33611-54-0

Basic information

• Product Name: α-(tert-Butyl)benzenemethaneimine
• Synonyms: 1-Phenyl-2,2-dimethylpropane-1-imine;α-(tert-Butyl)benzenemethaneimine;α-tert-Butylbenzenemethanimine
• CAS NO: 33611-54-0
• Molecular Formula: C₁₁H₁₅N
• Molecular Weight: 161.2435
• Mol File: 33611-54-0.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: α-(tert-Butyl)benzenemethaneimine(CAS DataBase Reference)
• NIST Chemistry Reference: α-(tert-Butyl)benzenemethaneimine(33611-54-0)
• EPA Substance Registry System: α-(tert-Butyl)benzenemethaneimine(33611-54-0)

Safety Data

• Hazardous Substances Data: 33611-54-0(Hazardous Substances Data)

Upstream product

• 110-89-4 piperidine 
• 25290-48-6 1-(4-Chloro-phenyl)-3-[2,2-dimethyl-1-phenyl-prop-(E)-ylidene]-urea 
• 594-19-4 tert.-butyl lithium 
• 4222-25-7 3-bromo-3-phenyl-3H-diazirine 
• 100-47-0 benzonitrile 
• 108-90-7 chlorobenzene 
• 630-18-2 tert-butyl isocyanide 
• 39509-28-9 1-chloro-1-phenyl-2,2-dimethylpropyl isocyanate 
• 33933-98-1 N-(Trimethylsilyl)-2,2-dimethyl-1-phenylpropanimine 
• 100-46-9 benzylamine 
• 23490-89-3 1-<1-Phenyl-2,2-dimethyl-propyliden>-3-phenyl-harnstoff 
• 677-22-5 tert-butylmagnesium chloride 

Downstream Products

• 108182-28-1 diimidotricarbonic bis<(2,2-dimethyl-1-phenylpropylidene)amide> 
• 25290-48-6 1-(4-Chloro-phenyl)-3-[2,2-dimethyl-1-phenyl-prop-(E)-ylidene]-urea 
• 39509-28-9 1-chloro-1-phenyl-2,2-dimethylpropyl isocyanate 
• 82388-65-6 N-(2,2-Dimethyl-1-phenylpropyliden)methansulfenamid 
• 82388-59-8 N-(2,2-Dimethyl-1-phenylpropyliden)ethansulfenamid 
• 82388-69-0 2,2-Dimethyl-1-phenyl-N-thiocyanato-1-propanimin 
• 82388-66-7 N-(2,2-Dimethyl-1-phenylpropyliden)benzolsulfenamid 
• 82388-62-3 4-Chlor-N-(2,2-dimethyl-1-phenylpropyliden)butansulfenamid 
• 54948-33-3 (C₄H₉)2BNC(C₆H₅)(t-C₄H₉) 
• 1219817-70-5 3-tert-butyl-3-phenyloxaziridine 
• 1448783-13-8 (S)-methyl N-(1-phenyl-2,2-dimethylpropylidene)phenylalaninate 
• 1448783-18-3 (S)-methyl N-(1-phenyl-2,2-dimethylpropylidene)tyrosinate 
• 1448783-19-4 (S)-methyl N-(1-phenyl-2,2-dimethylpropylidene)-4-nitrophenylalaninate 

Relevant articles and documents

Light-Driven Enantioselective Synthesis of Pyrroline Derivatives by a Radical/Polar Cascade Reaction

Herein, a light-driven, atom-economical process that provides access to enantiomerically enriched substituted chiral 1-pyrroline derivatives is introduced. The strategy involves the distal functionalization of acyl heterocycles through a hydrogen-atom transfer (HAT) process and the use of tailor-made ketimines as reliable electrophilic partners. This transformation is translated into an enantiomerically controlled radical/polar cascade reaction in which water is produced as the sole by-product and stereoselectivity is dictated by coordination to a chiral-at-rhodium catalyst.

AMINATION AND HYDROXYLATION OF ARYLMETAL COMPOUNDS

In one aspect, the present disclosure provides methods of preparing a primary or secondary amine and hydroxylated aromatic compounds. In some embodiments, the aromatic compound may be unsubstituted, substituted, or contain one or more heteroatoms within the rings of the aromatic compound. The methods described herein may be carried out without the need for transition metal catalysts or harsh reaction conditions.

An evaluation of substituent effects on aromatic edge-to-face interactions and CF-π versus CH-π interactions using an imino torsion balance model

A selection of imines derived from phenyl t-butyl ketones and substituted 2-phenylethylamines or phenylalanine exhibit slow rotation around the aryl-imino bond at ambient temperature, resulting in a large non-equivalence of the ortho hydrogens in the 1H NMR spectra. This facilitates assessment of aryl substituent effects on the face tilted-T CH-π interaction between a phenyl ring (A) on the imino carbon proximate to the terminal phenyl ring (B). Analysis of the marked temperature dependence of the chemical shift of the interacting ortho hydrogen affords estimates of the opposing enthalpic and entropic factors involved in the rapid equilibrium between the closed edge-to-face conformation and alternative open conformations devoid of a CH-π interaction while in solution. Above ca. 80 °C the entropy term (TΔS) cancels out the enthalpy (ΔH) favouring the closed conformation and open conformations are preferred. Accordingly, commonly reported binding free energies may not be a good measure of the energetic strength of intramolecular aromatic interactions. Investigation of an ortho fluoro substituted compound indicates that a CF-π interaction is at least 1.0 kcal mol-1 weaker in enthalpy than the CH-π interaction. Several X-ray crystal structures depicting an intramolecular edge-to-face interaction are presented.