54256-33-6

Basic information

• Product Name: (R)-5-phenyl-1,3-dioxolane-2,4-dione
• Synonyms: (R)-5-phenyl-1,3-dioxolane-2,4-dione
• CAS NO: 54256-33-6
• Molecular Formula: C₉H₆O₄
• Molecular Weight: 178.14154
• EINECS: 259-045-1
• Mol File: 54256-33-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 262.9°C at 760 mmHg
• Flash Point: 113.3°C
• Appearance: /
• Density: 1.391g/cm³
• Vapor Pressure: 0.0106mmHg at 25°C
• Refractive Index: 1.566
• CAS DataBase Reference: (R)-5-phenyl-1,3-dioxolane-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-5-phenyl-1,3-dioxolane-2,4-dione(54256-33-6)
• EPA Substance Registry System: (R)-5-phenyl-1,3-dioxolane-2,4-dione(54256-33-6)

Safety Data

• Hazardous Substances Data: 54256-33-6(Hazardous Substances Data)

Usage

Description

(R)-5-Phenyl-1,3-dioxolane-2,4-dione, also known as (R)-Phenylglycine, is a chiral chemical compound with the molecular formula C8H6O4. It is a white crystalline solid that is characterized by the presence of two chiral centers and exists as a pair of enantiomers, with (R)-5-Phenyl-1,3-dioxolane-2,4-dione being the enantiomer with the (R) configuration. (R)-5-Phenyl-1,3-dioxolane-2,4-dione is widely used in the synthesis of various pharmaceuticals and agrochemicals due to its valuable applications in the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Industry:
(R)-5-Phenyl-1,3-dioxolane-2,4-dione is used as a chiral building block for the production of chiral drugs. Its chiral nature allows for the efficient synthesis of enantiomerically pure compounds, which is crucial in the development of pharmaceuticals with desired therapeutic effects and reduced side effects.
Used in Agrochemical Industry:
(R)-5-Phenyl-1,3-dioxolane-2,4-dione is also used in the synthesis of various agrochemicals, contributing to the development of effective and targeted pest control solutions.
Used as a Resolving Agent:
(R)-5-Phenyl-1,3-dioxolane-2,4-dione is utilized as a resolving agent to separate enantiomers, which is essential in obtaining the desired enantiomer with specific biological activity and minimizing potential adverse effects associated with the other enantiomer.

InChI:InChI=1/C9H6O4/c10-8-7(12-9(11)13-8)6-4-2-1-3-5-6/h1-5,7H/t7-/m1/s1

Upstream product

• 611-71-2 (R)-Mandelic Acid 
• 503-38-8 trichloromethyl chloroformate 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 72730-04-2 (6R)-7t-((S)-2-hydroxy-2-phenyl-acetylamino)-8-oxo-(6rH)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester 
• 65360-91-0 (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-methyl-8-oxo-(6rH)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester 
• 55675-34-8 (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2,3-dicarboxylic acid 3-methyl ester 
• 63760-36-1 (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-methoxycarbonylmethyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 53116-61-3 (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-methoxy-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 52243-65-9 (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(methoxyimino-methyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 54003-21-3 (6R)-3-chloro-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 134789-79-0 3-<(R)-mandelyl>-5-methylthio-(2R)-phenyl-2,3-dihydro-1,3,4-thiadiazole 
• 134789-78-9 3-<(R)-mandelyl>-5-methylthio-(2S)-phenyl-2,3-dihydro-1,3,4-thiadiazole 
• 88010-33-7 diphenylmethyl 7β-(D-mandelylamino)-3α-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3β-methylthio-1-oxacephem-4α-carboxylate 
• 66204-09-9 (6R)-7t-((S)-2-hydroxy-2-phenyl-acetylamino)-8-oxo-(6rH)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 63881-91-4 (6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-methyl-8-oxo-(6rH)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 53994-71-1 (6R)-3-chloro-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 521284-19-5 (2R)-2-hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylethanamide 

Relevant articles and documents

Preparation of stereoregular isotactic poly(mandelic acid) through organocatalytic ring-opening polymerization of a cyclic O-carboxyanhydride

Poly(mandelic acid) (PMA) is an aryl analogue of poly(lactic acid) (PLA) and a biodegradable analogue of polystyrene. The preparation of stereoregular PMA was realized using a pyridine/mandelic acid adduct (Py·MA) as an organocatalyst for the ring-opening polymerization (ROP) of the cyclic O-carboxyanhydride (manOCA). Polymers with a narrow polydispersity index and excellent molecular-weight control were prepared at ambient temperature. These highly isotactic chiral polymers exhibit an enhancement of the glasstransition temperature (Tg) of 15°C compared to the racemic polymer, suggesting potential future application as highperformance commodity and biomedical materials.

Synthesis of mirabegron intermediate (R)-2-hydroxy-N-(4-nitrophenyl ethyl)-2-phenylacetamide

The invention discloses synthesis of mirabegron intermediate (R)-2-hydroxy-N-(4-nitrophenyl ethyl)-2-phenylacetamide. The synthesis method comprises the following steps: performing esterification reaction on R-mandelic acid and triphosgene in a solvent under the existence of alkali to generate a lactide intermediate I; and performing acylation reaction on the intermediate I and 4-nitrophenylethylamine in a solvent to obtain a target product. The synthesis method avoids use of EDCI and HOBt with high price, has the advantages of easily available raw materials, low cost, simplicity in operationand few impurities, and is suitable for industrialized production.