74927-72-3

Basic information

• Product Name: (R)-(-)-N-(3,5-DINITROBENZOYL)-ALPHA-PHENYLGLYCINE
• Synonyms: D-3,5-Dinitrobenzoylphenylglycine;(R)-(-)-N-(3,5-Dinitrobenzoyl)-á-phenylglycine;(R)-(-)-N-(3,5-DINITROBENZOYL) PHENYLGLYCINE 97+%;(2R)-2-[(3,5-DINITROBENZOYL)AMINO]-2-PHENYL-ACETIC ACID;(R)-(-)-N-(3,5-DINITROBENZOYL)-ALFA-PHENYLGLYCINE;Benzeneacetic acid, .alpha.-(3,5-dinitrobenzoyl)amino-, (.alpha.R)-;n-(3,5-dinitrobenzoyl)-d-α-phenylglycine;N-(3,5-dinitrobenzoyl)phenylglycine
• CAS NO: 74927-72-3
• Molecular Formula: C₁₅H₁₁N₃O₇
• Molecular Weight: 345.26
• Product Categories: chiral;Analytical Chemistry;e.e. / Absolute Configuration Determination (NMR);Enantiomer Excess & Absolute Configuration Determination;for Resolution of Bases;Optical Resolution;Synthetic Organic Chemistry
• Mol File: 74927-72-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 217-218 °C (dec.)
• Boiling Point: 480.21°C (rough estimate)
• Flash Point: 298.2 °C
• Appearance: white to light yellow crystal powder
• Density: 1.3660 (rough estimate)
• Vapor Pressure: 8.34E-14mmHg at 25°C
• Refractive Index: -102 ° (C=1, THF)
• Storage Temp.: Store below +30°C.
• BRN: 4719763
• CAS DataBase Reference: (R)-(-)-N-(3,5-DINITROBENZOYL)-ALPHA-PHENYLGLYCINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-N-(3,5-DINITROBENZOYL)-ALPHA-PHENYLGLYCINE(74927-72-3)
• EPA Substance Registry System: (R)-(-)-N-(3,5-DINITROBENZOYL)-ALPHA-PHENYLGLYCINE(74927-72-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 74927-72-3(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

(R)-(-)-N-(3,5-Dinitrobenzoyl)-alpha-phenylglycine

InChI:InChI=1/C15H11N3O7/c19-14(16-13(15(20)21)9-4-2-1-3-5-9)10-6-11(17(22)23)8-12(7-10)18(24)25/h1-8,13H,(H,16,19)(H,20,21)/t13-/m1/s1

Upstream product

• 875-74-1 (R)-phenylglycine 
• 99-33-2 3,5-dinitrobenoyl chloride 
• 2835-06-5 phenylglycin 
• 74958-71-7 (R)-(-)-N-(3,5-dinitrobenzoyl)-α-phenylglycine 

Downstream Products

• 69632-50-4 (R)-(-)-methyl N-(3,5-dinitrobenzoyl)-α-phenylglycinate 
• 1222074-04-5 (S)-(-)-2-(N-propylamino)-5-hydroxytetraline (-)-N-(3,5-dinitrobenzoyl)-α-phenylglycine salt 
• 1258400-16-6 (3S)-7-bromo-2,3-dihydro-1-benzofuran-3-aminium (2R)-{[(3,5-dinitrophenyl)carbonyl]amino}(phenyl)ethanoate 

Relevant articles and documents

Chiral High-Pressure Liquid Chromatographic Stationary Phases. 3. General Resolution of Arylalkylcarbinols

Enantiomers of arylalkylcarbinols (1) may be separated by chromatography upon a stationary phase comprised of chiral N-(3,5-dinitrobenzoyl)phenylglycine ionically bonded to γ-aminopropyl silanized silica.The order of elution of the enantiomers is related to the absolute configuration by a chiral recognition model.Hence, absolute configurations as well as enantiomeric purity can be conveniently determined on as little as nanogram quantities of carbinol.Alternatively, preparative separations can be performed upon the chiral phase, the scale being dictated by the column size.A convenient in situ method for preparation of efficient high-pressure liquid chromatography (HPLC) columns of this type is described.

Development of new HPLC chiral stationary phases based on native and derivatized cyclofructans

An unusual class of chiral selectors, cyclofructans, is introduced for the first time as bonded chiral stationary phases. Compared to native cyclofructans (CFs), which have rather limited capabilities as chiral selectors, aliphatic-and aromatic-functionalized CF6s possess unique and very different enantiomeric selectivities. Indeed, they are shown to separate a very broad range of racemic compounds. In particular, aliphatic-derivatized CF6s with a low substitution degree baseline separate all tested chiral primary amines. It appears that partial derivatization on the CF6 molecule disrupts the molecular internal hydrogen bonding, thereby making the core of the molecule more accessible. In contrast, highly aromaticfunctionalized CF6 stationary phases lose most of the enantioselective capabilities toward primary amines, however they gain broad selectivity for most other types of analytes. This class of stationary phases also demonstrates high "loadability" and therefore has great potential for preparative separations. The variations in enantiomeric selectivity often can be correlated with distinct structural features of the selector. The separations occur predominantly in the presence of organic solvents.

Chiral permselectivity in nanoporous opal films surface-modified with chiral selector moieties

The chiral permselectivity in thin opal films modified on the silica surface with chiral selector moieties was studied as a function of opal film geometry, supporting electrolyte concentration, solvent polarity, and chiral selector and linker structure. While opal film thickness, supporting electrolyte concentration and linker length and structure did not have a significant influence on the chiral permselectivity, the nanopore size, solvent polarity and selector structure had a pronounced effect. These observations are in agreement with the chiral selectivity mechanism in the opal films in which the permeating enantiomers are transported with different rates through the surface utilizing non-covalent interactions between the chiral permeant molecules and surface-bound chiral selectors. The chiral selectivity (transport rate ratio for S and R enantiomers) achieved in the present study was 4.5, which is one of the highest reported for chiral membranes. The Royal Society of Chemistry 2007.