42423-10-9

Basic information

• Product Name: Silanamine, 1,1,1-trimethyl-N-(1-methylethyl)-, lithium salt
• CAS NO: 42423-10-9
• Molecular Formula: C6H17NSi.Li
• Molecular Weight: 137.226
• Mol File: 42423-10-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Silanamine, 1,1,1-trimethyl-N-(1-methylethyl)-, lithium salt(CAS DataBase Reference)
• NIST Chemistry Reference: Silanamine, 1,1,1-trimethyl-N-(1-methylethyl)-, lithium salt(42423-10-9)
• EPA Substance Registry System: Silanamine, 1,1,1-trimethyl-N-(1-methylethyl)-, lithium salt(42423-10-9)

Safety Data

• Hazardous Substances Data: 42423-10-9(Hazardous Substances Data)

Upstream product

• 5577-65-1 N-isopropyl-N-trimethylsilylamine 
• 40102-97-4 Xanthenyllithium 
• 97254-20-1 C₉H₁₆LiN 
• 97254-18-7 <(pyridin-3-yl)phenylmethyl>lithium 

Downstream Products

• 42561-78-4 C₆H₅B{N(CH₃)2}{N(i-C₃H₇)Si(CH₃)3} 
• 76085-27-3 N_.N'-Diisopropyl-N''-phenyl-N'.N''-bis(trimethylsilyl)-triaminofluorsilan 
• 5577-65-1 N-isopropyl-N-trimethylsilylamine 
• 97254-20-1 C₉H₁₆LiN 
• 97254-18-7 <(pyridin-3-yl)phenylmethyl>lithium 

Relevant articles and documents

Divergent Kinetic and Theromodynamic Acidity in Organotransition-Metal Hydride Complexes: Synthesis, Structure, and Reactivity of the Rhenium Anion of Li+5-C5H5)Re(NO)(PPh3)>-

Reaction of hydride complex (η5-C5H5)Re(NO)(PPh3)(H) (1) and n-BuLi/TMEDA (THF, -78 deg C) gives (η5-C5H4Li)Re(NO)(PPh3)(H) (Li+-8), as shown by 31P NMR monitoring, deuterium labeling, and methylation (CH3OSO2CF3, -78 deg C) to (η5-C5H4CH3)Re(NO)(PPh3)(H) (9, 52 percent).Complex Li+-8 rearranges to the rhenium anion of Li+5-C5H5)Re(NO)(PPh3)>- (Li+-3; -32 deg C, 0.5 h) with ΔH* = 11.3 +/- 0.5 kcal/mol, ΔS* = -26.2 +/- 1.4 eu, and kH/kD (-22.4 deg C) = 1.16 +/- 0.08.Crossover experiments show hydrogen migration to be intramolecular, and K+-8 rearranges ca. 104 faster than Li+-8 at -91.6 deg C.Equilibration experiments show the η5-C5H5 and ReH proton pKa's (THF) in 1 to be ca. 36 and 26 - 30, respectively.Thus, the less acidic proton is abstracted kinetically, and a rationale is proposed.Reactions of Li+-3 with alkylating agents (CH3I, n-C4H9I, ClCH2CH=CH2, ClCH2COPh), benzoic anhydride, and D2O give the corresponding alkyl, acyl, and deuteride complexes (56 - 90 percent).IR data show Li+-3 to be a mixture of three ion pairs in THF.Pentamethyl analogue (η5-C5Me5)Re(NO)(PPh3)(H) (13) is prepared from methyl complex (η5-C5Me5)Re(NO)(PPh3)(CH3) (11; HCOOH, then 110 deg C; 43 percent).Reaction of 13 and n-BuLi/K+-t-BuO- gives principally K+5-C5Me5)Re(NO)(PPh3)>-, as assayed by 31P NMR and methylation (CH3I) to 11.