N-(Hydroxymethyl)phthalimide
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N-(Hydroxymethyl)phthalimide
structure -
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CAS No:
118-29-6
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Formula:
C9H7NO3
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Chemical Name:
N-(Hydroxymethyl)phthalimide
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Synonyms:
1H-Isoindole-1,3(2H)-dione,2-(hydroxymethyl)-;Phthalimide,N-(hydroxymethyl)-;2-(Hydroxymethyl)-1H-isoindole-1,3(2H)-dione;Phthalimidomethyl alcohol;(Hydroxymethyl)phthalimide;N-(Hydroxymethyl)phthalimide;N-Methylolphthalimide;NSC 27350;NSC 27471;NSC 39723;2-(Hydroxymethyl)isoindoline-1,3-dione;2-(Hydroxymethyl)-2,3-dihydro-1H-isoindole-1,3-dione;2-(Hydroxymethyl)isoindole-1,3-dione
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CAS No:
Description
N-(hydroxymethyl)phthalimide is a primary alcohol comprising phthalimide carrying an N-hydroxymethyl substituent. It is a primary alcohol and a member of phthalimides. It derives from a phthalimide.
N-(Hydroxymethyl)phthalimide Basic Attributes
177.15700
177.16
204-241-4
G8L8BA278J
39723|27471|27350
DTXSID1026954
29251995
Characteristics
57.61000
1.5
white powder
1.462 g/cm3
141-142 °C
332ºC at 760 mmHg
154.6±23.2 °C
1.644
Store in a cool, dry place. Store in a tightly closed container.
5.96E-05mmHg at 25°C
Safety Information
NONH for all modes of transport
3
S24/25
TI5270000
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 38 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
N-(Hydroxymethyl)phthalimide Use and Manufacturing
A mixture of phthalimide (41.14 g, 0.30 mol) and distilled water (100 mL) was stirred for 10 min at room temperature. After addition of formaldehyde solution (40percent, 27 mL, 0.36 mol), the resulting solution was refluxed for 1.5 h. After cooling to 0–5 °C, the resulting precipitate was collected by filtration, washed with cold water (0–5 °C, 200 mL) and dried in air to give the corresponding N-hydroxymethylphthalimide (51.01 g, 96percent yield).(0010)A solution of thionyl chloride (23.0 mL, 37.7 g, 0.32 mol) in dichloromethane (50 mL) was slowly added to a mixture of the resulting N-hydroxymethylphthalimide and dichloromethane (550 mL) and N, N-dimethylformamide (350 mL) during 30 min at room temperature with stirring. The resulting mixture was further stirred for 2 h at room temperature. After cooling to 0 °C, water (200 mL) was added slowly. And the solution was neutralized to pH 6.7–7.0 by using saturated aqueous NaHCOThe titled compound was prepared according to the method described in the literature 15. A mixture of phthalimide (0.1 mol), formalin (0.25 mol) and anhydrous potassium carbonate (1 g) was dissolved in water (50 mL) by heating on a water bath for 5 min. The resultant solution was stirred for 15 min and then refluxed on a sand-bath for 2 h. On cooling, a solid separated out which was filtered off and washed repeatedly with ice-cold water. The solid thus obtained, was dried and recrystallized from ethanol. A colorless needle was obtained. m.p., 149-150 °C, Yield-75 percent.General procedure: To a solution of 3, 4-dihydropyrimidinone (1) (1 mmol) and paraformaldehyde (2 mmol) in tetrachloroethylene (2 mL), diethyl phosphite was added (2 mmol). After completion monitored by TLC, the reaction mixture was concentrated under reduced pressure. The products were separated by silica gel column chromatography eluted with petroleum ethyl acetate/petroleum ether.
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.
1H-Isoindole-1,3(2H)-dione, 2-(hydroxymethyl)-: ACTIVE
Environmental transformation -> Pesticide transformation products (metabolite, successor)
PIMOH (N-Hydroxymethyl phthalimide acid is a known environmental transformation product of Phosmet.
Computed Properties
Molecular Weight:177.16
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:177.042593085
Monoisotopic Mass:177.042593085
Topological Polar Surface Area:57.6
Heavy Atom Count:13
Complexity:227
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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