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N-(2-Hydroxyethyl)phthalimide

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N-(2-Hydroxyethyl)phthalimide Basic information
Product Name:N-(2-Hydroxyethyl)phthalimide
Synonyms:AKOS BBS-00004429;2-PHTHALIMIDOETHANOL;2-(2-hydroxyethyl)-1h-isoindole-1,3(2h)-dione;N-(2-HYDROXYETHYL)PHTHALIMIDE;N-(BETA-HYDROXYETHYL)PHTHALIMIDE;TIMTEC-BB SBB003638;2-(2-hydroxyethyl)-1h-isoindole-3(2h)-dione;2-Hydroxyethylphthalimide
CAS:3891-07-4
MF:C10H9NO3
MW:191.18
EINECS:223-434-4
Product Categories:Building Blocks;Carbonyl Compounds;Chemical Synthesis;Cyclic Imides;Organic Building Blocks;N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Phthalimides;bc0001
Mol File:3891-07-4.mol
N-(2-Hydroxyethyl)phthalimide Structure
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
pka14.40±0.10(Predicted)
color White
BRN 147214
InChIInChI=1S/C10H9NO3/c12-6-5-11-9(13)7-3-1-2-4-8(7)10(11)14/h1-4,12H,5-6H2
InChIKeyMWFLUYFYHANMCM-UHFFFAOYSA-N
SMILESC1(=O)C2=C(C=CC=C2)C(=O)N1CCO
CAS DataBase Reference3891-07-4(CAS DataBase Reference)
NIST Chemistry ReferenceN-2-hydroxyethyl phthalimide(3891-07-4)
EPA Substance Registry System1H-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 Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
N-(2-Hydroxyethyl)phthalimide Usage And Synthesis
Chemical Propertieswhite crystalline powder
UsesN-(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 DescriptionN-(2-Hydroxyethyl)phthalimide is the precursor for chloromethyl ethers used in the synthesis of purine acyclic nucleosides.
SynthesisA 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.
synthesis of N-(2-Hydroxyethyl)phthalimide
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