1-N-(chloronickelio)-1-N-[2-(dimethylamino)phenyl]-2-N,2-N-dimethylbenzene-1,2-diamine

• ChemBase ID: 143491
• Molecular Formular: C16H20ClN3Ni
• Molecular Mass: 348.4965
• Monoisotopic Mass: 347.06991824
• SMILES: CN(C)c1ccccc1N(c1ccccc1N(C)C)[Ni]Cl
• Canonical SMILES: Cl[Ni]N(c1ccccc1N(C)C)c1ccccc1N(C)C
• 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;;/h5-12H,1-4H3;1H;/q-1;;+2/p-1
• InChIKey: IRLHVNUEEKJBEL-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-N-(chloronickelio)-1-N-[2-(dimethylamino)phenyl]-2-N,2-N-dimethylbenzene-1,2-diamine
• IUPAC Traditional name: 1-N-(chloronickelio)-1-N-[2-(dimethylamino)phenyl]-2-N,2-N-dimethylbenzene-1,2-diamine
• Synonyms: Nickamine; Chloro[N2-[2-(dimethylamino-κN)phenyl]-N1,N1-dimethyl-1,2-benzenediaminato-κN1,κN2]-nickel; Bis[(2-dimethylamino)phenyl]amine nickel(II) chloride; 氯[N2-[2-(二甲氨基-κN)苯基]-N1,N1-二甲基-1,2-苯二胺-κN1,κN2]-镍; 双[(2-二甲氨基)苯基]胺氯化镍(II)

Database IDs

• CAS Number: 1033772-47-2
• MDL Number: MFCD17015253
• PubChem SID: 162237710
• PubChem CID: 71310963

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.616219
• LogD (pH = 7.4): 3.6176813
• Log P: 3.6177
• Molar Refractivity: 99.057 cm^3
• Polarizability: 35.650185 Å^3
• Polar Surface Area: 9.72 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3

Product Information

• Purity: ≥97% (AT)
• Empirical Formula (Hill Notation): C16H20ClN3Ni

DETAILS

Sigma Aldrich - 728551

Packaging
100, 500 mg in glass bottle
Application
Catalyst for:
• Alkyl-alkyl Kumada coupling of secondary alkyl halides1
• Direct alkylation of heterocyclic C-H bonds2
• Sonogashira coupling of nonactivated alkyl halides3
• Kumada-Corriu-Tamao coupling of nonactivated alkyl halides with aryl and heteroaryl nucleophiles4Reactant of pincer NN2 ligand leading to selective carbon-carbon bond formation5