N-(hydroxymethyl)phthalimide

HCID 8354CAS 118-29-6
Substructure searchFind similar structures

Basic information

Standard SMILES
O=C1c2ccccc2C(=O)N1CO
InChIKey
MNSGOOCAMMSKGI-UHFFFAOYSA-N
Molecular formula
C9H7NO3
Average molar mass
177.16 g/mol
Monoisotopic mass
177.04259308

Overview

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 is functionally related to a phthalimide.

Names & identifiers

Preferred name
N-(hydroxymethyl)phthalimide
IUPAC
2-(hydroxymethyl)isoindole-1,3-dione
English name
N-(Hydroxymethyl)phthalimide
Molecular formula
C9H7NO3
Molecular weight
177.16

Names & synonyms

N-(Hydroxymethyl)phthalimide118-29-6N-HydroxymethylphthalimidePhthalimidomethyl alcoholHydroxymethylphthalimide2-(hydroxymethyl)isoindole-1,3-dione1H-Isoindole-1,3(2H)-dione, 2-(hydroxymethyl)-DTXSID1026954G8L8BA278JCHEBI:38816NSC-27350DTXCID506954
Show more names
N-Hydroxyl-Methyl phthalimideAURORA KA-454N-(HydroxymethyLAKOS BBS-00004724IFLAB-BB F0777-0575N-(Hydroxymethyl)phoxymethylphthalimide
RefChem:830141204-241-42-(hydroxymethyl)isoindoline-1,3-dioneN-MethylolphthalimidePhthalimidomethanolOxymethyl phthalimide2-(Hydroxymethyl)-1H-isoindole-1,3(2H)-dionePHTHALIMIDE, N-(HYDROXYMETHYL)-

Database identifiers

CAS
118-29-6
PubChem CID
8354
DTXSID
DTXSID1026954
ChEMBL
CHEMBL3183835
ChEBI
CHEBI:38816
UNII
G8L8BA278J
EC Number
204-241-4
Nikkaji
J16G

Properties

Computed structural properties

XLogP
1.5
Topological polar surface area
57.6 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
13

Experimental & physicochemical properties

PesticidesEnvironmental transformation -> Pesticide transformation products (metabolite, successor)

Physicochemical properties

Melting point
147 · 147-149 °C (lit.)
Boiling point
309.06 °C · 309.06°C (rough estimate)
Density
1.3312 · 1.3312 (rough estimate)
refractive index
1.52 · 1.5200 (estimate)
storage temp.
30 °C · Store below +30°C.
pka
13.17 · 13.17±0.10(Predicted)

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 88.1% (37 of 42) of all reports.

Warning

H315 (11.9%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information1H-Isoindole-1,3(2H)-dione, 2-(hydroxymethyl)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (11.9%)

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
rtecs
TI5270000
hs_code
29251995
Signal word
Warning

Chemistry & industry

Uses & manufacturing

Use ClassificationEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
General Manufacturing Information1H-Isoindole-1,3(2H)-dione, 2-(hydroxymethyl)-: ACTIVE

Applications

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.

Preparation methods · 1 item

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.

Upstream & downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

Additional notes

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

Related reactions

23 records
New reaction record

Linked notes

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