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    Nickamine

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      Nickamine

      SKU
      B0150

      Category: Building Blocks, Intermediates, Reagents

      Synonyms
      Bis[(2-dimethylamino)phenyl]amine nickel(II) chloride , Chloro[N2-[2-(dimethylamino-kN)phenyl]-N1,N1-dimethyl-1,2-benzenediaminato-kN1,kN2]-nickel
      1033772-47-2
      CAS-Number
      C16H20ClN3Ni
      Molecular Formula
      348.5
      Molecular Weight

      • Product Data
      • Handling
      • Safety Information
      • Details

      Specifications

      Purity
      ≥97% (NMR)
      Identity
      1H-NMR
      Appearance
      Grey powder

      Properties

      Solvents
      DMSO, THF, 1,4-dioxane, chloroform, dichloromethane, DMA and toluene, Inalkanes and water

      Downloads

      Safety Data Sheet
      CDX B0150 MSDS.pdf
      Short Term Storage
      +4°C
      Use / Stability
      Stable for at least 2 years after receipt when stored at +4°C.
      Handling Advice
      Protect from light and moisture.
      Long Term Storage
      +4°C
      Shipping
      AMBIENT
      Transportation
      Not dangerous goods
      Description
      Reagent used as a catalyst for cross-coupling reactions between alkyl halides and carbon nucleophiles. Catalyst for alkyl-alkyl Kumada coupling of secondary alkyl halides, direct alkylation of heterocyclic C-H bonds, Sonogashira coupling of nonactivated alkyl halides, Kumada-Corriu-Tamao coupling of nonactivated alkyl halides with aryl and heteroaryl nucleophiles. Reactant of pincer NN2 ligand leading to selective carbon-carbon bond formation.
      InChi
      InChI=1S/C16H20N3.ClH.Ni/c1-18(2)15-11-7-5-9-13(15)17-14-10-6-8-12-16(14)19(3)4
      References
      (1) Z. Csok, et al.: JACS 130, 8156 (2008) , (2) O. Vechorkin, et al.: JACS 131, 9756 (2009) , (3) O. Vechorkin, et al.: JACS 131, 12078 (2009) , (4) O. Vechorkin & X. Hu , Angew. Chem. Inter. Ed. 48, 2937 (2009) , (5) O. Vechorkin, et al.: Angew. Chem. Inter. Ed. 49, 3061 (2010) , (6) P. Ren, et al.: JACS 133, 7084 (2011) , (7) X. Hu , Chimia 66, 154 (2012) , (8) J. Breitenfeld & X. Hu , Chimia 68, 235 (2014)
      InChi Key
      IRLHVNUEEKJBEL-UHFFFAOYSA-M
      Smiles
      C[N]1(C)C2=CC=CC=C2N([Ni]13Cl)C4=C([N]3(C)C)C=CC=C4

      Reagent used as a catalyst for cross-coupling reactions between alkyl halides and carbon nucleophiles. Catalyst for alkyl-alkyl Kumada coupling of secondary alkyl halides, direct alkylation of heterocyclic C-H bonds, Sonogashira coupling of nonactivated alkyl halides, Kumada-Corriu-Tamao coupling of nonactivated alkyl halides with aryl and heteroaryl nucleophiles. Reactant of pincer NN2 ligand leading to selective carbon-carbon bond formation.

      SKU: B0150 Category: Building Blocks, Intermediates, Reagents
      • Additional information

      Additional information

      Synonyms

      Bis[(2-dimethylamino)phenyl]amine nickel(II) chloride, Chloro[N2-[2-(dimethylamino-kN)phenyl]-N1,N1-dimethyl-1,2-benzenediaminato-kN1,kN2]-nickel

      Purity

      ≥97% (NMR)

      Appearance

      Grey powder

      CAS-Number

      1033772-47-2

      Molecular Formula

      C16H20ClN3Ni

      Molecular Weight

      348.5

      Identity

      1H-NMR

      Solvents

      DMSO, THF, 1,4-dioxane, chloroform, dichloromethane, DMA and toluene, Inalkanes and water

      Smiles

      C[N]1(C)C2=CC=CC=C2N([Ni]13Cl)C4=C([N]3(C)C)C=CC=C4

      InChi Key

      IRLHVNUEEKJBEL-UHFFFAOYSA-M

      Shipping

      AMBIENT

      Short Term Storage

      +4°C

      Long Term Storage

      +4°C

      Handling Advice

      Protect from light and moisture.

      Use / Stability

      Stable for at least 2 years after receipt when stored at +4°C.

      Transportation

      Not dangerous goods

      References

      (1) Z. Csok, et al.: JACS 130, 8156 (2008), (2) O. Vechorkin, et al.: JACS 131, 9756 (2009), (3) O. Vechorkin, et al.: JACS 131, 12078 (2009), (4) O. Vechorkin & X. Hu, Angew. Chem. Inter. Ed. 48, 2937 (2009), (5) O. Vechorkin, et al.: Angew. Chem. Inter. Ed. 49, 3061 (2010), (6) P. Ren, et al.: JACS 133, 7084 (2011), (7) X. Hu, Chimia 66, 154 (2012), (8) J. Breitenfeld & X. Hu, Chimia 68, 235 (2014)

      InChi

      InChI=1S/C16H20N3.ClH.Ni/c1-18(2)15-11-7-5-9-13(15)17-14-10-6-8-12-16(14)19(3)4

      Quantity

      100 mg, 500 mg, Bulk

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