69632-32-2

Basic information

• Product Name: (R)-(-)-N-(3,5-DINITROBENZOYL)-ALPHA-PHENYLETHYLAMINE
• Synonyms: N-(3,5-dinitrobenzoyl)-alpha-methylbenzylamine;(-)-N-[(R)-α-Methylbenzyl]-3,5-dinitrobenzamide;N-[(1R)-1-Phenylethyl]-3,5-dinitrobenzamide;N-[(R)-1-Phenylethyl]-3,5-dinitrobenzamide;(R)-(-)-3,5-Dinitro-N-(1-phenylethyl)benzamide 98%;3,5-DINITRO-N-(1-PHENYLETHYL)BENZAMIDE;(R)-(-)-N-(3,5-DINITROBENZOYL) 1-PHENYLETHYALMINE;(R)-N-(3,5-DINITROBENZOYL)-1-PHENYLETHYLAMINE
• CAS NO: 69632-32-2
• Molecular Formula: C₁₅H₁₃N₃O₅
• Molecular Weight: 315.28
• Product Categories: e.e. / Absolute Configuration Determination (NMR);Enantiomer Excess & Absolute Configuration Determination;Analytical Chemistry
• Mol File: 69632-32-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: 158-161 °C(lit.)
• Boiling Point: 482.9°C at 760 mmHg
• Flash Point: 245.8°C
• Appearance: Off-white to pale yellow/Crystalline
• Density: 1.362g/cm³
• Vapor Pressure: 1.76E-09mmHg at 25°C
• Refractive Index: 1.627
• Solubility: almost transparency in Acetone
• PKA: 12.27±0.46(Predicted)
• BRN: 4268701
• CAS DataBase Reference: (R)-(-)-N-(3,5-DINITROBENZOYL)-ALPHA-PHENYLETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-N-(3,5-DINITROBENZOYL)-ALPHA-PHENYLETHYLAMINE(69632-32-2)
• EPA Substance Registry System: (R)-(-)-N-(3,5-DINITROBENZOYL)-ALPHA-PHENYLETHYLAMINE(69632-32-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 69632-32-2(Hazardous Substances Data)

Usage

Description

(R)-(-)-N-(3,5-DINITROBENZOYL)-ALPHA-PHENYLETHYLAMINE, also known as (R)-(?)-3,5-Dinitro-N-(1-phenylethyl)benzamide, is a chiral derivatizing agent used for converting enantiomers into diastereoisomers. This organic compound exhibits antiviral properties, particularly against the Hepatitis C virus (HCV) and other viral infections.

Uses

Used in Chiral Analysis:
(R)-(-)-N-(3,5-DINITROBENZOYL)-ALPHA-PHENYLETHYLAMINE is used as an NMR chiral shift reagent for determining the configuration of enantiomers in various chemical and pharmaceutical applications. Its ability to differentiate between enantiomers makes it a valuable tool in the field of stereochemistry.
Used in Standardization:
In the field of thermodynamics, (R)-(-)-N-(3,5-DINITROBENZOYL)-ALPHA-PHENYLETHYLAMINE is used as a standard for determining its standard molar enthalpy of combustion and formation using an isoperibolic micro-combustion calorimeter. This helps in the accurate measurement of energy changes during chemical reactions.
Used in Antiviral Applications:
(R)-(-)-N-(3,5-DINITROBENZOYL)-ALPHA-PHENYLETHYLAMINE is used as an antiviral agent for inhibiting the replication of the Hepatitis C virus (HCV) and other viral infections. Its effectiveness in combating viral replication makes it a potential candidate for the development of new antiviral drugs.
Used in Pharmaceutical Industry:
(R)-(-)-N-(3,5-DINITROBENZOYL)-ALPHA-PHENYLETHYLAMINE is used as a key intermediate in the synthesis of various pharmaceutical compounds, particularly those targeting viral infections. Its unique properties and reactivity contribute to the development of novel therapeutic agents.

InChI:InChI=1/C15H13N3O5/c1-10(11-5-3-2-4-6-11)16-15(19)12-7-13(17(20)21)9-14(8-12)18(22)23/h2-10H,1H3,(H,16,19)/t10-/m1/s1

Upstream product

• 3886-69-9 (+)-1-phenylethylamine 
• 99-33-2 3,5-dinitrobenoyl chloride 
• 118355-06-9 C₁₆H₁₈N₃OP 
• 14402-00-7 N-(3,5-dinitrobenzoyl)-1-phenylethanamine 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 99-34-3 3,5-dinitrobenzoic acid 
• 2627-86-3 (-)-α-methylbenzylamine 

Relevant articles and documents

A CONVENIENT FAMILY OF CHIRAL SHIFT REAGENTS FOR MEASUREMENT OF ENANTIOMERIC EXCESSES OF SULFOXIDES

(R)(-)-N-(3,5-dinitrobenzoyl)-α-phenylethylamine is a good chiral shift reagent for sulfoxides such as Ar-(SO)-CH3 (Ar=substituted phenyl, naphtyl) or R-(SO)-CH3 (R=t-Bu,Cyclohexyl,n-Octyl). 1-Naphthyl propyl sulfoxide was also successfully resolved.The s

Preparation of two new diasteromeric chiral stationary phases based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid and (R)- or (S)-1-(1-naphthyl)ethylamine and chiral tethering group effect on the chiral recognition

Two new diastereomeric chiral stationary phases (CSPs) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid as a chiral tethering group and a Π-basic chiral unit such as (R)-1-(1-naphthyl) ethylamine (CSP 1) or (S)-1-(1-naphthyl)ethylamine (CSP 2) were prepared. The two CSPs were applied to the enantiomeric separation of N-(3,5-dinitrobenzoyl)-1-phenylalkylamines and N-(3,5-dinitrobenzoyl)-α-amino acid derivatives using 20% isopropyl alcohol in hexane as a normal mobile phase. To elucidate the effect of the two chiral units on the chiral recognition, the chiral recognition abilities of the two CSPs were compared with each other and with that of a CSP (CSP 3) based on (R)-1-(1-naphthyl)ethylamine. From the chromatographic chiral recognition results, (R)-1-(1-naphthyl)ethylamine and (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid constituting CSP 1 were concluded to show a cooperative ("matched") effect on the chiral recognition while (S)-1-(1-naphthyl)ethylamine and (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid constituting CSP 2 were concluded to show an uncooperative ("mismatched") effect on the chiral recognition. From these results, it was concluded that (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid can be successfully used as a chiral tethering group for the preparation of new CSPs.

Thiolates chemically induce redox activation of BTZ043 and related potent nitroaromatic anti-tuberculosis agents

The development of multidrug resistant (MDR) and extensively drug resistant (XDR) forms of tuberculosis (TB) has stimulated research efforts globally to expand the new drug pipeline. Nitroaromatic compounds, including 1,3-benzothiazin-4-ones (BTZs) and related agents, are a promising new class for the treatment of TB. Research has shown that the nitroso intermediates of BTZs that are generated in vivo cause suicide inhibition of decaprenylphosphoryl- β-d-ribose 2′ oxidase (DprE1), which is responsible for cell wall arabinogalactan biosynthesis. We have designed and synthesized novel anti-TB agents inspired from BTZs and other nitroaromatic compounds. Computational studies indicated that the unsubstituted aromatic carbons of BTZ043 and related nitroaromatic compounds are the most electron-deficient and might be prone to nucleophilic attack. Our chemical studies on BTZ043 and the additional nitroaromatic compounds synthesized by us and others confirmed the postulated reactivity. The results indicate that nucleophiles such as thiolates, cyanide, and hydride induce nonenzymatic reduction of the nitro groups present in these compounds to the corresponding nitroso intermediates by addition at the unsubstituted electron-deficient aromatic carbon present in these compounds. Furthermore, we demonstrate here that these compounds are good candidates for the classical von Richter reaction. These chemical studies offer an alternate hypothesis for the mechanism of action of nitroaromatic anti-TB agents, in that the cysteine thiol(ate) or a hydride source at the active site of DprE1 may trigger the reduction of the nitro groups in a manner similar to the von Richter reaction to the nitroso intermediates, to initiate the inhibition of DprE1.