1200-14-2

Usage

Uses

Used in Flavor and Fragrance Industry:
4-N-Butylbenzaldehyde is used as a flavoring agent for imparting artificial cherry, almond, and rum flavors to food products. Its sweet and floral odor makes it a valuable ingredient in creating a wide range of food flavors, enhancing the sensory experience for consumers.
Used in Perfume and Fragrance Industry:
The pleasant aroma of 4-N-Butylbenzaldehyde also makes it a popular component in the production of perfumes and fragrances. It contributes to the creation of complex and long-lasting scents, adding depth and character to various fragrance compositions.
Used in Pharmaceutical Industry:
4-N-Butylbenzaldehyde is studied for its potential use as a precursor in pharmaceutical synthesis. Its chemical structure offers possibilities for the development of new compounds, particularly in the area of anti-cancer drug research. This application is still in the exploratory phase, but the compound's potential as a building block for medicinal chemistry is being actively investigated.

InChI:InChI=1/C11H14O/c1-2-3-4-10-5-7-11(9-12)8-6-10/h5-9H,2-4H2,1H3

Upstream product

• 542-88-1 bis(2-chloromethyl)ether 
• 104-51-8 1-butylbenzene 
• 28788-62-7 4-butylbenzoyl chloride 
• 83803-80-9 4-n-butyl benzaldehyde diethyl acetal 
• 4426-47-5 butylboronic acid 
• 1122-91-4 4-bromo-benzaldehyde 
• 121-43-7 Trimethyl borate 
• 15499-27-1 4-n-butylchlorobenzene 
• 1461-25-2 tetra-n-butyltin(IV) 
• 1239384-08-7 butyl[2-(2-hydroxyprop-2-yl)phenyl]diisopropylsilane 
• 218627-62-4 4-butylphenylallene 
• 75-52-5 nitromethane 
• 1156-55-4 N-(4-butylphenyl)-4-methylbenzenesulfonamide 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 

Downstream Products

• 1209-20-7 p-Butylzimtsaeure 
• 35684-20-9 C₁₈H₂₁NO₂ 
• 36078-54-3 1-butyl-4-(chloromethyl)benzene 
• 69824-75-5 2,5-bis(4-butylphenyl)thiazolo[5,4-d]thiazole 
• 90672-06-3 (4-Butyl-phenyl)-(3-methyl-isothiazol-5-yl)-methanol 
• 124856-02-6 (1Z,4Z,9Z,15Z)-5-(4-Bromo-phenyl)-10,15,20-tris-(4-butyl-phenyl)-porphyrin 
• 124856-07-1 10,15,20-Tris(4-butylphenyl)-5-(4'-formylphenyl)porphyrin 
• 75552-43-1 2-(4-Butyl-phenyl)-5-octyl-[1,3]dioxane 
• 81220-96-4 2-(4-Butyl-phenyl)-5-octyl-[1,3]dioxane 
• 74800-47-8 2-(4-Butyl-phenyl)-5-propyl-[1,3]dioxane 
• 81220-90-8 2-(4-Butyl-phenyl)-5-propyl-[1,3]dioxane 
• 62718-62-1 (E)-3-(4-n-butylphenyl)acrylic acid 
• 74800-63-8 2-(4-Butyl-phenyl)-5-hexyl-[1,3]dioxane 
• 81220-92-0 2-(4-Butyl-phenyl)-5-hexyl-[1,3]dioxane 

Relevant academic research and scientific papers

ESR line shape studies of N (4-n butyl benzilidine) 4-amino 2,2,6,6-tetramethyl piperidine 1-oxide (BBTMPO) in toluene

BBTMPO was synthesized by a condensation of 4-n butyl benzaldehyde and 4-amino 2,2,6,6- tetramethyl piperidine N oxide (4-tempamine).The shape of the resulting spin probe, estimated using the Dreiding models, is a spherocone of length 10.7 Angstroem capped by hemispheres of radii 6.6 and 4.0 Angstroem, respectively.The magnetic parameters of BBTMPO in toluene at 77 K were determined.Variable temperature ESR line shape studies in the temperature range of 142-211 K revealed that BBTMPO exhibited anisotropic rotational ditFusion in toluene along the long axis of the spherocone and in the direction parallel to the N-O bond.Rotational diffusion along the long axis was found to be 3+/-0.5 and 7+/-0.5 times faster for frozen and liquid toluene, respectively, than the other two axes.The line shapes have been simulated by using the stochastic Liouville theory of slow-motional effects on ESR spectrum.The slow tumbling spectrum (158 K) in the model-sensitive region showed good agreement for a Brownian model.The plot of τR vs 1/T over the whole temperature range yield a good linear fit with two slopes, with the activation energy for reorientation process of 4.9 kcal/mol in the liquid state, and 9.9 kcal/mol in the solid state.The higher activation energy of rotational reorientation coupled with a lower anisotropy of molecular reorientation (N) in the solid state, indicates that the rotational degrees of freedom is more restricted in the frozen state than in the liquid state.Molecular reorientation for BBTMPO in toluene was analyzed in terms of the hydrodynamic free space model for molecular relaxation in liquids.The stickiness factor S was found to be 0.6 while the anisotropic interaction parameter K which measures the coupling of rotation to translation was found to be 0.7.For perdeuterated 2,2,6,6-tetramethyl-4-piperidine N-oxide (PD-Tempone) in toluene the stickiness factor was calculated to be 0.3, and κ was 0.4.The doubling in size and weight in going from PD-Tempone to BBTMPO increases the stickiness factor and K from 0.3 to 0.6, and 0.4 to 0.7, respectively.The similarity in the structure of BBTMPO to that of liquid crystal methoxy benzilidine butyl aniline (MBBA) and its potential use as a spin probe for MBBA is discussed.

Synthesis of Unbranched 4-Alkylbenzaldehydes

The preparation of unbranched 4-alkylbenzaldehydes free of positional and branched-chain isomers by different methods is described.A one-step preparation of the aldehydes is reported which involves the direct hydrogenation of a Friedel-Craft's complex in the presence of Pd/C catalyst.

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.

The Role of LiBr and ZnBr2 on the Cross-Coupling of Aryl Bromides with Bu2Zn or BuZnBr

The impact of LiBr and ZnBr2 salts on the Negishi coupling of alkylZnBr and dialkylzinc nucleophiles with both electron-rich and -poor aryl electrophiles has been examined. Focusing only on the more difficult coupling of deactivated (electron-rich) oxidative addition partners, LiBr promotes coupling with BuZnBr, but does not have such an effect with Bu2Zn. The presence of exogenous ZnBr2 shuts down the coupling of both BuZnBr and Bu2Zn, which has been shown before with alkyl electrophiles. Strikingly, the addition of LiBr to Bu2Zn reactions containing exogenous ZnBr2 now fully restores coupling to levels seen without any salt present. This suggests that there is a very important interaction between LiBr and ZnBr2. It is proposed that Lewis acid adducts are forming between ZnBr2 and the electron-rich Pd0 centre and the bromide from LiBr forms inorganic zincates that prevent the catalyst from binding to ZnBr2. This idea has been supported by catalyst design as chlorinating the backbone of the NHC ring of Pd-PEPPSI-IPent to produce Pd-PEPPSI-IPentCl catalyst now gives quantitative conversion, up from a ceiling of only 50 % with the former catalyst.

Acceptorless Dehydrogenation of Alcohols Catalyzed by CuI N-Heterocycle Thiolate Complexes

CuI N-heterocycle thiolate clusters efficiently catalyze the acceptorless dehydrogenation of alcohols at 70 °C. A variety of secondary/primary benzylic, allylic, and aliphatic alcohols are dehydrogenated to the corresponding ketones and aldehydes in high yields of isolated product upon release of H2. This simple catalytic system is involved in the synthesis of imines through the one-pot reaction of alcohols and amines.

Metal-catalyzed formal amidation of alkenes under CO-free condition

An effective procedure for synthesis of amides from alkenes and [Formula presented] via Pd and Fe catalysts under mild conditions is described. A series of benzamides containing various functional groups can be obtained in reasonable yield and the possible reaction pathway is proposed in this Letter.

Destruction and Construction: Application of Dearomatization Strategy in Aromatic Carbon-Nitrogen Bond Functionalization

The formation of carbon-carbon bonds through the functionalization of aromatic carbon-nitrogen bonds is a highly attractive synthetic strategy in the synthesis of aromatic molecules. In this paper, we report a novel aromatic carbon-nitrogen bond functionalization reaction by using a simple dearomatization strategy. Through this process para-substituted anilines serve as a potential aryl source in the construction of a range of functionalized aromatic molecules, such as quaternary carbon centers, α-keto esters, and aldehydes.

Reductive carbonylation of aryl halides employing a two-chamber reactor: A protocol for the synthesis of aryl aldehydes including 13C- and D-isotope labeling

A protocol has been developed for conducting the palladium-catalyzed reductive carbonylation of aryl iodides and bromides using 9-methylfluorene-9- carbonyl chloride (COgen) as a source of externally delivered carbon monoxide in a sealed two-chamber system (COware), and potassium formate as the in situ hydride source. The method is tolerant to a wide number of functional groups positioned on the aromatic ring, and it can be exploited for the isotope labeling of the aldehyde group. Hence, reductive carbonylations run with 13COgen provide a facile access to 13C-labeled aromatic aldehydes, whereas with DCO2K, the aldehyde is specifically labeled with deuterium. Two examples of double isotopic labeling are also demonstrated. Finally, the method was applied to the specific carbon-13 labeling of the β-amyloid binding compound, florbetaben.

Identification of Trypanosoma brucei leucyl-tRNA synthetase inhibitors by pharmacophore- and docking-based virtual screening and synthesis

Human African trypanosomiasis (HAT), caused by the protozoan parasite Trypanosoma brucei, is a neglected fatal disease. Leucyl-tRNA synthetase (LeuRS), which has been successfully applied in the development of antifungal agent, represents a potential antiprotozoal drug target. In this study, a 3D model of T. brucei LeuRS (TbLeuRS) synthetic active site was constructed and subjected to virtual screening using a combination of pharmacophore- and docking-based methods. A new 2-pyrrolinone scaffold was discovered and the structure-activity relationship (SAR) studies aided by the docking model and organic synthesis were carried out. Compounds with various substituents on R1, R2 and R3 were synthesized and their SAR was discussed.

Gold-catalyzed oxidation of arylallenes: Synthesis of quinoxalines and benzimidazoles

A gold-catalyzed oxidation of arylallenes to form α-diketones and aldehydes in good yields is presented. Further directed synthesis of quinoxalines and benzimidazoles, via the condensation of the resulting α-diketones and aldehydes with benzene-1,2-diamine, was achieved in high yields.