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

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

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

• 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 
• 5455-98-1 2-oxiranylmethylisoindole-1,3-dione 
• 104-88-1 4-chlorobenzaldehyde 
• 67843-74-7 (S)-epichlorohydrin 
• 106-89-8 epichlorohydrin 

Downstream Products

• 131920-02-0 6-benzyloxy-4-cyano-4-ethoxycarbonyl-1H-2,3-dihydro-1-(N-phthalimidyl methylene)carbazole 
• 131920-01-9 5-(5-benzyloxy-3-indolyl)-4-cyano-4-ethoxycarbonyl-1-(N-phthalimidyl)pentan-2-one 
• 131920-03-1 6-benzyloxy-4-cyano-4-ethoxycarbonyl-1,2,3,4-tetrahydro-2-amino methylene>carbazole 
• 131920-15-5 6-benzyloxy-4-cyano-4-ethoxycarbonyl-1,2,3,4-tetrahydro-1-amino methylene>carbazole 
• 6284-28-2 2-oxo-5-phthalimidomethyl-tetrahydro-furan-3-carboxylic acid ethyl ester 
• 161596-47-0 (S)-N-glycidylphthalimide 
• 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 
• 34839-13-9 (2S)-1-amino-3-chloropropan-2-ol hydrogen chloride 
• 5455-98-1 2-oxiranylmethylisoindole-1,3-dione 
• 953747-19-8 1-amino-3-(cyclohexyl (methyl)amino)propan-2-ol 

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.

A practical and enantiospecific synthesis of (-)-(R)- and (+)-(S)-piperidin-3-ols

A highly enantiospecific, azide-free synthesis of (-)-(R)- and (+)-(S)-piperidin-3-ol in excellent yield was developed. The key step of the synthesis involves the enantiospecific ring openings of enantiomerically pure (R)- and (S)-2-(oxiran-2-ylmethyl)-1H-isoindole-1,3(2H)-diones with the diethyl malonate anion and subsequent decarboxylation.

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.

PROCESS FOR THE PREPARATION OF CHIRAL GLYCIDYLPHTHALIMIDE IN HIGHLY OPTICAL PURITY

The present invention relates to a process for the preparation of highly optical pure glycidylphthalimide. More particularly, the present invention relates to a process for the preparation of chiral glycidylphthalimide, which comprises the steps of reacting an optically active 3-susbstituted 1-amino-2-propanol acid addition salt with phthalic anhydride in a presence of a base to obtain N-(3-substituted-2-hydroxypropyl)phthalimide and subjecting the obtained compound to an epoxide cyclization reaction to prepare the targeted glycidylphthalimide. According to the process, the chirality of the starting material is substantially retained throughout overall procedures. Therefore, the process can prepare the targeted glycidylphthalimide in an optically pure form having 99%ee or higher. And, the reactions are carried out under mild conditions through overall procedures and in a single reaction vessel without any special purification. This increases the yield of the target compound.