50766-86-4

Usage

Uses

Used in Pharmaceutical Production:
3-Nitrobutyrophenone is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the formation of complex organic molecules that are integral to drug development.
Used in Organic Synthesis:
As a reagent, 3-Nitrobutyrophenone is utilized in organic synthesis to facilitate chemical reactions, enabling the creation of a range of organic compounds for research and industrial applications.
Used in Research of Psychoactive Substances:
3-Nitrobutyrophenone is used as a subject of study in the field of psychopharmacology due to its psychoactive properties, aiding researchers in understanding the effects and mechanisms of action of designer drugs.
Used in Chemical Education and Training:
Due to its unique properties and applications, 3-Nitrobutyrophenone can be employed as a teaching tool in chemical education to illustrate concepts of organic chemistry, synthesis, and the importance of safety in laboratory practices.

InChI:InChI=1/C10H11NO3/c1-2-4-10(12)8-5-3-6-9(7-8)11(13)14/h3,5-7H,2,4H2,1H3

Upstream product

• 495-40-9 propiophenone 
• 99-61-6 3-nitro-benzaldehyde 
• 108-03-2 1-Nitropropane 
• 645-00-1 m-iodonitrobenzene 
• 123-72-8 butyraldehyde 
• 71-43-2 benzene 

Downstream Products

• 2034-41-5 1-(3-aminophenyl)butan-1-one 
• 5369-17-5 m-(n-butyl)-aniline 
• 138563-23-2 1-(3-amino-phenyl)-butan-1-ol 
• 29067-54-7 (RS)-1-(3-nitrophenyl)butanol 
• 121-92-6 3-nitrobenzoic acid 
• 618-95-1 methyl 3-nitrobenzoate 
• 280760-10-3 C₁₀H₁₃N₃O₂ 
• 1366133-37-0 C₂₁H₃₄N₂O₂S 
• 23217-85-8 α-(3-Aminophenyl)valeriansaeure 
• 29193-31-5 2-(3-Butyrylamino-2,4,6-triiodo-phenyl)-pentanoic acid 
• 25709-24-4 2-(2,4,6-Triiodo-3-propionylamino-phenyl)-pentanoic acid 
• 23279-57-4 α-(3-Nitrophenyl)-valeriansaeure 
• 23279-56-3 α-(3-Nitrophenyl)-valeronitril 
• 29067-57-0 1-(1-Bromo-butyl)-3-nitro-benzene 

Relevant academic research and scientific papers

Palladium-Catalyzed Direct Oxidative Coupling of Iodoarenes with Primary Alcohols Leading to Ketones: Application to the Synthesis of Benzofuranones and Indenones

In the present study, a palladium-catalyzed direct oxidative acylation through cross-dehydrogenative coupling has been investigated, utilizing readily available primary alcohols as acylating sources. Overall, this oxidative coupling proceeds via three distinct transformations such as oxidation, radical formation, and cross-coupling in one catalytic process. This protocol does not involve the assistance of a directing group or activation of the carbonyl group by any other means. Furthermore, this reaction made use of no toxic CO gas as carbonylating agent; instead, feedstock primary alcohols have been utilized as acylation source. Notably, the synthesis of benzofuranones and indenones is enabled. This strategy was also applied to the synthesis of n-butylphthalide, fenofibrate, pitofenone, and neo-lignan.

Structure-Based Discovery of Novel and Selective 5-Hydroxytryptamine 2B Receptor Antagonists for the Treatment of Irritable Bowel Syndrome

Here we employed structure-based ligand discovery techniques to explore a recently determined crystal structure of the 5-hydroxytryptamine 2B (5-HT2B) receptor. Ten compounds containing a novel chemical scaffold were identified; among them, seven molecules were active in cellular function assays with the most potent one exhibiting an IC50 value of 27.3 nM. We then systematically probed the binding characteristics of this scaffold by designing, synthesizing, and testing a series of structural modifications. The structure-activity relationship studies strongly support our predicted binding model. The binding profiling across a panel of 11 5-HT receptors indicated that these compounds are highly selective for the 5-HT2B receptor. Oral administration of compound 15 (30 mg/kg) produced significant attenuation of visceral hypersensitivity in a rat model of irritable bowel syndrome (IBS). We expect this novel scaffold will serve as the foundation for the development of 5-HT2B antagonists for the treatment of IBS.

Palladium-Catalyzed Environmentally Benign Acylation

Recent trends in research have gained an orientation toward developing efficient strategies using innocuous reagents. The earlier reported transition-metal-catalyzed carbonylations involved either toxic carbon monoxide (CO) gas as carbonylating agent or functional-group-assisted ortho sp2 C-H activation (i.e., ortho acylation) or carbonylation by activation of the carbonyl group (i.e., via the formation of enamines). Contradicting these methods, here we describe an environmentally benign process, [Pd]-catalyzed direct carbonylation starting from simple and commercially available iodo arenes and aldehydes, for the synthesis of a wide variety of ketones. Moreover, this method comprises direct coupling of iodoarenes with aldehydes without activation of the carbonyl and also without directing group assistance. Significantly, the strategy was successfully applied to the synthesis n-butylphthalide and pitofenone.

Synthesis of enantiopure 1-aryl-1-butylamines and 1-aryl-3-butenylamines by diastereoselective addition of allylzinc bromide to imines derived from (R)-phenylglycine amide

The synthesis of enantiopure 1-aryl-1-butylamines via a highly diastereoselective addition of allylzinc bromide to imines derived from (R)-phenylglycine amide is reported. These are synthesised by a three-step procedure, which involves: (a) formation of the chiral imines; (b) asymmetric addition of the allylzinc reagent; (c) removal of the chiral auxiliary by means of a reductive or non-reductive method. The reductive method provides 1-aryl-1-butylamines whereas the non-reductive method preserves the double bond to afford 1-aryl-3-butenylamines. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

3-Azabicyclo[3.1.0]hexane derivatives useful in therapy

Compounds of formula (I), their salts and prodrugs thereof, where the substituents are as defined herein are disclosed as opiate binding agents useful in the treatment of opiate-mediated conditions. Also described are processes for making such substances.

HENRY CONDENSATION UNDER HIGH PRESSURE. 2. EFFECT OF AROMATIC ALDEHYDE TYPE AND PRESSURE ON THE YIELD OF ω-NITROSTYRENES AND SECONDARY PROCESSES

Condensation of aromatic aldehydes (I)-(XX) with EtNO2 and n-PrNO2 in AcOH in the presence of AcONH4 or i-BuNH2 gives primarily ω-nitrostyrenes (Ia, b) - (XXa, b) and small quantities of nitriles (Ic) - (XXc), oximes (Id) - (XXd), and ketones (Ie, f) - (XXe, f).The yields of (Ia, b) - (XXa, b) at P = 1 atm are higher for acceptor substitutents on the aromatic ring whereas at P = 10 kbar, they are higher for donor substituents.High pressures suppress the formation of (Ic-f) - (XXc-f) and the Z-isomers of (Ia, b) - (XXa, b).The high pressure technique is especially useful in the preparation of donor-substituted (Ia, b) - (XXa, b) which are intermediates in the synthesis of the psychotropic β-phenylethylamines.