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H41803

Sigma-Aldrich

N-(Hydroxymethyl)phthalimide

97%

Synonym(s):

Phthalimidomethanol

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About This Item

Empirical Formula (Hill Notation):
C9H7NO3
CAS Number:
118-29-6
Molecular Weight:
177.16
Beilstein/REAXYS Number:
140946
EC Number:
204-241-4
MDL number:
MFCD00005899
UNSPSC Code:
12352100
PubChem Substance ID:
24895627
NACRES:
NA.22

Quality Level

200

assay

97%

mp

147-149 °C (lit.)

SMILES string

OCN1C(=O)c2ccccc2C1=O

InChI

1S/C9H7NO3/c11-5-10-8(12)6-3-1-2-4-7(6)9(10)13/h1-4,11H,5H2

InChI key

MNSGOOCAMMSKGI-UHFFFAOYSA-N

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Application

For amidomethylation of aromatics in triflic acid.

Packaging

Safe reagent for the in situ generation of anhydrous formaldehyde in organic solvents.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis, 1077-1077 (1993)
[Effect of hydroxymethylphthalimide on embryogenesis in white rats].
Iu S Kagan et al.
Gigiena i sanitariia, (10)(10), 64-66 (1983-10-01)
Organic Letters (2007)
M N Khan
Journal of pharmaceutical and biomedical analysis, 7(6), 685-691 (1989-01-01)
The conversion of N-(hydroxymethyl)phthalimide (NHPH) to phthalimide could not be detected within 300 s at pH 9.0, whereas in 0.18 M NaOH complete conversion of NHPH to phthalimide was observed within 50 s. In the presence of 0.2-0.4 M 1,4-diazabicyclo[2.2.2]octane
Xiang-Bao Meng et al.
Carbohydrate research, 342(9), 1169-1174 (2007-04-05)
3,4,6-Tri-O-acetyl-D-galactal, 3,4,6-tri-O-acetyl-D-glucal and 3,6,2',3',4'6'-hexa-O-acetyl-D-lactal were reacted with N-hydroxymethylphthalimide and boron trifluoride etherate to produce the corresponding phthalimidomethyl unsaturated glycosides via Ferrier rearrangement. When the galactal derivative was used, a non-Ferrier rearrangement product was also isolated as a minor product under

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