69707-07-9

Basic information

• Product Name: C₁₀H₁₂⁽²⁾HN
• CAS NO: 69707-07-9
• Molecular Weight: 148.212
• Mol File: 69707-07-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: C₁₀H₁₂⁽²⁾HN(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₀H₁₂⁽²⁾HN(69707-07-9)
• EPA Substance Registry System: C₁₀H₁₂⁽²⁾HN(69707-07-9)

Safety Data

• Hazardous Substances Data: 69707-07-9(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 21175-64-4 1,1-dideuteriophenylmethanol 
• 3592-47-0 Benzaldehyde-d 
• 75-31-0 isopropylamine 

Relevant articles and documents

Reactions of N-Chloro-N-alkylbenzylamines with Amines in Acetonitrile. Origin of Steric Effect in Imine-Forming Elimination

Reaction of N-chloro-N-alkylbenzylamines in which the alkyl group is Me, Et, i-Pr, sec-Bu, and t-Bu with MeNH2 and Et2NH in MeCN have been studied kinetically.The eliminations are quantitative and regiospecific, producing only N-benzylidenealkylamines.The relative rates of elimination for Me/Et/i-Pr/sec-Bu/t-Bu alkyl substituents are 1/0.6/0.4/0.3/0.1 with MeNH2 and 1/0.5/0.3/0.2/0.03 with Et2NH, respectively.Comparison with published data reveals that Charton's value for the imine-forming elimination decreases with the variation of the base-solvent from MeONa-MeOH to MeNH2-MeCN but increases when the base is changed from MeNH2 to Et2NH.For a given base, Hammett ρ and kH/kD values decrease and the ΔH(excit.) and ΔS(excit.) values increase with bulkier alkyl substituents.From these results, the origin of the steric effect in imine-forming elimination is attributed to the repulsive interaction between the alkyl group and the base in the transition state.

Reactions of N-(arylsulfonoxy)-N-alkylbenzylamines with MeONa-MeOH. Steric effect on the structure of the imine-forming transition state

Elimination reactions of N-(arylsulfonoxy)-N-alkylbenzylamines 1-5 with MeONa-MeOH have been studied kinetically. The elimination reactions are regiospecific, producing only corresponding benzylidenalkylamines. The rate equation for the reactions is kobs = k0 + k2[MeONa], indicating that the reactions proceed by competing solvolytic- and base-promoted pathways. The relative rates of elimination for the k2 and k0 pathways are 1, 0.67, 0.53, 0.35, and 0.27 for R = Me, Et, i-Pr, s-Bu, and t-Bu and 1, 4.1, 5.1, and 8.7 for R = Et, i-Pr, s-Bu, and t-Bu, respectively. For MeONa-promoted elimination from 1-5, Hammett ρ and kH/kD decrease but ρ1g and |β1g| increase with a bulkier alkyl substituent. However, the values for the solvolytic eliminations are nearly the same for all substrates and are similar to those for the base-promoted pathway, except for the ρ values, which have opposite signs. From these results, the changes in transition-state structure wrought by variation of N-alkyl substituents are assessed.