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252611

Sigma-Aldrich

N-(Bromomethyl)phthalimide

96%

Synonym(s):

Phthalimidomethyl bromide

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5 G
$67.60
25 G
$236.00

About This Item

Empirical Formula (Hill Notation):
C9H6BrNO2
CAS Number:
5332-26-3
Molecular Weight:
240.05
Beilstein/REAXYS Number:
140943
EC Number:
226-239-2
MDL number:
MFCD00005897
UNSPSC Code:
12352100
PubChem Substance ID:
24855225
NACRES:
NA.22

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assay

96%

form

solid

mp

152-155 °C (lit.)

functional group

bromo
imide

SMILES string

BrCN1C(=O)c2ccccc2C1=O

InChI

1S/C9H6BrNO2/c10-5-11-8(12)6-3-1-2-4-7(6)9(11)13/h1-4H,5H2

InChI key

UUSLLECLCKTJQF-UHFFFAOYSA-N

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Application

N-(Bromomethyl)phthalimide was used as initiator in synthesis of α-phthalimidopoly(styrene) by atom transfer radical polymerisation[1]. It was also used in synthesis of functionalized 5-(aminomethyl)pyrimidine-2,4,6-trione analog[2] and new bis-C(cage)-substituted o-carborane[3].

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX5990
MKCT5777
MKCJ1862
MKCC0906
MKCG1525

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Approaches to phthalimido and amino end-functional polystyrene by atom transfer radical polymerisation (ATRP).
Postma A, et al.
Reactive functional Polymers, 66(1), 137-147 (2006)
James J-W Duan et al.
Bioorganic & medicinal chemistry letters, 17(1), 266-271 (2006-10-10)
Using a pyrimidine-2,4,6-trione motif as a zinc-binding group, a series of selective inhibitors of tumor necrosis factor-alpha converting enzyme (TACE) was discovered. Optimization of initial lead 1 resulted in a potent inhibitor (51), with an IC(50) of 2 nM in
Synthesis and crystal structure of 1, 2-bis (phthalimidomethyl)-1, 2-dicarba-closo-dodecaborane (12): a precursor to polyamines.
Zhu Y, et al.
Inorganic Chemistry Communications, 4(8), 447-449 (2001)
Leonardo P Giglio et al.
Nitric oxide : biology and chemistry, 98, 41-49 (2020-03-10)
Polymeric biomaterials capable of delivering nitric oxide (NO) topically can be used to enhance skin blood flow (SkBF) and accelerate wound healing. Herein, we used reversible addition-fragmentation chain transfer radical (RAFT) polymerization to synthesize the first poly(vinyl alcohol) (PVA) functionalized

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