422665

4,5-Dichlorphthalimid

97%

• Empirische Formel (Hill-System): C₈H₃Cl₂NO₂
• CAS-Nummer: 15997-89-4
• Molekulargewicht: 216.02
• MDL-Nummer: MFCD00015886
• UNSPSC-Code: 12352100
• PubChem Substanz-ID: 24866447
• NACRES: NA.22

Eigenschaften

• Assay: 97%
• mp (Schmelzpunkt): 217-219 °C (lit.)
• Funktionelle Gruppe: 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)
• InChIKey: QJPBDGMPYPSJSF-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

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]

Anwendung

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:

• 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]

Sicherheitshinweise

• Piktogramme: GHS07
• Signalwort: Warning
• H-Sätze: H315,H319,H335
• P-Sätze: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Gefahreneinstufungen: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Zielorgane: Respiratory system
• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: dust mask type N95 (US), Eyeshields, Gloves