N-(Hydroxymethyl)phthalimide

N-(Hydroxymethyl)phthalimide Basic information
Product Name:N-(Hydroxymethyl)phthalimide
Synonyms:2-methylolisoindoline-1,3-quinone;N-(HydroxymethyL;PHTHALIMIDOMETHANOL;N-(HYDROXYMETHYL)PHTHALIMIDE;HYDROXYMETHYL PHTHALIMIDE;IFLAB-BB F0777-0575;AURORA KA-454;2-(hydroxymethyl)-1h-isoindole-3(2h)-dione
CAS:118-29-6
MF:C9H7NO3
MW:177.16
EINECS:204-241-4
Product Categories:N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Phthalimides;pharmacetical;intermediates;fine chemicals
Mol File:118-29-6.mol
N-(Hydroxymethyl)phthalimide Structure
N-(Hydroxymethyl)phthalimide Chemical Properties
Melting point 147-149 °C (lit.)
Boiling point 309.06°C (rough estimate)
density 1.3312 (rough estimate)
refractive index 1.5200 (estimate)
storage temp. Store below +30°C.
pka13.17±0.10(Predicted)
form Fine Crystalline Powder
color White
BRN 140946
InChIKeyMNSGOOCAMMSKGI-UHFFFAOYSA-N
CAS DataBase Reference118-29-6(CAS DataBase Reference)
NIST Chemistry Reference1H-isoindole-1,3(2h)-dione, 2-(hydroxymethyl)-(118-29-6)
EPA Substance Registry SystemN-(Hydroxymethyl)phthalimide (118-29-6)
Safety Information
Safety Statements 22-24/25
WGK Germany 3
RTECS TI5270000
TSCA Yes
HS Code 29251995
MSDS Information
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N-(Hydroxymethyl)phthalimide Usage And Synthesis
Chemical Propertieswhite crystalline powder
UsesN-(Hydroxymethyl)phthalimide is used as a reactant in the synthesis of 5-[(3-aralkyl amido/imidoalkyl)phenyl]-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines as antiviral agents.
UsesFor amidomethylation of aromatics in triflic acid.
DefinitionChEBI: A primary alcohol comprising phthalimide carrying an N-hydroxymethyl substituent.
PreparationTo a flask equipped with a mechanical stirrer and condenser is added 511 gm (3.47 moles) of phthalimide, 260 ml of 40% formalin (3.47 moles), and 1750 ml of water. The mixture is refluxed for about 5-10 min or until a clear solution results (if any insoluble material remains, it is first filtered). Then the mixture is cooled for several hours. The resulting product is filtered with suction, washed with cold water, and air-dried to afford 594 gm (96%), m.p. 137-141°C.
NOTE: The product should not be oven-dried since it decomposes with the loss of formaldehyde. Recrystallization of the product from ethanol affords 94% recovery of the original material with the same melting point range.
Preparation of N-Hydroxymethylphthalimide

Synthesis Reference(s)Journal of the American Chemical Society, 77, p. 1913, 1955 DOI: 10.1021/ja01612a068
N-(Hydroxymethyl)phthalimide Preparation Products And Raw materials
Raw materialsAmmonium hydroxide-->Formaldehyde-->Phthalic anhydride-->Phthalimide
Preparation ProductsPHTHALAMIDE-->N-(Bromomethyl)phthalimide-->A-(HYDROXYMETHYL)BENZENACETIC ACID METHYL ESTER
N-CHLOROSACCHARIN N-Hydroxyphthalimide N-(Chloromethyl)phthalimide N-Hydroxyethylphthalimide O-Phthalimide N-(Hydroxymethyl)phthalimide Isoindoline 4-NITRO-N-CARBOETHOXYPHTHALIMIDE 2-[(3-CHLOROPHENOXY)METHYL]-1H-ISOINDOLE-1,3(2H)-DIONE N-Carbethoxyphthalimide AURORA KA-8051 3,4,5,6-Tetrahydro-N-(hydroxymethyl)phthalimide

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