1584722-83-7

Basic information

• Product Name: 2-ethynyl-1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholene
• Synonyms: 2-ethynyl-1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholene
• CAS NO: 1584722-83-7
• Molecular Weight: 432.589
• Mol File: 1584722-83-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-ethynyl-1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ethynyl-1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholene(1584722-83-7)
• EPA Substance Registry System: 2-ethynyl-1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholene(1584722-83-7)

Safety Data

• Hazardous Substances Data: 1584722-83-7(Hazardous Substances Data)

Upstream product

• 884639-92-3 2-chloro-1,3-bis(diisopropylphenyl)-1,3-dihydro-1,3,2-diazaphosphol 
• 65032-27-1 ethynylmagnesium chloride 

Downstream Products

• 1584722-80-4 1,2-bis[1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholene]ethyne 

Relevant articles and documents

Specific and reversible alkynyl transfer reactions of an n-heterocyclic phosphane

Reaction of P-chloro-1,3,2-diazaphospholenes with alkynyllithium or Grignard reagents produced N-heterocyclic alkynylphosphanes 3a-c. Terminal alkynylphosphane 3c reacted in the presence of a catalytic amount of CuCl with formation of bis-phosphanylalkyne 4, ethyne and chlorodiazaphospholene 2b, which was converted into the appropriate azide 6 upon addition of LiN3. Detailed studies allowed us to explain the formal alkynyl/Cl metathesis and alkynyl scrambling as arising from a combination of Cu-catalysed cross-coupling steps and the reverse processes, which involved Cu-induced P-C bond breaking. The superposition of individual steps allows the formulation of an equilibrium reaction: 2 3c [lrarr2] 4 + HCCH. Shift of the equilibrium by enforced release of acetylene into the gas phase enabled quantitative conversion of 3c into 4. Traces of P-C bond-activation products were also detected upon action of CuCl on 3b with an internal triple bond, but alkynylphosphanes with Ph2P or (iPr2N)2P moieties were unreactive. Alkynylphosphanes 3a-c and 4 were characterised by spectroscopic data and single-crystal X-ray diffraction studies. The presence of notably elongated P-C bonds points to a bond-weakening effect, which is responsible for explaining the unusual P-C bond reactivity.