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100919

Sigma-Aldrich

N-(4-Bromobutyl)phthalimide

98%

Synonym(s):

1-Phthalimido-4-bromobutane, 2-(4-Bromobutyl)-2,3-dihydro-1H-isoindole-1,3-dione, 2-(4-Bromobutyl)phthalimide, 4-Bromobutylphthalimide

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About This Item

Empirical Formula (Hill Notation):
C12H12BrNO2
CAS Number:
5394-18-3
Molecular Weight:
282.13
Beilstein/REAXYS Number:
164119
EC Number:
226-401-2
MDL number:
MFCD00005905
UNSPSC Code:
12352111
PubChem Substance ID:
24846427
NACRES:
NA.22

Quality Level

200

assay

98%

reaction suitability

reagent type: cross-linking reagent
reagent type: linker

mp

76-80 °C (lit.)

functional group

bromo

polymer architecture

functionality: heterobifunctional

SMILES string

O=C1N(CCCCBr)C(C2=CC=CC=C21)=O

InChI

1S/C12H12BrNO2/c13-7-3-4-8-14-11(15)9-5-1-2-6-10(9)12(14)16/h1-2,5-6H,3-4,7-8H2

InChI key

UXFWTIGUWHJKDD-UHFFFAOYSA-N

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Application

N-(4-Bromobutyl)phthalimide can be used to synthesize:
  • Biologically important N4,N9-disubstituted 4,9-diaminoacridine derivatives.
  • Imidazo[4,5-b]pyridine derivatives applicable in the preparation of ketolide antibiotics.
  • Calix[4]arene and thiacalix[4]arene-based oxamate ligands.

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
STBJ7745
STBF4613V
STBB4363V
STBB4363
MKBC8931

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Synthesis of multivalent oxamate ligands based on calix [4] arene and thiacalix [4] arene backbones in 1, 3-Alternate conformation
Noamane MH, et al.
Tetrahedron, 73, 4259-4264 (2017)
Zhanhui Wang et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 971, 10-13 (2014-09-28)
The application of antibodies to small molecules in the field of bioanalytics requires antibodies with stable biological activity and high purity; thus, there is a growing interest in developing rapid, inexpensive and effective procedures to obtain such antibodies. In this
Synthesis of derivatives of imidazo [4,5-b] pyridine: Novel sulfur contained side chains for macrolide antibiotics
Liu L, et al.
Chinese Chemical Letters = Zhongguo Hua Xue Kuai Bao, 19, 1-4 (2008)
Development of a synthetic route towards N4, N9-disubstituted 4, 9-diaminoacridines: On the way to multi-stage antimalarials
Fonte M, et al.
Tetrahedron Letters, 60, 1166-1169 (2019)

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