68239-22-5

Basic information

• Product Name: 1-(2-hydroxy-2-phenylethyl)pyrrolidine-2,5-dione
• Synonyms: 1-(2-hydroxy-2-phenylethyl)pyrrolidine-2,5-dione;1-(2-Hydroxy-2-phenylethyl)-2,5-pyrrolidinedione;2,5-Pyrrolidinedione, 1-(2-hydroxy-2-phenylethyl)-;Einecs 269-434-8;N-(2-Hydroxy-2-phenylethyl)succinimide
• CAS NO: 68239-22-5
• Molecular Formula: C₁₂H₁₃NO₃
• Molecular Weight: 219.23652
• EINECS: 269-434-8
• Mol File: 68239-22-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 445.4°Cat760mmHg
• Flash Point: 223.2°C
• Appearance: /
• Density: 1.294g/cm³
• Vapor Pressure: 1.03E-08mmHg at 25°C
• Refractive Index: 1.596
• CAS DataBase Reference: 1-(2-hydroxy-2-phenylethyl)pyrrolidine-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-hydroxy-2-phenylethyl)pyrrolidine-2,5-dione(68239-22-5)
• EPA Substance Registry System: 1-(2-hydroxy-2-phenylethyl)pyrrolidine-2,5-dione(68239-22-5)

Safety Data

• Hazardous Substances Data: 68239-22-5(Hazardous Substances Data)

Usage

General Description

1-(2-hydroxy-2-phenylethyl)pyrrolidine-2,5-dione, also known as (S)-HPHPD, is a chemical compound with a molecular formula C12H13NO3. It is a derivative of the amino acid proline and is classified as a pyrrolidine-2,5-dione. 1-(2-hydroxy-2-phenylethyl)pyrrolidine-2,5-dione has been studied for its potential as a pharmaceutical agent, particularly for its use as an inhibitor of the enzyme prolyl hydroxylase. Prolyl hydroxylase is involved in the regulation of hypoxia-inducible factor (HIF), which plays a role in oxygen homeostasis and is associated with diseases such as cancer and ischemic heart disease. (S)-HPHPD may have therapeutic applications in the treatment of these conditions by modulating the HIF pathway. Further research is needed to fully understand the potential uses and mechanisms of action of this compound.

InChI:InChI=1/C12H13NO3/c14-10(9-4-2-1-3-5-9)8-13-11(15)6-7-12(13)16/h1-5,10,14H,6-8H2

Upstream product

• 54553-14-9 succinic acid N-(chloromethyl)imide 
• 100-52-7 benzaldehyde 
• 123-56-8 Succinimide 
• 96-09-3 styrene oxide 

Downstream Products

• 120542-02-1 N-[(E)-2-phenylvinyl]succinimide 
• 110057-85-7 tris-(β-hydroxy-phenethyl)-amine 
• 79365-85-8 bis-(β-hydroxy-phenethyl)-amine 
• 91974-40-2 1-(2-(4-nitrophenyl)-2-oxoethyl)pyrrolidine-2,5-dione 
• 7568-93-6 2-Amino-1-phenylethanol 
• 99989-77-2 N-(4-nitro-β-nitryloxy-phenethyl)-succinimide 
• 106272-54-2 N-(β-acetoxy-phenethyl)-succinimide 

Relevant articles and documents

Preparation and Reactivity of Highly Functionalized Organometallics at the α Position of Oxygen or Nitrogen

α-Halogenoalkyl carboxylates (FG-R1CH(X)(OCOR2); FG = COOR, CN, SR; X = I, Br) were readily prepared by the addition of an acid chloride or bromide (R2COX; X = Br or Cl) to an aldehyde (FG-RCHO) in the presence of a catalytic amount of ZnCl2.They insert efficiently zinc dust in THF-DMSO (X = Br, 8 - 10 deg C, 6 - 10 h) affording the corresponding zinc organometallics at the α position to oxygen FG-RCH(ZnBr)(OAc).After the addition of the THF-soluble copper salt CuCN*2LiCl, the corresponding copper reagents FG-RCH(Cu(CN)ZnBr)(OAc) are formed and reacted with variousclasses of electrophiles such as acid chlorides, aldehydes, enones, allylic and alkynyl halides, activated alkynes, nitro olefins and alkylidenemalonates providing polyfunctional molecules in excellent yields.Similarly, zinc organometallics at the α position to the nitrogen of cyclic imides were prepared by the zinc insertion to cyclic α-chloromethyl (or α-chloroethyl) imides.After their transmetalation to the corresponding copper organometallic ((R1CO)2NCH(R)(Cu(CN)ZnCl); R = Me or H), they were reacted with allylic and alkynyl halides and ethyl propiolate affording polyfunctional imides.The reaction of cyclic N-(chloromethyl)imides with aldehydes in the presence of chromium(II) chloride in THF furnishes protected amino alcohols in 36 - 95percent yield.