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422665

Sigma-Aldrich

4,5-Dichlorophthalimide

97%

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About This Item

Fórmula empírica (notación de Hill):
C8H3Cl2NO2
Número de CAS:
15997-89-4
Peso molecular:
216.02
MDL number:
MFCD00015886
UNSPSC Code:
12352100
PubChem Substance ID:
24866447
NACRES:
NA.22

assay

97%

mp

217-219 °C (lit.)

SMILES string

Clc1cc2C(=O)NC(=O)c2cc1Cl

InChI

1S/C8H3Cl2NO2/c9-5-1-3-4(2-6(5)10)8(13)11-7(3)12/h1-2H,(H,11,12,13)

InChI key

QJPBDGMPYPSJSF-UHFFFAOYSA-N

General description

4,5-Dichlorophthalimide (5,6-dichloro-1H-isoindole-1,3(2H)-dione) is a phthalimide derivative. It has been synthesized from 5,6-dichloro-1,3-isobenzofurandione and characterized by 1H ,13C-NMR and IR. The dipole moment, polarizability and first-order hyperpolarizability of 4,5-dichlorophthalimide have been investigated using ab initio and density functional theory calculations.

Application

4,5-Dichlorophthalimide (5,6-dichloro-1H-isoindole-1,3(2H)-dione) is suitable as a reactant in the synthesis of 5′-N-(4′′,5′′-dichlorophthaloyl)-3′-azido-2′,3′-dideoxythymidine and 2-amino-4,5-dichlorobenzoic acid.
It may be used in the following studies:
  • As a reactant in the synthesis of 4,5-dichloro-1,2-benzenedicarboxamide.
  • As an additive in the Ir-BICP catalyzed asymmetric hydrogenation of 2,3,3-trimethylindolenine to improve enantioselectivity.
  • As a reactant in the synthesis of octachloro-Cu-phthalocyanine.
  • As a reagent in the synthesis of 7-tert-butylthianthrene-2,3-dicarboxylic imide.
  • As a starting material in the synthesis of N-(3-bromopropyl)-4,5-dichlorophthalimide.
  • As a nucleophilic partner in the phosphine-catalyzed allylic substitution of Morita-Baylis-Hillman acetates to form N-protected β-amino phosphonic acid esters.

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

Certificados de análisis (COA)

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Sigma-Aldrich

158801

Tetrachlorophthalonitrile

Elizabeth Sharlow et al.
Probe Reports from the NIH Molecular Libraries Program, 2010 Dec 15 (Updated 2011 24) (2011-10-01)
The unicellular eukaryote
Jan Balzarini et al.
Antiviral chemistry & chemotherapy, 14(3), 139-144 (2003-10-03)
A variety of substituted 5'-N-phthaloyl-3'-azido-2',3'-dideoxythymidine derivatives has been evaluated for their activity against HIV-1, HIV-2 and Moloney murine sarcoma virus (MSV) in cell culture. Most of the 3'-azido-2',3'-dideoxythymidine (AZT, zidovudine) derivatives showed antiviral activity in the lower micromolar concentration range
Additive effects in Ir-BICP catalyzed asymmetric hydrogenation of imines.
Zhu G and Zhang X.
Tetrahedron Asymmetry, 9(14), 2415-2418 (1998)
Conversion of phthalimides to isoindolines by diborane.
8 Strassert CA and Awruch J.
Monatshefte fur Chemie / Chemical Monthly, 137(12), 1499-1503 (2006)
HaeIl Park et al.
The Journal of organic chemistry, 71(20), 7892-7894 (2006-09-26)
A series of N-protected beta-amino phosphonic acid esters have been prepared by phosphine-catalyzed allylic substitution of 2-(diethylphosphonyl)-substituted allylic acetates employing 4,5-dichlorophthalimide as nucleophilic partner. These organocatalytic allylic substitutions exhibit exceptionally high levels of regiospecificity by virtue of a tandem S(N)2'-S(N)2'
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