84478-42-2

Basic information

• Product Name: 2-[4-chloro-2-fluoro-5-(prop-2-yn-1-yloxy)phenyl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione
• Synonyms: 1H-Isoindole-1,3(2H)-dione, 2-(4-chloro-2-fluoro-5-(2-propynyloxy)phenyl)-4,5,6,7-tetrahydro-; 2-(4-Chloro-2-fluoro-5-(2-propynyloxy)phenyl)-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione
• CAS NO: 84478-42-2
• Molecular Formula: C₁₇H₁₃ClFNO₃
• Molecular Weight: 333.7414
• Mol File: 84478-42-2.mol

Chemical Properties

• Boiling Point: 499.7°C at 760 mmHg
• Flash Point: 256°C
• Density: 1.43g/cm³
• Vapor Pressure: 4.05E-10mmHg at 25°C
• Refractive Index: 1.619
• CAS DataBase Reference: 2-[4-chloro-2-fluoro-5-(prop-2-yn-1-yloxy)phenyl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[4-chloro-2-fluoro-5-(prop-2-yn-1-yloxy)phenyl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione(84478-42-2)
• EPA Substance Registry System: 2-[4-chloro-2-fluoro-5-(prop-2-yn-1-yloxy)phenyl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione(84478-42-2)

Safety Data

• Hazardous Substances Data: 84478-42-2(Hazardous Substances Data)

Upstream product

• 2426-02-0 3,4,5,6-Tetrahydrophthalic anhydride 
• 84478-65-9 4-chloro-2-fluoro-5-(2-propynyloxy)benzenamine 

Relevant articles and documents

Two isomeric 2-[4-chloro-2-fluoro-5-(prop-2-ynyloxy)phenyl]hexahydro- isoindole-1,3-dione compounds

The molecular structures of 2-[4-chloro-2-fluoro-5-(prop-2-ynyloxy)phenyl]- 1,3,4,5,6,7-hexahydroisoindole-1,3-dione, C17H13ClFNO 3, (I), and the isomeric compound 2-[4-chloro-2-fluoro-5-(prop-2- ynyloxy)phenyl]-cis-1,3,3a,4,7,-7a-hexahydroisoindole-1,3-dione, (II), are, as anticipated, significantly different in their conformations and in the distances between the farthest two atoms. The six-membered ring of the 1,3,4,5,6,7-hexahydroisoindole-1,3-dione moiety in (I) adopts a half-chair conformation. The dihedral angle between the five-membered dione ring of (I) and the benzene ring is 50.96 (7)°. The six-membered ring of the cis-1,3,3a,4,7,7a-hexahydroisoindole-1,3-dione moiety in (II) adopts a boat conformation. The dihedral angle in (II) between the five-membered dione ring and the benzene ring is 61.03 (13)°. In the crystal structures, the molecules are linked by C-H...O hydrogen bonds and weak π-π interactions. Compound (I) is a much more potent herbicide than (II). The Cl...H distances between the farthest two atoms in (I) and (II) are 11.37 and 9.97 A, respectively.

Hydrolysis and Phytotoxic Activity of Cyclic Imides

In order to explain the close phytotoxic activities of N-aryl-3,4,5,6-tetrahydrophthalimides and their hydrolyzed products, N-aryl-3,4,5,6-tetrahydrophthalamic acids, five sets of both types of compounds possessing the same aryl residues were prepared.Their phytotoxic activity against sawa millett (E. utilis) and green microalga (S. acutus), and the relationship of interconversion between the imides and amide acids during the bioassay were investigated.In almost all cases, the imides showed stronger activity than the corresponding amide acids.The hydrolysis of the imides and the cyclization of amide acids were observed in respect of the aryl residues.The phytotoxicity caused by the imides and amide acids tested was influenced by this interconversion.