25628-09-5

Basic information

• Product Name: tetramethylammonium trifluoromethanesulphonate
• Synonyms: tetramethylammonium trifluoromethanesulphonate
• CAS NO: 25628-09-5
• Molecular Weight: 223.216
• Mol File: 25628-09-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: tetramethylammonium trifluoromethanesulphonate(CAS DataBase Reference)
• NIST Chemistry Reference: tetramethylammonium trifluoromethanesulphonate(25628-09-5)
• EPA Substance Registry System: tetramethylammonium trifluoromethanesulphonate(25628-09-5)

Safety Data

• Hazardous Substances Data: 25628-09-5(Hazardous Substances Data)

Upstream product

• 74-87-3 methylene chloride 
• 191666-77-0 [Cp(*)Ir(η(3)-CHPhCHCH2)(NCMe)](OTf) 
• 75-50-3 trimethylamine 
• 1825-61-2 Trimethylmethoxysilane 
• 335-05-7 Trifluoromethanesulfonyl fluoride 

Downstream Products

• 361440-67-7 [1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester 
• 13377-46-3 exo-tricyclo[3.2.1.0(2,4)]octane 
• 37904-33-9 (2-cyclopropylethyl)benzene 
• 278-72-8 exo-tricyclo[3.2.1.0-2,4]octane 
• 286-60-2 bicyclo[6.1.0]nonane 
• 75-19-4 cyclopropane 
• 1126-76-7 1,2-Epoxy-4-phenylbutane 
• 18366-49-9 1-tert-butyl-2-phenylaziridine 
• 2952-05-8 1,2-diphenylaziridine 
• 3923-51-1 1,1-diphenylprop-2-en-1-ol 
• 180348-14-5 2-Phenyl-2-propyloxirane 
• 882-59-7 1,1-diphenyloxirane 
• 873-49-4 cyclopropylbenzene 
• 1138-47-2 trans-1,2-diphenylcyclopropane 

Relevant articles and documents

Activation of acetonitrile in [Cp*Ir(η3-CH2CHCHPh)(NCMe)]+: Crystal structures of iridium-amidine, imino-ether, amido, and amide complexes

Reactions of [Cp*Ir(η3-CH2CHCHPh)(NCMe)]OTf (1) with protic amines, alcohols, and water produce amidine complexes [Cp*Ir(η3-CH2CHCHPh)(NH=C(NR2)Me)]OTf (2) (R2 = (Me)2 (a), (Me)(H) (b), (i-Pr)(H) (c), (-CH2(CH2)3CH2-) (d)), imino-ether complexes [Cp*Ir-(η3-CH2CHCHPh)(NH=C(OR′)Me)]OTf (4) (R′ = Me (a), Et (b), i-Pr (c)), and amido complex Cp*Ir(η3-CH2CHCHPh)(NHC(=O)Me) (5-K), respectively. The keto form amido complex 5-K undergoes tautomerization to give the enol form complex Cp*Ir(η3-CH2CHCHPh)(N= C(OH)Me) (5-E) in polar solvents. Tertiary amines (NMe3, NEt3) react with 1 in chlorinated solvents (XCl) to give the chloro complex Cp*IrCl(η3-CH2CHCHPh) (3) and quaternary ammonium salts [R3NX]OTf(R = Me, Et and X = CH2Cl, CH3, CHCl2, CCl3, PhCH2). Crystal structures of 2a, 4a, 5-K, and [Cp*Ir(NH=C(OH)Me)(OH2)(PPh3)]OTf2 (6) have been determined by single-crystal X-ray diffraction analysis, which lead us to suggest hybrid structures, Ir--NH-C(=N+Me2)Me (2a′) for 2a and Ir--NH-C(=O+Me)Me (4a′) for 4a to some extent. Complexes 2 and 4 react with PPh3 to give an iridium(III) complex [Cp*Ir(η3-CH2CHCHPh)(PPh3)]OTf (7) and the free amidines NH=C(NR2)Me (8) and imino-ethers NH=C(OR′)Me (9), respectively. Nitrile complexes 1 and [Cp*Ir(η3-CH2CHCHPh)(NCCH= CHMe)]OTf(10) catalyze the hydration of the nitriles in the presence of Na2CO3 to produce amides, and the benzonitrile complex [Cp*Ir(η3-CH2CHCHPh)(NCPh)]OTf(11) catalyzes the methanolysis of benzonitrile in the presence of Na2CO3 to produce NH=C(OMe)Ph. Plausible mechanisms for these catalytic reactions are suggested with the amido and imino-ether complexes such as 4 and 5 being involved.