68527-72-0

Usage

InChI:InChI=1/C11H13N/c1-11(2,3)10-7-5-4-6-9(10)8-12/h4-7H,1-3H3

Upstream product

• 67-56-1 methanol 
• 2944-48-1 2-tert-butylanisole 
• 143-33-9 sodium cyanide 
• 253185-03-4 tert-butylbenzene 
• 460-19-5 ethanedinitrile 
• 104876-31-5 1-(tert-butyl)-2-isocyanobenzene 
• 109-65-9 1-bromo-butane 
• 507-19-7 t-butyl bromide 
• 91-15-6 phthalonitrile 
• 542-69-8 1-iodo-butane 
• 558-17-8 tert-Butyl iodide 
• 85-01-8 phenanthrene 
• 1184-88-9 sodium pivalate 
• 75-05-8 acetonitrile 

Downstream Products

• 273218-96-5 2-tert-butylbenzyl isothiocyanate 
• 91338-95-3 2-tert-butylbenzylamine 

Relevant academic research and scientific papers

Acetonitrile as a cyanating reagent: Cu-catalyzed cyanation of arenes

A novel approach to the Cu-catalyzed cyanation of simple arenes using acetonitrile as an attractive cyano source has been documented. The C-H functionalization of arenes without directing groups involves a sequential iodination/cyanation to give the desired aromatic nitriles in good yields. A highly efficient Cu/TEMPO system for acetonitrile C-CN bond cleavage has been discovered. TEMPO is used as a cheap oxidant and enables the reaction to be catalytic in copper. Moreover, TEMPOCH2CN 6 has been identified as the active cyanating agent and shows high reactivity for forming the -CN moiety.

Decarboxylative photosubstitution of dicyanobenzenes with aliphatic carboxylate ions

The photoreaction of dicyanobenzenes with aliphatic carboxylate ions afforded alkylcyanobenzenes and alkyldicyanobenzenes via decarboxylative substitution. The redox-photosensitized reaction system was effective in improving the product yield. The efficie

Characterization of the binding site of the histamine H3 receptor. 2. Synthesis, in vitro pharmacology, and QSAR of a series of monosubstituted benzyl analogues of thioperamide

A series of monosubstituted benzyl analogues of the histamine H3 receptor antagonist thioperamide were synthesized and evaluated for their histamine H3 receptor activity on the guinea pig jejunum. Incorporation of Cl, Br, and I at th

Reductive activation of arenes. XII. Reaction of the product of phthalonitrile one-electron reduction with butyl halides in liquid ammonia

The product of one-electron reduction of the phthalonitrile with metallic potassium in liquid ammonia reacts with butyl halides (BuCl, BuBr, BuI, s-BuBr, t-BuBr, t-BuI) to yield compounds of alkyl bonding in ipso(2-butylbenzonitriles) and unsubstituted (4-butyl-1,2-dicyanobenzenes and 2,5-dibutylbenzonitriles) positions of the aromatic ring of the original dinitrile. The dependence of the product composition on the character of alkyl moiety and halogen atom in the butyl halide is rationalized by reaction mechanism including at the first stage electron transfer from the anion-radical of the phthalonitrile to the alkyl halide and followed by recombination of the alkyl radical produced with another molecule of anionradical.

Anodic Cyanation of tert-Butylated Anisoles: Competitive Aromatic Additions and Substitutions

The electrooxidation of sevral tert-butylated anisoles has been carried out in ,ethanol containing sodium cyanide at a Pt anode in a divided cell.Two types of reactions occured competitively, aromatic-ring addition and substitution.Increasing the level of tert-butyl substitution raises the relative extent of addition to the aromatic ring.An MO calculation has indicated that the order of orientational preference for substitution of the aromatic hydrogen of alkylanisole cation radicals is explained in terms of the LUMO electron densities calculated for the cation radicals.The effect of structure on the oxidation potential of alkylanisoles has also been studied. para Substitution lowers the oxidation potential while ortho substitution raises the potential.

On the Chemistry of (2,4,6-Tri-tert-butylphenyl)isocyanide

The thermal rearrangement of (2,4,6-tri-tert-butylphenyl)isocyanide, available from 1,3,5-tri-tert-butylbenzene in 45percent yield by a four-step synthesis, offers a high-yield access to 2,4,6-tri-tert-butylbenzonitrile and -benzoic acid.The rate of this rearrangement is only slightly retarded by the bulky ortho substituents, confirming the pericyclic transition state proposed earlier. - Key Words: Crowded molecules/ Isocyanide rearrangement/ Steric effects

The Synthetic Potential of the Isocyanide-Cyanide Rearrangement

Excellent chemical and optical yields (>96percent retention) of cyanides are achieved by vapor phase thermolysis or short contact flow thermolysis of isocyanides. trans-2-Butenyl isocyanide rearranges without concomitant allylic isomerization to trans-2-butenyl cyanide.Optically active 1-(formyloxymethyl)-2-phenylethyl cyanide is obtained from optically active L-phenylalanine as a new type of chiral pool synthon.

The Isonitrile-Nitrile Rearrangement. A Reaction without a Structure-Reactivity Relationship

Reproducible rates of isomerisation of aliphatic isonitriles to nitriles in solution can be measured by GLC or IR when free-radical inhibitors are added to suppress a competing radical chain reaction.The reactivities of 19 primary, secondary, tertiary, cyclic, bicyclic, bridgehead, benzyl, substituted-benzyl, α-carbomethoxymethyl, and triphenylmethyl isocyanides in this rearrangement reaction vary by only a factor of 67 in rate or by +/- 2 kcal mol-1 in ΔG(excit.).This is explained by a tight hypervalent three-membered cyclic transition state in agreement with a previous prediction by ab initio calculation.The slower rate of 9-triptycyl isocyanide is proposed to be due to steric hindrance by the three peri hydrogens.Aromatic isocyanides isomerize about 10 times faster independent of polar para substituents and bulky ortho substituents.A hypervalent orthogonal transition state with retention of the aromatic sextet is proposed in contrast to the popular phenonium-type transition states for aryl migration in other 1,2-rearrangements.The reactivity data and the transition-state structures are discussed in context with other cationotropic 1,2-shifts.

Cyanation of Aromatic Compounds in a Gaseous Plasma

Aromatic compounds are directly cyanated by passing cyanogen and the respective compounds through a radio-frequency generated and inductively coupled glow discharge zone.Benzene and a wide variety of substituted benzenes (C6H5X: X = CH3, t-Bu, CF3, OH, F, Cl, Br, CHO) are cyanated providing a good yield of ortho-, meta-, para-, and ipso-substituted products.The relative amount of ipso product increases as the carbon-X bond dissociation energy decreases.The ratio of ortho to meta to para cyanated products demonstrates a slight preference for substitution on electron-rich positions.A plot of the meta/para yield ratio against ?m - ?p gives a ρ value of -0.5.It is proposed that electron impact on cyanogen produces CN., which in turn attacks the aromatic, causing substitution.