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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:
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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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