N-(2-Hydroxyethyl)phthalimide Chemical Properties

Melting point:

126-128 °C(lit.)

Boiling point:

326.92°C (rough estimate)

Density 

1.2722 (rough estimate)

refractive index 

1.5310 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Crystalline Powder

pka

14.40±0.10(Predicted)

color 

White

BRN 

147214

InChI

InChI=1S/C10H9NO3/c12-6-5-11-9(13)7-3-1-2-4-8(7)10(11)14/h1-4,12H,5-6H2

InChIKey

MWFLUYFYHANMCM-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C=CC=C2)C(=O)N1CCO

CAS DataBase Reference

3891-07-4(CAS DataBase Reference)

NIST Chemistry Reference

N-2-hydroxyethyl phthalimide(3891-07-4)

EPA Substance Registry System

1H-Isoindole-1,3(2H)-dione, 2-(2-hydroxyethyl)- (3891-07-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-26-36/37/39-24/25

WGK Germany 

3

TSCA 

TSCA listed

HS Code 

29251900

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

N-(2-Hydroxyethyl)phthalimide Usage And Synthesis

Chemical Properties

white crystalline powder

Uses

N-(2-Hydroxyethyl)phthalimide is used as a reagent to synthesize (-)-R-rolipram is a phosphodiesterase 4 inhibitor that is used to treat depression. N-(2-Hydroxyethyl)phthalimide is also used as a reagent to synthesize FR252921, a compound that acts as an immunosuppressant. Amlodipine Impurity 6

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 4, p. 106, 1963
The Journal of Organic Chemistry, 24, p. 1122, 1959 DOI: 10.1021/jo01090a601

General Description

N-(2-Hydroxyethyl)phthalimide is the precursor for chloromethyl ethers used in the synthesis of purine acyclic nucleosides.

Synthesis

A synthetic method of N-(2-Hydroxyethyl)phthalimide. It was prepared by allowing 147.2g (1.0 mole) of phthalimide to react in an autoclave with 53.0g (1.20 moles) of ethylene oxide in the presence of 1.47g (1%) of active chromium III tri-2-ethylhexanoate (COT) and 400 ml of methylisobutyl ketone (MiBK) at 160° to 165°C for two hours. On cooling, the N-(2-Hydroxyethyl)phthalimide crystallized and was collected by filtration. A 94.7% yield of the hydroxyethyl imide was obtained.

N-(2-Hydroxyethyl)phthalimide(3891-07-4)Related Product Information

• 3-Nitrophthalimide
• Bismaleimide
• N-Methylphthalimide
• Succinimide
• 4-Nitrophthalimide
• 2-(METHYLSULFONYL)ETHANOL
• Methyl 2-hydroxyethyl cellulose
• Hydroxyethyl starch
• Hydroxyethyl Cellulose
• O-Phthalimide
• 4-Aminophthalimide
• N-Hydroxyphthalimide
• Aztreonam Amide
• N-CHLOROSACCHARIN
• N-(Hydroxymethyl)phthalimide
• Potassium phthalimide
• Desmethyl amolodipine
• Amlodipine Impurity 26