19667-37-9

Basic information

• Product Name: 2-(3-Chloro-2-hydroxypropyl)-2H-isoindole-1,3-dione
• Synonyms: 2-(3-Chloro-2-hydroxypropyl)-2H-isoindole-1,3-dione;N-(3-Chloro-2-hydroxypropyl)phthalimide
• CAS NO: 19667-37-9
• Molecular Formula: C₁₁H₁₀ClNO₃
• Molecular Weight: 239.655
• Mol File: 19667-37-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 405.4°Cat760mmHg
• Flash Point: 199°C
• Appearance: /
• Density: 1.444g/cm³
• Vapor Pressure: 2.68E-07mmHg at 25°C
• Refractive Index: 1.615
• CAS DataBase Reference: 2-(3-Chloro-2-hydroxypropyl)-2H-isoindole-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-Chloro-2-hydroxypropyl)-2H-isoindole-1,3-dione(19667-37-9)
• EPA Substance Registry System: 2-(3-Chloro-2-hydroxypropyl)-2H-isoindole-1,3-dione(19667-37-9)

Safety Data

• Hazardous Substances Data: 19667-37-9(Hazardous Substances Data)

Usage

Uses

2-(3-Chloro-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione has been used in yeast biosynthesis of (S)-adrenergic β-blockers by stereoselective reduction of haloketones. It has also been used in a validated LC-?MS?/MS method for the determination of three genotoxic impurities in rivaroxaban drug substance.

InChI:InChI=1/C11H10ClNO3/c12-5-7(14)6-13-10(15)8-3-1-2-4-9(8)11(13)16/h1-4,7,14H,5-6H2

Upstream product

• 136918-14-4 phthalimide 
• 106-89-8 epichlorohydrin 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 67843-74-7 (S)-epichlorohydrin 
• 5455-98-1 2-oxiranylmethylisoindole-1,3-dione 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 3920-12-5 2-hydroxy-3-chloropropylamine 
• 6284-28-2 2-oxo-5-phthalimidomethyl-tetrahydro-furan-3-carboxylic acid ethyl ester 
• 5455-98-1 2-oxiranylmethylisoindole-1,3-dione 
• 953747-19-8 1-amino-3-(cyclohexyl (methyl)amino)propan-2-ol 
• 161596-47-0 (S)-N-glycidylphthalimide 
• 62037-46-1 rac-1-amino-3-chloro-2-propanol hydrochloride 
• 181140-34-1 (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione 
• 131920-15-5 6-benzyloxy-4-cyano-4-ethoxycarbonyl-1,2,3,4-tetrahydro-1-amino methylene>carbazole 
• 131920-03-1 6-benzyloxy-4-cyano-4-ethoxycarbonyl-1,2,3,4-tetrahydro-2-amino methylene>carbazole 
• 131920-01-9 5-(5-benzyloxy-3-indolyl)-4-cyano-4-ethoxycarbonyl-1-(N-phthalimidyl)pentan-2-one 
• 131920-02-0 6-benzyloxy-4-cyano-4-ethoxycarbonyl-1H-2,3-dihydro-1-(N-phthalimidyl methylene)carbazole 
• 35750-02-8 2-(3-chloro-2-oxopropyl)-1H-isoindole-1,3(2H)-dione 
• 10554-11-7 N-(3-anilino-2-hydroxy-propyl)-phthalimide 

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.