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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:
164119
EC Number:
226-401-2
MDL number:
MFCD00005905
UNSPSC Code:
12352111
PubChem Substance ID:
24846427
NACRES:
NA.22

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 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 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)
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
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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