148857-42-5

Basic information

• Product Name: (S)-2-(3-chloro-2-hydroxypropyl)isoindoline-1,3-dione
• Synonyms: (S)-2-(3-chloro-2-hydroxypropyl)isoindoline-1,3-dione;Rivaroxaban Impurity 49;2-[(2S)-3-Chloro-2-hydroxypropyl]-1H-isoindole-1,3(2H)-dione
• CAS NO: 148857-42-5
• Molecular Formula: C₁₁H₁₀ClNO₃
• Molecular Weight: 239.655
• Mol File: 148857-42-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 405.4±35.0 °C(Predicted)
• Appearance: /
• Density: 1.444±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: 13.25±0.20(Predicted)
• CAS DataBase Reference: (S)-2-(3-chloro-2-hydroxypropyl)isoindoline-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(3-chloro-2-hydroxypropyl)isoindoline-1,3-dione(148857-42-5)
• EPA Substance Registry System: (S)-2-(3-chloro-2-hydroxypropyl)isoindoline-1,3-dione(148857-42-5)

Safety Data

• Hazardous Substances Data: 148857-42-5(Hazardous Substances Data)

Usage

Description

(S)-2-(3-chloro-2-hydroxypropyl)isoindoline-1,3-dione is an organic compound characterized by its unique molecular structure, which features a chloro group and a hydroxy group attached to a propyl chain that is connected to an isoindoline-1,3-dione backbone. (S)-2-(3-chloro-2-hydroxypropyl)isoindoline-1,3-dione is known for its potential applications in various industries due to its chemical properties.

Uses

Used in Pharmaceutical Industry:
(S)-2-(3-chloro-2-hydroxypropyl)isoindoline-1,3-dione is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with specific therapeutic properties.
Used in Biocatalyst Preparation:
(S)-2-(3-chloro-2-hydroxypropyl)isoindoline-1,3-dione is used to prepare Diplogelasinospora grovesii IMI 171018, a new whole cell biocatalyst for stereoselective reduction of ketones. This application highlights the compound's utility in the field of biocatalysis, where it can contribute to the development of more efficient and environmentally friendly processes for producing enantiomerically pure compounds.

Upstream product

• 5455-98-1 2-oxiranylmethylisoindole-1,3-dione 
• 104-88-1 4-chlorobenzaldehyde 
• 136918-14-4 phthalimide 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 85-44-9 phthalic anhydride 
• 34839-13-9 (2S)-1-amino-3-chloropropan-2-ol hydrogen chloride 
• 67843-74-7 (S)-epichlorohydrin 
• 106-89-8 epichlorohydrin 

Downstream Products

• 3920-12-5 2-hydroxy-3-chloropropylamine 
• 161596-47-0 (S)-N-glycidylphthalimide 
• 5455-98-1 2-oxiranylmethylisoindole-1,3-dione 
• 6284-28-2 2-oxo-5-phthalimidomethyl-tetrahydro-furan-3-carboxylic acid ethyl ester 
• 39849-46-2 1-amino-3-piperidino-propan-2-ol 
• 874340-08-6 N-[3-phthalimido-2-(R)-hydroxypropyl]-3-fluoro-4-(4-morpholinyl)aniline 
• 446292-08-6 2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione 
• 1429334-03-1 (S)-1-phthalimido-2-((phenyloxycarbonyl)oxy)-3-propylchloride 
• 1373348-82-3 (S)-3-Chloro-1-(1,3-dioxoisoindolin-2-yl)propan-2-yl-3-fluoro-4-morpholinophenylcarbamate 
• 168828-89-5 2-({(5S)-2-oxo-3-[(4-morpholino-3-fluorophenyl)]-4,5-dihydro-1,3-oxazole-5-yl}methyl)-isoindole-1,3-dione 
• 953747-19-8 1-amino-3-(cyclohexyl (methyl)amino)propan-2-ol 
• 62037-46-1 rac-1-amino-3-chloro-2-propanol hydrochloride 
• 34839-13-9 (2S)-1-amino-3-chloropropan-2-ol hydrogen chloride 
• 181140-34-1 (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione 

Relevant articles and documents

Taking advantage of lithium monohalocarbenoid intrinsic α-elimination in 2-MeTHF: controlled epoxide ring-openingen routeto halohydrins

The intrinsic degradative α-elimination of Li carbenoids somehow complicates their use in synthesis as C1-synthons. Nevertheless, we herein report how boosting such an α-elimination is a straightforward strategy for accomplishing controlled ring-opening of epoxides to furnish the corresponding β-halohydrins. Crucial for the development of the method is the use of the eco-friendly solvent 2-MeTHF, which forces the degradation of the incipient monohalolithium, due to the very limited stabilizing effect of this solvent on the chemical integrity of the carbenoid. With this approach, high yields of the targeted compounds are consistently obtained under very high regiocontrol and, despite the basic nature of the reagents, no racemization of enantiopure materials is observed.

2-Methyltetrahydrofuran as a suitable green solvent for phthalimide functionalization promoted by supported KF

An efficient chemoselective nitrogen functionalization of phthalimides by using KF-Alumina in 2-methyltetrahydrofuran, a solvent obtained from renewal sources, is described.