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

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