583-47-1

Basic information

• Product Name: 4-benzyloxazolidine-2,5-dione
• Synonyms: 4-benzyloxazolidine-2,5-dione;4-Benzyl-2,5-oxazolidinedione;4-(benzyl)oxazolidine-2,5-quinone;4-(phenylmethyl)-1,3-oxazolidine-2,5-dione;DL-Phenylalanine N-carboxy anhydride;N-Carboxyl-DL-phenylalanine anhydride;NSC 36252
• CAS NO: 583-47-1
• Molecular Formula: C₁₀H₉NO₃
• Molecular Weight: 191.18336
• EINECS: 209-503-1
• Mol File: 583-47-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 128 °C (decomp)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.299g/cm³
• Refractive Index: 1.569
• Storage Temp.: 2-8°C
• PKA: 9.32±0.40(Predicted)
• CAS DataBase Reference: 4-benzyloxazolidine-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 4-benzyloxazolidine-2,5-dione(583-47-1)
• EPA Substance Registry System: 4-benzyloxazolidine-2,5-dione(583-47-1)

Safety Data

• Hazardous Substances Data: 583-47-1(Hazardous Substances Data)

Usage

General Description

4-benzyloxazolidine-2,5-dione, also known as benzyl oxazolidine-2,5-dione, is a chemical compound commonly used as a reagent in organic synthesis. It is a white crystalline solid with the molecular formula C10H9NO3 and a molecular weight of 191.18 g/mol. 4-benzyloxazolidine-2,5-dione is a cyclic urethane derivative and is typically utilized in the preparation of various pharmaceuticals, agrochemicals, and other fine chemicals. It is known for its ability to undergo various reactions such as ring opening and acylation, making it a versatile building block for the synthesis of complex organic molecules. 4-benzyloxazolidine-2,5-dione is an important reagent in the field of organic chemistry and is widely used in research and industrial applications.

InChI:InChI=1/C10H9NO3/c12-9-8(11-10(13)14-9)6-7-4-2-1-3-5-7/h1-5,8H,6H2,(H,11,13)

Upstream product

• 150-30-1 Phenylalanine 
• 79-22-1 methyl chloroformate 
• 37534-65-9 D-2-carbamoylamino-3-phenylpropionic acid 
• 124-38-9 carbon dioxide 
• 7497-12-3 bis(2,4-dinitrophenyl) carbonate 
• 5070-13-3 bis-(p-nitrophenyl) carbonate 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 23338-68-3 β-phenylalanine sodium salt 
• 63-91-2 L-phenylalanine 
• 75-44-5 phosgene 
• 1213763-83-7 S-benzyltetrahydrothiophenium phenylalanine salt 
• 1213763-81-5 butyl-triphenylphosphonium phenylalanine salt 
• 133565-25-0 phenylalanine, tetrabutylammonium carboxylate salt 
• 63-91-2 L-phenylalanine 

Downstream Products

• 92008-08-7 C₁₃H₂₀N₂O₂ 
• 14348-35-7 2-Amino-N-{2-[2-(2-amino-3-phenyl-propionylamino)-ethyldisulfanyl]-ethyl}-3-phenyl-propionamide 
• 103676-09-1 2-amino-N-benzyl-3-phenylpropionamide 
• 97437-86-0 Phenylalanin-<4-chlor-anilid> 
• 97811-40-0 Phenylalanin- 
• 131100-60-2 Phenylalanin-aethylamid 
• 127643-68-9 2-amino-N-(4-methoxyphenyl)-3-phenylpropanamide 
• 23961-07-1 3-DL-Phenylalanylaminooxy-propionsaeure 
• 24063-56-7 4-DL-Phenylalanylaminooxy-buttersaeure 
• 23961-21-9 4-phenylalanylamino-benzoic acid 
• 23961-11-7 N-phenylalanyl-anthranilic acid 
• 23961-10-6 2-DL-Phenylalanylamino-benzoesaeure-aethylester 
• 23961-20-8 4-DL-Phenylalanylamino-benzoesaeure-aethylester 
• 54774-16-2 o-nitrophenylsulfenyl-DL-phenylalanyl-N-carboxyanhydride 

Relevant articles and documents

N-carboxyl-DL-phenylalanine anhydride

The N1-H1 imino group of the five-membered ring of the title compound, C10H9NO3, forms intermolecular hydrogen bonds between O1 along the a axis and between O3 along the b axis. Thus, a two-dimensional hydrogen-bonding network forms a layer perpendicular to the c axis. The layer, which consists of one of two independent molecules, stacks alternately along the c axis and produces a sandwich structure.

Synthesis of sterically hindered N-acylated amino acids from N-carboxyanhydrides

Sterically hindered N-acyl, gem-disubstituted amino acids are easily prepared via the addition of organometallic reagents to N-carboxyanhydrides (NCA). The process tolerates a wide variety of functional groups and allows the synthesis of amide products not readily accessible by traditional acylation chemistry. The existence of an isocyanate intermediate was established by in situ IR spectroscopy.

PROCESS FOR PRODUCING AMINO ACID N-CARBOXYANHYDRIDE

The present invention provides a process for producing an amino acid N-carboxyanhydride, which comprises reacting an amino acid or a derivative thereof with a compound represented by the following formula (1): wherein R1 and R2 represent the same or different electron-withdrawing substituents and each independently are an optionally substituted acyl group, an optionally substituted alkyloxycarbonyl group, an optionally substituted perfluoroalkyl group, an optionally substituted perchloroalkyl group, a cyano group, a halogen atom, or a nitro group; and a and b are the same or different and each are an integer of 1-5.