79092-33-4

Basic information

• Product Name: C₈H₄KLi
• CAS NO: 79092-33-4
• Molecular Weight: 146.159
• Mol File: 79092-33-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₈H₄KLi(CAS DataBase Reference)
• NIST Chemistry Reference: C₈H₄KLi(79092-33-4)
• EPA Substance Registry System: C₈H₄KLi(79092-33-4)

Safety Data

• Hazardous Substances Data: 79092-33-4(Hazardous Substances Data)

Upstream product

• 536-74-3 phenylacetylene 

Downstream Products

• 84416-64-8 2-(phenylsulfonamido)phenyl-acetylene 
• 84416-67-1 2-(phenylsulfonamido)-1-ethylbenzene 
• 766-50-7 (2-iodophenyl)-acetylene 
• 766-46-1 2-bromo-1-ethynylbenzene 
• 873-31-4 2-chlorophenylacetylene 
• 52670-38-9 2-ethynylaniline 

Relevant articles and documents

Dimetallation of phenylacetylene. Synthesis of ortho-susbtituted derivatives of phenylacetylene, benzoselenophene and benzotellurophene

Phenylacetylene can be dimetallated in two ways. o-K-C6H4-CC-Li is formed by treating phenylacetylene at -70 deg C with two equivalents of butyllithium and one equivalent of potassium tert-butoxide in a mixture of tetrahydrofuran and hexane.The dimetallation with BuLi*N,N,N',N'-tetramethylethanediamine (TMEDA) affords a mixture of about 15percent (m + p)-Li-C6H4-CCLi and 85percent o-LiC6H4-CC-Li.Ortho-K-C6H4-CC-Li can be transformed into the dilithio or di-Grignard derivatives by addition of anhydrous lithium bromide or magnesium bromide etherate.Reaction of the dilithio derivative with elemental selenium and tellurium, followed by successive addition of tert-butyl alcohol and hexamethylphosphoric triamide (HMPT), gives benzoselenophene and benzotellurophene in good yields.Regiospecific functionalization of the nucleus via dimetal derivatives succeeds in the case of alkylation, halogenation, sulfenylation and acylation (with dimethylformamide and dimethylacetamide).Trimethylchlorosilane, chloromethyl methyl ether, aldehydes and ketones do not however react regiospecifically.