105872-07-9

Usage

Classification

Aromatic nitrile

Common uses

Intermediate in the synthesis of pharmaceuticals and agrochemicals

Medical applications

Production of pharmaceutical drugs for various medical treatments

Synthesis

Building block in the synthesis of other organic compounds

Industrial applications

Potential use in the development of new materials

Versatility

Range of uses in the pharmaceutical, agricultural, and industrial fields

Upstream product

• 10531-16-5 p-butylbenzylbromide 
• 143-33-9 sodium cyanide 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 199608-28-1 4-iodobenzyl methanesulfonate 
• 109-72-8 n-butyllithium 
• 16532-79-9 4-Bromophenylacetonitrile 
• 4426-47-5 butylboronic acid 
• 14377-19-6 [4-(n-Butyl)phenyl]acetic acid 
• 7677-24-9 trimethylsilyl cyanide 
• 18282-51-4 4-iodo-benzyl alcohol 
• 60834-63-1 p-butylbenzyl alcohol 
• 1200-14-2 4-(n-butyl)benzaldehyde 
• 28788-62-7 4-butylbenzoyl chloride 
• 63676-96-0 lithium tri-n-butylzincate 

Downstream Products

• 14377-19-6 [4-(n-Butyl)phenyl]acetic acid 
• 743355-59-1 4-butyl-phenethylamine 
• 960048-18-4 2-(4-n-butylphenyl)-3-oxo-4-phenylbutanenitrile 
• 103167-96-0 (4-butyl-phenyl)-acetic acid dodecyl ester 
• 950508-68-6 2-(4-n-butylphenyl)-3-phenylpropan-2-one 

Relevant academic research and scientific papers

Synthesis of phenylenevinylene oligothiophene derivatives with and without cyano side substitution and evaluation of optoelectronic characteristics

Two types of phenylenevinylene terthiophene with and without cyano side substitution were synthesized to investigate the effect of the molecular structure on optoelectronic properties. The oligothiophene with cyano side substitution exhibited large bathoc

ALPHA,BETA UNSATURATED METHACRYLIC ESTERS WITH ANTI-INFLAMMATORY PROPERTIES

The invention relates to compounds of formula (I): wherein A, RA1, RA2, RB, RC and RD are as defined herein, and associated aspects.

CARBOXY DERIVATIVES WITH ANTIINFLAMMATORY PROPERTIES

The invention relates to compounds of formula (I) and to their use in treating or preventing an inflammatory disease or a disease associated with an undesirable immune response: (I) wherein, RA1, RA2, RC and RD are as defined herein.

Scalable Negishi Coupling between Organozinc Compounds and (Hetero)Aryl Bromides under Aerobic Conditions when using Bulk Water or Deep Eutectic Solvents with no Additional Ligands

Pd-catalyzed Negishi cross-coupling reactions between organozinc compounds and (hetero)aryl bromides have been reported when using bulk water as the reaction medium in the presence of NaCl or the biodegradable choline chloride/urea eutectic mixture. Both C(sp3)-C(sp2) and C(sp2)-C(sp2) couplings have been found to proceed smoothly, with high chemoselectivity, under mild conditions (room temperature or 60 °C) in air, and in competition with protonolysis. Additional benefits include very short reaction times (20 s), good to excellent yields (up to 98 %), wide substrate scope, and the tolerance of a variety of functional groups. The proposed novel protocol is scalable, and the practicability of the method is further highlighted by an easy recycling of both the catalyst and the eutectic mixture or water.

Making a difference on excited-state chemistry by controlling free space within a nanocapsule: Photochemistry of 1-(4-alkylphenyl)-3-phenylpropan-2-ones

The free space within a reaction cavity plays a determining role during the excited-state reaction of 1-(4-alkylphenyl)-3-phenylpropan-2-ones included within a capsule formed by two molecules of a deep cavity cavitand. By controlling the free space within the reaction cavity through remote alkyl substitution on the reactant ketone it is possible to control the yield of the rearrangement product shown above.

A novel 1,2-migration of arylzincates bearing a leaving group at benzylic position: Application to a three-component coupling of p-iodobenzyl derivatives, trialkylzincates, and electrophiles leading to functionalized p- substituted benzenes

A three-component coupling of p-iodobenzyl derivatives, trialkylzincates, and electrophiles is described. Lithium trialkylzincates (R3ZnLi) react with p-iodobenzyl methanesulfonate to give benzylzinc reagents p-RC6H4CH2Zn(L). The reaction proceeds through a mechanism involving initial iodine/zinc exchange and the 1,2-migration of the resulting arylzincates. The benzylzinc reagents, thus prepared, are subsequently used in coupling reaction with electrophiles such as aldehydes, ketones, acyl chlorides, tosyl cyanide, and chlorosilanes to give a variety of functionalized p-substituted benzenes. Reactions under Barbier conditions in which the corresponding benzylzinc reagents are generated in the presence of electrophiles work well for Me3ZnLi and for magnesium zincates R3ZnMgBr derived from Grignard reagents. Generation of secondary benzylzinc reagents starting from diethyl 1-(p-iodophenyl)ethyl phosphate and their reaction with electrophiles are also achieved under Barbier conditions. Ketones, allyl bromides, and chlorosilanes are successfully used as electrophiles under these conditions.

Benzylimidazolines as h5-HT(1B/1D) serotonin receptor ligands: A structure-affinity investigation

Benzylimidazolines may represent a class of 5-HT(1D) ligands that has yet to be exploited. On the basis of a previous report that the 2- (substituted-benzyl)imidazoline α-adrenergic agonist oxymetazoline (8) binds with high affinity at calf brain 5-HT(1D) receptors, we explored the structure-affinity relationships of a series of related derivatives. Each of the aromatic substituents was removed and then reinstated in a systematic manner to determine the influence of the individual substituents on binding. It was found that all of the aromatic substituents of 8 act in concert to impart high affinity. However, although the 3-hydroxy group could be removed without significantly reducing affinity for h5-HT(1D) (i.e., human 5- HT(1Dα)) receptors, this modification reduced h5-HT(1B) (i.e., human 5- HT(1Dβ)) receptor affinity by nearly 50-fold. The 2,6-dimethyl groups also contribute to binding but seem to play a greater role for h5-HT(1B) binding than h5-HT(1D) binding. With the appropriate structural modifications, several compounds were identified that display 20- to > 100-fold selectivity for h5-HT(1D) versus h5-HT(1B) receptors. Preliminary functional data suggest that these compounds behave as agonists. Given that 5-HT(1D) agonists are currently being explored for their antimigraine action and that activation of h5-HT(1B) receptors might be associated with cardiovascular side effects, h5- HT(1D)selective agents may offer a new lead for the development of therapeutically efficacious agents.