120776-55-8

Basic information

• Product Name: 1-(2,3,5,6-tetrafluoropyridyl)-2-phenylethyne
• Synonyms: 1-(2,3,5,6-tetrafluoropyridyl)-2-phenylethyne
• CAS NO: 120776-55-8
• Molecular Weight: 251.183
• Mol File: 120776-55-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1-(2,3,5,6-tetrafluoropyridyl)-2-phenylethyne(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,3,5,6-tetrafluoropyridyl)-2-phenylethyne(120776-55-8)
• EPA Substance Registry System: 1-(2,3,5,6-tetrafluoropyridyl)-2-phenylethyne(120776-55-8)

Safety Data

• Hazardous Substances Data: 120776-55-8(Hazardous Substances Data)

Upstream product

• 16297-19-1 2,3,5,6-tetrafluoropyridin-4-yliodine 
• 18784-61-7 1,1-diphenylbis(phenylethynyl)silane 
• 52026-98-9 4-chloro-2,3,5,6-tetrafluoropyridine 
• 536-74-3 phenylacetylene 
• 932-88-7 1-iodo-2-phenylethyne 
• 41831-90-7 2,3,5,6-tetrafluoropyridyl-copper 
• 700-16-3 Pentafluoropyridine 
• 1362969-55-8 4-(2,3,5,6)-tetrafluoropyridylphosphonium tetrafluoroborate 
• 591-50-4 iodobenzene 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 

Relevant articles and documents

Triplet acetylenes as synthetic equivalents of 1,2-bicarbenes: Phantom n,π* state controls reactivity in triplet photocycloaddition

Diaryl acetylenes, in which one of the aryl groups is either a pyridine or a pyrazine, undergo efficient triplet state photocycloaddition to 1,4-cyclohexadiene with formation of 1,5-diaryl substituted tetracyclo[3.3.0. 02,8.04,6]octa

One-pot desilylation-Sonogashira coupling

Coupling of diethynyldiphenylsilane (1) with aryl halides under Sonogashira conditions affords the symmetrical diarylacetylenes bis(2-methylpyridin-5-yl)acetylene (2), bis(4-fluorophenyl)acetylene (3) and bis(4-trifluoromethylphenyl) acetylene (4) in 60% to 82% yield. In the case of 2, the by-product bis(2-methylpyridin-5-yl)butadiyne (2a) was isolated in 12% yield. The occurring desilylation reaction was investigated by treating bis(phenylethynyl)diphenylsilane (5) under the same conditions. The formation of 1-fluoro-4-(phenylethynyl)benzene (6), 1-trifluoromethyl- 4-(phenylethynyl)benzene (7) and (tetrafluoropyridin- 4-yl)ethynylbenzene (8) in 70 to 84% yield and the cleavage of hexaphenylcyclotrisiloxane were observed in all cases.

Preparation of p-substituted tetrafluoropyridyl derivatives via the tetrafluoropyridylcopper reagent

A new and improved preparation of 4-iodo-2,3,5,6-tetrafluoropyridine from pentafluoropyridine is described. This iodopyridine is utilized for the in situ preparation of the 4-tetrafluoropyridylcopper reagent, 1, via two methods. The first method involves metathesis of the 4-tetrafluoropyridylcadmium reagent with Cu(I)Br at room temperature. The requisite cadmium reagent was readily prepared in situ via reaction between 4-iodotetrafluoropyridine with acid-washed cadmium powder in DMF at room temperature. The second method involves the in situ reaction of 4-tetrafluoropyridyltributyl-phosphonium tetrafluoroborate with Na2CO3 and Cu(I)Br in DMF at room temperature. 1 readily undergoes reaction with allylic halides, vinyl iodides, aryl halides, acid chlorides and acetylenic iodides at room temperature to stereospecifically afford the corresponding 4-tetrafluoropyridyl derivatives. An alternative route to the alkyne derivatives was developed via the Pd(0) catalyzed reaction of 4-iodotetrafluoropyridine with 1-alkynes.