFORMATE(53526-74-2)
• EPA Substance Registry System: 2,3,4,5,6-PENTAFLUOROBENZYL CHLOROFORMATE(53526-74-2)

Safety Data

• Hazard Codes: Xi,T,C
• Statements: 36/37/38
• Safety Statements: 3/7-9-23-36/37/39
• HazardClass: TOXIC, CORROSIVE
• Hazardous Substances Data: 53526-74-2(Hazardous Substances Data)

Usage

General Description

2,3,4,5,6-Pentafluorobenzyl chloroformate is a chemical compound with the formula C8H2ClF5O2. It is a chloroformate ester that is commonly used as a reagent in organic synthesis, particularly in the creation of new pharmaceutical compounds. 2,3,4,5,6-PENTAFLUOROBENZYL CHLOROFORMATE is a clear, colorless liquid that is highly reactive and has a strong odor. It is often used as a protecting group for alcohols and amines during the synthesis of complex organic molecules. 2,3,4,5,6-Pentafluorobenzyl chloroformate is known for its ability to selectively react with hydroxyl and amino groups, making it a valuable tool in the field of organic chemistry.

InChI:InChI=1/C8H2ClF5O2/c9-8(15)16-7(14)2-1-3(10)5(12)6(13)4(2)11/h1,7H

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 440-60-8 (2,3,4,5,6-pentafluorophenyl)methanol 
• 75-44-5 phosgene 

Downstream Products

• 133230-76-9 (2,3,4,5,6-pentafluorobenzyloxycarbonyl)-L-phenylalanyl-L-histidine methyl ester 
• 133230-87-2 (2,3,4,5,6-pentafluorobenzyloxycarbonyl)-L-phenylalanyl-L-histdine 
• 133230-68-9 (2,3,4,5,6-pentafluorobenzyloxycarbonyl)-L-Phe-OH 
• 125489-16-9 pentafluorobenzyl (N,N-isopropyl-p-chlorobenzyl)carbamate 
• 125489-18-1 pentafluorobenzyl-N-isopropylanilate 
• 125489-17-0 pentafluorobenzyl (N,N-isopropyl-p-chlorophenyl)carbamate 
• 1363443-04-2 C₁₃H₁₀F₅NO₄ 
• 1363443-02-0 C₁₃H₉ClF₅NO₃ 

Relevant articles and documents

Three-Component Aminoarylation of Electron-Rich Alkenes by Merging Photoredox with Nickel Catalysis

A three-component 1,2-aminoarylation of vinyl ethers, enamides, ene-carbamates and vinyl thioethers by synergistic photoredox and nickel catalysis is reported. 2,2,2-Trifluoroethoxy carbonyl protected α-amino-oxy acids are used as amidyl radical precursors. anti-Markovnikov addition of the amidyl radical to the alkene and Ni-mediated radical/transition metal cross over lead to the corresponding 1,2-aminoarylation product. The radical cascade, which can be conducted under practical and mild conditions, features high functional group tolerance and broad substrate scope. Stereoselective 1,2-aminoarylation is achieved using a L-(+)-lactic acid derived vinyl ether as the substrate, offering a novel route for the preparation of protected enantiopure α-arylated β-amino alcohols. In addition, 1,2-aminoacylation of vinyl ethers is achieved by using an acyl succinimide as the electrophile for the Ni-mediated radical coupling.

(S)-(-)-N-(Pentafluorobenzylcarbamoyl)prolyl chloride: A chiral derivatisation reagent designed for gas chromatography/negative ion chemical ionisation mass spectrometry of amino compounds

RATIONALE The synthesis of a novel chiral derivatisation reagent, (S)-(-)-N-(pentafluorobenzylcarbamoyl)prolyl chloride is described which is preferably useful for negative-ion chemical ionisation mass spectrometry. METHODS Preparation of the reagent followed a general strategy used to prepare enantioselective reagents based on the N-substitution of L-proline. Pentafluorobenzyl chloroformate smoothly reacted with L-proline to give the desired derivatisation reagent after conversion into the acyl chloride. The product was sufficiently pure to be used in the following steps without any additional purification. RESULTS The reagent was tested against selected chiral and non-chiral analytical targets. Chromatographic enantioseparation was at least equal to the commonly used (S)-(-)-N-(heptafluorobutyryl)prolyl derivatives. The derivatives exhibit excellent mass spectral properties under negative ion chemical ionisation, i.e. reduced fragmentation and thus high ion current for the targeted m/z during analysis. With electron ionisation, the fragmentation that occurs is mainly directed by the introduced group. Enantioseparation with gas chromatography/negative-ion chemical ionisation mass spectrometry of the derivatives was demonstrated for the enantiomers of amphetamine, α-aminocaprylic acid methyl ester and threo-methylphenidate. CONCLUSIONS The new derivatisation reagent shows highly improved mass spectral properties for negative-ion chemical ionisation mass spectrometry and is thus suitable for sensitive chiral detection of amino compounds. The reagent extends the applicability of dissociative resonance electron capture using pentafluorobenzyl derivatives to chiral analysis. Copyright

SYNTHESIS OF NITROGEN ANALOGS OF PHENVALERATE

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