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.

form 

Fine Crystalline Powder

pka

13.17±0.10(Predicted)

color 

White

BRN 

140946

InChIKey

MNSGOOCAMMSKGI-UHFFFAOYSA-N

CAS DataBase Reference

118-29-6(CAS DataBase Reference)

NIST Chemistry Reference

1H-isoindole-1,3(2h)-dione, 2-(hydroxymethyl)-(118-29-6)

EPA Substance Registry System

N-(Hydroxymethyl)phthalimide (118-29-6)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

TI5270000

TSCA 

Yes

HS Code 

29251995

MSDS

• Language:English Provider:N-(Hydroxymethyl)phthalimide
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

N-(Hydroxymethyl)phthalimide Usage And Synthesis

Chemical Properties

white crystalline powder

Uses

N-(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.

Uses

For amidomethylation of aromatics in triflic acid.

Preparation

To 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.

Definition

ChEBI: A primary alcohol comprising phthalimide carrying an N-hydroxymethyl substituent.

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 1913, 1955 DOI: 10.1021/ja01612a068

N-(Hydroxymethyl)phthalimide(118-29-6)Related Product Information

• N-Hydroxyethylphthalimide
• N-Hydroxyphthalimide
• N-CHLOROSACCHARIN
• N-(Chloromethyl)phthalimide
• Isoindoline
• O-Phthalimide
• 3,4,5,6-Tetrahydro-N-(hydroxymethyl)phthalimide
• N-(Hydroxymethyl)phthalimide
• 2-[(3-CHLOROPHENOXY)METHYL]-1H-ISOINDOLE-1,3(2H)-DIONE
• AURORA KA-8051
• 4-NITRO-N-CARBOETHOXYPHTHALIMIDE
• N-Carbethoxyphthalimide