15274-43-8

Basic information

• Product Name: DICHLOROBIS(TRIBUTYLPHOSPHINE)NICKEL(II)
• Synonyms: BIS(TRIBUTYLPHOSPHINE)NICKEL(II) CHLORIDE;BIS(TRI-N-BUTYLPHOSPHINE)NICKEL(II) CHLORIDE;DICHLOROBIS(TRIBUTYLPHOSPHINE)NICKEL(II);Bis(tri-N-butylphosphine)nickel(Ⅱ)chloride;Bis(tri-N-butylphosphine)nickel()chloride;NSC 54233
• CAS NO: 15274-43-8
• Molecular Formula: C₂₄H₅₄Cl₂NiP₂
• Molecular Weight: 534.23
• Product Categories: Catalysis and Inorganic Chemistry;Chemical Synthesis;Ni
• Mol File: 15274-43-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 43-45 °C(lit.)
• Appearance: red to purple powder or crystals
• Storage Temp.: 2-8°C
• CAS DataBase Reference: DICHLOROBIS(TRIBUTYLPHOSPHINE)NICKEL(II)(CAS DataBase Reference)
• NIST Chemistry Reference: DICHLOROBIS(TRIBUTYLPHOSPHINE)NICKEL(II)(15274-43-8)
• EPA Substance Registry System: DICHLOROBIS(TRIBUTYLPHOSPHINE)NICKEL(II)(15274-43-8)

Safety Data

• Hazard Codes: T
• Statements: 45-20/21/22-34-42/43
• Safety Statements: 53-22-26-27-28-36/37/39-45
• RIDADR: UN 1759 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 15274-43-8(Hazardous Substances Data)

Usage

Description

Dichlorobis(tributylphosphine)nickel(II), a metal catalyst, can be used in various coupling reactions.

Uses

Catalyst for:Wenkert arylationsRegioselective [2+2+2] cycloadditionsPolymerization reactions

InChI:InChI=1/2C12H27P.2ClH.Ni/c2*1-4-7-10-13(11-8-5-2)12-9-6-3;;;/h2*4-12H2,1-3H3;2*1H;/q;;;;+2

Upstream product

• 998-40-3 tributylphosphine 
• 13463-39-3 tetracarbonyl nickel 
• 83864-14-6 nickel dichloride 
• 51266-28-5 (Bu₃P)2Ni(cyclo-octa-1,5-diene) 
• 98-09-9 benzenesulfonyl chloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 40759-64-6 C₁₀H₁₂O₂NiC₈H₁₂-1,5-cyclo 
• 126085-14-1 {(Cl-P=CTMS₂)Ni(PBu₃)2} 

Downstream Products

• 51266-28-5 (Bu₃P)2Ni(cyclo-octa-1,5-diene) 
• 15554-59-3 Ni{MeCN}6⁽²⁺⁾ 
• 998-40-3 tributylphosphine 
• 16887-00-6 chloride 
• 28101-79-3 Ni(PBu₃)4 
• 105057-23-6 (NiCl(P(CH₂CH₂CH₂CH₃)3)2)2C₆H₅CCC₆H₅ 
• 201548-83-6 Ni(CH₂SC₆H₅)2(P((CH₂)3CH₃)3)2 
• 201548-81-4 Ni(CH₂SC(CH₃)3)2(P((CH₂)3CH₃)3)2 
• 256338-95-1 Ni(P(C₄H₉)3)2(C₂Cl₂) 
• 256338-96-2 NiCl(P(C₄H₉)3)2(CCCl) 
• 256339-00-1 NiCl₂(P(C₄H₉)3)(C₆Cl₄P(C₄H₉)3) 
• 256338-97-3 NiCl(P(C₄H₉)3)2(CCP(C₄H₉)3)⁽¹⁺⁾*Cl^(1-)=[NiCl(P(C₄H₉)3)2(CCP(C₄H₉)3)]Cl 
• 913371-18-3 Pt(C₂H₄)(P(C₄H₉)3)2 
• 256339-14-7 NiCl(P(C₄H₉)3)2(CCP(C₄H₉)3)⁽¹⁺⁾*B(C₆H₅)4^(1-)=[NiCl(P(C₄H₉)3)2(CCP(C₄H₉)3)][B(C₆H₅)4] 

Relevant articles and documents

Scalable Synthesis of β-Lactamase Inhibitor QPX7728 by Sequential Nickel-Catalyzed Boron Insertion into a Benzofuran Substrate and Enantioselective Cyclopropanation of the Resulting Vinylboronate

We report the scalable, high-yielding, and highly selective synthesis of the β-lactamase inhibitor QPX7728 featuring two key synthetic steps: nickel-catalyzed boron insertion of benzofuran 1 followed by enantioselective cyclopropanation of the resulting cyclic vinylboronate 2. The identification of the key reagents (catalyst and chiral auxiliary) for both steps relied on the use of high-throughput experimentation. Further optimization allowed for the cost-effective and scalable production of QPX7728.

Synthesis and fluxional behavior of [bis(trialkylphosphine)nickelio]anthracene (alkyl = Et, Bu)

The title compounds were prepared from the respective (R3P)2NiCl2 complexes and magnesium-anthracene-(THF)3 (or anthracene in the presence of Mg or C8K). The assignment of the anthracene proton NMR si