260908

Sigma-Aldrich

N-Bromophthalimide

95%

Empirical Formula (Hill Notation):
C8H4BrNO2
CAS Number:
Molecular Weight:
226.03
Beilstein/REAXYS Number:
131211
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

95%

mp

194-198 °C (lit.)

SMILES string

BrN1C(=O)c2ccccc2C1=O

InChI

1S/C8H4BrNO2/c9-10-7(11)5-3-1-2-4-6(5)8(10)12/h1-4H

InChI key

MARXMDRWROUXMD-UHFFFAOYSA-N

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Application

N-Bromophthalimide has been used:
  • as reagent in allylic amination reactions of alkenes
  • brominating reagent in enantioselective synthesis of multisubstituted biaryl derivatives by chiral phosphoric acid catalyzed asymmetric bromination
  • as a titrant in titrimetric determination of isoniazid in pure form or in tablets

Packaging

25 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

V Krishnakumar et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 62(4-5), 918-925 (2005-06-14)
Fourier transform infrared (FT-IR) spectra of phthalimide and N-bromophthalimide have been recorded in the range of 4000-400 cm-1. With the hope of providing more and effective information on the fundamental vibrations, a normal coordinate analysis has been performed on phthalimide...
Ying Wei et al.
Organic letters, 15(20), 5186-5189 (2013-10-10)
Allylic amination reactions of alkenes, with an NBP (N-bromophthalimide) or NBS (N-bromosuccinimide)/DBU combination, were developed, in which both internal and external nitrogen nucleophiles can be installed directly. Dual activation of NBS or NBP by DBU leads to more electrophilic bromine...
Feng Chen et al.
Journal of the American Chemical Society, 135(4), 1232-1235 (2013-01-15)
A catalytic asymmetric bromocyclization of trisubstituted olefinic amides that uses a C(2)-symmetric mannitol-derived cyclic selenium catalyst and a stoichiometric amount of N-bromophthalimide is reported. The resulting enantioenriched pyrrolidine products, which contain two stereogenic centers, can undergo rearrangement to yield 2,3-disubstituted...
Titrimetric determination of para-aminobenzoic acid using N-bromophthalimide and N-bromosaccharin.
K G Kumar et al.
Journal of pharmaceutical and biomedical analysis, 7(5), 627-631 (1989-01-01)
A M el-Brashy et al.
Journal of pharmaceutical and biomedical analysis, 10(6), 421-426 (1992-06-01)
Two methods are proposed for the determination of isoniazid in pure form or in tablets. In the first method chlorpromazine hydrochloride, when treated with 2-iodoxybenzoic acid as an oxidant in 50% w/v o-phosphoric acid solution, is oxidized to chlorpromazine free...

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