5659-38-1

Basic information

• Product Name: 2H-Pyran-2-one, 3,4,5-trichloro-
• Synonyms: 3,4,5-Trichlor-2H-pyran-2-on;3,4,5-Trichlor-2-pyron;3,4,5-Trichlor-2-pyranon;2H-Pyran-2-one,3,4,5-trichloro;3,4,5-trichloro-pyran-2-one
• CAS NO: 5659-38-1
• Molecular Formula: C5HCl3O2
• Molecular Weight: 199.421
• Mol File: 5659-38-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2H-Pyran-2-one, 3,4,5-trichloro-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Pyran-2-one, 3,4,5-trichloro-(5659-38-1)
• EPA Substance Registry System: 2H-Pyran-2-one, 3,4,5-trichloro-(5659-38-1)

Safety Data

• Hazardous Substances Data: 5659-38-1(Hazardous Substances Data)

Upstream product

• 80674-03-9 (2Z)-2,3,4,5-Tetrachlor-5-phenylthio-2,4-pentadienal 
• 76827-74-2 (Z,Z)-2,3,4,5-Tetrachlor-2,4-pentadienthiosaeure-S-pentachlorphenylester 

Relevant articles and documents

Umlagerungen vinyloger Carbonsaeurechloride, XXX. Thermische Umlagerungen von chlor- und organylthiosubstituierten (2Z,4Z)-2,4-Pentadienalen und -onen zu (2Z,4Z)-2,4-Pentadienthiosaeure-S-estern

The pentadienals 2 are prepared by reduction of the corresponding acyl chlorides 1.The ketone 2d is synthesized from 1b with lithium tert-butyl(phenylthio)cuprate.Elimination of methyl chloride and cyclization occurs on treatment of 1a with AlCl3 giving the 2H-thiopyran-2-one 8.In boiling carbontetrachloride the aldehydes 2 rearrange by 1,5-chlorine shift completely and stereospecifically into the thiolates 3.The analogous reaction 2d -> 3d is non stereospecific.As expected, compounds 2 and 3 may be converted into the same 4H-pyran-4-ones 6.The rearrangement 2 -> 3 is accelerated by RS-groups instead of chlorine in the 5-position and decelerated in the 3-position.The substituent influences and the reaction mechanism are discussed.