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About This Item
Empirical Formula (Hill Notation):
C8H3Cl2NO2
CAS Number:
Molecular Weight:
216.02
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
assay
97%
mp
217-219 °C (lit.)
functional group
chloro
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.[1] The dipole moment, polarizability and first-order hyperpolarizability of 4,5-dichlorophthalimide have been investigated using ab initio and density functional theory calculations.[2]
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[3] and 2-amino-4,5-dichlorobenzoic acid.[4]
It may be used in the following studies:
It may be used in the following studies:
- As a reactant in the synthesis of 4,5-dichloro-1,2-benzenedicarboxamide.[1]
- As an additive in the Ir-BICP catalyzed asymmetric hydrogenation of 2,3,3-trimethylindolenine to improve enantioselectivity.[5]
- As a reactant in the synthesis of octachloro-Cu-phthalocyanine.[6]
- As a reagent in the synthesis of 7-tert-butylthianthrene-2,3-dicarboxylic imide.[7]
- As a starting material in the synthesis of N-(3-bromopropyl)-4,5-dichlorophthalimide.[8]
- As a nucleophilic partner in the phosphine-catalyzed allylic substitution of Morita-Baylis-Hillman acetates to form N-protected β-amino phosphonic acid esters.[9]
signalword
Warning
hcodes
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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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'
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
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