54837-90-0

Basic information

• Product Name: Benzenamine, 4-methyl-N-propyl-
• Synonyms: N-Propyl-p-toluidin;N-(4-methylphenyl)n-propylamine;Benzenamine,4-methyl-N-propyl;Benzenamine, 4-methyl-N-propyl-;N-n-propyl-4-methylbenzenamine;N-propyl-p-tolylamine;N-propyl-4-methylaniline;N-propyl-p-toluidine
• CAS NO: 54837-90-0
• Molecular Formula: C10H15N
• Molecular Weight: 149.236
• Mol File: 54837-90-0.mol

Chemical Properties

• Melting Point: 1.08°C (estimate)
• Boiling Point: 238.5°C
• Density: 0.9243
• Refractive Index: 1.5367
• CAS DataBase Reference: Benzenamine, 4-methyl-N-propyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, 4-methyl-N-propyl-(54837-90-0)
• EPA Substance Registry System: Benzenamine, 4-methyl-N-propyl-(54837-90-0)

Safety Data

• Hazardous Substances Data: 54837-90-0(Hazardous Substances Data)

Upstream product

• 71-23-8 propan-1-ol 
• 106-49-0 p-toluidine 
• 123-38-6 propionaldehyde 
• 74-85-1 ethene 
• 623-08-5 N-methyl-p-toluidine 
• 107-10-8 propylamine 
• 29540-83-8 p-tolyl triflate 
• 504-63-2 trimethyleneglycol 
• 5720-05-8 4-methylphenylboronic acid 
• 3739-64-8 allyl n-butyl ether 
• 102-69-2 tri-n-propylamine 
• 624-31-7 4-tolyl iodide 
• 2272-45-9 benzal-p-toluidine 
• 99-99-0 1-methyl-4-nitrobenzene 

Downstream Products

• 1304501-71-0 1,2-dipropyl-1,2-dip-tolylhydrazine 
• 55239-82-2 C₁₁H₁₄ClNO 
• 64062-60-8 3-(2-Methoxy-aethoxycarbonyl-amino)-phenyl-4-methyl-N-propylcarbanilat 

Relevant articles and documents

Dehydrogenation and α-functionalization of secondary amines by visible-light-mediated catalysis

A visible-light-mediated process for dehydrogenation of amines has been described. The given protocol showed a broad substrate scope, mild reaction conditions and excellent results without the requirement of tedious purification. This process can be applied in one-pot functionalization of secondary amines with various nucleophiles through the cooperation of visible-light and Lewis acid catalysis, leading to the structurally varied essential components of biologically active molecules. In addition, Stern-Volmer studies and quenching experiments revealed the role of a catalyst and led to the proposed mechanism of this transformation.

Titanium-Catalyzed Hydroaminoalkylation of Ethylene

The first examples of titanium-catalyzed hydroaminoalkylation reactions of ethylene with secondary amines are presented. The reactions can be achieved with various titanium catalysts and they do not require the use of high pressure equipment. In addition, the first solid-state structure of a titanapyrrolidine that is formed by insertion of an alkene into the Ti?C bond of a titanaaziridine is reported.

Use of a Droplet Platform to Optimize Pd-Catalyzed C-N Coupling Reactions Promoted by Organic Bases

Recent advances in Pd-catalyzed carbon-nitrogen cross-coupling have enabled the use of soluble organic bases instead of insoluble or strong inorganic bases that are traditionally employed. The single-phase nature of these reaction conditions facilitates their implementation in continuous flow systems, high-throughput optimization platforms, and large-scale applications. In this work, we utilized an automated microfluidic optimization platform to determine optimal reaction conditions for the couplings of an aryl triflate with four types of commonly employed amine nucleophiles: anilines, amides, primary aliphatic amines, and secondary aliphatic amines. By analyzing trends in catalyst reactivity across different reaction temperatures, base strengths, and base concentrations, we have developed a set of general recommendations for Pd-catalyzed cross-coupling reactions involving organic bases. The optimization algorithm determined that the catalyst supported by the dialkyltriarylmonophosphine ligand AlPhos was the most active in the coupling of each amine nucleophile. Furthermore, our automated optimization revealed that the phosphazene base BTTP can be used to facilitate the coupling of secondary alkylamines and aryl triflates.

Breaking the Base Barrier: An Electron-Deficient Palladium Catalyst Enables the Use of a Common Soluble Base in C-N Coupling

Due to the low intrinsic acidity of amines, palladium-catalyzed C-N cross-coupling has been plagued continuously by the necessity to employ strong, inorganic, or insoluble bases. To surmount the many practical obstacles associated with these reagents, we utilized a commercially available dialkyl triarylmonophosphine-supported palladium catalyst that facilitates a broad range of C-N coupling reactions in the presence of weak, soluble bases. The mild and general reaction conditions show extraordinary tolerance for even highly base-sensitive functional groups. Additionally, insightful heteronuclear NMR studies using 15N-labeled amine complexes provide evidence for the key acidifying effect of the cationic palladium center.

Heterogeneous borrowing hydrogen reactions with Pd/C and ZnO: Diol scope

A borrowing hydrogen reaction with different diols was employed for the preparation of complex beta- gamma- or epsilon-amino alcohols from p-toluidine and tetrahydroquinoline with the aim of better understanding the applicability of the Pd/C ZnO heterogeneous catalyst.

Room temperature N-alkylation of amines with alcohols under UV irradiation catalyzed by Cu-Mo/TiO2

It is highly desirable to develop efficient heterogeneous photocatalysts for organic reactions. Here, we show the preparation and catalytic performance of a novel TiO2 (P25) supported Cu and Mo photocatalyst (Cu-Mo/TiO2) for N-alkylation of amines with alcohols under UV irradiation at room temperature. A variety of aromatic and aliphatic amines were selectively converted into the corresponding secondary amines or tertiary amines in moderate to excellent yields without the addition of any co-catalysts such as bases and organic ligands. Noteworthy, this catalytic system is feasible in the alkylation of anilines containing halogen substituents with alcohols and the yields of the desired products are up to 95%.

Ligand-free cross-coupling of boronic acids with Cu(NO3) 2 complexes of amines in aqueous media

The efficient conversion of boronic acids, both arylboronic acids and alkylboronic acids, to the corresponding amines in water was accomplished in moderate to good yields using Cu(NO3)2 complexes of amines as the nitrogen source. The

Assembly of substituted 2-alkylquinolines by a sequential palladium-catalyzed Ci-N and Ci-C bond formation

Diversity: A range of substituted 2-alkylquinolines can be prepared in a general and efficient synthetic approach that employs mild reaction conditions (see scheme). The synthesis is based on a sequential palladium-catalyzed Ci-N and Ci-C bond formation, followed by palladium-catalyzed aromatization, and results in the formation of the desired compounds in one step. Copyright

Microwave-promoted selective mono-n-alkylation of anilines with tertiary amines by heterogeneous catalysis

A palladium-catalyzed N-alkylation of anilines with tertiary amines that occurs under heterogeneous transfer-hydrogenation conditions has been developed (see scheme). This protocol of transamination, which uses a relatively cheap and easily recyclable heterogeneous catalyst, can be efficiently applied to different substrates and is suitable for large-scale preparations.

HETEROCYCLIC DERIVATIVE HAVING INHIBITORY ACTIVITY ON TYPE-I 11 -HYDROXYSTEROID DEHYDROGENASE

Disclosed is a compound which is useful as an 11β-hydroxysteroid dehydrogenase type 1 inhibitor. A compound represented by the formula: its pharmaceutically acceptable salt, or a solvate thereof, wherein X is O or S, a broken line and a wavy line represent the presence or the absence of a bond, (i) when a broken line represents the presence of a bond, a wavy line represents the absence of a bond, R2 and R3 are each independently hydrogen, halogen, cyano, hydroxy, carboxy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl or the like, (ii) when a broken line represents the absence of a bond, a wavy line represents the presence of a bond, R1 and R4 are each independently hydrogen, halogen or the like, R2 and R3 are each independently hydrogen, halogen, cyano, hydroxy, carboxy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl or the like, and R5 and R6 are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl or the like.