178422-67-8

Basic information

• Product Name: 2-[1-(3-Chloro-phenyl)-meth-(Z)-ylidene]-2,3-dihydro-benzo[1,4]dioxine
• Synonyms: 2-[1-(3-Chloro-phenyl)-meth-(Z)-ylidene]-2,3-dihydro-benzo[1,4]dioxine
• CAS NO: 178422-67-8
• Molecular Weight: 258.704
• Mol File: 178422-67-8.mol

Chemical Properties

• CAS DataBase Reference: 2-[1-(3-Chloro-phenyl)-meth-(Z)-ylidene]-2,3-dihydro-benzo[1,4]dioxine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[1-(3-Chloro-phenyl)-meth-(Z)-ylidene]-2,3-dihydro-benzo[1,4]dioxine(178422-67-8)
• EPA Substance Registry System: 2-[1-(3-Chloro-phenyl)-meth-(Z)-ylidene]-2,3-dihydro-benzo[1,4]dioxine(178422-67-8)

Safety Data

• Hazardous Substances Data: 178422-67-8(Hazardous Substances Data)

Upstream product

• 120-80-9 benzene-1,2-diol 
• 203173-96-0 2-[3-(3-Chloro-phenyl)-prop-2-ynyloxy]-phenol 
• 625-99-0 3-iodochlorobenzene 
• 14817-38-0 2‐(prop‐2‐yn‐1‐yloxy)phenol 

Relevant articles and documents

Palladium-Catalyzed Heteroannulation Leading to Heterocyclic Structures with Two Heteroatoms: A Highly Convenient and Facile Method for a Totally Regio- and Stereoselective Synthesis of (Z)-2,3-Dihydro-2-(ylidene)-1,4-benzo- and -naphtho [2,3-b]dioxins

A facile method for the synthesis of (Z)-2,3-dihydro-2-(ylidene)-1,4-benzo- and naphthodioxins (3) has been developed using palladium-copper catalysis. Aryl halides 2 were found to react with mono-prop-2-ynylated catechol (la) or 2-hydroxy-3-(prop-2-ynyloxy)naphthalene (Ib) in the presence of (PPh3)2PdCl2 (3.5 mol %) and CuI (7 mol %) in triethylamine by stirring at room temperature for 20 h followed by heating at 100°C for 16 h to give products 3 in good yields. The method is regioand stereoselective and also amenable to bisheteroannulation. The Z-stereochemistry of products 3 was established firmly from 1H NMR, 3JCH values (between vinylic proton and methylenic carbon of the heterocyclic ring), proton NOE measurements, and finally from X-ray analysis. Based on experimental observations and known palladium chemistry, a mechanism has been proposed to explain the regio- and stereoselective product formation. Some of the products 3 were also converted , to 1,4-benzodioxan derivatives 6 using hydrogenation procedure. A uracil derivative of possible biological interest, possessing a 1,4-benzodioxinyl functionality at the C-5 position, has been synthesized.

A totally stereoselective synthesis of (Z)-2-arylidene-1,4-benzodioxanes using palladium-copper catalysis

A convenient and general synthesis of (Z)-2-Arylidene-1,4-benzodioxanes from a mono-prop-2-ynylated catechol and aromatic halides by palladium catalysis is described.